Phytochemistry Letters 7 (2014) v–xvii

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Phytochemistry Letters

journal homepage: www.elsevier .com/locate/phytol

Contents

Phytochemicals from the aerial parts of Ligularia thomsonii and their radical scavenging activity

Syed Hamid Hussain, Abdul Latif, Russell J. Cox, Thomas J. Simpson, Mumtaz Ali, Mohammad Arfan and Ghias Uddin

� Three new and nine reported compounds were isolated and characterized. � The known compounds are reported for the fi rst time from the genus. � All compounds were evaluated for their antioxidant activities.

doi:10.1016/S1874-3900(14)00015-9

Nigrosphaerin A a new isochromene derivative from the endophytic fungus Nigrospora sphaerica

Ahmed M. Metwaly, Hazem A. Kadry, Atef A. El-Hela, Abd-Elsalam I. Mohammad, Guoyi Ma, Stephen J. Cutler and Samir A. Ross

� The phytochemical and biological properties of the endophytic fungus Nigrospora sphaerica were examined. Nigrosphaerin A, a new isochromene derivative, along with nineteen known compounds was isolated and identifi ed. Four compounds showed good in vitro antileukemic activity. Three compounds showed moderate in vitro antileishmanial activity. One compound showed good antifungal activity.

pp 1–5

pp 6–10

pp 173–181Role of plants in anticancer drug discovery

Jabeena Khazir, Bilal Ahmad Mir, Lynne Pilcher and Darren L. Riley

� Cancer is second deadly disease after cardiovascular diseases. � There is a tremen-dous need to discover novel safer and more effective anticancer agents. � Plants serve as a basis for promising therapeutic agents for cancer treatment. � Important plant derived anticancer agents have been discussed here. � Some potential plant derived lead molecules have also been discussed.

INVITED MINI REVIEWS

LETTERS

vi Phytochemistry Letters 7 (2014) v–xvii

A new nortriterpenoid from the fruiting bodies of Ganoderma tropicum

Li-li Hu, Qing-yun Ma, Sheng-zhuo Huang, Zhi-kai Guo, Hai-xia Ma, Jian-chun Guo, Hao-fu Dai and You-xing Zhao

� A C-24 lanostane nortriterpene was isolated from Ganoderma tropicum. � A new C-29 lanostane nortriterpene was isolated from Ganoderma tropicum. � The lanostane triterpenoids from Ganoderma tropicum were found for the fi rst time.

Guaianolides and elemanolides from Vernonia anthelmintica

Li Zhang, Yong-Liang Shao, Lei Hua, Ya Li, Syed Hamid Hussain, Mohammad Arfan and Kun Gao

� Two new guaianolides and two known elemanolides were isolated from Vernonia anthelmintica Willd. � Their biosyn-thetic relationships were discussed. � Compounds 1–4 were evaluated for their cytotoxicity against HL-60 and SMMC-7721 cell lines.

Development and validation of a gas chromatographic method for the quantifica-tion of D-pinitol in decoctions of Desmodium adscendens

Ines van Dooren, Nina Hermans, Liene Dhooghe, Tania Naessens, Reinhilde Vermeylen, Magda Claeys, Arnold Vlietinck, Luc Pieters and Sandra Apers

� A GC method for quantifi cation of pinitol in D. adscendens was developed. � Different internal standards and derivatization methods were evaluated. � The fi nal method was validated. � The calibration model was linear, the precision and accuracy were acceptable.

Simalin A and B: Two new aromatic compounds from the stem bark of Bombax ceiba

Khem Raj Joshi, Hari Prasad Devkota and Shoji Yahara

� Two new aromatic compounds; simalin A (1) and simalin B (2) were isolated from the stem barks of Bombax ceiba. � Five known compounds (3–7) were also isolated together with these two new compounds. � Compounds 6 and 7 were isolated for the fi rst time from B. ceiba.

pp 26–29

pp 19–25

pp 14–18

pp 11–13

Phytochemistry Letters 7 (2014) v–xvii vii

Monoterpene indole alkaloids and monoterpene diglycosides from the roots of Triosteum pinnatifidum

Xiong Huang, Ying Li, Yanfang Su, Xin Chai and Shilun Yan

� One new indole alkaloid and one new diglycoside were isolated from T. pinnatifidum. � Structures were deduced by 1D and 2D NMR spectra and X-ray crystallographic analysis. � It is the fi rst report of 13C NMR data of urceolide and all compounds from Triosteum.

