31
Review Article Traditional Uses, Phytochemistry, and Bioactivities of Cananga odorata (Ylang-Ylang) Loh Teng Hern Tan, 1 Learn Han Lee, 1 Wai Fong Yin, 2 Chim Kei Chan, 3 Habsah Abdul Kadir, 3 Kok Gan Chan, 2 and Bey Hing Goh 1 1 Jeffrey Cheah School of Medicine and Health Sciences, Monash University Malaysia, 46150 Bandar Sunway, Selangor Darul Ehsan, Malaysia 2 Division of Genetic and Molecular Biology, Faculty of Science, Institute of Biological Sciences, University of Malaya, 50603 Kuala Lumpur, Malaysia 3 Biomolecular Research Group, Biochemistry Program, Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia Correspondence should be addressed to Bey Hing Goh; [email protected] Received 30 April 2015; Revised 4 June 2015; Accepted 9 June 2015 Academic Editor: Mark Moss Copyright © 2015 Loh Teng Hern Tan et al. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Ylang-ylang (Cananga odorata Hook. F. & omson) is one of the plants that are exploited at a large scale for its essential oil which is an important raw material for the fragrance industry. e essential oils extracted via steam distillation from the plant have been used mainly in cosmetic industry but also in food industry. Traditionally, C. odorata is used to treat malaria, stomach ailments, asthma, gout, and rheumatism. e essential oils or ylang-ylang oil is used in aromatherapy and is believed to be effective in treating depression, high blood pressure, and anxiety. Many phytochemical studies have identified the constituents present in the essential oils of C. odorata. A wide range of chemical compounds including monoterpene, sesquiterpenes, and phenylpropanoids have been isolated from this plant. Recent studies have shown a wide variety of bioactivities exhibited by the essential oils and the extracts of C. odorata including antimicrobial, antibiofilm, anti-inflammatory, antivector, insect-repellent, antidiabetic, antifertility and antimelanogenesis activities. us, the present review summarizes the information concerning the traditional uses, phytochemistry, and biological activities of C. odorata. is review is aimed at demonstrating that C. odorata not only is an important raw material for perfume industry but also considered as a prospective useful plant to agriculture and medicine. 1. Introduction Cananga odorata Hook. F. & omson, which is commonly called ylang-ylang, is a fast growing tree and can found natively in tropical Asia such as Philippines, Malaysia, Indonesia, and some other islands of Indian Ocean, mainly the Comoro, Nossi Be, and Madagascar islands. is plant has been well-known for its fragrant flower and has been introduced to China, India, Africa, and America. Ylang-ylang essential oils have already been widely utilized in the food industry as well as in the perfume industry and aromatherapy. Primarily, the ylang-ylang essential oil is derived from the flower of the C. odorata plant via water or water and steam distillation. Ylang-ylang oil has been described to possess medium to strong initial aroma with fresh, floral, slightly fruity fragrant yet delicate. Furthermore, the flower is also described to produce intensely sweet scent which is similar to jasmine [1]. Ylang-ylang oil has been approved to be generally recognized as safe by Flavor and Extract Manufacturers Asso- ciation (FEMA) and is widely used as flavouring agent and adjuvant. Currently, ylang-ylang oil can be found in various cosmetic and households products such as the massage oils, moisturizing creams, perfumes, and even scented candles. It is also believed that the medicinal properties exhibited by ylang-ylang oil are one of the main factors that contribute to its increasing popularity in the field of aromatherapy. Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2015, Article ID 896314, 30 pages http://dx.doi.org/10.1155/2015/896314

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Page 1: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Review ArticleTraditional Uses Phytochemistry and Bioactivities ofCananga odorata (Ylang-Ylang)

Loh Teng Hern Tan1 Learn Han Lee1 Wai Fong Yin2 Chim Kei Chan3

Habsah Abdul Kadir3 Kok Gan Chan2 and Bey Hing Goh1

1 Jeffrey Cheah School of Medicine and Health Sciences Monash University Malaysia 46150 Bandar SunwaySelangor Darul Ehsan Malaysia2Division of Genetic and Molecular Biology Faculty of Science Institute of Biological Sciences University of Malaya50603 Kuala Lumpur Malaysia3Biomolecular Research Group Biochemistry Program Institute of Biological Sciences Faculty of Science University of Malaya50603 Kuala Lumpur Malaysia

Correspondence should be addressed to Bey Hing Goh gohbeyhingmonashedu

Received 30 April 2015 Revised 4 June 2015 Accepted 9 June 2015

Academic Editor Mark Moss

Copyright copy 2015 Loh Teng Hern Tan et al This is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work is properlycited

Ylang-ylang (Cananga odorata Hook F amp Thomson) is one of the plants that are exploited at a large scale for its essential oilwhich is an important rawmaterial for the fragrance industryThe essential oils extracted via steam distillation from the plant havebeen usedmainly in cosmetic industry but also in food industry TraditionallyC odorata is used to treat malaria stomach ailmentsasthma gout and rheumatismThe essential oils or ylang-ylang oil is used in aromatherapy and is believed to be effective in treatingdepression high blood pressure and anxiety Many phytochemical studies have identified the constituents present in the essentialoils of C odorata A wide range of chemical compounds including monoterpene sesquiterpenes and phenylpropanoids have beenisolated from this plant Recent studies have shown a wide variety of bioactivities exhibited by the essential oils and the extractsof C odorata including antimicrobial antibiofilm anti-inflammatory antivector insect-repellent antidiabetic antifertility andantimelanogenesis activitiesThus the present review summarizes the information concerning the traditional uses phytochemistryand biological activities of C odorata This review is aimed at demonstrating that C odorata not only is an important raw materialfor perfume industry but also considered as a prospective useful plant to agriculture and medicine

1 Introduction

Cananga odorata Hook F amp Thomson which is commonlycalled ylang-ylang is a fast growing tree and can foundnatively in tropical Asia such as Philippines MalaysiaIndonesia and some other islands of Indian Ocean mainlythe Comoro Nossi Be and Madagascar islands This planthas been well-known for its fragrant flower and has beenintroduced toChina India Africa andAmerica Ylang-ylangessential oils have already been widely utilized in the foodindustry aswell as in the perfume industry and aromatherapyPrimarily the ylang-ylang essential oil is derived from theflower of the C odorata plant via water or water and steam

distillation Ylang-ylang oil has been described to possessmedium to strong initial aroma with fresh floral slightlyfruity fragrant yet delicate Furthermore the flower is alsodescribed to produce intensely sweet scent which is similar tojasmine [1] Ylang-ylang oil has been approved to be generallyrecognized as safe by Flavor and ExtractManufacturers Asso-ciation (FEMA) and is widely used as flavouring agent andadjuvant Currently ylang-ylang oil can be found in variouscosmetic and households products such as the massage oilsmoisturizing creams perfumes and even scented candles Itis also believed that the medicinal properties exhibited byylang-ylang oil are one of the main factors that contribute toits increasing popularity in the field of aromatherapy

Hindawi Publishing CorporationEvidence-Based Complementary and Alternative MedicineVolume 2015 Article ID 896314 30 pageshttpdxdoiorg1011552015896314

2 Evidence-Based Complementary and Alternative Medicine

Although the uses of ylang-ylang oil and its safety as foodingredient have been also reviewed previously [2] during thattime period the studies on the pharmacological activities ofthe Cananga odorata plant were still very limited Basicallya very brief review was done covering the antibacterialantifungal amebicidal and cytotoxic activities of the ylang-ylang essential oil [2] Perhaps it is due to the improvementin different biological assays and accessibility of chemicalpurification and identification techniques and it has seemedgreatly impacted by the research activities carried out byresearchers In particular an apparent increase in the differ-ential biological activities investigation on medicinal plantshas enabled diversified applications of existing knownnaturalproducts For instance the recent extensive explorations ofdifferential pharmacological properties of ylang-ylang andtheir active compounds have significantly opened up its newcommercial avenues for agriculture [3] Insightfully there isa great increase in number of pharmacological studies doneon C odorata in recent years particularly surrounding itsbiological properties and chemical components [4ndash8]There-fore the current review aimed to compile or summarize theseimportant findings and further highlight the importance ofCodorata as a potential promising drug discovery candidate forfuture

2 Taxonomic Classification and Nomenclatureof Cananga odorata

Taxonomic classification and nomenclature ofCananga odor-ata are as follows

kingdom Plantae plantssubkingdom Tracheobionta vascular plantssuperdivision Spermatophyta seed plantsdivision Magnoliophyta flowering plantsclass Magnoliopsida dicotyledonssubclass Magnoliidaeorder Magnolialesfamily Annonaceae custard-apple familygenus Cananga (DC) Hook f amp Thomson ylang-ylangspecies Cananga odorata (Lam) Hook f amp Thom-son ylang-ylang

3 Botany

31 Botanical Name

311 Common Names C odorata is commonly known asylang-ylangTheEnglish names ofC odorata are ylang-ylangperfume tree Cananga and cadmia Meanwhile the othercommon names for C odorata are listed in Table 1

32 Synonyms According to the plant list there are morethan twenty synonyms which have been recorded for C

odorata For instance Cananga mitrastigma (F Muell)DominCanangiummitrastigma (FMuell) DominCanangaodorata var odorata Cananga odoratum (Lam) Baillex King Canangium odoratum (Lam) Baill ex KingCanangium odoratum var velutinum Koord amp ValetonCananga scortechinii King Canangium scortechinii KingFitzgeraldia mitrastigma F Muell Unona cananga SprengUnona leptopetalaDCUnona odorata (Lam) DunalUnonaodorata (Lam) Baill Unona odoratissima Blanco Unonaossea Blanco Uvaria axillaris Roxb Uvaria cananga BanksUvaria odorata Lam Uvaria ossea (Blanco) Blanco andUvaria trifoliata Gaertn [50]

4 Botanical Description and Distribution

C odorata belong to the Annonaceae family with 125 generaand 2050 species To date the Cananga genus consists of twospecies of plant namelyC odorata andC latifoliaC odoratais a perennial tropical tree which grows natively in South-EastAsia countries such as Philippines and Malaysia and it alsooccurs naturally in several Pacific islands including AustraliaAfter that it has been introduced into China India Africaand America due to its economic importance [51]

The morphological features of the C odorata plant arebriefly described in Table 2 and illustrated in Figure 1 Basi-cally C odorata is a medium-sized evergreen tree which-generally grows up to 15 meters height with long droopingbranches [9]

5 Ethnomedicinal Uses

C odorata has a variety of medicinal properties and tradi-tional uses The strongly fragrant yellow flower of C odoratahas been reported to be used to enhance the scent of coconutoil before being used formassage by Polynesians live in SouthPacific islands [52] In Java the dried flowers ofC odorata areused to treat malaria andmalaria-like symptoms Similarly itis also recognized as medicinal plants used against malariatraditionally in Vietnam [27] Meanwhile it has been alsoreported that the pounded fresh flowers paste being usedto treat asthma The flowers and bark of C odorata areused to treat pneumonia and stomach ache by the localcommunities and traditional healers fromNorthernMarianaIslands [53] In Indonesia ylang-ylang oil is used to enhanceeuphoria feel during sex and also reduce sexual anxiety [54]In line with the above mentioned traditional usage ylang-ylang has been reported to be used as antidepressant to treatdepression and nervousness It has been also reported to haveblood pressure lowering effect suggesting its potential use inmanaging hypertension [51]

According to both of the folks from India and islandersof the Indian Ocean the leaves of C odorata is believed torelieve itchiness by direct topical application and also to treatdandruff [55] Indian has also used ylang-ylang oil to treatheadaches eye inflammation and gout [52] Apart from thatthe traditional healers from Papuan New Guinea believe thatby consuming the decoction of the heated inner bark of Codorata is ableto treat gout [56] Besides that the bark of the

Evidence-Based Complementary and Alternative Medicine 3

Table 1 The common names of C odorata from different regions

Regions Common namesGeneral Ylang-ylang perfume tree Cananga and cadmia (English)

Oceania

Canang odorant (French)Chirang irang (Palau)Derangerang derangirang (Nauru)Ilahnglahng ilanlang (Kosrae)Ilang-ilang alang-ilang (Guam)Ilangilang lengileng alangilang pur-n-wai pwurenwai seir en wai (Pohnpei)Ilanilan (Marshall Islands)Lanalana (Hawailsquoi)Makosoi mokohoi makasui mokosoi (Fiji)Mohokoi (Tonga)Mosolsquooi (Samoa)Motolsquoi (French Polynesia)Motolsquooi matalsquooi matolsquooi (Cook Islands Niue Tahiti)Motoi (Marquesas-Nuku Hiva Niue)Mutui (Marquesas-Fatu Hiva)Pwalang (Puluwat atoll)Pwanang pwuur pwalang (Chuuk)Salsquoo (Solomon islands Kwaralsquoae)

South East Asia

Ilang-ilang alang-ilang (Philippines)Sagasein kedatngan kadatnyan (Myanmar)Kernanga (Indonesia)Fereng kradang naga (Thailand)Kenanga chenanga ylang-ylang (Malaysia)

India Apurvachampaka chettu sampangi karumugai (India)Adapted from [9] with slight modifications

Table 2 The morphological features of C odorata leaves stems flowers fruits and seeds

Part Descriptions

LeavesColour dark shiny green (above) duller and lighter green (beneath)Arrangement alternate single plane along twigsLength 9ndash21 cm width 4ndash9 cmShape ovate-oblong to broadly elliptic with wavy margin rounded and unequal base acuminate apex

Twigspetiole Petiole colour light green twig colour light green (young) brown (old)Petiole length 6ndash15mm

Flowers

Odor highly fragrantLength 75 cmArrangement hanging axillary in a group of 4ndash12 flowers with umbellate arrangement scattering around theolder parts of twigsPedicels short 1ndash25 cm longCalyx three broad pointed and hairyPetals six slightly thicken twisted pointed hairy 4ndash6 cm long green (young) yellow to yellowish-brown(mature)

FruitsColour dark green to black (ripe)Shape ovoidLength 15ndash23 cm long

SeedsShape hard flattened ovoid and pittedSize 6mm diameterColour pale brown

Summarized from [9] with slight modifications

4 Evidence-Based Complementary and Alternative Medicine

(a) (b) (c)

(d)

Figure 1 Morphology of C odorata (a) Mature C odorata flower with yellow petals (b) young yellowish-green C odorata flower (c) youngC odorata plant in Rimba Ilmu Botanic Garden University of Malaya and (d) leaves of C odorata plant (images are obtained from DrSugumaran (a) and Mr Cheah ((b)ndash(d)) from University of Malaya)

plant is believed to be effective in treating stomach ailmentsIt is also being used as laxative by communities in Tonga andSamoaMeanwhile the Indian used the decoction of the barkof the plant to treat rheumatism phlegm ophthalmia ulcersand fevers [57]

6 Phytochemistry

The phytochemistry of C odorata is well documented Codorata is well known for its essential oil Essential oils arereferred as the natural complex and volatile compoundswhich exhibit distinctive scent that are produced by aromaticplants as secondary metabolites [58] Generally the essentialoils can be extracted from the aromatic plants by steam orhydrodistillation However various combinations of extrac-tion methods are necessary to extract all the volatile phyto-chemicals present in the C odorata Besides the steam andhydrodistillation extraction methods simultaneous steamdistillation-solvent extraction and supercritical fluid extrac-tion (SFE) were also developed to completely isolate mostof the volatile secondary metabolites of ylang-ylang flower[13] More advanced methods have been employed to ana-lyze the volatile components of C odorata due to several

disadvantages presented by using distillation method suchas time consuming and thermal degradation For instanceHeadspace-Solid Microextraction method coupled with GasChromatography-Mass Spectrometry (HS-SPME-GC-MS)was used to characterize all the volatile compounds of Codorata flower at different stages of development [59]

Numerous chemical composition studies have beenconducted on the essential oil of different parts of C odorataIn one of the earliest reports ylang-ylang essential oil wasshown to contain monoterpene hydrocarbons oxygen-containing monoterpenes sesquiterpene hydrocarbonsoxygen-containing sesquiterpenes benzenoids acetatesbenzoates and phenols To date many compounds havebeen identified from the essential oil of ylang-ylangEssentially most of the compounds identified from theessential oil from different part of C odorata plant arelisted in Table 3 In 1986 a total of 52 compounds from thevolatile oxygenated and hydrocarbon fractions of first gradeylang-ylang essential oil fromMadagascar were identified bycombined gas chromatography-mass spectrometry (GC-MS)and proton nuclear magnetic resonance (1H NMR) Thestudy revealed that the main components identified from

Evidence-Based Complementary and Alternative Medicine 5

Table 3 The constituents identified from the essential oil of C odorata

Class Constituents Plant parts ReferenceMonoterpenes (E)-120573-Ocimene Leaf fruit [10ndash12]

(Z)-120573-Ocimene Leaf fruit [10ndash12]18-Cineole Leaf flower fruit [10 12ndash14]

Bornyl acetate Leaf [11]Camphene Leaf flower [11]Geraniol Leaf flower [11]

Geranyl acetate Flower [11 13]Limonene Leaf flower fruit [10ndash14]Linalool Leaf flower [10ndash13]

Linalyl acetate Leaf [11]Myrcene Leaf fruit [10ndash12]Neral Flower [15]Nerol Flower [14]

Neryl acetate Flower [15]p-Cymene Leaf fruit [11 12]Plinol a Flower [16]Plinol d Flower [16]Sabinene Leaf fruit [10ndash12]