A new aromatic amine from fungus Pestalotiopsis vaccinii

Xuefeng Zhou, Xiuping Lin, Wanlei Ma, Wei Fang, Zhefang Chen, Bin Yang and Yonghong Liu

� A new and fi ve known compounds were isolated from fungus Pestalotiopsis vaccinii. � The structure of the new compound was determined by spectroscopic methods, especially 2D NMR analyses. � The new compound pestalamine A (1) showed cytotoxicities against MCF-7, HeLa, and HepG2 human cancer cell lines.

Effect of nicotinic acid, nicotinamide and trigonelline on the proliferation of lettuce cells derived from protoplasts

Hamako Sasamoto and Hiroshi Ashihara

� The effect of pyridine compounds on growth of lettuce cells derived from protoplasts was investigated. � Nicotinic acid inhibited the division and colony formation of the cell, but trigonelline did not. � Trigonelline formation from nicotinic acid appears to be a detoxifi cation reaction.

Compounds from Simarouba berteroana which inhibit proliferation of NF1-defective cancer cells

Krishna P. Devkota, Jennifer A. Wilson, Curtis J. Henrich, James B. McMahon, Karlyne M. Reilly and John A. Beutler

� A novel canthine glycoside was identifi ed from Simarouba berteroana. � Known quassinoids from this plant possessed the best cell growth inhibition against NF1-defi cient cancer cells. � A lignan was also identifi ed as having modest activity, but was also toxic.

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viii Phytochemistry Letters 7 (2014) v–xvii

Two new acylated drimane-type sesquiterpene glucosides from Petrorhagia saxifraga

Monica Scognamiglio, Brigida D’Abrosca, Valeria Severino, Angela Chambery, Pietro Monaco and Antonio Fiorentino

� Two new acylated drimane glucosides have been isolated from Petrorhagia saxifraga. � Structures were elucidated by 2D NMR and Q-TOF HRMS2 analyses. � Drimane gluco-sides could represent a chemotaxonomic marker for Petrorhagia genus.

Further cycloartane and friedelane triterpenoids from the leaves of Caloncoba glauca

James D. Simo Mpetga, Hong-Ping He, Xiao-Jiang Hao, Ying Leng and Pierre Tane

� Isolation and elucidation of new cycloartane and friedelane-type triterpenoids. � Caloncobalactone C (2) is a 9,10-seco-cycloartane triterpenoid. � Isolates were evaluated for their inhibition of mouse and human 11�-HSD1 and 11�-HSD2. � Caloncobic acid C (1) exhibited a better selectivity on mouse enzymes.

New diterpene polyester and phenolic compounds from Pycnocycla spinosa Decne. Ex Boiss with relaxant effects on KCl-induced contraction in rat ileum

Mustafa Ghanadian, Hassan Sadraei, Samar Yousuf, Gholamreza Asghari, M. Iqbal Choudhary and Masood Jahed

� We investigated the activity-guided isolation of spasmolytics from Pycnocycla spinosa. � A new myrsinane diterpene, and a new phenolic compound were isolated. � The new polycyclic diterpene is likely the main active ingredient of the extract. � It is the fi rst that a myrsinane diterpene is reported to have spasmolytic effect.

Steroidal saponins from the leaves of Cordyline fruticosa (L.) A. Chev. and their cyto-toxic and antimicrobial activity

Romuald T. Fouedjou, Rémy B. Teponno, Luana Quassinti, Massimo Bramucci, Dezemona Petrelli, Luca A. Vitali, Dennis Fiorini, Léon A. Tapondjou and Luciano Barboni

� Three new steroidal saponins were isolated from the leaves of Cordyline fruticosa. � The new compounds were tested for cytotoxic and antimicrobial activity. � Two of the compounds showed cytotoxicity against three human tumour cell lines. � One compound showed a moderate antibacterial activity against Enterococcus faecalis.

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Phytochemistry Letters 7 (2014) v–xvii ix

Acylated cyanidin glycosides from the pale-violet flowers of Ionopsidium acaule (Desf.) Rchb. (Brassicaceae)

Fumi Tatsuzawa, Narumi Takahashi, Kazuhisa Kato, Koichi Shinoda, Norio Saito and Toshio Honda

� New anthocyanins were isolated from the pale-violet fl owers of Ionopsidium acaule. � The structures were elucidated on the basis of chemical and spectroscopic data. � Anthocyanins were based on 3-sambubioside-5-glucosides of cyanidin. � The antho-cyanin glycosylation and acylation pattern had chemotaxonomic signifi cance.

Portulacerebroside A induces apoptosis via activation of the mitochondrial death pathway in human liver cancer HCCLM3 cells

Guo-Yin Zheng, Li-Ping Qu, Xiao-Qiang Yue, Wei Gu, Hong Zhang and Hai-Liang Xin

� Portulacerebroside A was found to induce apoptosis of tumor cells for the fi rst time. � Portulacerebroside A facilitates the protein phosphorylation of p38 MAPK and JNK. � Portulacerebroside A disrupts mitochondrial membrane potential. � Portulacerebroside A induces apoptosis via activation of the mitochondrial death pathway in HCCLM cells.

Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides

Maryan Bruzual de Abreu, Abeer Temraz, Antonio Vassallo, Alessandra Braca and Nunziatina De Tommasi

� Phytochemical study of Tabebuia argentea and Catalpa bignonioides was performed. � One new lignan and one new phenolic glycosides were identifi ed. � Plants of Bignoniaceae are a source of phenolic glycosides.

New enantiomeric isoquinoline alkaloids from Coptis chinensis

Lei Wang, Sheng-Yuan Zhang, Liang Chen, Xiao-Jun Huang, Qing-Wen Zhang, Ren-Wang Jiang, Fen Yao and Wen-Cai Ye

� Ten isoquinoline alkaloids were isolated from the rhizoma of Coptis chinensis. � The chiral separation and structure elucidation of a pair of new enantiomeric isoquinoline alkaloids were described. � Berberine (8) displayed synergistic antibacterial activity against MRSA in combination with ceftazidime and cefepime.

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x Phytochemistry Letters 7 (2014) v–xvii

Two new labdane-type diterpenes from the wood of Cunninghamia konishii

Chi-I Chang, Yen-Cheng Li, Yong-Han Hong, Wei-Yi Cheng, Che-Yi Chao, Minoru Tsuzuki, Sakae Amagaya, Ching-Jang Huang and Yueh-Hsiung Kuo

� Two new labdane-type diterpenes were isolated and characterized from Cunninghamia konishii. � Four known labdane-type diterpenoids were isolated from C. konishii. � Structures of these isolates were elucidated by spectroscopic methods.

A new cryptoporic acid derivative from cultures of the basidiomycete Poria albocincta BCC 26244

Masahiko Isaka, Panida Chinthanom, Kannawat Danwisetkanjana and Rattaket Choeyklin

� A new cryptoporic acid derivative was isolated from cultures of Poria albocincta. � The structure was elucidated on the basis of spectroscopic data interpretations. � Biological activities of the cryptoporic acid derivatives were evaluated.

pp 107–110

1 R1=CH2OH, R2=CH32 R1=CH3, R2=COOH

R1R2

OH

H

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Four new sesquiterpene polyol esters from Celastrus angulatus

Hai-Yan Zhang, Tian-Zeng Zhao, Jian-Jun Dong, Rong-Feng Chen, Zhi-Hong Li and Hai-Lin Qin

� More information about the chemical constituents of Celastrus angulatus were given. � Four new sesquiterpene polyol esters were discovered from Celastrus angulatus. � The new sesquiterpene polyol esters were identifi ed as �-dihydroagarofuran sesquiterpene.

A new 5,6-dihydro-2-pyrone derivative from Phomopsis amygdali, an endophytic fungus isolated from hazelnut (Corylus avellana)

Seref Akay, Güner Ekiz, Fatma Kocabas, E. Esin Hames-Kocabas, Kemal S. Korkmaz, andErdal Bedir

� Endophytic fungi of Corylus avellana L. (hazelnut). � Two fungi, namely Phomopsis amygdali and Fusarium oxysporium, were identifi ed. � P. amygdali provided a new sec-ondary metabolite. � 5,6-Dihydro-2H-pyran-2-one derivative was encountered for the fi rst time in Phomopsis genus.