Terpinen-4-ol Leaf fruit [10ndash12]Terpinolene Leaf fruit [10ndash12]Thujanol Fruit [12]

trans-Linalool oxide acetate Flower [15]trans-120573-Ocimene Flower [13 14]120572-Phellandrene Leaf fruit [10ndash12]120572-Pinene Leaf flower fruit [10ndash14]120572-Pyronene Fruit [16]120572-Terpinene Leaf fruit [10ndash12]120572-Terpineol Leaf fruit [10 12ndash14]120572-Thujene Leaf fruit [11 12]120573-Myrcene Flower [13 14]120573-Phellandrene Leaf [11]120573-Pinene Leaf flower fruit [10ndash14]120574-Terpinene Leaf fruit [10ndash12]

Sesquiterpenes (EE)-Farnesal Leaf [11](EE)-Farnesol Leaf flower [11]

(EE)-120572-Farnesene Flower [11 13ndash15](EZ)-Farnesal Leaf [11](2E2Z)-Farnesal Flower [15]

(2Z6E)-Farnesyl acetate Flower [15]110-diepi-Cubenol Flower [15]

1H-Indole Flower [16]1-epi-Cubenol Flower [15]5-Indanol Flower [15]

Aromadendrene Leaf [11]Bicycloelemene Flower [15]

Bicyclogermacrene Leaf [10ndash12]Calamene Flower [13]

Caryophyllene epoxide Leaf [10]Caryophyllene oxide Leaf flower [11 12 14]

Cedrol Flower [13 14]

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

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Disease Markers

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OncologyJournal of

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Oxidative Medicine and Cellular Longevity

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The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Research and TreatmentAIDS

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Gastroenterology Research and Practice

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Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 2: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

2 Evidence-Based Complementary and Alternative Medicine

Although the uses of ylang-ylang oil and its safety as foodingredient have been also reviewed previously [2] during thattime period the studies on the pharmacological activities ofthe Cananga odorata plant were still very limited Basicallya very brief review was done covering the antibacterialantifungal amebicidal and cytotoxic activities of the ylang-ylang essential oil [2] Perhaps it is due to the improvementin different biological assays and accessibility of chemicalpurification and identification techniques and it has seemedgreatly impacted by the research activities carried out byresearchers In particular an apparent increase in the differ-ential biological activities investigation on medicinal plantshas enabled diversified applications of existing knownnaturalproducts For instance the recent extensive explorations ofdifferential pharmacological properties of ylang-ylang andtheir active compounds have significantly opened up its newcommercial avenues for agriculture [3] Insightfully there isa great increase in number of pharmacological studies doneon C odorata in recent years particularly surrounding itsbiological properties and chemical components [4ndash8]There-fore the current review aimed to compile or summarize theseimportant findings and further highlight the importance ofCodorata as a potential promising drug discovery candidate forfuture

2 Taxonomic Classification and Nomenclatureof Cananga odorata

Taxonomic classification and nomenclature ofCananga odor-ata are as follows

kingdom Plantae plantssubkingdom Tracheobionta vascular plantssuperdivision Spermatophyta seed plantsdivision Magnoliophyta flowering plantsclass Magnoliopsida dicotyledonssubclass Magnoliidaeorder Magnolialesfamily Annonaceae custard-apple familygenus Cananga (DC) Hook f amp Thomson ylang-ylangspecies Cananga odorata (Lam) Hook f amp Thom-son ylang-ylang

3 Botany

31 Botanical Name

311 Common Names C odorata is commonly known asylang-ylangTheEnglish names ofC odorata are ylang-ylangperfume tree Cananga and cadmia Meanwhile the othercommon names for C odorata are listed in Table 1

32 Synonyms According to the plant list there are morethan twenty synonyms which have been recorded for C

odorata For instance Cananga mitrastigma (F Muell)DominCanangiummitrastigma (FMuell) DominCanangaodorata var odorata Cananga odoratum (Lam) Baillex King Canangium odoratum (Lam) Baill ex KingCanangium odoratum var velutinum Koord amp ValetonCananga scortechinii King Canangium scortechinii KingFitzgeraldia mitrastigma F Muell Unona cananga SprengUnona leptopetalaDCUnona odorata (Lam) DunalUnonaodorata (Lam) Baill Unona odoratissima Blanco Unonaossea Blanco Uvaria axillaris Roxb Uvaria cananga BanksUvaria odorata Lam Uvaria ossea (Blanco) Blanco andUvaria trifoliata Gaertn [50]

4 Botanical Description and Distribution

C odorata belong to the Annonaceae family with 125 generaand 2050 species To date the Cananga genus consists of twospecies of plant namelyC odorata andC latifoliaC odoratais a perennial tropical tree which grows natively in South-EastAsia countries such as Philippines and Malaysia and it alsooccurs naturally in several Pacific islands including AustraliaAfter that it has been introduced into China India Africaand America due to its economic importance [51]

The morphological features of the C odorata plant arebriefly described in Table 2 and illustrated in Figure 1 Basi-cally C odorata is a medium-sized evergreen tree which-generally grows up to 15 meters height with long droopingbranches [9]

5 Ethnomedicinal Uses

C odorata has a variety of medicinal properties and tradi-tional uses The strongly fragrant yellow flower of C odoratahas been reported to be used to enhance the scent of coconutoil before being used formassage by Polynesians live in SouthPacific islands [52] In Java the dried flowers ofC odorata areused to treat malaria andmalaria-like symptoms Similarly itis also recognized as medicinal plants used against malariatraditionally in Vietnam [27] Meanwhile it has been alsoreported that the pounded fresh flowers paste being usedto treat asthma The flowers and bark of C odorata areused to treat pneumonia and stomach ache by the localcommunities and traditional healers fromNorthernMarianaIslands [53] In Indonesia ylang-ylang oil is used to enhanceeuphoria feel during sex and also reduce sexual anxiety [54]In line with the above mentioned traditional usage ylang-ylang has been reported to be used as antidepressant to treatdepression and nervousness It has been also reported to haveblood pressure lowering effect suggesting its potential use inmanaging hypertension [51]

According to both of the folks from India and islandersof the Indian Ocean the leaves of C odorata is believed torelieve itchiness by direct topical application and also to treatdandruff [55] Indian has also used ylang-ylang oil to treatheadaches eye inflammation and gout [52] Apart from thatthe traditional healers from Papuan New Guinea believe thatby consuming the decoction of the heated inner bark of Codorata is ableto treat gout [56] Besides that the bark of the

Evidence-Based Complementary and Alternative Medicine 3

Table 1 The common names of C odorata from different regions

Regions Common namesGeneral Ylang-ylang perfume tree Cananga and cadmia (English)

Oceania

Canang odorant (French)Chirang irang (Palau)Derangerang derangirang (Nauru)Ilahnglahng ilanlang (Kosrae)Ilang-ilang alang-ilang (Guam)Ilangilang lengileng alangilang pur-n-wai pwurenwai seir en wai (Pohnpei)Ilanilan (Marshall Islands)Lanalana (Hawailsquoi)Makosoi mokohoi makasui mokosoi (Fiji)Mohokoi (Tonga)Mosolsquooi (Samoa)Motolsquoi (French Polynesia)Motolsquooi matalsquooi matolsquooi (Cook Islands Niue Tahiti)Motoi (Marquesas-Nuku Hiva Niue)Mutui (Marquesas-Fatu Hiva)Pwalang (Puluwat atoll)Pwanang pwuur pwalang (Chuuk)Salsquoo (Solomon islands Kwaralsquoae)

South East Asia

Ilang-ilang alang-ilang (Philippines)Sagasein kedatngan kadatnyan (Myanmar)Kernanga (Indonesia)Fereng kradang naga (Thailand)Kenanga chenanga ylang-ylang (Malaysia)

India Apurvachampaka chettu sampangi karumugai (India)Adapted from [9] with slight modifications

Table 2 The morphological features of C odorata leaves stems flowers fruits and seeds

Part Descriptions

LeavesColour dark shiny green (above) duller and lighter green (beneath)Arrangement alternate single plane along twigsLength 9ndash21 cm width 4ndash9 cmShape ovate-oblong to broadly elliptic with wavy margin rounded and unequal base acuminate apex

Twigspetiole Petiole colour light green twig colour light green (young) brown (old)Petiole length 6ndash15mm

Flowers

Odor highly fragrantLength 75 cmArrangement hanging axillary in a group of 4ndash12 flowers with umbellate arrangement scattering around theolder parts of twigsPedicels short 1ndash25 cm longCalyx three broad pointed and hairyPetals six slightly thicken twisted pointed hairy 4ndash6 cm long green (young) yellow to yellowish-brown(mature)

FruitsColour dark green to black (ripe)Shape ovoidLength 15ndash23 cm long

SeedsShape hard flattened ovoid and pittedSize 6mm diameterColour pale brown

Summarized from [9] with slight modifications

4 Evidence-Based Complementary and Alternative Medicine

(a) (b) (c)

(d)

Figure 1 Morphology of C odorata (a) Mature C odorata flower with yellow petals (b) young yellowish-green C odorata flower (c) youngC odorata plant in Rimba Ilmu Botanic Garden University of Malaya and (d) leaves of C odorata plant (images are obtained from DrSugumaran (a) and Mr Cheah ((b)ndash(d)) from University of Malaya)

plant is believed to be effective in treating stomach ailmentsIt is also being used as laxative by communities in Tonga andSamoaMeanwhile the Indian used the decoction of the barkof the plant to treat rheumatism phlegm ophthalmia ulcersand fevers [57]

6 Phytochemistry

The phytochemistry of C odorata is well documented Codorata is well known for its essential oil Essential oils arereferred as the natural complex and volatile compoundswhich exhibit distinctive scent that are produced by aromaticplants as secondary metabolites [58] Generally the essentialoils can be extracted from the aromatic plants by steam orhydrodistillation However various combinations of extrac-tion methods are necessary to extract all the volatile phyto-chemicals present in the C odorata Besides the steam andhydrodistillation extraction methods simultaneous steamdistillation-solvent extraction and supercritical fluid extrac-tion (SFE) were also developed to completely isolate mostof the volatile secondary metabolites of ylang-ylang flower[13] More advanced methods have been employed to ana-lyze the volatile components of C odorata due to several

disadvantages presented by using distillation method suchas time consuming and thermal degradation For instanceHeadspace-Solid Microextraction method coupled with GasChromatography-Mass Spectrometry (HS-SPME-GC-MS)was used to characterize all the volatile compounds of Codorata flower at different stages of development [59]

Numerous chemical composition studies have beenconducted on the essential oil of different parts of C odorataIn one of the earliest reports ylang-ylang essential oil wasshown to contain monoterpene hydrocarbons oxygen-containing monoterpenes sesquiterpene hydrocarbonsoxygen-containing sesquiterpenes benzenoids acetatesbenzoates and phenols To date many compounds havebeen identified from the essential oil of ylang-ylangEssentially most of the compounds identified from theessential oil from different part of C odorata plant arelisted in Table 3 In 1986 a total of 52 compounds from thevolatile oxygenated and hydrocarbon fractions of first gradeylang-ylang essential oil fromMadagascar were identified bycombined gas chromatography-mass spectrometry (GC-MS)and proton nuclear magnetic resonance (1H NMR) Thestudy revealed that the main components identified from

Evidence-Based Complementary and Alternative Medicine 5

Table 3 The constituents identified from the essential oil of C odorata

Class Constituents Plant parts ReferenceMonoterpenes (E)-120573-Ocimene Leaf fruit [10ndash12]

(Z)-120573-Ocimene Leaf fruit [10ndash12]18-Cineole Leaf flower fruit [10 12ndash14]

Bornyl acetate Leaf [11]Camphene Leaf flower [11]Geraniol Leaf flower [11]

Geranyl acetate Flower [11 13]Limonene Leaf flower fruit [10ndash14]Linalool Leaf flower [10ndash13]

Linalyl acetate Leaf [11]Myrcene Leaf fruit [10ndash12]Neral Flower [15]Nerol Flower [14]

Neryl acetate Flower [15]p-Cymene Leaf fruit [11 12]Plinol a Flower [16]Plinol d Flower [16]Sabinene Leaf fruit [10ndash12]

Terpinen-4-ol Leaf fruit [10ndash12]Terpinolene Leaf fruit [10ndash12]Thujanol Fruit [12]

trans-Linalool oxide acetate Flower [15]trans-120573-Ocimene Flower [13 14]120572-Phellandrene Leaf fruit [10ndash12]120572-Pinene Leaf flower fruit [10ndash14]120572-Pyronene Fruit [16]120572-Terpinene Leaf fruit [10ndash12]120572-Terpineol Leaf fruit [10 12ndash14]120572-Thujene Leaf fruit [11 12]120573-Myrcene Flower [13 14]120573-Phellandrene Leaf [11]120573-Pinene Leaf flower fruit [10ndash14]120574-Terpinene Leaf fruit [10ndash12]

Sesquiterpenes (EE)-Farnesal Leaf [11](EE)-Farnesol Leaf flower [11]

(EE)-120572-Farnesene Flower [11 13ndash15](EZ)-Farnesal Leaf [11](2E2Z)-Farnesal Flower [15]

(2Z6E)-Farnesyl acetate Flower [15]110-diepi-Cubenol Flower [15]

1H-Indole Flower [16]1-epi-Cubenol Flower [15]5-Indanol Flower [15]

Aromadendrene Leaf [11]Bicycloelemene Flower [15]

Bicyclogermacrene Leaf [10ndash12]Calamene Flower [13]

Caryophyllene epoxide Leaf [10]Caryophyllene oxide Leaf flower [11 12 14]

Cedrol Flower [13 14]

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

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Diabetes ResearchJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 3: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 3

Table 1 The common names of C odorata from different regions

Regions Common namesGeneral Ylang-ylang perfume tree Cananga and cadmia (English)

Oceania

Canang odorant (French)Chirang irang (Palau)Derangerang derangirang (Nauru)Ilahnglahng ilanlang (Kosrae)Ilang-ilang alang-ilang (Guam)Ilangilang lengileng alangilang pur-n-wai pwurenwai seir en wai (Pohnpei)Ilanilan (Marshall Islands)Lanalana (Hawailsquoi)Makosoi mokohoi makasui mokosoi (Fiji)Mohokoi (Tonga)Mosolsquooi (Samoa)Motolsquoi (French Polynesia)Motolsquooi matalsquooi matolsquooi (Cook Islands Niue Tahiti)Motoi (Marquesas-Nuku Hiva Niue)Mutui (Marquesas-Fatu Hiva)Pwalang (Puluwat atoll)Pwanang pwuur pwalang (Chuuk)Salsquoo (Solomon islands Kwaralsquoae)

South East Asia

Ilang-ilang alang-ilang (Philippines)Sagasein kedatngan kadatnyan (Myanmar)Kernanga (Indonesia)Fereng kradang naga (Thailand)Kenanga chenanga ylang-ylang (Malaysia)

India Apurvachampaka chettu sampangi karumugai (India)Adapted from [9] with slight modifications

Table 2 The morphological features of C odorata leaves stems flowers fruits and seeds

Part Descriptions

LeavesColour dark shiny green (above) duller and lighter green (beneath)Arrangement alternate single plane along twigsLength 9ndash21 cm width 4ndash9 cmShape ovate-oblong to broadly elliptic with wavy margin rounded and unequal base acuminate apex

Twigspetiole Petiole colour light green twig colour light green (young) brown (old)Petiole length 6ndash15mm

Flowers

Odor highly fragrantLength 75 cmArrangement hanging axillary in a group of 4ndash12 flowers with umbellate arrangement scattering around theolder parts of twigsPedicels short 1ndash25 cm longCalyx three broad pointed and hairyPetals six slightly thicken twisted pointed hairy 4ndash6 cm long green (young) yellow to yellowish-brown(mature)

FruitsColour dark green to black (ripe)Shape ovoidLength 15ndash23 cm long

SeedsShape hard flattened ovoid and pittedSize 6mm diameterColour pale brown

Summarized from [9] with slight modifications

4 Evidence-Based Complementary and Alternative Medicine

(a) (b) (c)

(d)

Figure 1 Morphology of C odorata (a) Mature C odorata flower with yellow petals (b) young yellowish-green C odorata flower (c) youngC odorata plant in Rimba Ilmu Botanic Garden University of Malaya and (d) leaves of C odorata plant (images are obtained from DrSugumaran (a) and Mr Cheah ((b)ndash(d)) from University of Malaya)

plant is believed to be effective in treating stomach ailmentsIt is also being used as laxative by communities in Tonga andSamoaMeanwhile the Indian used the decoction of the barkof the plant to treat rheumatism phlegm ophthalmia ulcersand fevers [57]

6 Phytochemistry

The phytochemistry of C odorata is well documented Codorata is well known for its essential oil Essential oils arereferred as the natural complex and volatile compoundswhich exhibit distinctive scent that are produced by aromaticplants as secondary metabolites [58] Generally the essentialoils can be extracted from the aromatic plants by steam orhydrodistillation However various combinations of extrac-tion methods are necessary to extract all the volatile phyto-chemicals present in the C odorata Besides the steam andhydrodistillation extraction methods simultaneous steamdistillation-solvent extraction and supercritical fluid extrac-tion (SFE) were also developed to completely isolate mostof the volatile secondary metabolites of ylang-ylang flower[13] More advanced methods have been employed to ana-lyze the volatile components of C odorata due to several

disadvantages presented by using distillation method suchas time consuming and thermal degradation For instanceHeadspace-Solid Microextraction method coupled with GasChromatography-Mass Spectrometry (HS-SPME-GC-MS)was used to characterize all the volatile compounds of Codorata flower at different stages of development [59]