OAcR7

R3

R5

OHO

R4

R2

R6

R1OAc

OAcR3

R5

O

R4

R2

R6

R1

Phytochemistry Letters 7 (2014) v–xvii xi

New cyclohexylethanoids from the leaves of Clerodendrum trichotomum

Rui-Lan Xu, Rui Wang, Wei Ha and Yan-Ping Shi

� Two new cyclohexylethanoids were isolated and elucidated by extensive NMR experiments. � This series cyclohexylethanoids are characteristic of the Clerodendrum genus. � The new cyclohexylethanoids were evaluated for cytotoxicity against the A549 human tumor cell line.

Beckmann rearrangement products of methyl 3-oxo-tirucall-8, 24-dien-21-oate from Boswellia serrata gum and their anti-tumor activity

Suvarna Shenvi, K. Rijesh, Latha Diwakar and G. Chandrasekara Reddy

� Isolated 3-oxo-tirucall-8, 24-dien-21-oic acid from Boswellia serrata. � Synthesized novel A-ring modifi ed compounds (2–6). � Tested in vitro inhibitory activities against fi ve human tumor cell lines. � Compounds 4 and 6 exhibited good anti-tumor activity against prostate cancer cell line.

Antioxidant metabolites from marine alga-derived fungus Aspergillus wentii EN-48

Xin Li, Xiao-Ming Li, Gang-Ming Xu, Chun-Shun Li and Bin-Gui Wang

� Metabolites of the marine alga-derived endophytic fungus Aspergillus wentii EN-48 were investigated. � A new seco-anthraqui-none and a new benzamide derivative were obtained. � Compounds 2–8 exhibited signifi cant scavenging activity against DPPH.

The potential of Leucosidea sericea against Propionibacterium acnes

Richa Sharma, Navneet Kishore, Ahmed Hussein and Namrita Lall

� Signifi cant anti-bacterial and antioxidant activity were displayed by crude extract of Leucosidea sericea and isolated compound. � In the present study, four known and one new compound have been isolated for the fi rst time from ethanolic extract of L. sericea. � The plant exhibited anti-infl amma-tory effi cacy by suppressing pro-infl ammatory cytokines (IL 8 and TNF �). � Electron microscopy studies proved the lethal effects of plant extract and compound 5 on the cells of P. acnes.

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xii Phytochemistry Letters 7 (2014) v–xvii

Flavanones from Miconia prasina

Amer H. Tarawneh, Francisco León, Mohamed Ali Ibrahim, Sara Pettaway, Christopher R. McCurdy and Stephen J. Cutler

� Phytochemical study of Miconia prasina. � One new fl avanone glycoside and fi ve known fl avanones were isolated. � In vitro binding assays using cannabinoid receptors (CB1 and CB2) were evaluated.

Isolation and characterization of two new phenolic acids from cultured cells of Saussurea involucrata

Xiaowei Zou, Dan Liu, Yaping Liu, Yanhun Fu, Xiaozhe Zhang, Zhilong Xiu and Hongbin Xiao

� Two new phenolic acids were obtained from cultured cells of Saussurea involucrata. � The new compounds belong to caffeoyl quinic acids with an additional maloyl group. � The new phenolic acids showed strong radical scavenging abilities.

Abrusamide A and B, two hepatoprotective isomeric compounds from Abrus mollis Hance

Xujiang Yuan, Li Lin, Xuqian Zhang and Shaodong Deng

� Two isomeric compounds, abrusamide A and B were isolated. � Their structures were elucidated by UV, HR–ESI–MS, 1H NMR, 13C NMR and 2D NMR spectrum. � Their plausible biogenetic pathways were proposed. � Their hepatoprotective activities were evaluated by CCL4-induced injury of L-02 cells model with MTT method.

Mid-infrared spectroscopy and short wave infrared hyperspectral imaging—A novel approach in the qualitative assessment of Harpagophytum procumbens and H. zeyheri (Devil’s Claw)

Nontobeko Mncwangi, Ilze Vermaak and Alvaro M. Viljoen

� Two Harpagophytum species are used interchangeably to treat infl ammation and are resolved by spectral methods here. � Chemical congruency and bio-equivalence of the two species have not been proven. � Multivariate analysis models for species authenti-cation were developed. � The two developed models had good statistics with R2X values of 0.86 and 0.99 for MIR and SWIR data, respectively.