Numerous chemical composition studies have beenconducted on the essential oil of different parts of C odorataIn one of the earliest reports ylang-ylang essential oil wasshown to contain monoterpene hydrocarbons oxygen-containing monoterpenes sesquiterpene hydrocarbonsoxygen-containing sesquiterpenes benzenoids acetatesbenzoates and phenols To date many compounds havebeen identified from the essential oil of ylang-ylangEssentially most of the compounds identified from theessential oil from different part of C odorata plant arelisted in Table 3 In 1986 a total of 52 compounds from thevolatile oxygenated and hydrocarbon fractions of first gradeylang-ylang essential oil fromMadagascar were identified bycombined gas chromatography-mass spectrometry (GC-MS)and proton nuclear magnetic resonance (1H NMR) Thestudy revealed that the main components identified from

Evidence-Based Complementary and Alternative Medicine 5

Table 3 The constituents identified from the essential oil of C odorata

Class Constituents Plant parts ReferenceMonoterpenes (E)-120573-Ocimene Leaf fruit [10ndash12]

(Z)-120573-Ocimene Leaf fruit [10ndash12]18-Cineole Leaf flower fruit [10 12ndash14]

Bornyl acetate Leaf [11]Camphene Leaf flower [11]Geraniol Leaf flower [11]

Geranyl acetate Flower [11 13]Limonene Leaf flower fruit [10ndash14]Linalool Leaf flower [10ndash13]

Linalyl acetate Leaf [11]Myrcene Leaf fruit [10ndash12]Neral Flower [15]Nerol Flower [14]

Neryl acetate Flower [15]p-Cymene Leaf fruit [11 12]Plinol a Flower [16]Plinol d Flower [16]Sabinene Leaf fruit [10ndash12]

Terpinen-4-ol Leaf fruit [10ndash12]Terpinolene Leaf fruit [10ndash12]Thujanol Fruit [12]

trans-Linalool oxide acetate Flower [15]trans-120573-Ocimene Flower [13 14]120572-Phellandrene Leaf fruit [10ndash12]120572-Pinene Leaf flower fruit [10ndash14]120572-Pyronene Fruit [16]120572-Terpinene Leaf fruit [10ndash12]120572-Terpineol Leaf fruit [10 12ndash14]120572-Thujene Leaf fruit [11 12]120573-Myrcene Flower [13 14]120573-Phellandrene Leaf [11]120573-Pinene Leaf flower fruit [10ndash14]120574-Terpinene Leaf fruit [10ndash12]

Sesquiterpenes (EE)-Farnesal Leaf [11](EE)-Farnesol Leaf flower [11]

(EE)-120572-Farnesene Flower [11 13ndash15](EZ)-Farnesal Leaf [11](2E2Z)-Farnesal Flower [15]

(2Z6E)-Farnesyl acetate Flower [15]110-diepi-Cubenol Flower [15]

1H-Indole Flower [16]1-epi-Cubenol Flower [15]5-Indanol Flower [15]

Aromadendrene Leaf [11]Bicycloelemene Flower [15]

Bicyclogermacrene Leaf [10ndash12]Calamene Flower [13]

Caryophyllene epoxide Leaf [10]Caryophyllene oxide Leaf flower [11 12 14]

Cedrol Flower [13 14]

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Oxidative Medicine and Cellular Longevity

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Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 4: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

4 Evidence-Based Complementary and Alternative Medicine

(a) (b) (c)

(d)

Figure 1 Morphology of C odorata (a) Mature C odorata flower with yellow petals (b) young yellowish-green C odorata flower (c) youngC odorata plant in Rimba Ilmu Botanic Garden University of Malaya and (d) leaves of C odorata plant (images are obtained from DrSugumaran (a) and Mr Cheah ((b)ndash(d)) from University of Malaya)

plant is believed to be effective in treating stomach ailmentsIt is also being used as laxative by communities in Tonga andSamoaMeanwhile the Indian used the decoction of the barkof the plant to treat rheumatism phlegm ophthalmia ulcersand fevers [57]

6 Phytochemistry

The phytochemistry of C odorata is well documented Codorata is well known for its essential oil Essential oils arereferred as the natural complex and volatile compoundswhich exhibit distinctive scent that are produced by aromaticplants as secondary metabolites [58] Generally the essentialoils can be extracted from the aromatic plants by steam orhydrodistillation However various combinations of extrac-tion methods are necessary to extract all the volatile phyto-chemicals present in the C odorata Besides the steam andhydrodistillation extraction methods simultaneous steamdistillation-solvent extraction and supercritical fluid extrac-tion (SFE) were also developed to completely isolate mostof the volatile secondary metabolites of ylang-ylang flower[13] More advanced methods have been employed to ana-lyze the volatile components of C odorata due to several

disadvantages presented by using distillation method suchas time consuming and thermal degradation For instanceHeadspace-Solid Microextraction method coupled with GasChromatography-Mass Spectrometry (HS-SPME-GC-MS)was used to characterize all the volatile compounds of Codorata flower at different stages of development [59]

Numerous chemical composition studies have beenconducted on the essential oil of different parts of C odorataIn one of the earliest reports ylang-ylang essential oil wasshown to contain monoterpene hydrocarbons oxygen-containing monoterpenes sesquiterpene hydrocarbonsoxygen-containing sesquiterpenes benzenoids acetatesbenzoates and phenols To date many compounds havebeen identified from the essential oil of ylang-ylangEssentially most of the compounds identified from theessential oil from different part of C odorata plant arelisted in Table 3 In 1986 a total of 52 compounds from thevolatile oxygenated and hydrocarbon fractions of first gradeylang-ylang essential oil fromMadagascar were identified bycombined gas chromatography-mass spectrometry (GC-MS)and proton nuclear magnetic resonance (1H NMR) Thestudy revealed that the main components identified from

Evidence-Based Complementary and Alternative Medicine 5

Table 3 The constituents identified from the essential oil of C odorata

Class Constituents Plant parts ReferenceMonoterpenes (E)-120573-Ocimene Leaf fruit [10ndash12]

(Z)-120573-Ocimene Leaf fruit [10ndash12]18-Cineole Leaf flower fruit [10 12ndash14]

Bornyl acetate Leaf [11]Camphene Leaf flower [11]Geraniol Leaf flower [11]

Geranyl acetate Flower [11 13]Limonene Leaf flower fruit [10ndash14]Linalool Leaf flower [10ndash13]

Linalyl acetate Leaf [11]Myrcene Leaf fruit [10ndash12]Neral Flower [15]Nerol Flower [14]

Neryl acetate Flower [15]p-Cymene Leaf fruit [11 12]Plinol a Flower [16]Plinol d Flower [16]Sabinene Leaf fruit [10ndash12]

Terpinen-4-ol Leaf fruit [10ndash12]Terpinolene Leaf fruit [10ndash12]Thujanol Fruit [12]

trans-Linalool oxide acetate Flower [15]trans-120573-Ocimene Flower [13 14]120572-Phellandrene Leaf fruit [10ndash12]120572-Pinene Leaf flower fruit [10ndash14]120572-Pyronene Fruit [16]120572-Terpinene Leaf fruit [10ndash12]120572-Terpineol Leaf fruit [10 12ndash14]120572-Thujene Leaf fruit [11 12]120573-Myrcene Flower [13 14]120573-Phellandrene Leaf [11]120573-Pinene Leaf flower fruit [10ndash14]120574-Terpinene Leaf fruit [10ndash12]

Sesquiterpenes (EE)-Farnesal Leaf [11](EE)-Farnesol Leaf flower [11]

(EE)-120572-Farnesene Flower [11 13ndash15](EZ)-Farnesal Leaf [11](2E2Z)-Farnesal Flower [15]

(2Z6E)-Farnesyl acetate Flower [15]110-diepi-Cubenol Flower [15]

1H-Indole Flower [16]1-epi-Cubenol Flower [15]5-Indanol Flower [15]

Aromadendrene Leaf [11]Bicycloelemene Flower [15]

Bicyclogermacrene Leaf [10ndash12]Calamene Flower [13]

Caryophyllene epoxide Leaf [10]Caryophyllene oxide Leaf flower [11 12 14]

Cedrol Flower [13 14]

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

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PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 5: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 5

Table 3 The constituents identified from the essential oil of C odorata

Class Constituents Plant parts ReferenceMonoterpenes (E)-120573-Ocimene Leaf fruit [10ndash12]

(Z)-120573-Ocimene Leaf fruit [10ndash12]18-Cineole Leaf flower fruit [10 12ndash14]

Bornyl acetate Leaf [11]Camphene Leaf flower [11]Geraniol Leaf flower [11]

Geranyl acetate Flower [11 13]Limonene Leaf flower fruit [10ndash14]Linalool Leaf flower [10ndash13]

Linalyl acetate Leaf [11]Myrcene Leaf fruit [10ndash12]Neral Flower [15]Nerol Flower [14]

Neryl acetate Flower [15]p-Cymene Leaf fruit [11 12]Plinol a Flower [16]Plinol d Flower [16]Sabinene Leaf fruit [10ndash12]

Terpinen-4-ol Leaf fruit [10ndash12]Terpinolene Leaf fruit [10ndash12]Thujanol Fruit [12]

trans-Linalool oxide acetate Flower [15]trans-120573-Ocimene Flower [13 14]120572-Phellandrene Leaf fruit [10ndash12]120572-Pinene Leaf flower fruit [10ndash14]120572-Pyronene Fruit [16]120572-Terpinene Leaf fruit [10ndash12]120572-Terpineol Leaf fruit [10 12ndash14]120572-Thujene Leaf fruit [11 12]120573-Myrcene Flower [13 14]120573-Phellandrene Leaf [11]120573-Pinene Leaf flower fruit [10ndash14]120574-Terpinene Leaf fruit [10ndash12]

Sesquiterpenes (EE)-Farnesal Leaf [11](EE)-Farnesol Leaf flower [11]

(EE)-120572-Farnesene Flower [11 13ndash15](EZ)-Farnesal Leaf [11](2E2Z)-Farnesal Flower [15]

(2Z6E)-Farnesyl acetate Flower [15]110-diepi-Cubenol Flower [15]

1H-Indole Flower [16]1-epi-Cubenol Flower [15]5-Indanol Flower [15]

Aromadendrene Leaf [11]Bicycloelemene Flower [15]

Bicyclogermacrene Leaf [10ndash12]Calamene Flower [13]

Caryophyllene epoxide Leaf [10]Caryophyllene oxide Leaf flower [11 12 14]

Cedrol Flower [13 14]

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 6: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

6 Evidence-Based Complementary and Alternative Medicine

Table 3 Continued

Class Constituents Plant parts ReferenceCopaborneol Flower [15]Cyperene Flower [15]

Germacrene D Leaf flower fruit [10ndash14]Globulol Leaf [11]Guaiol Flower [15]

Isogermacrene D Flower [15]Jejunol Flower [15]

Levoglucosenone Flower [16]Selina-4(15)5-diene Flower [15]

Spathulenol Leaf [11]t-Cadinol Leaf [10 12]t-Muurolol Flower [13 14]

trans-Nerolidol Flower [13 14]Viridiflorol Leaf [11]Zonarene Flower [15]120572-Amorphene Leaf flower [10 12]120572-Bisabolol Flower [13 14]120572-Bulnesene Leaf [11]120572-Cadinol Leaf [10 12]120572-Cedrene Flower [13]120572-Copaene Leaf flower [10ndash12]120572-Cubebene Leaf [11]120572-Gurjunene Leaf [11 12]120572-Humulene Leaf flower fruit [10ndash14]120572-Muurolene Leaf [10 12]120572-Ylangene Leaf flower [10 12ndash14]120573-Bourbonene Leaf flower [11 14 15]120573-Caryophyllene Leaf flower fruit [10ndash12]120573-Copaene Leaf [12]120573-Cubebene Leaf flower [10ndash12 14]120573-Elemene Leaf [11 12]120574-Cadinene Leaf [10 12]120574-Muurolene Flower fruit [13]120575-Cadinene Leaf flower [10ndash12]120575-Cadinol Flower [13 14]120575-Elemene Leaf [10 12]120576-Cadinene Flower [13]120591-Cadinene Flower [13]120591-Cadinol Flower [13 14]120591-Muurolene Flower [13]

Aliphatic compounds (2E6E)-Farnesyl acetate Flower [11 13 14 17](E)-Hex-2-enal Leaf [10 12](E)-Hex-2-enol Leaf flower [10 12](Z)-Hex-3-enol Leaf flower [10 12]2-Hexenyl acetate Flower [13 14]

2-Methyl-3-buten-2-ol Flower [13 14]3-Hexenyl acetate Flower [13 14]

3-Methyl-2-buten-1-ol Flower [13 14]3-Methyl-2-buten-1-yl acetate (prenyl acetate) Flower [14 17]

Benzyl alcohol Flower [13 14]Decane Flower [16]

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 7: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 7

Table 3 Continued

Class Constituents Plant parts ReferenceDiethyl 15-pentanedioate Flower [16]

Dodecane Flower [16]Methyl 3-methylbutanoate Flower [16]

Methyl caprylate Flower [16]n-Hexanol Leaf fruit [10 12]Heptanal Flower [15]

Tetracosane Flower [15]Tricosane Flower [15]Undecane Flower [16]

Phenylpropanoids (E)-Cinnamyl acetate Flower [11 13]14-Dimethylbenzene Flower [14]

1-Methoxy-1-propylbenzene Flower [16]1-Phenyl-2-propen-1-ol Flower [16]1-Phenylallyl acetate Flower [16]

2-Methoxy-4-methylphenol Flower [14]2-Phenylethyl acetate Flower [13]34-Dimethoxytoluene Flower [14]3-Buten-2-ol benzoate Flower [14]3-Hexen-1-ol benzoate Flower [14]

3-Methyl-2-buten-1-yl benzoate Flower [15]4-(2-Propenyl)-phenol Flower [14]4-Allyl-phenyl-acetate Flower [15]

4-Methoxy benzaldehyde Flower [16]4-Methoxyphenyl acetate Flower [14]

Anethol Flower [13 14]Benzyl acetate Flower [11 13 14]Benzyl benzoate Flower [11 13 14]Benzyl salicylate Flower [11 13 14]Benzylaldehyde Flower [14]Benzyl-n-butyrate Flower [14]Butyl benzoate Flower [14]

Cinnamyl alcohol Flower [14]Ethyl benzoate Flower [13 14]Isoeugenol Flower [14]

Methoxyphenol Flower [14]Methyl benzoate Flower [11 13 14]

Methyl-2-methoxybenzoate Flower [14]Methyl-4-methoxybenzoate Flower [14]

Methyleugenol Flower [13 14]p-Cresyl methyl ether (p-methylanisole) Flower [13 17 18]

p-Vinyl-guaiacol Flower [15]Vanillin Flower [15]Veratrole Flower [15]

Nitrogen-bearing compounds Phenylacetonitrile Flower [14]2-Phenyl-1-nitroethane Flower [14]Methyl anthranilate Flower [14]

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 8: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

8 Evidence-Based Complementary and Alternative Medicine

the oxygenated fraction of ylang-ylang essential oil were p-methylanisole (1) methyl benzoate (2) and benzyl benzoate(3) benzyl acetate (4) geranyl acetate (5) cinnamyl acetate(6) and (EE)-farnesyl acetate (7) linalool (8) geraniol (9)and benzyl salicylate (10) and their molecular structuresare shown in (Figure 2) Linalool (8) was shown to be maincomponent present in oxygenated fraction (28) that isresponsible for the floral smell of ylang-ylang Meanwhilethe hydrocarbon fraction of ylang-ylang oil consisted ofmainly sesquiterpenes and monoterpenes whereby bothgermacrene D (11) and 120573-caryophyllene (12) represented63 of the total hydrocarbon fraction of ylang-ylang oil[60] 120574-Muurolene (13) and (EE)-farnesyl acetate (7)were both sesquiterpenes identified for the first time inylang-ylang oil in [60] In 2012 Benini and colleagues[15] demonstrated a total of 32 compounds which were notpreviously reported in ylang-ylang oil were detected from theC odorata flower samples obtained from Grande ComoreMayotte Nossi Be and Ambanja (Table 3) Furthermorethe characterization of ylang-ylang essential oils was furtherimproved by the use of comprehensive two-dimensionalGC coupled to time-of-flight MS (GCtimesGC-TOFMS) bythe similar group of researchers Brokl and colleagues [16]demonstrated that GCtimesGC-TOFMS was able to revealmore chemical components present in ylang-ylang flower(Table 3) suggesting that this technology is capable ofproviding better insight on chemical polymorphism as wellas of studying the different parameters of ldquoterroir effectrdquo onphytoconstituents

There are various factors that can influence the chemicalcomposition and quality of the volatile secondarymetabolitesbeing extracted from the aromatic plants and flowers partic-ularly the extraction method extraction time and the flowerconditions [13] The essential oil extracted from the flower ofC odorata is the important main raw material for perfumeindustry To date four grades of ylang-ylang oil have beendeveloped and are commercially available the Extra FirstSecond andThirdwhich contain different chemical composi-tions that determine the quality and uses of the oil The Extraquality of ylang-ylang oil is highly recommended to be usedin production of high-grade perfumes This is because theExtra grade oil is rich in strongly odoriferous molecules suchas linalool (8)p-cresyl methyl ether (p-methylanisole) (1)methyl benzoate (2) benzyl acetate (4) and geranyl acetate(5) which are the volatile compounds that give the fragranceMeanwhile the other grades contain increasing amount ofsesquiterpene hydrocarbons which are less volatile such as 120573-caryophyllene (12) germacreneD (11) and (EE)-120572-farnesene(14) For instance the First and Second grades are used incosmetics Lastly the Third grade oil is being used for scent-ing of soaps Besides depending on the fractionation basedon distillation times the chemical composition of ylang-ylang essential oils can be varied significantly depending onthe stages of flower maturity [59 61] and also geographicalarea which presents different environmental and agronomicconditions [15 17] Qin and colleagues [59] revealed highlevel of volatile polymorphism occurring along the 7 differentflower development stages with only 5245 of Bray-Curtissimilarity value among all stages The study showed that

large amounts of volatile compounds including hydrocarbonesters and alcohols were detected in the full bloom stage ofCodorata which was the most suitable period for harvesting asthose volatile compoundsmay have contributed to the aromaprofile of C odorata [59]