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Phytochemistry Letters 7 (2014) v–xvii xiii

Constituents from Zhuyeqing Liquor and their inhibitory effects on nitric oxide production

Hong-ying Gao, Hang-yu Wang, Guo-yu Li, Xiao-wei Du, Xiu-ting Zhang, Ying Han, Jian Huang, Xiao-xiao Li and Jin-hui Wang

� Four new compounds along with 57 known compounds were obtained from Zhuyeqing Liquor. � The biosynthetic pathways leading to compounds 2, 5, 6, 7 and 8 were proposed. � Anti-infl ammatory activity of the isolates was evaluated. � All the isolates were unequivocally identifi ed for their source by UPLC/TOF-MS.

New broad-spectrum antibacterial and antifungal alkaloids from Kopsia hainanensis

Jia Chen, Mei-Li Yang, Jun Zeng and Kun Gao

� The alkaloidal fraction from Kopsia hainanensis showed antimicrobial activity. � Four new and eleven known alkaloids were isolated from the alkaloidal fraction. � Their structures were identifi ed by spectroscopic data. � Compounds 2 and 8 exhibited broad-spectrum antibacterial and antifungal activities.

Guanacastane-type diterpenoids from Coprinus plicatilis

Yuanzhen Liu, Chunhua Lu and Yuemao Shen

� Four new guanacastane-type diterpenoids were reported. � Plicatilisin F gives a keto-enol tautomerization in the solution. � ‘‘OSMAC (One Strain-Many Compounds) approach’’ was used to explore novel metabolites.

Naturally occurring prenylated coumarins from Micromelum integerrimum twigs

Wong Phakhodee, Mookda Pattarawarapan, Preetiya Pongparn and Surat Laphookhieo

� Secondary metabolites from twigs of Micromelum integerrimum were inves-tigated. � Two new prenylated coumarins were isolated along with 9 known coumarin derivatives. � The coumarin structures were elucidated by extensive spectroscopic interpretation.

pp 165–168

OH3CO O

O

OH OH

O HHH3C OHO O

O

O

OHH

OHH3C

O

(1)Dhydramicromelin (2)integerrimelin

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xiv Phytochemistry Letters 7 (2014) v–xvii

pp 186–189Isopimarane diterpenes and flavan derivatives from the twigs of Caesalpinia furfuracea

Ittipon Siridechakorn, Sarot Cheenpracha, Thunwadee Ritthiwigrom, Wong Phakhodee, Suwanna Deachathai, Theeraphan Machan, Nirun Ruankeaw and Surat Laphookhieo

� The fi rst phytochemical investigation of Caesalpinia furfuracea twigs. � Four new compounds including two isopimarane diterpenes and two fl avan derivatives. � Caesalfurfuric acid A exhibited antibacterial activity against MRSA SK1with an MIC value of 16 �g/mL.

A new macrocyclic lactone and a new quinoflavan from Celastrus hindsii

Xian-Qing Hu, Wei Han, Zhu-Zhen Han, Qing-Xin Liu, Xi-Ke Xu, Peng Fu and Hui-Liang Li

� Two new compounds were isolated from Celastrus hindsi. � The structures were determined by extensive spectroscopic analysis. � The X-ray crystallography of 1 was reported for the fi rst time. � Compounds 1–5 showed weak cytotoxicity activity in vitro.

A new flavone sulfonic acid from Phyllanthus urinaria

Nguyen Van Thanh, Phan Thi Thanh Huong, Nguyen Hoai Nam, Nguyen Xuan Cuong, Nguyen Phuong Thao, Bieke Dejaegher, Andrea Gordien, Yvan Vander Heyden, Joëlle Quetin-Leclercq and Chau Van Minh

� A new fl avone derivative urinariafl avone (1) and eight compounds from Phyllanthus urinaria were isolated. � Cytotoxic activity against CHO and J774 cancer cell lines of all isolates was assessed. � Compounds 4, 5, and 7 showed cytotoxic effects (IC50s ∼ 6.00–41.30 �M) on both CHO and J774 cancer cell lines.