In term of geographical locations by comparing theessential oil in the flower and fruits the fruits of C odoratafrom Cameroon were found to contain more abundant ofmonoterpenic essential oil such as sabinene (15) myrcene(16) 120572-pinene (17) and terpinen-4-ol (18) while the com-position of essential oils present in the leaves of C odoratafrom Cameroon was quite similar as compared to floweressential oil [10] Similarly another study [11] revealed thatthe composition of essential oil present in the leaves of Codorata from Australia was relatively similar to the findingsfrom Cameroon [10] but with larger amounts of hexanol (19)and absence of sabinene (15) More recently a study focusedon the variation in the chemical profiles of essential oilsfrom C odorata among the Western Indian Ocean islandssuch as Union of Comoros Madagascar and Mayotte asthey are known to be the current main producers of ylang-ylang essential oils [15] The study revealed that there is asignificantly high variation in terms of the proportion ofessential oils constituents fromeach area of origin throughoutthe Western Indian Ocean islands [15]

With the advancement of bioinformatics a numberof genes responsible for volatile compounds biosynthesispathway were elucidated with use of high-throughput RNAsequencing technology Jin and colleagues [61] successfullycharacterized the functionality of four full-length of terpenesynthases (TPSs) CoTPS1 CoTPS2 CoTPS3 and CoTPS4extracted from yellow flower of C odorata One of the TPSsspecifically known as CoTPS2 was found to be novel andmultifunctional in which it could catalyze the synthesis ofsesquiterpenes including 120573-ylangene (20) 120573-copaene (21)and 120573-cubebene (22) [61]

Besides the extensive studies on the phytoconstituentsin the essential oil of C odorata the medicinal propertiesof nonvolatile constituents from the plant part have beeninvestigated and reported as well Several new compoundswere isolated from the methanolic extract of the seedsof C odorata in 1999 [62] The study revealed a newstereoisomer of ushinsunine-120573-N-oxide (23) and another10 newly discovered compounds from this species for thefirst time The isolated compounds from this extract arelisted in (Table 4) For instance liriodenine (24) a cyto-toxic oxoaporphine alkaloid isolated from C odorata wasdemonstrated to be a potent inhibitor of topoisomerase IIin both in vitro and in vivo [62] Besides the cytotoxic andantineoplastic activity of this compound liriodenine (24)was also shown to be active against Gram-positive bacteriayeast and filamentous fungi Sampangine (25) was anotheralkaloid isolated from the chloroform extract of the stem barkof C odorata [19] Literatures revealed that sampangine (25)a copyrine alkaloid exhibited antifungal antimycobacterialantimalarial activities and demonstrated cytotoxic effectstoward humanmalignantmelanoma cells [63] Amore recentstudy isolated and characterized four compounds from the

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

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Diabetes ResearchJournal of

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 9: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 9

O

O

Benzyl acetate (4)

O

Methyl benzoate (2)

O

O

Benzyl benzoate (3)p-Methylanisole (1)

O

OCH3

O

O

Geranyl acetate (5) Cinnamyl acetate (6)

O

O

(EE)-Farnesyl acetate (7)

O

O

H3C

HO

Linalool (8)

OH

Geraniol (9)

O

OH

O

Benzyl salicylate (10) Germacrene D (11) 120573-Caryophyllene (12)

H HH2C

HO

Terpinen-4-ol (18)

OH

Hexanol (19)

H

OH

120573-Ylangene (20)

HH

H

120573-Copaene (21) 120573-Cubebene (22)

H

HH

H

CH2

(+)-Ushinsunine-120573-N-oxide (23)

N

O

H3CO

H3CON

O

O

O

Liriodenine (24)

N N

O

Sampangine (25)

N

OH

Cananodine (26)

O

O

Linalyl acetate (13) Sabinene (15)

CH2

Myrcene (16) 120572-Pinene (17)(EE)-120572- Farnesene (14)

Figure 2 Continued

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

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PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 10: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

10 Evidence-Based Complementary and Alternative Medicine

OHH

O

O OHOH

OH

Cryptomeridiol 11-120572-L-rhamnoside (27)

O

OOH

OHOH

120574-Eudesmol 11-120572-L-rhamnoside (28)

OH

120574-Eudesmol (29)

O

O

Methyl isoeugenol (30)

O

HO

O

Isosiphonodine (31)

O H

OH

O

O

Canangone (32)

O

OH

OH

OGlc

Canangaionoside (33)

O

OH

OH

CHO

OGlc

HO

HO

O

O

O

OHC

OGlc

OH

Canangalignan I (34)

HO

HO

O

O

O

OH

CHOOGlc

O

HOCHO

OGlc

OH

H

Canangalignan II (35)

Canangaterpene I (36)

O

O

OH

O

HO

HO

OCH3

OCH3

H

HOO

O

Canangaterpene II (37)

OHC

OH

H

H

Canangaterpene III (38)Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

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Diabetes ResearchJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 11: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 11

H

HO

O

O

O

OMe

OMe

HO

Canangaterpene IV (39)

MeO

HO

O

O

O

OMe

OMe

HO

Canangaterpene V (40)

OHCH

OH

Canangaterpene VI (41) Canangafruticoside A (42)

CHO

OHHO

OGlc(1998400)

Canangafruticoside B (43)

CHO

OHO

O

OGlc(1998400)

Canangafruticoside C (44)

CHO

OHOHO

HO O

OGlc(1998400)

Canangafruticoside D (45)

CHO

OO

HO

OGlc(1998400)

Canangafruticoside E (46)

CHO

OHO

OHO

HO

OGlc(1998400) O

OHCH

(3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47)

N-trans-Feruloyltyramine (48)

HO

N

OHO

H

H3CON

O

O

Cleistopholine (49)

NH

O

O

H

(minus)-Anonaine (50)Figure 2 Continued

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 12: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

12 Evidence-Based Complementary and Alternative Medicine

HO

120573-Sitosterol (58)

HO

Stigmasterol (59)

(+)-Nornuciferine (51)

NH

HH3CO

H3CO

(+)-N-Acetylnornuciferine (52)

N

HH3CO

H3CO

COCH3

NH

O

OHH

OH

N

O

OH

OH

CH3

(minus)-Ushinsunine (53) (minus)-Norushinsunine (54)

Corchoionoside (64)

O

O

H

OH

O

HO

HO

HOH

OH

CH3 CH3

CH3

H3C

Citroside A (63)

C

H

O

OGlcHO

Lyscamine (60)

O

O

H

OHH

Ominus

N+ CH3

COOH

O

OH

OH

OGlc

Breyniaionoside (62)Trans-cinnamic acid (61)

(+)-Reticuline (57)

N

HHO

HO

H3CO

H3CO

CH3

NH

HO

HH3CO

(minus)-Asimilobine (55) (minus)-Anaxagoreine (56)

NH

HO

H

HOH

H3CO

Figure 2 Continued

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

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OncologyJournal of

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Oxidative Medicine and Cellular Longevity

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PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 13: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 13

(+)-Syringaresinol 4-O-120573-D-glucopyranoside (65)

OH

HO

O

HH

H

OO

OHHOHO

HOH2C

OCH3

OCH3

OCH3

H3CO

Figure 2 The molecular structures of the constituents isolated from different part of C odorata

fruits of C odorata including cananodine (26) new guaipyri-dine sesquiterpenes cryptomeridiol 11-120572-L-rhamnoside (27)and 120574-eudesmol 11-120572-L-rhamnoside (28) both being neweudesmane sesquiterpenes and lastly the 120574-eudesmol (29)a previously known eudesmane sesquiterpene [20] Thestudy also demonstrated that all the identified compoundsdisplayed cytotoxicity against both hepatocarcinoma cancercell lines Hep G2 and Hep 2215 Cryptomeridiol 11-120572-L-rhamnoside (27) and 120574-eudesmol (29) exhibited the mostpotent cytotoxic activity against Hep G2 and Hep 2215 celllines Moreover Ragasa and colleagues [33] revealed theisolation of methyl isoeugenol (30) benzyl benzoate (3)and farnesyl acetate (7) from dichloromethane extract of airdried flower of C odorata The study further showed thatthe compoundmethyl isoeugenol (30) exhibited antibacterialand antifungal activities [33]

Furthermore two lactone compounds have been isolatedfrom the leaves and stems of C odorata in conjunction withthe searching for bioactive constituents from the C odorataplant by a group of researchers [21] Isosiphonodin (31) anda new spirolactone named as canangone (32) were the twolactones isolated and identified from the acetone extract ofdried leaves and stems of C odorata [21] Recently a newmegastigmane glucoside named as canangaionoside (33)wasidentified from the methanolic extract of the dried leaves ofC odorata [22]Three new lignan dicarboxylates and six newterpenoid derivatives were also isolated by Matsumoto andcolleagues from the methanolic extract of C odorata flowerbuds [8 23] The new lignans isolated from the flower budsof C odorata were named as canangalignans I (34) and II(35) [8] whereas canangaterpenes I II III IV V and VI (36ndash41)were the six new terpenoid derivatives identified from themethanolic extract of C odorata flower buds [8 23] Theyalso indicated that one of the newly discovered terpenoidscanangaterpene I (36) exhibited potent antimelanogenesisactivity [8] Lastly five usual monoterpene glucosides werealso isolated and named as canangafruticosides A-E (42ndash46)by Nagashima and colleagues [24] The chemical structuresof both nonvolatile and volatile chemical compounds men-tioned above are illustrated in Figure 2

7 Bioactivities of C odorata

Various biological activities of C odorata have been exten-sively studied over the past decadesThe detailed informationof respective biological activities of C odorata is being dis-cussed as below A summarized form of biological activitiesof C odorata is then provided in Table 6

8 Antimicrobial Activity

In the last decade the emergence of multidrug resistancepathogens and strains with reduced susceptibility due toindiscriminate use of antibiotics has become a global concern[64] as the clinical efficacy of many existing antibioticshas been compromised As a consequence the therapy ofthe infections inflicted by the multidrug resistant pathogenis complicated and has led to substantial increased hos-pitalizations and greater risk for morbidity and mortality[65] This issue has necessitated the scientist to screen fornovel antimicrobial substances from various medicinal plantsources including the essential oils or the extracts from aro-matic plantswhich have been reported to possess phytochem-icals with antimicrobial activities [66] The antimicrobialproperties of the essential oils and extracts of C odoratahave been tested against various Gram-positive and Gram-negative pathogens as well as pathogenic fungi (Table 5)

Recently the stem bark extracts of C odorata obtainedfrom Indonesia were shown to exhibit potent antimicrobialactivities using the agar well disc diffusion assay The studyhas demonstrated that n-hexane ethyl acetate and ethanolicextracts of C odorata stem bark possessed good activityagainst Propionibacterium acnes and Candida albicans Theethanolic extract of C odorata at the dose of 400120583gwellexhibited an inhibition zone of 19 plusmn 158mm when testedagainst P acnes In fact the activity index stands at 063when being relative to the standard drug which is knownas chloramphenicol [26] Among the three extracts of Codorata tested the n-hexane extracts of C odorata stem barkshowed the highest inhibitory effect on C albicans growth(17 plusmn 158mm) at the dose of 100 120583gwell It represents the

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 14: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

14 Evidence-Based Complementary and Alternative Medicine

Table 4 The identified chemical constituents from different extracts of C odorata

Extracts Family Name of constituents References

Methanolic extract of C odorata seed

Quinoline alkaloids

(+)-Ushinsunine-120573-N-oxide [18]

Cleistopholine [18]

Liriodenine [18]

(minus)-Anonaine [18]

(+)-Nornuciferine [18]

(+)-N-Acetylnornuciferine [18]

(minus)-Ushinsunine [18]

(minus)-Norushinsunine [18]

(minus)-Asimilobine [18]

(+)-Reticuline [18]

Lyscamine [18]

(minus)-Anaxagoreine [18]

Phytosterols Stigmasterol [18]

120573-Sitosterol [18]

Phenylpropanoids N-trans-Feruloyltyramine [18]

trans-Cinnamic acid [18]

Chloroform extract of C odorata stembark

Quinoline alkaloids Liriodenine [19]

Sampangine [19]

Methanolic extract of C odorata fruit

Guaipyridine alkaloids Cananodine [20]

Cycloeudesmane sesquiterpenoids

Cryptomeridiol11-120572-L-rhamnoside

[20]

120574-Eudesmol11-120572-L-rhamnoside

[20]

120574-Eudesmol [20]

Quinoline alkaloidsCleistopholine [20]

(+)-Ushinsunine-120573-N-oxide [20]

Lyscamine [20]Phenylpropanoids N-trans-Feruloyltyramine [20]

Acetone extract of C odorata stems andleaves

Lactones Isosiphonodine [21]

Canangone [21]

Methanol extract of dried leaves of Codorata

Megastigmane glycosideCanangaionoside [22]

Breyniaionoside A [22]

Citroside A [22]

Methanol extract of flower buds of Codorata

LignansCanangalignan I [8]

Canangalignan II [8]

Canangaterpene I [8]

Terpenoids

Canangaterpene II [8]

Canangaterpene III [8]

Canangaterpene IV [23]

Canangaterpene V [23]

Canangaterpene VI [23](3R3aR8aS)-3-Isopropyl-8a-methyl-8-oxo-1233a6788a-

octahydroazulene-5-carbaldehyde

[8]

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 15: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 15

Table 4 Continued

Extracts Family Name of constituents References

Methanol extract of leaves of C odoratavar fruticosa

Monoterpene glucosides

Canangafruticoside A [24]Canangafruticoside B [24]Canangafruticoside C [24]Canangafruticoside D [24]Canangafruticoside E [24]

Ionone glucosides Corchoionoside C [24]

Lignans (+)-Syringaresinol4-O-120573-D-glucopyranoside [24]

activity index of 056 when being relative to the standarddrug known as nystatin [26] Meanwhile in another studythe researchers have taken the research to another next levelof assessment The purified constituents from the bark ofplant were used to evaluate the antimicrobial activity ondifferent species of bacteria Besides they have also examinedthe antifungi activities of these purified compounds [28]In that particular research those three tested compoundswhich are known asO-methylmoschatoline liriodenine (24)and 34-dihydroxybenzoic acid were showing a significantantibacterial and antifungal activities at their respective doseat 200120583gdisc and 400120583gdisc Among the three purifiedcompounds liriodenine (24) emerged as the strongest com-pound in exerting its antibacterial and antifungal activitiesagainst Klebsiella sp and C albicans respectively [25]

On the other hand a study was conducted specifically onthe antimicrobial activity of theC odorata leaf extractsThreedifferent extracts of C odorata leaf were prepared and testedagainst selected Gram-positive and Gram-negative bacteriaas well as different fungal strains [26]Themethanolic extractof C odorata exhibited the highest antimicrobial activitiesas compared to petroleum ether and chloroform extractsMoreover the study also suggested that the Gram-negativebacteria demonstrated higher resistance than the Gram-positive bacteria against all the extracts ofC odorata leaf [31]Similarly the antimicrobial activity of the essential oil of Codorata showed high inhibitory effect with MIC

90 valuesat 023mgmL against S aureus ATCC 25923 and clinicalstrains S aureus [32] However both E coli ATCC 25922andPseudomonas aeruginosaATCC27853 showed high resis-tance towards the essential oils of C odorata which did notshow inhibitory capacity up to the maximum concentration(2712mgmL) tested in the study [32] The study also hascharacterized the essential oil ofC odorata usingGC-MS andrevealed that the essential oil ofC odorata contained trans-120573-caryophyllene (1292) linalool (8) (1138) germacrene D(11) (1121) benzyl acetate (4) (1034) and geranyl acetate(5) (987) [32]

Meanwhile the essential oil of C odorata obtained fromsteam distillation was shown to exhibit weak antibacterialactivity against P acnes strains [67] The inhibition zones ofC odorata essential oils against 5 strains of P acnes wereonly ranging from 88 plusmn 07mm to 95 plusmn 07mm [67] whichwere relatively smaller as compared to ethanolic extract ofC odorata described in [26] In effort of discovering the

potential usage of ylang-ylang oil as alternative treatmentfor irritable bowel syndrome three different antibacterialassays namely disc diffusion assay turbidometric assay andzone of clearance assay were conducted against E coli [68]However essential oil of C odorata demonstrated relativelylow antibacterial activity against E coli where the essentialoil of C odorata did not inhibit the growth of E coli ineither the agar plate or liquid culture and also did not showany killing ability against E coli from the zone clearanceassay [68] The essential oil of C odorata has also showed toexhibit no inhibitory effect againstMalassezia furfur which isa fungal pathogen associated with seborrheic dermatitis [69]In contrast another study demonstrated that the essentialoils of C odorata which contained germacrene D (11) (20)and 120573-caryophyllene (12) (17) exhibited slight fungicidalactivity (12 plusmn 2mm) against Trichophyton mentagrophytesTIMM2789 using agar diffusion assay [70]

The synergistic effects of ylang-ylang oil with differentcombinations of essential oils for treatment of microbialinfections have also been reported For an example a studyhas proven that the combinations of ylang-ylang oil andthyme oil were significantly more effective against S aureusATCC 25923 and its synergistic effect was observed betweenboth of the essential oils in which the inhibition zone wasincreased by 384 as compared to thyme oil alone [71]However a slight antagonism effect was then observed whenylang-ylang oil was used together with thyme oil againstEscherichia coliATCC25922 the inhibition zonewas reducedby 489 when compared to thyme oil alone [71] Similarlyanother study revealed that blended essential oil preparationwhich is comprised of lavender clary sage and ylang-ylangoils in the ratio 3 4 3 displayed a strong antibacterial andantifungal activities against Staphylococcus aureus ATCC6538 Staphylococcus epidermidis Escherichia coli ATCC25923 Pseudomonas aeruginosa ATCC 9027 and Candidaalbicans ATCC 10231 [72] The results also revealed that thepreparation showed a synergistic antimicrobial effect againstall the tested microorganisms The increased antimicrobialactivities displayed from the blended essential oil preparationas compared to the single or pure essential oil were believedto be contributed by the increased active components suchas linalool (8) and linalyl acetate (13) present in the blendedpreparation [72]

Besides that antiplasmodial activity of C odorata wasalso evaluated by a group of researchers from Vietnam [27]

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 16: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

16 Evidence-Based Complementary and Alternative Medicine

Table 5 The antimicrobial activities screening of different C odorata extracts

Plant part Extracts Pathogens tested Screening assay ReferenceBark na Gram-positive bacteria Disc diffusion assay [25]

Bacillus subtilisBacillus megateriumStaphylococcus aureusSarcina luteaStreptococcus-120573-haemolyticus

Gram-negative bacteriaEscherichia coliPseudomonas aeruginosaShigella flexneriShigella shigaShigella boydiiShigella dysenteriaeShigella sonneiSalmonella typhiKlebsiella

FungiAspergillus flavusAspergillus nigerAspergillus versicolorCandida albicans

n-hexane Gram-positive bacteria Well diffusion assay [26]Propionibacterium acnes

FungiCandida albicans

Ethyl acetate Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Gram-positive bacteria [26]Propionibacterium acnes

FungiCandida albicans

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chlorideMethanolic

Whole plant Essential oils Gram-positive bacteria Disc diffusion assay [28]Methicillin-resistant Staphylococcus aureus ATCC 700699

Gram-positive bacteria [29]Bacillus cereusBacillus subtilisBacillus megateriumBacillus polymyxaStreptococcus-120573-haemolyticusStreptococcus aureusStreptococcus lutea

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 17: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 17

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceGram-negative bacteriaEscherichia coliShigella dysenteriaeShigella flexneriShigella sonneiPseudomonas aeruginosaSalmonella typhi BSalmonella paratyphi ASalmonella paratyphi B

Fungi [30]Rhizopus oryzaeAspergillus nigerAspergillus fumigatusAspergillus krusliCandida albicansSaccharomyces cerevisiae

FungiCandida albicans ATCC 48274Rhodotorula glutinis ATCC 16740Schizosaccharomyces pombe ATCC 60232Saccharomyces cerevisiae ATCC 2365Yarrowia lipolytica ATCC 16617

Leaf Methanolic Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Protozoan parasite In vitro bioassay [27]Plasmodium falciparum FcB1 strain

Petroleum ether Gram-positive bacteria Well diffusion assay [31]Staphylococcus aureus

Gram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 18: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

18 Evidence-Based Complementary and Alternative Medicine

Table 5 Continued

Plant part Extracts Pathogens tested Screening assay ReferenceChloroform Gram-positive bacteria Well diffusion assay [31]

Staphylococcus aureusGram-negative bacteriaSalmonella typhiEscherichia coliVibrio cholera

FungiEpidermophyton floccosumMicrosporum gypseumTrichophyton mentagrophytes

Ethanolic Protozoan parasite In vitro bioassay [27]Cyclohexane Plasmodium falciparum FcB1 strain

Methylene chloridena not available

Nyugen-Pouplin and colleague revealed that the cyclohexaneextract of C odorata leaves at 10 120583gmL exerted moderateantiplasmodial activity (75 inhibition) against Plasmodiumfalciparum FcB1 strain with IC

50value of 125 plusmn 39 120583gmL

[27] The result of present study somehow ascertains thefolkloric claim on C odorata used as medicinal plant totreat malaria and malaria-like symptoms in Indonesia andVietnam

Overall ylang-ylang oil and different extracts of Codorata showed better antibacterial activities against Gram-positive bacteria than Gram-negative bacteria For instanceS aureus showed high susceptibility to the essential oilsand extracts of C odorata as compared to other testedGram-negative bacteria Studies also showed that C odorataexhibited a remarkable antifungal activity Disc and welldiffusion assay were the most common tests being employedto evaluate the antimicrobial activity of the essential oil andextracts of C odorata Although the antimicrobial activityof C odorata tested was not as potent as other essentialoils and extracts of other plants studies have demonstratedthat the synergistic effects observed from the combinationsof different medicinal plants and herbs may potentiate theantimicrobial activities against pathogens

9 Antibiofilm Properties

Many bacteria possess the ability to form biofilm which isa slimy layer comprised of bacterial cells that protected byself-synthesizedmatrices of polysaccharides andproteins thatallows attachment to various surfaces such as polystyreneglass and stainless steel in different environments [73] Theformation of microbial biofilms poses a significant chal-lenge to current clinical and industrial settings as microbialbiofilms are associated with dramatically enhanced toler-ance towards most antimicrobial agents and disinfectantchemicals as well as the bodyrsquos immune system Hence theincreased resistance developed by the formation of biofilmcontributes to the chronicity of microbial infections andleading to therapy failure [74] Although many approaches

have been implemented in controlling biofilms the discoveryfor novel natural and effective antibiofilm agents is stillundergoing in order to cope with the increased biofilm-associated health problems The plant-derived essential oilshave been explored extensively to combat biofilm formationFor instance oregano oil [75] eucalyptus oil [76] tea treeoil [77] cinnamon oil [73] and lemon grass [78] havebeen demonstrated to exhibited potent antibiofilm activitiesagainst wide range of bacteria Recently the antibiofilmactivity of cananga oil also has been evaluated in severalstudies [5] A study revealed that ylang-ylang oil exhibitedstrong antibiofilm activity at dose-dependent manner againstbiofilm formation of Staphylococcus aureus ATCC 6538 [5]The study utilized a static biofilm formation assay confocallaser microscopy and also scanning electron microscopy toexamine the effect of cananga oil on biofilm formation of Saureus [5] It was found that 001 (vv) of ylang-ylang oilshowed more than 80 inhibition against biofilm formationof S aureus as compared to the control group but did notinhibit the growth of S aureus Furthermore the study alsosuggested that both cis-nerolidol and trans-nerolidol were theconstituents in ylang-ylang oil that is responsible for the inhi-bition of biofilm formation [5] Furthermore another studycombined the unique properties of magnetic nanoparticleswhich have been reported to be effective delivery systemswith the ylang-ylang oil as a coating agent for surfaces ofimplantations with the intention to reduce the developmentof biofilm [79] The study has shown the incorporation ofylang-ylang oil with iron oxideC

14nanoparticles effective

in inhibiting the initial adherence phase of clinical strains ofboth S aureus andKlebsiella pneumoniawithmore than 2-logreduction to the coated catheter specimens [79] The resultsof the study have suggested the potential use of ylang-ylangoil in nanobiosystems with antibiofilm activity [79]

10 Antioxidant Properties

The generation of free-radical intermediates through oxida-tive stress has been known to cause disturbances inmetabolic

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 19: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 19

Table6Bioactivities

ofC

odorataessentialoils

andextracts

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Antim

icrobial

(i)Antibacteria

l(ii)A

ntifu

ngal

(iii)Antiprotozoal

(i)Who

leplant

(ii)B

ark

(iii)Leaf

(i)Essentialoil

(ii)n

-Hexane

(iii)Ethylacetate

(iv)E

thanolic

(v)M

ethano

lic(vi)Cy

clohexane

(vii)

Petro

leum

ether

(viii)C

hloroform

(i)Welld

iffusionassay100ndash

400120583

gwelltestedagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i(i)

Linalool

(ii)L

inalylacetate

(iii)Lirio

denine

(iv)O

-Methylm

oschatoline

(v)3

4-D

ihydroxybenzoica

cid

(vi)Methyleugenol

(vii)

na

(viii)n

a

[26]

(ii)D

iscdiffu

sionassay200ndash

400120583

gdisc

teste

dagainst

varie

tyof

Gram-positiveG

ram-negativeb

acteria

and

fung

i[28]

(iii)023

mgmL(M

IC90)a

gainstSaureus

[32]

(iv)125plusmn39120583

gmL(IC 5

0)againstPfalcip

arum

FcB1

strain

[33]

Antibiofilm

Flow

erEssentialoil

(i)001(vv)sho

wed

80inhibitio

nagainstb

iofilm

forS

aureusA

TCC6538

(i)cis-N

erolidol

(ii)trans-N

erolidol

[5]

(ii)Inh

ibitadherencep

hase

ofbo

thclinicalstrains

ofS

aureus

andK

pneumonia(2

logs

redu

ction)

Antioxidant

(i)Ba

rk(ii)L

eaf

(iii)Flow

er

(i)Ethylacetate

(ii)M

ethano

lic(iii)Essentialoil

(i)79DPP

Hinhibitio

nteste

dat50

ppm

(i)na

[26]

(ii)2

900plusmn131

offerricredu

cing

power

at05120583

gmL

(ii)n

a[34]

(iii)638plusmn045of

DPP

Hinhibitio

n(iii)na

[30]

(iv)7

55plusmn051inhibitio

nin

the120573

-caroteneb

leaching

test

(v)D

PPHradicalscaveng

ingactiv

ity(8006plusmn002)

Insecticidal

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

Diru

s(mosqu

itoes)

Flow

erEssentialoil

(i)Teste

d1

5and

10(w

v)o

nA

aegyptiC

quinquefa

sciatusandAn

Diru

sLC

50values

of97

7

882and

499respectively

(i)na

[35]

(ii)10

insoybeanoilexh

ibitedoviposition

-deterrent

andovicidalactiv

ities

(ii)n

a[36]

(iii)01m

gmLshow

edlarvicidalactiv

ityagainstA

aegypti

(iii)na

[37]

(iv)L

D50at5296p

pmagainstimmatures

tage

ofA

aegypti

(iv)n

a[38]

(iv)M

usadomestica

(hou

sefly)

(v)P

reparedin

ethylalcoh

olLT 5

0of

5208ho

ursand

LC50of

2936

towards

Musadomestica

(v)n

a[39]

(v)R

speratus(term

ite)

(vi)2m

gfiltersho

wed

180plusmn58

and940plusmn40

mortalitiesa

fter2

and7days

ofexpo

sure

(vi)na

[40]

(vi)Szeam

ais(agric

ulture

pest)

(vii)

LD50valueo

f3314120583gadult

(vii)

Linalool

[41]

(viii)L

D50valueo

f1477

mgL(vapou

rphase

toxicity

bioassay)

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Computational and Mathematical Methods in Medicine

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 20: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

20 Evidence-Based Complementary and Alternative Medicine

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Insectrepellent

(i)A

aegypti

(ii)C

quinquefasciatus

(iii)An

diru

s(mosqu

itoes)

(iv)T

castaneum

(beetle)

(i)Flow

er(ii)L

eaf

Essentialoil

(i)Prepared

insoybeanoilED

50of

00452149and

lt0003m

gcm

2againstA

aegypti

Adirusa

ndC

quinquefa

sciatusrespectively

(i)Linalool

[42]

(ii)P

rotectiontim

etow

ards

AaegyptiA

dirusandC

quinquefa

sciatus(84240and

600minutesresp)

(iii)Prepared

inethylalcoh

olprotectiontim

eagainst

AaegyptiandC

quinquefa

sciatus(8667plusmn1040and

1260plusmn1577minutes)at0

33120583Lcm

2(ii)n

a[43]

(iv)S

trongestrepellent

effectat5120583Lgof

oats

(iii)na

[3]

(v)9

8repellencyaft

er2and4ho

urse

xposure

Antim

elanogenesis

(i)Flow

erbu

dMethano

lic

(i)Inhibitio

non

melanin

prod

uctio

nin

B16melanom

a4A

5cells

(i)Ca

nang

aterpenesI

(ii)(3R

3aR

8aS)-3-Isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-

carbaldehyde

[8]

(ii)T

erpeno

idderiv

ativescanangaterpenes

I(IC

50=

36120583

M)and(3R3aR8aS)-3-isop

ropyl-8

a-methyl-8

-oxo-12

33a6

788a-octahydroazulene-5-carbaldehyde

(IC 5

0=25120583

M)

(ii)S

eed

(iii)Inhibitio

non

tyrosin

asep

rotein

expressio

nin

mou

seB16melanom

acells

(iii)N-tran

s-Feruloyltyramine

[18]

Anti-infl

ammatory

(i)na

(ii)L

eaf

(iii)Fruit

(i)Essentialoil

(ii)M

ethano

lic(iii)Ethano

lic

(i)Strong

lipoxygenaseinh

ibito

ryeffect(sim80)at

05120583

gmL

(i)Linalool

[6]

(ii)Inh

ibition

onnitricoxider

eleaseinRA

W2647(979

plusmn146)at50120583

gmL

(ii)L

inalylacetate

[34]

(iii)In

carrageenanindu

cedpawedem

amod

elpaw

volumeinh

ibition

of629at100m

gkg

(iii)na

[44]

Sedativ

erelaxing

and

harm

onizingeffect

na

Essentialoil

(i)Re

ducedsysto

licanddiastolic

BPthroug

hsniffi

ng(i)

na

[45]

(ii)D

ecreased

pulse

rateandstr

esslevel

(iii)Increasedalertness

(iv)T

ransderm

aladministratio

nresulteddecrease

inbo

thph

ysiologicaland

behaviou

rallevel

(ii)n

a[46]

Effecto

nmoo

dandcogn

itive

perfo

rmance

na

Essentialoil

Redu

cedalertnessm

oodandcalm

nessbu

twith

out

increasedcogn

itive

perfo

rmance

na

[47]

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Disease Markers

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OncologyJournal of

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Oxidative Medicine and Cellular Longevity

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Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 21: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 21

Table6Con

tinued

Bioactivities

Partused

Type

ofextracts

DosageRe

sults

Suggestedconstituentsw

ithrespectiv

eactiv

ities

References

Spermatotoxic

Root

bark

Ethano

lic(i)

Immob

ilizedratrsquossperm

with

insecond

s(i)

A52

kdprotein

[48]

(ii)5

0mg100g

body

weightd

ayredu

cedsperm

motility

(ii)n

a[49]

(iii)100m

g100g

body

weightd

aycaused

94

abno

rmalsperm

morph

olog

y

Antihyperglycem

ic(i)

Leafand

stem

(ii)F

lower

buds

(i)Dichlorom

ethane

(ii)M

ethano

lic

(i)Alpha-amylaseinh

ibito

ryeffectw

ith226plusmn13

(le

af)a

nd253plusmn33

(stem)inh

ibition

at78120583gmL

(i)na

[7]

(ii)A

ldoser

eductase

inhibitory

effectIC

50at12

15

and08120583

Mby

canang

aterpene

I(E)-[(1R3R5S6S8S)-6-hydroxy-13

-dim

etho

xy-2-

oxaspiro[45]decan-8-yl]m

ethyl]caffeateand

canang

afruiticosid

eErespectiv

ely

(ii)C

anangaterpeneI

(iii)(E)-[(1R3R5S6S8S)-6-Hydroxy-13-

dimetho

xy-2-oxaspiro

[45]decan-8-

yl]m

ethyl]caffeate

(iv)C

anangafruitic

osideE

[23]

IC50halfm

axim

alinhibitory

concentration

LD50m

edianlethaldo

se

LT50m

edianlethaltim

eED

50m

edianeffectiv

edose

nano

tavailable

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 22: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

22 Evidence-Based Complementary and Alternative Medicine

processes They are known to be responsible for cellularinjuries and disease formation due to the destruction ofunsaturated lipids proteins and DNA The implications ofoxidative damage have been linked to many human diseasessuch as cancer cardiovascular diseases inflammatory pro-cesses cataracts and even the normal ageing process [80]Recently natural occurring antioxidants have been of greatinterest because of peoplersquos concerns over the use of syn-thetic antioxidants such as butylated hydroxyanisole (BHA)butylated hydroxytoluene (BHT) propyl gallate and tert-butylhydroquinone (TBHQ) which may have adverse effectson human health [81] The antioxidant activity of C odorataextracts was evaluated using DPPH assay to determine thefree radical scavenging abilities of the extracts The result ofthe study revealed that the ethyl acetate extract of the stembark of C odorata exhibited the highest percentage of DPPHinhibition (79) as compared to other tested plant extracts[26] Besides the DPPH assay the antioxidant activity ofmethanolic extract of C odorata leaves was also determinedby ferric ion reducing power assayThe extract showed a totalof 2900 plusmn 131 of ferric reducing power at 05120583gmL [34]