CO2HAcOOH

H

H

Caesalfurfuric acid A (1)

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pp 169–172

Thymol derivatives from Eupatorium fortunei and their inhibitory activities on LPS-induced NO production

Yuli Wang, Jinming Li, Hao Wang, Da-Qing Jin, Hongqiang Chen, Jing Xu, Yasushi Ohizumi and Yuanqiang Guo

� Two new thymol derivatives were isolated from Eupatorium fortunei. � Their structures were elucidated on the basis of 1D and 2D NMR and mass spectroscopic data analyses. � The phytochemical investigation further revealed the chemical constituents of Eupatorium fortunei. � The inhibitory activities on LPS-induced NO production of isolated compounds were evaluated.

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Phytochemistry Letters 7 (2014) v–xvii xv

Three new antioxidant furofuran lignans from Callicarpa nudiflora

Yue-Hua Luo, Zhi-Qiang Zhou, Shuang-Cheng Ma and Hui-Zheng Fu

� Three new lignans were isolated from the leaves of Callicarpa nudiflora. � Compounds 1–3 were evaluated for their antioxidant activities. � Compounds 1–3 exhibited antioxidant activities with EC50 values of 19.8, 18.5, and 8.3 �M, respectively.

Polyacetylenes from Bidens bipinnata L. and their biological activities

Xiao-Yu Wang, Guan-Ru Chen, Chun-Xiao Pan, Zi-Yun Deng, Jin-Fang Ge, Ning Li and Fei-Hu Chen

� New polyacetylenes from Bidens bipinnata L. were isolated and identifi ed. � Six polyacetylenes were isolated in total and two are new. � All the compounds exhibited anti-infl ammatory activity in vitro.

Guaianolides and phenolic constituents from Crepis dioscoridis L., growing wild in Greece

Michail Tsoukalas, Chrysoula Gousiadou and Helen Skaltsa

� Phytochemical study of Crepis dioscoridis L. � One new, namely 11�,13-dihydro-crepiside C, and nine known guaianolides of costus type were isolated and characterized. � The main sesquiterpene lactones were by order of their abundance integrifolin 3�-D-glucopyranoside, crepiside C and 8-epi-grosheimin.

Two new components from the rhizome of Anemarrhena asphodeloides Bge. and their antiplatelet aggregative activity

Yu Sun, Linguang Li, Chunting Liu, Qingbo Liu, Lingzhi Li, Ying Peng and Shaojiang Song

� Two new components have been isolated from Anemarrhena asphodeloides Bge. � The isolated components were evaluated for their antiplatelet aggregative activity. � The structures were elucidated by spectroscopic data and CD analysis.

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xvi Phytochemistry Letters 7 (2014) v–xvii

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Ex situ volatile survey of ground almond and pistachio hulls for emission of spiro-ketals: Analysis of hull fatty acid composition, water content, and water activity

Noreen E. Mahoney, Wai S. Gee, Bradley S. Higbee and John J. Beck

� Analysis of ground almond hull and shell emissions detected the spiroketals conoph-thorin and chalcogran. � Conophthorin is an important semiochemical of the insect pest navel orangeworm. � The spiroketals appear to be produced by damaged hull tissue.

Isolation and structure characterization of two new diterpenoids from Clerodendrum bungei

Lin Sun, Zhenzhong Wang, Gang Ding, Yuan Bi, Zhaoqing Mengand Wei Xiao

Two tetrahydroisoquinoline alkaloids from the fruit of Averrhoa carambola

Dan Yang, Haihui Xie, Bao Yang and Xiaoyi Wei

� Six compounds including two new alkaloids were isolated from star fruit in China. � It is the fi rst report of all the compounds except for ferulic acid from this species. � Two alkaloids and 8,9,10-trihydroxythymol showed weak antioxidant activity.

2�-(Z)-Cinnamoylsalicortin: A novel salicinoid isolated from Populus tremula

Ken Keefover-Ring, Marcus Carlsson and Benedicte Riber Albrectsen

� 2�-(Z)-Cinnamoylsalicortin was isolated and identified in P. tremula. � 2�-(Z)-Cinnamoylsalicortin and 2�-(E)-cinnamoylsalicortin co-occur in salicaceous species. � The structure and relatively high concentration of the regioisomers in P. tremula foliage may shape defense properties of this salicaceous species.

Phytochemistry Letters 7 (2014) v–xvii xvii

Announcements of the Phytochemical Society of Europe pp I–II

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