Normally a series of antioxidant assays will be uti-lized to examine different aspects of antioxidant propertyof plant extract In a particular study antioxidant activityof the C odorata essential oils was assessed using freeradical-scavenging 120573-carotene bleaching and the luminol-photochemiluminescence assays [30] The results of thestudy revealed that all the tests indicated that essentialoil of C odorata was a decent source of antioxidant Indetail the free radical-scavenging activity of C odoratawas 638 plusmn 045 of DPPH inhibition and the value wastwice higher than that of trolox one of the reference oilswith potent antioxidant activity Furthermore the resultswere further supported by the lipid peroxidation inhibitoryactivity displayed by the essential oil of C odorata (755 plusmn051 inhibition) in the 120573-carotene bleaching test Theluminol-photochemiluminescence assay also showed that theessential oil of C odorata exhibited effective superoxideradical scavenging activity [30] Consistently the essentialoils extracted from the flower of C odorata originated fromMadagascar also exhibited good DPPH radical scavengingactivity (8006 plusmn 002) [82]

11 AntivectorInsecticidalAntipest Properties

Dengue disease which is a tropical and subtropicalmosquito-borne viral illness has become a public health concernworldwide According to World Health Organization [83]statistics showed that approximately 25 billion people livein countries that are endemic for dengue and estimatedthat 50ndash100 million infections occur annually There wasdramatic increase in the number of reported cases of denguedisease in Malaysia particularly in 2013 where incidences ofdengue fever (14327 per 100000 population) were doubledas compared to 2012 (722 per 100000 population) [84 85]However the prevention of dengue fever is only restricted tomanaging the vector Aedes aegypti due to absence of effectiveprophylactics or vaccine against the infection Generallysynthetic insecticides such as DDT and other chlorinated

hydrocarbons are used to control the mosquitoes Howeverthe continuous application of these synthetic compounds hasresulted in the development of resistant strains of mosquitovectors particularly A aegypti Hence considerable studyhas shifted the interest towards natural products which maybe effective in controlling the vector population Larvicidalovicidal and repellent properties of essential oils and extractsfrom several plant species against mosquito vector havebeen evaluated including Cananga odorata Studies havedemonstrated that the essential oil of Cananga odorata pos-sessed repellent properties as well as oviposition-deterrentand ovicidal activities against several mosquito species In2011 the insecticidal activity of the essential oils of Canangaodorata prepared in soybean oil was evaluated using standardWHO susceptibility testing protocols It was found that theessential oil extracted from ylang-ylang flower at doses of1 5 and 10 (wv) exhibited low insecticidal activity andknockout rate against all three types of adultmosquito speciesincluding the Aedes aegypti Culex quinquefasciatus andAnopheles dirus with LC

50values of 977 882 and 499

respectively [35] Targeting the breeding sites of mosquitoesis one of the effective strategies to control and eradicate thepopulation density of themosquito vectors Furthermore themosquito life cycle can be disrupted by preventing them fromundergoing oviposition which is an important event shapingboth individual fitness and vectorial capacity in life history ofmosquito [86] Study has revealed that the essential oil of Codorata may serve as a potential mosquito egg control agentagainst the species of Aedes aegypti Anopheles dirus andCulex quinquefasciatus It was found that 10 C odorata insoybean oil exhibited significantly high oviposition-deterrentand ovicidal activities against all three tested mosquitospecies However further study was suggested by the authoras most of the results obtained from previous studies relatedto oviposition-deterrent and ovicidal were not promising andmost of the mosquito eggs were shown to be tolerant to theaction of insecticides [36] Besides that larvicidal and pupi-cidal activities of the essential oil of Cananga odorata againstthree immature stages of Aedes aegypti Anopheles dirus andCulex quinquefasciatus were evaluated [87] Although theessential oil of C odorata was not as effective as the essentialoil of Syzygium aromaticum which was the most effectiveagainst all immature stages of the three tested mosquitospecies in the study higher larvicidal and pupicidal activitieswere demonstrated by C odorata essential oils against allimmature stages of both C quinquefasciatus and Anophelesdirus as compared to A aegypti [87] Similar results were alsodemonstrated in [37] whereby the essential oils of C odorataexhibited low larvicidal activity against A aegypti with only400 plusmn 41 mortality observed at dose of 01mgmL In amore recent study on the larvicidal activity of C odorata thechemical composition of the essential oils was determinedwith GC-MS and was evaluated together with the insecticidalactivity of the plants against the third and fourth instar stageof A aegypti [38] The study revealed that the essential oilsof C odorata demonstrated moderate insecticidal activitywith LD

50at 5296 ppm against the immature stage of A

aegypti among the plants evaluated [38] Benzyl acetate (4)linalool (8) and benzyl benzoate (3) were the three major

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

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OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

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PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 23: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 23

compounds identified from the essential oils of C odoratawith the percentage of 182 141 and 123 respectively[38]

Moreover recent study also showed that C odorata oilprepared in ethyl alcohol possessed larvicidal effect andoviposition-deterrent activity as well against house flyMuscadomestica The control of house fly is also essential as it isknown to be a serious disease causing pest which can trans-mit pathogenic organisms such as protozoa cysts parasitesenteropathogenic bacteria and enterovirus to human andlivestock The study demonstrated that C odorata oil exhib-ited larvicidal effect against the 3rd instar larvae of house flywith median lethal time (LT

50) value of 5208 hours and LC

50

value of 2936 as compared to cypermethrin (10wv) acommon chemical insecticide with LT

50and LC

50of 3163

hours and 1145 respectively [39] Furthermore excellentoviposition-deterrent activity was also demonstrated by Codorata oil with 100 effective repellency value againstthe female house fly from undergoing oviposition at bothconcentrations of 165120583Lcm2 and 330 120583Lcm2 [39]

Seo and colleague [40] also assessed the insecticidalactivities of the essential oil from C odorata flower againstJapanese termite Reticulitermes speratus Kolbe The fumi-gation bioassay employed by the study [40] found thatthe essential oil C odorata at 2mgfilter paper resulted incumulative mortalities of 180 plusmn 58 and 940 plusmn 40 of thetermites after 2 and 7 days of exposure respectively

Besides that the essential oil of C odorata leaves hasbeen demonstrated to possess antipest properties as well andcould be considered to have the potential to be developed aspossible natural fumigant or insecticide for control of insectassociated with storage products [41] The study showed thattopical application of essential oil of C odorata leaves exhib-ited toxicity against Sitophilus zeamais which is a pest asso-ciated with corn storage with a LD

50value of 3314 120583gadult

[41] Furthermore fumigant activity of C odorata essentialoil against S zeamais was also evaluated using vapour phasetoxicity bioassay The results showed that the essential oilof C odorata leaves exhibited fumigant toxicity against Szeamais with a LD

50value of 1477mgL The study also

suggested that linalool (8) which is a competitive inhibitorof acetylcholinesterase might be the active component thataccounted for the insecticidal activity of C odorata essentialoil [41]

12 Insect-Repellent Properties

Insect repellent is known to be one of the most effectiveways to reduce the transmission of vector-borne diseasesespecially frommosquito [88] With the fact that no effectivevaccine against dengue is available protection frommosquitobites could be only achieved by preventing physical contactwith mosquitoes using repellents Studies have indicated thatthe essential oil of Cananga odorata prepared in soybeanoil possessed certain degree of repellent activity against theadult mosquito of A aegypti A dirus and C quinquefas-ciatus with the ED

50of 0045 2149 and lt0003mgcm2

The essential oil of Cananga odorata also demonstrated amoderate time of protection against A aegypti A dirus

and C quinquefasciatus at a duration of 84 240 and 600minutes respectively [42] even though the protection timeof DEET-based repellent which remains the gold standard ofprotection in which 238DEET showed a complete 5 hoursprotection against A aegypyi bites [89] Meanwhile anotherstudy revealed that the protection time was improved by Codorata oil prepared in ethyl alcohol at 033 120583Lcm2 againstA aegypti and C quinquefasciatus with 8667 plusmn 1040 and1260 plusmn 1577 minutes respectively [43] Similarly a morerecent study revealed that essential oil of C odorata preparedin coconut oil at 033 120583Lcm2 showed a better activity with989 protection from bites of A aegypti with an improvedprotection time for 887 plusmn 104 minutes among the threetested diluents [4] The discrepancy between the studies maybe due to many factors that might affect the efficacy of therepellent such as the species and density of mosquito theage gender and biochemical attractiveness of the subject aswell as the experimental conditions [43] Most of the studiesindicated above have shown that indeed the essential oils ofC odorata demonstrated goodmosquito-repelling propertiesagainst different species of mosquitoes

Besides the repellent activity against mosquito the essen-tial oil ofC odorata leaves has been shown to exhibit repellentactivity against Tribolium castaneum a red flour beetle whichis known to be the pest associated with stored productshence protecting the stored products from insect damage[3 90] The essential oil of C odorata leaves was shown tohave the strongest repellent effect against T castaneum atconcentration of 5120583L per gram of oats as compared to othertested essential oils in the study [90] Caballero-Gallardo andcolleagues [3] also demonstrated that essential oil from Codorata exhibited the highest percentage of repellency of 98at 02 120583gcm2 after both exposure times of 2 and 4 hoursagainst T castaneum suggesting that it can be consideredexcellent candidates as natural repellents

13 Antimelanogenesis

Melanin production or melanogenesis determines the skincolor of animals and humans Although melanogenesis isa major protective mechanism against UV-induced skininjury the excessive production of melanin due to exten-sive UV exposure can lead to dermatological disordersThere has been increasing interest towards the findingsof alternative herbal for treatment of hyperpigmentationbecause of the increased reports of potential mutagenicityand cases of ochronosis due the use of tyrosinase inhibitorsuch as hydroquinone which is one of the most widelyprescribed compounds found in nowadays cosmetic prod-ucts and depigmenting agents [91] Recently the methano-lic extract of the flower buds of C odorata was foundto exhibit inhibitory effect against melanogenesis [8] Theinhibitory effect of the constituents extracted from theflower buds of C odorata was demonstrated by the detec-tion of the melanin content in theophylline-stimulated B16melanoma 4A5 cells via photometric method at 405 nm[8] The study indicated that several compounds isolatedfrom the methanolic extract of the flower buds of C odor-ata displayed the inhibitory effect on melanogenesis and

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 24: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

24 Evidence-Based Complementary and Alternative Medicine

without induced any cytotoxicity to B16 melanoma 4A5cells Furthermore there were two terpenoid derivatives(compound 5 canangaterpenes I (36) (IC

50= 36 120583M) and

compound 12 (3R3aR8aS)-3-isopropyl-8a-methyl-8-oxo-1233a6788a-octahydroazulene-5-carbaldehyde (47) (IC

50

= 25 120583M)) exhibited stronger activity in inhibiting the pro-duction of melanin than the positive control arbutin (IC

50=

174 120583M) [8] Also the study found that lignans with a catecholmoiety and without the glucosyl moieties are essential forthe inhibitory activity of melanogenesis [8] Therefore thestudy showed that the flower buds of C odorata containterpenoid derivatives which may have high potential for thetreatment of skin disorder or cosmetic industry Besides thatN-trans-feruloyltyramine (48) whichwas a phenylpropanoidisolated from themethanolic extract of the seeds ofC odorata[18] may be another constituent that is responsible for thesuppression of melanogenesis as this compound has beenreported to show more potent inhibitory activity on theexpression of tyrosinase protein (an important enzyme inmelanin biosynthesis) in mouse B16 melanoma cells than thekojic acid (a tyrosinase inhibitor) [92] In contrast a studyshowed that the aqueous extract of C odorata did not inhibitdopachrome formation (minus198 plusmn 07) which indicated thatno antityrosinase activity exhibited by the aqueous extractof C odorata [93] These observations deduced that theinhibitory effects on melanogenesis of C odorata extracts areinvolving the regulation of tyrosinase gene expression ratherthan the direct inhibition of tyrosinase activity

14 Anti-Inflammatory Properties

Inflammatory diseases such as rheumatism arthritis andpelvic inflammatory disease continue to be one of themajor health concerns worldwide Traditional remedies havebeen known to be one of the most common ways to treatinflammatory diseases For instance the folkloric practice oftreating joint pain with Willow (Salix alba) bark has led tothe discovery of aspirin as the most commonly used painreliever for 100 years [94] Despite that many steroidal andnonsteroidal anti-inflammatory drugs (NSAIDs) have beenintroduced to treat various inflammatory disordersHoweveradverse side effects including renal problems gastrointestinalirritation and even myocardial infarction and strokes havebeen reported due to the prolonged use of steroidal andNSAIDs [94] Hence researchers have becoming more inter-ested in evaluating the anti-inflammatory potential of plantstraditionally used for relieving aches asthma and pains forthe discovery and development of potent anti-inflammatorydrugs Traditionally different parts of C odorata plants havebeen exploited and used to treat fever asthma and painsSeveral scientific evaluationswere also conducted on the anti-inflammatory activities of C odorata

Wei and Shibamoto [6] demonstrated that the essential oilof C odorata displayed anti-inflammatory properties using15-lipoxygenase inhibitor screening assay Lipoxygenases areenzymes that catalyze the metabolism of arachidonic acid inproducing metabolites that regulate inflammatory responsein mammals The essential oil of C odorata showed stronglipoxygenase inhibitory effect (sim80) at a concentration

of 05 120583gmL and also exhibited lipoxygenase inhibitoryactivity that appeared similar to nordihydroguaiaretic acida standard lipoxygenase inhibitory chemical in a reversedose-response manner [6] The study also suggested that thelipoxygenase inhibitory effect was accounted by the majorconstituents present in the essential oils such as linalool (8)linalyl acetate (13) and other volatile constituents [6] Thesechemical constituents are normally found to possess anti-inflammatory activities in previous experimentations [95]Furthermore the methanolic extract of C odorata leaveswas shown to possess moderate inhibitory effect (979 plusmn146) on nitric oxide release in macrophage RAW2647cells with low cytotoxicity (cell viability 897 plusmn 05) at50 120583gmL [34] Although nitric oxide is produced to actas a defense and regulatory molecule during inflammatoryreactions it may damage normal tissue when it is excessivelyproduced [34 96] Overall the findings indicated that themethanolic extract of C odorata leaves may be a potentialanti-inflammatory agent as the release of nitric oxide bymacrophages has long been associated with inflammation

Besides the in vitro studies mentioned above the anti-inflammatory activity of C odorata also had been evalu-ated in experimental animals recently The ethanolic extractof C odorata fruit was shown to exhibit significant anti-inflammatory activity in the carrageenan induced paw edemamodel of Wistar albino rats with LD

50gt 2000mgkg [44]

The acute oral toxicity study indicated that the ethanolicextract C odorata fruit was more effective in inhibition ofpaw volume (629) at dose of 100mgkg than aspirin withinhibition of 6014 at dose of 300mgkg Furthermore theauthor of the study suggested that anti-inflammatory effectof the extract might be due to the presence of flavonoids andtannins which is responsible for inhibiting both cyclooxyge-nase and lipoxygenase pathway [44]

15 Sedative Relaxing andHarmonizing Effects

The essential oil obtained from the leaves of C odorata usinghydrodistillation method extraction was shown to possesssedative effect and certain degree of physiological influenceon human [45] The study indicated that sniffing C odorataoil decreased the systolic and diastolic blood pressure ofhuman from 10643 plusmn 1151mmHg to 10520 plusmn 1072mmHgand 7060plusmn1053mmHg to 6920plusmn1171mmHg respectivelydemonstrating that the oil exhibited sedative effect Theresults were further supported by the decreased pulse rateafter sniffing C odorata (7340 plusmn 738 bpm) as comparedto the control (7533 plusmn 755 bpm) On top of that thestudy also found that C odorata essential oil exhibitedrelaxing effect on the volunteers after sniffing the oil reducingthe stress index from high level (7333 KUL) to mediumlevel (4950KUL) The stress level was also determined bymeasuring the alpha brain wave of the volunteers and theresults showed that sniffing the essential oil of C odorataincreased an individualrsquos alpha brain wave or also decreasedonersquos stress level [45] Similar results were also evidenced byHongratanaworakit and Buchbauer [46] whereby the inhala-tion of ylang-ylang oil significantly decreased both systolic

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

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PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 25: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 25

and diastolic blood pressure and pulse rate indicating thatinhalation of ylang-ylang oil decreased autonomic nervoussystem arousal Besides that the similar study [46] evaluatedthe effect of inhalation of ylang-ylang on the behavioural levelof subjects in the aspect of alertness and attentiveness Thestudy demonstrated that the subjects felt more attentive andmore alert after inhaling the oil suggesting that the effect ofinhalation of ylang-ylang oil is characterized as ldquoharmoniza-tionrdquo which resulted in uncoupling of physiological (reducedANS arousal) and behavioural arousal process (increasedbehavioural activation) [46] Meanwhile the similar group ofresearchers found that transdermal administration of ylang-ylang oil to healthy subjects resulted in both decreasedphysiological arousal and deactivation of behavioural levelwhereby the subjects experienced more calm and relaxedafter transdermal administration [97] The findings of thesestudies indicated that the differential effects of essential oilsdepend on the route of administration whereby inhalationand percutaneous administration of the essential oils givedifferent pharmacological and psychological effects eitherwith or without involving the olfactory processing [97]Moreover themost recent study evaluated the sedative effectsof ylang-ylang oil with the use of sphygmomanometer andelectrocardiogram (EKG) to determine the blood pressureand heart rate respectively of the subjects after the inhalationof the fragrance of the oil [98] Similarly this study alsoindicated that ylang-ylang oil showed sedative effectivenesswhere declination of 12-lead EKG demonstrating decreasedheart rate was observed in the group treated with ylang-ylang oil [98] Overall the available studies have shownthat the essential oil of C odorata indeed possess sedativerelaxing and also harmonization effects on human and alsoexplained its usefulness in aromatherapy and medicine suchas reduction of blood pressure or relief of depression andstress in human

16 Effects on Mood andCognitive Performance

Studies have shown that the mood and cognitive perfor-mance of a healthy individual can be modulated by aromasof essential oils A study revealed that ylang-ylang aromaacted significantly different on the cognitive performanceof the healthy volunteers as compared to the control groupand the peppermint aroma [47] Ylang-ylang aroma pro-duced a reduced alertness mood and increased calmnessof the healthy volunteers but absence in the enhancementof cognitive performance and also lengthened processingspeed [47] Ishiguchi and colleagues evaluated the effect ofinhalation of ylang-ylang essential oil by detecting the elec-troencephalography background activity of the volunteers[99]They revealed that alpha 1 (8ndash99Hz) brain waves whichpresent in deep relaxation was increased significantly duringinhalation of ylang-ylang essential oil and also reducedalertness mood of the volunteers [99] Thus Ishiguchi andcolleagues suggested that the lowering effect of alertness andincreased alpha 1 brain waves may be the physiological basisfor relaxation effect of aromatherapy with ylang-ylang [99]Furthermore reduction of the amplitude of auditory P300

which is associated with the higher cognitive processing wasobserved in healthy volunteers during inhalation of ylang-ylang aroma suggesting a relaxing effect of aroma on cogni-tive function Watanabe and colleagues [100] elucidated theeffect of ylang-ylang aroma on the auditory P300 of healthyindividual and patientwith temporal lobe epilepsy (TLE)whohave impaired odor identification The study demonstratedexposure to ylang-ylang aroma prolonged latencies of P300 inboth control and TLE groups while only significant reductionof P300 amplitudes in healthy volunteers was observedThe absence of P300 amplitudes reduction in TLE patientssuggested that their information processing was not alteredduring the exposure to ylang-ylang aroma or the fact thatTLE patients had lower P300 amplitudes under odourlesscondition as compared to the controls [100]

17 Spermatotoxic Properties

Overpopulation is known to be a global issue and pub-lic health concern The ever-increasing human populationcauses various detrimental effects including environmentaldegradation poverty and rise in unemployment Thereforemany studies have been focusing on the discovery and devel-opment of novel and more potent contraceptive Currentlymedicinal plants have also received huge attention for its useas contraceptives due to their little side effects C odoratawas also found to possess spermicidal activity in both invitro and in vivo study [48] In the in vitro study the spermsobtained from healthy male rats were immobilized by 50ethanolic extract of root bark of C odorata within secondsIn the in vivo study the administration of crude extract at50mg100 g body weightday reduced the motility of spermof the rat significantly (5 plusmn 038 seconds) as compared tothe control rat (30 plusmn 198 seconds) Furthermore reducedsperm count and 94 abnormal sperm morphology werealso observed when 100mg100 g body weightday of crudeextract was administrated into ratsThe biochemical findingsof the study indicated that the crude extract of C odorataroot bark reduced the production of testosterone altered themetabolism of stored spermatozoa in the testes and led tothe deficiency in nutrients for proper spermmaturation [48]Comparison between the antifertility effects of extract of Codorata bark and gossypol which is a well-studied antifertilityagent has been conducted as well [49] The study suggestedthat C odorata bark extract may be a better antifertility agentthan gossypol as reversibility in the motility of sperm wasobserved in the C odorata treated group after withdrawalof the extract The study also managed to isolate the activecomponent of the extract and was determined as a 52 kdprotein which immobilized the sperm in vitrowithin seconds[49]

18 Antihyperglycemic Effects and AntidiabeticComplications Properties

Diabetes mellitus is a common metabolic disorder charac-terized by chronic hyperglycemia as a result from defects ininsulin production and insulin action Currently there is aneed to develop safe and treatment for diabetes as most of the

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 26: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

26 Evidence-Based Complementary and Alternative Medicine

available medications have several adverse effects Accordingto [101] it was found that approximately 1200 species ofplants were used as traditional medicine in treating diabetesglobally The leaves and stem extracts of C odorata werefound to exhibit alpha-amylase inhibitory effects [7] Bothleaves and stem extracts of C odorata demonstrated 226 plusmn13 and 253 plusmn 33 inhibition respectively at 78 120583gmLon porcine pancreatic 120572-amylase enzyme However bothleaves and stem extracts of C odorata did not exhibit anyinhibitory effect on 120572-glucosidase enzyme [7] The results ofthe study suggested that the extracts of C odorata may havethe potential to be used as 120572-amylase inhibitor in managingpostprandial hyperglycemia Another study revealed thatseveral terpenoid derivatives and flavonoids isolated fromthe flower buds of C odorata possessed inhibitory effectson aldose reductase [23] Aldose reductase is an enzyme inthe polyol pathway that reduces glucose to sorbitol with theuse of NADPH The accumulation of intracellular sorbitolas a result of abnormal activation of polyol pathway maylead to chronic complications of diabetes such as diabeticneuropathy retinopathy nephropathy and cataract [102]Hence the inhibition of aldose reductase activity may helpin preventing diabetic complications The study showedthat canangaterpene I (E)-[(1R3R5S6S8S)-6-hydroxy-13-dimethoxy-2- oxaspiro[45]decan-8-yl]methyl caffeate andcanangafruticoside E exhibited potent inhibitory effects onaldose reductase with IC

50at 12 15 and 08 120583M respectively

with comparison to a reference compound chlorogenic acidwith IC

50at 07 120583M [23]

19 Commercial Uses

Many patents exist which describe the commercial appli-cation of ylang-ylang oil Of the 866 references to ldquoylang-ylangrdquo that were located by ldquoScifinderrdquo 533 of these (615)were patents At the time of writing recent patents involvingylang-ylang oil showed that a majority of the inventionshave focused on field of health products and cosmetic usesYlang-ylang oil has been reported to be ingredients for manycosmetic products such as skin care products [103 104] hairprotecting products [105] hair growth promoter [106] andsunscreen compositions [107] Besides that the essential oilsof C odorata also present applications in agriculture andfood industry The essential oil of C odorata has also beenreported to be one of the ingredients for an invention usedas repellent against insects arachnids and other arthropods[108] In additionC odorata oil has also been incorporated asone of ingredients into a beverage formulations for the use asnutritional supplement [109] All these patents demonstrate astrong commercial value and wide range of uses of C odorataessential oil

20 Conclusion

Extensive literature survey demonstrated that C odoratais a medicinal and aromatic plant with a vast spectrumof pharmacological activities having considerable impor-tance in agricultural and consumer products industriesThe constituents such as O-methylmoschatoline liriodenine

(24) 34-dihydroxybenzoic acid germacrene D (11) and 120573-caryophyllene (12) have been recognized as the bioactivemolecules that possess antimicrobial activities Linalool (8)is another compound that has been shown to exhibit insec-ticidal and anti-inflammatory activities Besides that it hasbeen experimentally proven that C odorata also possessantibiofilm antioxidant antidiabetic antifertility antime-lanogenesis insect-repellent antihyperglycemic sedativeand relaxing properties And overall this review emphasizesthe potential ofC odorata to be used as new therapeutic drugsand also provides sufficient baseline information for futureworks and commercial exploitation

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

Acknowledgments

This work was supported by the Monash University MalaysiaECR Grant (5140077-000-00) MOSTI eScience Fund (02-02-10-SF0215) and University of Malaya for High ImpactResearch Grant (Grant no H-50001-A000027 and noA000001-50001) The authors are thankful to Dr SugumaranManickam and Mr Cheah Yih Horng for providing theimages of the plant taken from Rimba Ilmu Botanic GardenUniversity of Malaya

References

[1] K R Goodrich ldquoFloral scent in Annonaceaerdquo Botanical Journalof the Linnean Society vol 169 no 1 pp 262ndash279 2012

[2] G A Burdock and I G Carabin ldquoSafety assessment of Ylang-Ylang (Cananga spp) as a food ingredientrdquo Food and ChemicalToxicology vol 46 no 2 pp 433ndash445 2008

[3] K Caballero-Gallardo J Olivero-Verbel and E E StashenkoldquoRepellent activity of essential oils and some of their individualconstituents against Tribolium castaneum herbstrdquo Journal ofAgricultural and Food Chemistry vol 59 no 5 pp 1690ndash16962011

[4] M Soonwera and S Phasomkusolsil ldquoEfficacy of Thai herbalessential oils as green repellent against mosquito vectorsrdquo ActaTropica vol 142 pp 127ndash130 2015

[5] K Lee J-H Lee S-I Kim M H Cho and J Lee ldquoAnti-biofilm anti-hemolysis and anti-virulence activities of blackpepper cananga myrrh oils and nerolidol against Staphylococ-cus aureusrdquoAppliedMicrobiology and Biotechnology vol 98 no22 pp 9447ndash9457 2014

[6] AWei and T Shibamoto ldquoAntioxidantlipoxygenase inhibitoryactivities and chemical compositions of selected essential oilsrdquoJournal of Agricultural and Food Chemistry vol 58 no 12 pp7218ndash7225 2010

[7] M M Jemain M N Nik Musarsquoadah A Rohaya L A Rashidand I NorHadiani ldquoIn vitro antihyperglycaemic effects of someMalaysian plantsrdquo Journal of Tropical Forest Science vol 23 no4 pp 467ndash472 2011

[8] T Matsumoto S Nakamura S Nakashima et al ldquoLignandicarboxylates and terpenoids from the flower buds ofCananga

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

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Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 27: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 27

odorata and their inhibitory effects on melanogenesisrdquo Journalof Natural Products vol 77 no 4 pp 990ndash999 2014

[9] H IManner andC R ElevitchCananga odorata (ylang-ylang)Species Profiles for Pacific Island Agroforestry 2006

[10] P Zollo L Biyiti F Tchoumbougnang C Menut G Lamatyand P Bouchet ldquoAromatic plants of tropical Central AfricaPart XXXII Chemical composition and antifungal activity ofthirteen essential oils from aromatic plants of CameroonrdquoFlavour and Fragrance Journal vol 13 no 2 pp 107ndash114 1998

[11] J Brophy R Goldsack and P Forster ldquoEssential oils from theleaves of some Queensland Annonaceaerdquo Journal of EssentialOil Research vol 16 no 2 pp 95ndash100 2004

[12] J-C Chalchat R-P Garry C Menut G Lamaty R Malhuretand J Chopineau ldquoCorrelation between chemical compositionand antimicrobial activity VI Activity of someAfrican essentialoilsrdquo Journal of Essential Oil Research vol 9 no 1 pp 67ndash751997

[13] E Stashenko J R Martinez C MacKu and T ShibamotoldquoHRGC and GC-MS analysis of essential oil from Colombianylangminusylang (Cananga odorata Hook fil Et Thomson formagenuina)rdquo Journal of High Resolution Chromatography vol 16no 7 pp 441ndash444 1993

[14] E E Stashenko W Torres and J R M Morales ldquoA studyof the compositional variation of the essential oil of ylang-ylang (Cananga odorataHook Fil etThomson forma genuina)during flower developmentrdquo Journal of High Resolution Chro-matography vol 18 no 2 pp 101ndash104 1995

[15] C Benini M Ringuet J-P Wathelet G Lognay P du Jardinand M-L Fauconnier ldquoVariations in the essential oils fromylang-ylang (Cananga odorata [Lam] Hook f amp Thomsonforma genuina) in the Western Indian Ocean islandsrdquo Flavourand Fragrance Journal vol 27 no 5 pp 356ndash366 2012

[16] M Brokl M-L Fauconnier C Benini G Lognay P du Jardinand J-F Focant ldquoImprovement of ylang-ylang essential oilcharacterization by GCtimesGC-TOFMSrdquoMolecules vol 18 no 2pp 1783ndash1797 2013

[17] C Benini G Mahy J P Bizoux et al ldquoComparative chemicaland molecular variability of Cananga odorata (Lam) HookF amp Thomson forma genuina (ylangminusylang) in the WesternIndian Ocean Islands implication for valorizationrdquo Chemistryamp Biodiversity vol 9 no 7 pp 1389ndash1402 2012

[18] T-J Hsieh F-R Chang and Y-C Wu ldquoThe constituents ofCananga odoratardquo Journal of the Chinese Chemical Society vol46 no 4 pp 607ndash611 1999

[19] J U M Rao G S Giri T Hanumaiah and K V J RaoldquoSampangine a new alkaloid from Cananga odoratardquo Journalof Natural Products vol 49 no 2 pp 346ndash347 1986

[20] T-J Hsieh F-R Chang Y-C Chia C-Y Chen H-F Chiuand Y-C Wu ldquoCytotoxic constituents of the fruits of Canangaodoratardquo Journal of Natural Products vol 64 no 5 pp 616ndash6192001

[21] E Caloprisco J-D Fourneron R Faure and F-E DemarneldquoUnusual lactones from Cananga odorata (Annonaceae)rdquo Jour-nal of Agricultural and Food Chemistry vol 50 no 1 pp 78ndash802002

[22] K Matsunami J Nagashima S Sugimoto et al ldquoMegastig-mane glucosides and an unusual monoterpene from the leavesof Cananga odorata var odorata and absolute structures ofmegastigmane glucosides isolated from C odorata var odorataandBreynia officinalisrdquo Journal of NaturalMedicines vol 64 no4 pp 460ndash467 2010

[23] T Matsumoto S Nakamura K Fujimoto et al ldquoStructure ofconstituents isolated from the flower buds of Cananga odorataand their inhibitory effects on aldose reductaserdquo Journal ofNatural Medicines vol 68 no 4 pp 709ndash716 2014

[24] J Nagashima K Matsunami H Otsuka D Lhieochaiphantand S Lhieochaiphant ldquoThe unusual canangafruticosides A-E five monoterpene glucosides two monoterpenes and amonoterpene glucoside diester of the aryldihydronaphthalenelignan dicarboxylic acid from leaves of Cananga odorata varfruticosardquo Phytochemistry vol 71 no 13 pp 1564ndash1572 2010

[25] M M Rahman S S Lopa G Sadik et al ldquoAntibacterialand cytotoxic compounds from the bark of Cananga odoratardquoFitoterapia vol 76 no 7-8 pp 758ndash761 2005

[26] I W Kusuma Murdiyanto E T Arung Syafrizal and Y KimldquoAntimicrobial and antioxidant properties of medicinal plantsused by the Bentian tribe from Indonesiardquo Food Science andHuman Wellness vol 3 no 3-4 pp 191ndash196 2014

[27] J Nguyen-Pouplin H Tran H Tran et al ldquoAntimalarial andcytotoxic activities of ethnopharmacologically selected medici-nal plants from South Vietnamrdquo Journal of Ethnopharmacologyvol 109 no 3 pp 417ndash427 2007

[28] S Chao G Young C Oberg and K Nakaoka ldquoInhibition ofmethicillin-resistant Staphylococcus aureus (MRSA) by essentialoilsrdquo Flavour and Fragrance Journal vol 23 no 6 pp 444ndash4492008

[29] M A Kaisa ldquoA review on phytochemicals from somemedicinalplants of Bangladeshrdquo Journal of Pharmacy and NutritionSciences vol 1 no 1 2011

[30] G Sacchetti S Maietti M Muzzoli et al ldquoComparativeevaluation of 11 essential oils of different origin as functionalantioxidants antiradicals and antimicrobials in foodsrdquo FoodChemistry vol 91 no 4 pp 621ndash632 2005

[31] I Indrakumar V Selvi R Gomathi and S Karpagam ldquoEvalua-tion of antimicrobial activity of Cananga odorata (Lam) HookF amp Thomson leaf extract an in vitro studyrdquo Mintage Journalof Pharmaceutical and Medical Sciences vol 1 no 1 pp 21ndash222012

[32] B F M T Andrade L N Barbosa I da Silva Probst and AF Junior ldquoAntimicrobial activity of essential oilsrdquo Journal ofEssential Oil Research vol 26 no 1 pp 34ndash40 2014

[33] C Y Ragasa B Tamboong and J Rideout ldquoSecondarymetabo-lites from Jasminum sambac and Cananga odoratardquo ACGCChemical Research Communications vol 16 pp 40ndash47 2003

[34] E-M Choi and J-K Hwang ldquoScreening of Indonesian medic-inal plants for inhibitor activity on nitric oxide production ofRAW2647 cells and antioxidant activityrdquo Fitoterapia vol 76no 2 pp 194ndash203 2005

[35] S Phasomkusolsil and M Soonwera ldquoEfficacy of herbal essen-tial oils as insecticide against Aedes aegypti (Linn) Culex quin-quefasciatus(Say) and Anopheles Dirus (Peyton and Harrison)rdquoSoutheast Asian Journal of Tropical Medicine and Public Healthvol 42 no 5 pp 1083ndash1092 2011

[36] S Phasomkusolsil and M Soonwera ldquoThe effects of herbalessential oils on the ovipositiondeterrent and ovicidal activitiesofAedes aegypti (Linn)Anopheles dirus (Peyton and Harrison)and Culex quinquefasciatus (say)rdquo Tropical Biomedicine vol 29no 1 pp 138ndash150 2012

[37] S-M Seo H-M Park and I-K Park ldquoLarvicidal activity ofajowan (Trachyspermum ammi) and peru balsam (Myroxylonpereira) oils and blends of their constituents against mosquitoAedes aegypti acute toxicity on water fleaDaphnia magna and

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 28: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

28 Evidence-Based Complementary and Alternative Medicine

aqueous residuerdquo Journal of Agricultural and Food Chemistryvol 60 no 23 pp 5909ndash5914 2012

[38] S S Vera D F Zambrano S CMendez-Sanchez F Rodrıguez-Sanabria E E Stashenko and J E Duque Luna ldquoEssentialoils with insecticidal activity against larvae of Aedes aegypti(Diptera Culicidae)rdquo Parasitology Research vol 113 no 7 pp2647ndash2654 2014

[39] M Soonwera ldquoLarvicidal and oviposition deterrent activitiesof essential oils against house fly (Musca domestica L DipteraMuscidae)rdquo Journal of Agricultural Technology vol 11 no 3 pp657ndash667 2015

[40] S-M Seo J Kim S-G Lee C-H Shin S-C Shin andI-K Park ldquoFumigant antitermitic activity of plant essentialoils and components from ajowan (Trachyspermum ammi)allspice (Pimenta dioica) caraway (Carum carvi) dill (Anethumgraveoiens) geranium (Pelargonium graveoiens) and litsea(Litsea cubeba) oils against Japanese termite (Reticulitermessperatus kolbe)rdquo Journal of Agricultural and FoodChemistry vol57 no 15 pp 6596ndash6602 2009

[41] J Cheng K Yang N N Zhao X G Wang S Y Wang and ZL Liu ldquoComposition and insecticidal activity of the essential oilof Cananga odorata leaves against Sitophilus zeamaismotschul-sky (Coleoptera Curculionidae)rdquo Journal of Medicinal PlantsResearch vol 6 no 19 2012

[42] S Phasomkusolsil and M Soonwera ldquoComparative mosquitorepellency of essential oils against Aedes aegypti (Linn)Anopheles dirus (Peyton and Harrison) and Culex quinquefas-ciatus (Say)rdquo Asian Pacific Journal of Tropical Biomedicine vol1 no 1 pp S113ndashS118 2011

[43] M Soonwera and S Phasomkusolsil ldquoMosquito repellent fromThai essential oils against dengue fever mosquito (Aedes aegypti(L)) and filarial mosquito vector (Culex quinquefasciatus(Say))rdquo African Journal of Microbiology Research vol 8 no 17pp 1819ndash1824 2014

[44] Y A Maniyar and C H J Devi ldquoEvaluation of anti-inflammatory activity of ethanolic extract of Cananga odorataLam in experimental animalsrdquo International Journal of Basic ampClinical Pharmacology vol 4 no 2 pp 354ndash357 2015

[45] C N Wang ldquoEffect ofMelaleuca leucadendron Cananga odor-ata and Pogostemon cablin oil odors on human physiologicalresponsesrdquoWood Research vol 3 no 2 p 100 2012

[46] T Hongratanaworakit and C Buchbauer ldquoEvaluation of theharmonizing effect of ylang-ylang oil on humans after inhala-tionrdquo Planta Medica vol 70 no 7 pp 632ndash636 2004

[47] M Moss S Hewitt L Moss and K Wesnes ldquoModulation ofcognitive performance andmood by aromas of peppermint andylang-ylangrdquo International Journal of Neuroscience vol 118 no1 pp 59ndash77 2008

[48] P Anitha andM Indira ldquoImpact of feeding ethanolic extract ofroot bark of Cananga odorata (Lam) on reproductive functionsinmale ratsrdquo Indian Journal of Experimental Biology vol 44 no12 pp 976ndash980 2006

[49] A Pankajakshy and I Madambath ldquoSpermatotoxic effects ofCananga odorata (Lam) a comparison with gossypolrdquo Fertilityand Sterility vol 91 no 5 pp 2243ndash2246 2009

[50] The Plant List ldquoCananga odorata (Lam) Hook F ampThomsonrdquohttpwwwtheplantlistorgtpl11recordkew-2695745

[51] N Saedi and G H Crawford ldquoBotanical briefs ylang-ylangoilmdashextracts from the tree Cananga odoratardquo Cutis vol 77 no3 pp 149ndash150 2006

[52] D K Holdsworth ldquoTraditional medicinal plants of RarotongaCook Islands part Irdquo Pharmaceutical Biology vol 28 no 3 pp209ndash218 1990

[53] D Nandwani J A Calvo J Tenorio F Calvo and L ManglonaldquoMedicinal plants and traditional knowledge in the northernMariana Islandsrdquo Journal of Applied Biosciences vol 8 no 2 pp323ndash330 2008

[54] S Holt ldquoPart 2 stimulants and dietary supplementsrdquo Alterna-tive and Complementary Therapies vol 5 no 5 pp 279ndash2851999

[55] S Jain and S Srivastava ldquoTraditional uses of some Indianplants among islanders of the Indian Oceanrdquo Indian Journal ofTraditional Knowledge vol 4 no 4 pp 345ndash357 2005

[56] D K Holdsworth and L Corbett ldquoTraditional medicinal plantsof the north solomons province Papua new guinea part IIrdquoPharmaceutical Biology vol 26 no 1 pp 45ndash50 1988

[57] A Roloff H Weisgerber P Schutt U M Lang and B StimmEnzyklopadie Der Holzgewachse Handbuch Und Atlas DerDendrologie Wiley-VCH 2012

[58] F Bakkali S Averbeck D Averbeck and M Idaomar ldquoBio-logical effects of essential oilsmdasha reviewrdquo Food and ChemicalToxicology vol 46 no 2 pp 446ndash475 2008

[59] X-W Qin C-Y Hao S-Z He et al ldquoVolatile organic com-pound emissions from different stages of Cananga odorataflower developmentrdquo Molecules vol 19 no 7 pp 8965ndash89802014

[60] E M Gaydou R Randriamiharisoa and J-P Bianchini ldquoCom-position of the essential oil of ylang-ylang (Cananga odorataHook Fil et Thomson forma genuina) from MadagascarrdquoJournal of Agricultural and Food Chemistry vol 34 no 3 pp481ndash487 1986

[61] J Jin M J Kim S Dhandapani et al ldquoThe floral transcrip-tome of ylang ylang (Cananga odorata var fruticosa) uncoversbiosynthetic pathways for volatile organic compounds and amultifunctional and novel sesquiterpene synthaserdquo Journal ofExperimental Botany vol 66 no 13 pp 3959ndash3975 2015

[62] S H Woo M C Reynolds N J Sun J M Cassady andR M Snapka ldquoInhibition of topoisomerase II by liriodeninerdquoBiochemical Pharmacology vol 54 no 4 pp 467ndash473 1997

[63] J Kluza A M Clark and C Bailly ldquoApoptosis induced bythe alkaloid sampangine in HL-60 leukemia cells correlationbetween the effects on the cell cycle progression and changesof mitochondrial potentialrdquo Annals of the New York Academy ofSciences vol 1010 no 1 pp 331ndash334 2003

[64] I Ahmad and A Z Beg ldquoAntimicrobial and phytochemicalstudies on 45 Indian medicinal plants against multi-drugresistant human pathogensrdquo Journal of Ethnopharmacology vol74 no 2 pp 113ndash123 2001

[65] P Dahiya and S Purkayastha ldquoPhytochemical screening andantimicrobial activity of some medicinal plants against multi-drug resistant bacteria from clinical isolatesrdquo Indian Journal ofPharmaceutical Sciences vol 74 no 5 p 443 2012

[66] E Christaki E Bonos I Giannenas and P Florou-Paneri ldquoAro-matic plants as a source of bioactive compoundsrdquo Agriculturevol 2 no 3 pp 228ndash243 2012

[67] S Luangnarumitchai S Lamlertthon and W TiyaboonchaildquoAntimicrobial activity of essential oils against five strains ofPropionibacterium acnesrdquo Mahidol University Journal of Phar-maceutical Sciences vol 34 no 1ndash4 pp 60ndash64 2007

[68] A Thompson D Meah N Ahmed et al ldquoComparison of theantibacterial activity of essential oils and extracts of medicinal

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 29: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Evidence-Based Complementary and Alternative Medicine 29

and culinary herbs to investigate potential new treatments forirritable bowel syndromerdquo BMC Complementary and Alterna-tive Medicine vol 13 article 338 2013

[69] J-H Lee and J-S Lee ldquoChemical composition and antifungalactivity of plant essential oils againstMalassezia furfurrdquo KoreanJournal ofMicrobiology andBiotechnology vol 38 no 3 pp 315ndash321 2010

[70] S Inouye K Uchida and S Abe ldquoVapor activity of 72 essentialoils against a Trichophyton mentagrophytesrdquo Journal of Infectionand Chemotherapy vol 12 no 4 pp 210ndash216 2006

[71] K Kon and M Rai ldquoAntibacterial activity of Thymus vulgarisessential oil alone and in combination with other essential oilsrdquoNusantara Bioscience vol 4 no 2 pp 50ndash56 2012

[72] S Tadtong S Suppawat A Tintawee P Saramas S Jareonvongand T Hongratanaworakit ldquoAntimicrobial activity of blendedessential oil preparationrdquoNatural Product Communications vol7 no 10 pp 1401ndash1404 2012

[73] Y-G Kim J-H Lee S-I Kim K-H Baek and J Lee ldquoCinna-mon bark oil and its components inhibit biofilm formation andtoxin productionrdquo International Journal of Food Microbiologyvol 195 pp 30ndash39 2015

[74] P S Stewart and J W Costerton ldquoAntibiotic resistance ofbacteria in biofilmsrdquoThe Lancet vol 358 no 9276 pp 135ndash1382001

[75] A Nostro A S Roccaro G Bisignano et al ldquoEffects of oreganocarvacrol and thymol on Staphylococcus aureus and Staphylococ-cus epidermidis biofilmsrdquo Journal of Medical Microbiology vol56 no 4 pp 519ndash523 2007

[76] J C Goldbeck J E do Nascimento R G Jacob A MFiorentini and W P da Silva ldquoBioactivity of essential oils fromEucalyptus globulus and Eucalyptus urograndis against plank-tonic cells and biofilms of Streptococcus mutansrdquo IndustrialCrops and Products vol 60 pp 304ndash309 2014

[77] M Sandasi C M Leonard and A M Viljoen ldquoThe in vitroantibiofilm activity of selected culinary herbs and medicinalplants against Listeria monocytogenesrdquo Letters in AppliedMicro-biology vol 50 no 1 pp 30ndash35 2010

[78] S Taweechaisupapong P Ngaonee P Patsuk W Pitiphat andW Khunkitti ldquoAntibiofilm activity and post antifungal effect oflemongrass oil on clinical Candida dubliniensis isolaterdquo SouthAfrican Journal of Botany vol 78 pp 37ndash43 2012

[79] M Bilcu A M Grumezescu A E Oprea et al ldquoEfficiencyof vanilla patchouli and ylang ylang essential oils stabilizedby iron oxideC

14nanostructures against bacterial adherence

and biofilms formed by Staphylococcus aureus and Klebsiellapneumoniae clinical strainsrdquoMolecules vol 19 no 11 pp 17943ndash17956 2014

[80] M G Miguel ldquoAntioxidant activity of medicinal and aromaticplants A reviewrdquo Flavour and Fragrance Journal vol 25 no 5pp 291ndash312 2010

[81] F Shahidi ldquoAntioxidants in food and food antioxidantsrdquoFoodNahrung vol 44 no 3 pp 158ndash163 2000

[82] H-F Wang Y-K Wang and K-H Yih ldquoDPPH free-radicalscavenging ability total phenolic content and chemical com-position analysis of forty-five kinds of essential oilsrdquo Journal ofCosmetic Science vol 59 no 6 pp 509ndash522 2008

[83] World Health Organization Dengue Guidelines for DiagnosisTreatment Prevention and Control WorldHealth OrganizationGeneva Switzerland 2009

[84] Ministry of Health Malaysia Health Facts 2014 Ministryof Health Malaysia 2014 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202014pdf

[85] Ministry of Health Malaysia ldquoHealth facts 2013rdquo 2013 httpwwwmohgovmyimagesgallerypublicationsHEALTH20FACTS202013pdf

[86] M V Cardo D Vezzani and A E Carbajo ldquoOvipositionstrategies of temporary pool mosquitoes in relation to weathertidal regime and land use in a temperate wetlandrdquo Bulletin ofEntomological Research vol 102 no 6 pp 651ndash662 2012

[87] S Phasomkusolsil and M Soonwera ldquoEfficacy of Thai herbalessential oils against three immature stages of Aedes aegypti(Linn) Anopheles dirus (Peyton and Harrison) and Culexquinquefasciatus (say)rdquoTopclass Journal of HerbalMedicine vol2 pp 25ndash35 2013

[88] R K Gupta and L C Rutledge ldquoRole of repellents in vectorcontrol and disease preventionrdquoThe American Journal of Tropi-cal Medicine and Hygiene vol 50 no 6 supplement pp 82ndash861994

[89] M S Fradin and J F Day ldquoComparative efficacy of insectrepellents against mosquito bitesrdquo The New England Journal ofMedicine vol 347 no 1 pp 13ndash18 2002

[90] J Olivero-Verbel I Tirado-Ballestas K Caballero-Gallardoand E E Stashenko ldquoEssential oils applied to the food actas repellents toward Tribolium castaneumrdquo Journal of StoredProducts Research vol 55 pp 145ndash147 2013

[91] S Parvez M Kang H-S Chung et al ldquoSurvey and mechanismof skin depigmenting and lightening agentsrdquo PhytotherapyResearch vol 20 no 11 pp 921ndash934 2006

[92] M Efdi K Ohguchi Y Akao Y Nozawa M Koketsu and HIshihara ldquoN-trans-feruloyltyramine as a melanin biosynthesisinhibitorrdquoBiological and Pharmaceutical Bulletin vol 30 no 10pp 1972ndash1974 2007

[93] C-C Lin C-H Yang P-S Wu C-C Kwan and Y-S ChenldquoAntimicrobial anti-tyrosinase and antioxidant activities ofaqueous aromatic extracts from forty-eight selected herbsrdquoJournal of Medicinal Plant Research vol 5 no 26 pp 6203ndash6209 2011

[94] S Basu and B Hazra ldquoEvaluation of nitric oxide scavengingactivity in vitro and ex vivo of selected medicinal plants tradi-tionally used in inflammatory diseasesrdquo Phytotherapy Researchvol 20 no 10 pp 896ndash900 2006

[95] A T Peana P S DrsquoAquila F Panin G Serra P Pippia and MD LMoretti ldquoAnti-inflammatory activity of linalool and linalylacetate constituents of essential oilsrdquo Phytomedicine vol 9 no8 pp 721ndash726 2002

[96] S Moncada R M J Palmer and E A Higgs ldquoNitric oxidephysiology pathophysiology and pharmacologyrdquo Pharmaco-logical Reviews vol 43 no 2 pp 109ndash142 1991

[97] T Hongratanaworakit and G Buchbauer ldquoRelaxing effect ofylang ylang oil on humans after transdermal absorptionrdquoPhytotherapy Research vol 20 no 9 pp 758ndash763 2006

[98] D j Jung J Y Cha S E Kim I G Ko and Y S Jee ldquoEffects ofYlang-Ylang aroma on blood pressure and heart rate in healthymenrdquo Journal of Exercise Rehabilitation vol 9 no 2 pp 250ndash255 2013

[99] A Ishiguchi A Saitou K Suenaga K Ohta and M Matsuuraldquo14 Effects of odors on electroencephalogram and subjectivealterationsrdquo Clinical Neurophysiology vol 119 no 6 article e782008

[100] S Watanabe K Hara K Ohta et al ldquoAroma helps to preserveinformation processing resources of the brain in healthy sub-jects but not in temporal lobe epilepsyrdquo Seizure vol 22 no 1pp 59ndash63 2013

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 30: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

30 Evidence-Based Complementary and Alternative Medicine

[101] Y-J Hsu T-H Lee C L-T Chang Y-T Huang and W-CYang ldquoAnti-hyperglycemic effects and mechanism of Bidenspilosawater extractrdquo Journal of Ethnopharmacology vol 122 no2 pp 379ndash383 2009

[102] M Saraswat P Muthenna P Suryanarayana J M Petrash andG B Reddy ldquoDietary sources of aldose reductase inhibitorsprospects for alleviating diabetic complicationsrdquo Asia PacificJournal of Clinical Nutrition vol 17 no 4 pp 558ndash565 2008

[103] T FlorenceMHines andDGan ldquoCosmetic compositions anduses thereofrdquo Google Patents 2014

[104] C Drapeau S Kukulcan and G S Jensen ldquoSkin care compo-sitions containing combinations of natural ingredientsrdquo GooglePatents 2014

[105] J Humphreys and J Sherman ldquoCompositions and methods fortreating keratin based fibersrdquo Google Patents 2014

[106] C S Darsale ldquoNourishing oil composition pomade compo-sition for promoting hair growth shampoo conditioner hairroot stimulator and methods for making and using the samerdquoGoogle Patents 2014

[107] H EThaggard ldquoReduced-alcohol sunscreen compositions andmethodsrdquo Google Patents 2014

[108] G E Hoag and D K Anderson ldquoNatural volatile plant oils torepel arthropodsrdquo Google Patents 2014

[109] B J West C J Jensen A K Palu S Deng and J A WasdenldquoMorinda citrifolia and iridoid based formulationsrdquo GooglePatents 2014

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom

Page 31: Review Article Traditional Uses, Phytochemistry, …jonnsaromatherapy.com/pdf/Tan_Uses_Phytochemistry_of_Cananga...Review Article Traditional Uses, Phytochemistry, and Bioactivities

Submit your manuscripts athttpwwwhindawicom

Stem CellsInternational

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

MEDIATORSINFLAMMATION

of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Behavioural Neurology

EndocrinologyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Disease Markers

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

BioMed Research International

OncologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Oxidative Medicine and Cellular Longevity

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

PPAR Research

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Immunology ResearchHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

ObesityJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Computational and Mathematical Methods in Medicine

OphthalmologyJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Diabetes ResearchJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Research and TreatmentAIDS

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Gastroenterology Research and Practice

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Parkinsonrsquos Disease

Evidence-Based Complementary and Alternative Medicine

Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom