Journal of Scientific & Industrial Research

Vol. 59, November 2000, pp 893-903

Novel Constituents of Gardenia Species - A Review Virinder S Parmar*, Sunil K Sharma & Poonam

Department of Chemistry, University of Delhi, Delhi-It 0 007, India

The secondary metabolites from Gardenia species for the period 1907 to December 1999 have been reviewed. One hundred fifteen chemical constituents belonging to different classes of bioactive compounds e.g. tlavonoids , iridoids , terpenoids, steroids, acids, esters, alcohols, etc. have been reported from different Gardenia species. A number of these compounds have been found to possess potent biological activities, i. e. anti-invasive, antiviral , anti-inflammatory, anti­fungal, estrogenic, neurosurgical , etc.

Introduction

The genus Gardenia belongs to the family Rubiaceae and has more than 80 species spread among tropical and subtropical regions of the World . The plants of Gardenia genus have high medicinal value and hence are of commercial importance. Some exotic species are grown in gardens. Several Gardenia species yield timber which is used as substitute of boxwood. The destructive distillation of wood 1 of Gardenia Lucida yields charcoal, 30.1, pyroligeneous acid, 39.5; tar, 10.8; pitch and losses, 1.3; acid, 5.4; ester, 4.6; acetone, 3.8, and methanol, 1.2 per cent. Gardenia species play important role as a fragrance modifier. The recent perfumes2 containing Gardenia and its components are Vent Vert , Charlie, Michelle, Adolfo, etc. The fresh flowers of G. jasminoides on maceration with petroleum and distillation of the extract yield about 0 .07 per cent of a clear yellowi sh essential oil. The oil contains benzyl acetate, styrene acetate, linalool, linalyl acetate, terpeneol and methyl anthranilate. The fragrance is mainly due to styrene acetate 1

• The leaf buds and the young shoots of G. gummifera and G. Lucida yield a res inous exudation , commercially known as Dikamali gum or Cumbi gum containing res in , 89 .9 ; steam­volatile oil, 0 .1; and plant impurites, I 0.0 per cent. The acid, iodine and saponin values for the resin were 87 . I , 80.8 and 172.3, respective ly. It has a pigment, gardenin (5-hydroxy-3, 6, 8, 3', 4', 5'-hexamethoxy fl avone, 1, 1.4 per cent), which can be obtained by digesting the res in with hot alcohol 1

• It may be mentioned that despite hi gh medicinal and

commercial importance, no review on Gardenia species has so far been published .

Biological Activity

Gardenia species are used medicinally in various ways . Gardeniae Fructus, the fruit of G. jasminoides is an important crude drug and has been used in China and Japan and reported to have laxative, anti-inflammatory, antipyretic, diuretic , antihepatitis, cholagolic and hemostatic effects3.4 . The fruit extract decreased cholesterol level in serum of rats5. The flowers of G. jasminoides are used in Chinese folk medicine for birth control6• The ethyl acetate extract of flowers showed significant effects on terminating early pregnancy in rats6• In Malaya, its leaves are frequently used in poultices 1• Root of the plant is used in dyspepsia and nervous disorders1•

G. erubescens is a local medicinal plant found in Nigeria, its methanolic crude extract and saponins separated from it showed sedative, analges ic, hypotensive and diuretic effects in vivo on rats, mice and cats7

. Water decoctions of the aerial parts are used locally in Northern Nigeria as a multipurpose remedy, particularly for the treatment of gonorrhoea, abdominal disorders, loss of apetite and insomnia8·9.

The resinous exudates of G. gummifera and G. Lucida exhibit anti spasmodic, expectorant, carmi­native, diaphoretic and anthelmintic effects. It is given to children in nervous disorders and di arrhoea due to dentiti on 1• It is a lso used to clean foul ulcers. A decoction of the resi n is used in fever. The resin is extensively employed in veterinary medicine to keep

894 J SCI JND RES VOL 59 NOVEMBER 2000

away flies from sores and for destroying maggots in wounds' . Ether extract of the leaves of G. Lucida showed antibiotic activity against Staphylococcus aureus and Escherichia coli 10 , and leaves of the plant are used in cutaneous disease ''·

A preparation from roots of G. turgida is used by the Santals (an Indian tribe) as a remedy for indigestion in children. Crushed roots form a lather with water, which is applied in headache' . Fruits of the species are used in affections of mammary glands . Saponin isolated from G. turgida decreased the formation of, and inhibited the spasmogenic effects of the slow reacting substance anaphylaxis in sensitised guinea pigs. The use of saponin as antiasthmatic drug has also been reported 12 •

Flavonoids

So far thirty three flavonoids have been isolated from Gardenia species, most are highly oxygenated flavones and only two are flavanones (Tab le I ). Of various Gardenia species, mainly two, viz., G. gummifera and G. Lucida are quite rich in flavonoid s and account for seventeen flavones (> 50 per cent of total). Interestingly all of these lack a subs tituent at the C-3 position .

Gunatilaka et al. 13 isolated flavonoids 6 , 8, 10, 21, 32 from two Sri Lankan species G. fosbergii and G. cramerii in which the C-3 position is oxygenated . Thus the compounds isolated from the above spec ies are of chemotaxonomic significance and presence of oxidising enzymes was also indicated. Gardenin was the first flavonoid isolated way back in 1877 from thi s genus 14 • The structure assigned to it earlier as 5-hydroxy-3 ,6,8,3',4',5'-hexamethoxyflavone (1) 15· 16 was revised by Rao and Venkataraman 17 on the basis of its NMR and mass spectra as 5-hydroxy-6,7,8,3',4',5'­hexamethoxyflavone (13) which is now known as gardenin A. Miller et a/. 18 examined five Fijian Gardenia species, viz., G. gordonii, G. grievi, G. hillii, G. storckii and G. taitensis . The bud exudates of these species had a less complex flavonoid profile as compared to that of Asian Gardmia gum exudates which are reported to contain several polyoxygenated flavonoids.

Due to its high commercia l and medicinal importance and high flavonoid content, the phytochemical examination of Dikamali gum was undertaken to isolate highly oxygenated flavo nes, viz., gardenin A, gardenin B, gardenin E and

xanthomicrol (2), and the last was reported for the first time (Parmar, V.S., personal comunnication).

As a part of the ongoing research programme, a few of the highly oxygenated flavones were screened for various biological activities and gardenin B (14) exhibited antiinvas ive activity, without any histological signs of cytotoxicity in MCF-7 and HBL-1 00 cells and also showed antiviral activity against Encepehalomyocarditis virus (EMV) in vitro 19.

Gardenin A and B were compared for their ability to modulate cytochrome P-450 dependent mixed function oxidases (MFO) and gardenin B was more e ffective in stimulation of MFO activity (Parmar et al., unpublished resu lts). A few of these flavones were also active against the Natura l killer cells (NK cell s) (Parmar, V.S., personal comunnication).

Table 1- Flavonoids from Gardenia species

Compound

Accrosin (3)

Apigenin (4)

7,4'-Dihydroxytlavone (5)

5,3'-Dihydroxy-3,6, 7 ,4',5 '­

pentamethoxytlavone (6)

5 ,5'-Dihydrox y-3,6, 7,3 ',4'­

pentamethoxytlavone (7)

5,4'-Di hydrox y-3 ,6, 7,8-

letramethoxytlavone (8)

5 ,5'-Di hydrox y-6, 7 ,2' ,3 '­

lelramelhoxytlavone (9)

5 ,4'-Di hydroxy-3 ,6, 7-

trimethoxyflavone ( I 0)

3',4'-Dihydroxywogonin ( II )

3',4'-Dimethoxywogonin ( 12)

Gardenin A ( 13)

Garclenin 8 (14)

Garden inC ( 15)

Garden in D ( 16)

Garden in E ( 17)

Gardenin-A-5-0-• -D­

glucopyranoside ( 18)

5- Hydroxy-7 ,4'-dimethoxyllavanone

( 19)

5-Hydroxy-7,4'-climethoxyllavone

(20)

Plant//Component

Dikamali gum20

Dikama/i gum20

G. sootepen.1·ii1

G . .fosbergi/3

G. cramerii22

G. fosbergi/'· 22

G. cramerii22

G. fosbe rgii 22

G . .fosbergi/-1

Dikamali gum23

Dikamali gum20·

23

Dikamali gum 14'

20·

24

G. lucida25

G. turgida26

Dikamali gum20·

24

G. /ucidc/5

G. turgida26

G. lucida25

G. lucida25

Dikamali gum20

G. lucidc/' G. lllrgida2r,

G. j7orida27

G. erubesceni 'i

G. em bescen/ 8

PARMAR eta/.: CONSTITUENTS OF GARDENIA SPECIES 895

5-Hydrox y-3 ,6, 7,3 ',4' ,5'­

hexamethoxy flavone (21)

5-Hydroxy-6, 7,3 ',4' ,5'­

pentamethoxyflavone (22)

5-Hydroxy-7,3',4'­

trimethoxyflavanone (23)

4'-Hydroxywogonin (24)

3-0-Methylkaempferol (25)

Nevadensin (26)

5 ,6, 7 ,4'-Tetrahydroxy-3 ,3 ',5'­

trimethoxyflavone (27)

5,7 ,3',4'-Tetrahydroxy-6,8-

dimethoxyflavone (28)

5, 7 ,3',5'-Tetrahydrox y-8,4'­

dimethoxyflavone (29)

5,7 ,4'-Trihydroxy-3,6-

dimethoxytlavone (30)

5,7 ,4'-Trihydroxy-6,8-

dimethoxyflavone (3 1)

5,3',5'-Trihydroxy-3 ,6,7,4'­

tetramethoxyflavone (32)

3',4',5'-Trihydroxywogonin (33)

3',4',5'-Trimethoxywogonin (34)

Iridoids

G. fosbergii'-1

G. cramerii12

G. fosbergii/.1 . 22

G. erubescen.1.2x

Dikamali gum211

G. gordonii18

G. grievi18

G. hillii'8

G. storckii'x

Dikamali gum211' 24

G. fosbergii 13

Dikamali gum2~

Dikamali gum311

G. gordonii'8

G. grievi'x

G. hiflii1x

G. storckii'8

G. taitensis'8

Dikamali gum211

G. cramerii12

G. fosb ergii /.1. 22

Dikamali gum23

Dikamali gum211•

24

The iridoid glucosides are a group of naturall y occurring compounds characterised by the cyclopentano pyran ring system. In most of the compounds, a ~-glucosyloxy group is present on C-1 and a double bond between C-3 and C-4 givi ng rise to the characteristic enol ether. Several names were applied to this group of compounds and fin ally iridoid glucosides was selected as suggested by Briggs et aP 1

•

Iridoids are not commonly found in Gardellio species, however, G. jasminoides is an exception as most of the iridoids have been isolated from it (Table-2) . The only other Gardenia species from which iridoids have been isolated are G. augusta and G. lutea . Probably due to the presence of irido ids'' the fruits of G. jasminoides are used as an anti­inflammatory and tranqiuilizer and hold an important position in Chinese medicine. Cerbinal (36), a pseudoazulene iridoid is a potent antifungal compound against Puccina fun gi·13

. Iridoid g lycoside, gcmpm (42) showed choleretic ac tivity . Harada et

0

1 R,=Re=H; Rs=OH; R2=R3=R4=Rs=R7=Rg=OCH3

2 R,=R2=R4=Rs=H; R3=Rs=OH; R7=Re=Rg=OCH3

3 R1=R4=Rs=H; R2=Rs=Re=OH; R3=R7=R9=0CH3

4 R1=R2=R4=Rs=R7= Rg=H; R3=R6=R8=0H

5 R1=R2=R4=Rs=Rs=R7=Rg=H; R3=Re=OH

6 R, =Rg=H; R2=Rs=OH; R3=R4=Rs=R7=R8=0CH3

7 R,=Rg=H; R4=Rs=OH; R2=R3=Rs=R7=Re=OCH3

8 R1=R2=R4=H ; R3=Rs=OH; Rs=R7=Re=R9=0CH3

9 R3=Rs=Rg=H; R4=Rs=OH; R,=R2=~1=Re=OCH3 10 R1=R2=R4=Rg=H; R3=Rs=OH; R5=R7=Re=OCH3

11 R1=R4=Rs=R1=H; R2=R3=Rs=Re=OH; R9=0CH3 12 R1=R4=Rs=R7=H; Rs=Re=OH; R2=R3=R9=0CH3

13 R,=Rs=H ; Rs=OH; R2=R3=R4=R7=Re=R9=0CH3

14 R1=R2=R4=Rs=H; Rs=OH; R3=R7=R8=Rg=OCH3

15 R1 =Rs=H; R2=Rs=OH; R3=R4=R7=Re=R9=0CH3

16 R1=R4=Rs=H; R2=Rs=OH; R3=R7=R8=R9=0CH3

17 R,=Rs=H; R2=R4=Rs=OH; R3=R7=Re=Rg=OCH3

18 R,=Rs=H ; R2=R3=R4=Rs=R7=Rg=OCH3; R6=0-glucopyranosyl

20 R1=R2=R4=Rs=R7=Rg=H; R6=0H; R3=Re=OCH3 21 R,=Rg=H; Rs=OH; R2=R3=R4=Rs=R7=R8=0CH3 22 R1=Rs=Rg=H; Rs=OH; R2=R3=R4=R7=R8=0CH3 24 R1=R2=R4=Rs=R7=H; R3=Rs=R8=0H; R9=0CH3 25 R1=R2=R4=R7=R9=H; R3=R6=R8=0H; Rs=OCH3 26 R1=R2=R4=R s=H; Rs=Re=OH; R3=R7=R9=0CH3 27 R1=R9=H; R3=R6=R7=R8=0H; R2=R4=R5=0CH3 28 R,=R4=Rs=H; R2=R3=R6=R8=0H; R7=R9=0CH3 29 R1=Rs=R7=H; R2=R4=Rs=R8=0H; R3=R9=0CH3 30 R1=R2=R4=Rg=H; R3=R6=R8=0H; R5=R7=0CH3 31 R1=R2=R4=R5=H; R3=R6=R8=0H; R7=R9=0CH3 32 R,=Rg=H ; R2=R4=R6=0H; R3=R5=R7=R8=0CH3 33 R1=Rs=R1=H; R2=R3=R4=Rs=R8=0H; R9=0CH3 34 R1=Rs=R1=H ; Rs=Re=OH; R2=R3=R4=R9=0CH3

0

Rs

R4 0

19 R1=R3=Rs=H; R4=0H; R2=R6=0CH3

23 R1=R2=Rs=OCH3; R3=R5=H; R4=0H

a/.4, reported that genipin (42) and geniposide (44)

induced bile secretion , inhibited both spontaneous contraction and pliocarpine induced contraction of rat stomach. Geniposide has also been used as a

896 J SCII ND RES VOL 59 NOVEMB ER 2000

35 R1=J3-D-Gic; R2=CH3; R3=H; R4=Ac

37 R1=R2=R3=R4=H 38 R1=J3-D-Gic; (6, 1J3) Glc(=p-coumaroyl

gentiobiose); R2=CH3; R3=R4=H

39 R1=J3-D-Gic; R2=R4=H; R3=a-OH

42 R1=R3=R4=H; R2=CH3 43 R1=p-D-Gic(6, 1J3) Glc(=gentiobiose);

R2=CH3; R3=R4=H 44 R1=J3-D-Gic; Rr CH3; R3=R4=H

45 R1=J3-D-Gic; Rr R3=R4=H

46 R1=J3-D-Gic; R2=CH3; R3=a-OH; R4=H 50 R1=J3-D-Gic; R2=CH3; R3=!3-0 H; R4=H

40 R1=0H; R2=CH20H 47 R1=CH20H; RrOH

COOH HD C CH3

CH20H I HO~O CH3

HO OH 49

36

,,{Q'' R4 O-J3-D-Gic

41 R1=CH3; R2=H; R3=J3-0H; R4==CH2 51 R1=H; R2=J3-0H; R3=H; R•=a.-CH 3; J3-0H

purgat ive\ and its pentaacetate is biologically acti ve as an an titumor agent against C-6 glioma cell s in cu lture34 .

48

Compound

Table 2- lridoids from Gardeni a species

Plant/Component

Acetyl geniposide (35)

Cerbinal (36)

Cho leretic geniposidic acid

aglycon (37)

6"-p-Coumaroyl geni pin

genti obioside (38)

Deacetyl aspeluros idi c acid (39)

Gardenoside (40)

Gardoside ( 41 )

Genipin (42)

Genipin gentiobioside (43)

Geniposide (44)

Geniposid ic acid (45)

Methyl deacetyl

aspelurosidate (46)

Monotropein methyl ester (47)

Penta acetyl geniposide (48)

Picrocrocinic acid (49)

Scancloside methyl ester (50)

G. jasminoides15· .M

G. jasminoides33

G. j asm inoide/7

G. jasminoides fruir1x

G. j asminoides35

G. j asminoides35. 3Y. 4o. 41 . 42

G. j asminoides fruit43

G. j asminoides35· 44

G. jasminoides35· 39.4

2

G. jasminoides fruit43·

45

G. jasminoides35· 39' 4~

G. augusta47

G. jasmilwide/1"1~"141' 4243.411. ,.).5/ll/

G. lu/ea52

G. sooletJensis5·1

G. jasminoides35· 41' 42

G. j asminoides35· 39

G. jasminoides fruit43

G. soolepensis53

G. j asminoides fmi t43

G. jasminoides34

G. jasminoides36

G. jasminoides35· 44

G. jasminoides fru i t~ -1

G . . 1·oo1epensis53

Shanzhi side (5 1) G. jasminoide/5· 39· 54

Tarennoside (52) G. jasminoide/1 ~~~~~~----------~~~ ~~~-------

Terpenoids and Steroids

A number of steroids and terpenoids have been iso lated from Gardenia species (Table 3). Oleanolic ac id 3-0-glucoside (75) showed high molluscicidal

PARMAR et al.: CONSTITUENTS OF GARDENIA SPECIES 897

HO

R,

0

57 R,=CH2-CH=CH-CH=C.(CH3)2; R2=CH3

58 R,=CH2-CH2-CH7CH=C.(CH3)2; R2=CH3

59 R,=CH2-CH2-(CO)-CH=C.(CH3)2; R2=CH3

60 R,=CH2-CHT(CO)-CH2-CH(CH3)2; R2=CH3

61 R,=CH2-CHTCHT(CO)-CH(CH3)2; R2=CH3

72 R,=CH2-CHT(CO)-CH=C.(CH3)2; R2=H

0

actiVIty against Bulinus truncatus and Biomphalaria pfeifferi52 • ~-Sitosteroi (78) and ursolic acid (81) inhibited arachidonic acid-induced platelet aggregation in decreasing order of potency55. ~­Sitosterol and ursolic acid inhibited platelet activating factor induced aggregation while only the former inhibited ADP-induced platelet aggregat ion. Ursolic acid (@25-100 mg kg-1) exhibited a concentration dependant anti-inflammatory effect55 . ~-Sitosterol has been reported to possess estrogenic activity and to stimulate uterine tissue; it also serves as plant steroid precursor for cortisone production 56-58 . Most terpenes isolated from the genus Gardenia are triterpenoids.

Recently Zhao et al.'9, reported the presence of two novel monoterpenoids, gardendiol (65) and gardenone (67) in the fruits of G. jasminoides. Though many iridoid compounds have been isolated so far from G. jasminoides, it is interesting that gardendiol (65) is different from the above iridoids as it has a 8-lactone structure .

Table3- Steroids and terpenoids from Gardenia species

Compound Plant/Component

o.-Amyrin (53) G. turgida2~

~-Amyrin (54) G. Lucida~0

G. Lutea52

3-epi-~-Amyrin (55)

~-Amyrin acetate (56)

Cycloartadienone (57)

Cycloartenone (58)

9, 19-Cyclolanost-24-ene-3,23-dione

(59)

9, 19-Cyclolanostane-3 ,23-dione (60)

9, 19-Cyclolanostane-3,24-dione (61)

3o., 19o.-Dihydroxy-olean-12-ene-28-

oic acid (62)

Erubescenone (63)

Erythrodiol (64)

Gardendiol (65)

Gardenic acid

Gardenolic acid (66)

Gardenone (67)

Gypsogenic acid (68)

Hederagenin (69)

(3 ~-23-Dihydroxyolean-12-ene-28-oic

acid)

Hydroxycitronell al

1 9-~-Hydroxyerythrodiol (70)

Linalool (7 1)

4-Nor-9 , 19-cyclolanost-24-ene-3,23-

dione (72)

Oleanolic acid (73)

G. imperialil''

G. imperialis01

G. gordonil-62

G. ltiflc-62

G. storckii02

G. gordonic-62

G. grievet2

G. hilll-62

G. storckit-62

G. gordonil2

G. hilll'2

G. storckic.fJ2

G. taitensil'2

G. gordonic.fJ2

G. g rievel2

G. hillt2

G. storckit2

G. latifolia63

G. erubescenl>4

G. gwmnifera~5

G. jasminoidesw

G. jasminoidei' G. jasminoidel'· tSO

G. jasminoides5Y

G. turgida67

G. latifolia68

G. turgida67

G. jasminoide/'Y

G. gummiferc/' G. tahitensi/0

G. gardonic.fJ2

G. hilliM G. storckil.fJ2

G. erubescens''4

G. latifolicP

G. sootepensis21

G. turgida26·

67

898

Oleanolic acid acetate (74)

Oleanolic acid 3-0-glucoside (75)

Oleanonic aldehyde (76)

Spinosic acid (77)

~- s itosterol (78)

~-Sitosterol-3 -0-~-D-glucopyranosyl

( 1-4)-0-a L-rhamno-pyranoside (79)

Stigmasterol (80)

Styrolaceta~e

Ursolic acid (8 1)

R

R

54 R=OH; R1=H

55 R=H; R1=0H

56 R=OCOCH3; R,=H

H 62 R=R,=~-oH ; R2=H

OH n R=R1= ~-H ; R2=H

70 R=OH

J SCI IND RES VOL 59 NOVEMBER 2000

G. erubescen/'4

G. jasminoide/1

G. lutea52

G. gwnmifercl5

G. fatifolia6x

G. gummifera65

G. jasminoides72

G. latifolianx

G. Lucida60

G. lutea51

G. sootepensii'· 53

G. turgida26· n?

G. lucida73

G. erubescens64

G. jasminoides 71

G. lutea51

G. jasminoideiy

G. erubescens64

73

74

75

Miscellaneous Compounds

Besides the above mentioned group of compounds, several acids, alkanes, esters and glycosides have been isolated from Gardenia species . Crocetin (85) and crocin (87) are the yellow pigments isolated from G. jasminoides. The demand for crocin as a natural material for yellow colouration in food stuffs is increasing. Crocin is an important colouring agent in a wide variety of foods in Japan. The acids 83, 84, 88 and 90 are found to be lipoxygenase inhibitors and compound 88 has been found to be the most potent inhibitor38 .

D-Mannitol , isolated from a number of Gardenia species (Table 4), is quite a valuable compound as it is used in medicaments for the prevention of renal failure and in neuro surgical activity. D-Mannitol was shown to have dialating effects on vascular smooth muscle in the cerebral micro circulation 74

.

HO OHC CH3 68

~" 71

R,=R2=H R, =-COCHJ, R2=H R 1=H, R2=0-glucos1de 76

PARMAR eta/.: CONSTITUENTS OF GARDENIA SPECIES 899

Table 4- Miscellaneous Compounds from Gardenia Species

Compounds Plant/Component

Benzyl acetate Bornyi-6-0-~-D-xylopyranosyi-~-D­

glucopyranoside (82)

3-0-Caffeoyl-4-0-sinapoyi-quinic acid (83)

Chlorogenic acid (84)

Crocef6n (85)

Crocetin mono (~-gentiobiosyl) (86) Crocin (87)

3,4-Di-0-caffeoylquinic acid (88)

3,4-Di -caffeoyl-5 -(3-hydroxy-3-methyl)glutaroyl quinic acid (89)

3,5-Di-0-caffeoyl-4-0-(3-hydroxy-3-methyl-) glutaroylquinic acid (90)

6,7-Dimethylacsculetin (9 1)

Eugenol (92)

Heneicosane

Heptacosanol

Hexaacetyl D-mannitol Hexacosyl-p-coumarate (93)

cis-3-Hexenyl benzoate

7-Keto-octadec-cis-1 1- enoic acid (94)

G. jasminoidesm

G. jasminoide/5

G. jasminoides fruit 38

· 70

G. jasminoides

fruit38

G. grandiflora77

G. jasminoide.r11 18

G. jasminoide.1.7x

G. jasminoides48·

50·

51. 77

G. jasminoides

fruit 38

G. jasminoides fruit 7

Y

G. jasminoides fruir'x

G. jasminoides fruit 4

-'· 45

G. jasminoidesm

G. sootepen.si/1

G. sootepensii 1

G. turgida26

Dika/imali gum80

G. tahitensi/'' G. lucidast

(R)-Li nalyl-6-0-a-L-arabinopyranosyl- G. jasminoide/5

~-D-glucopyranoside (95) Linoleic acid

Linolenic acid

D-Mannitol

D-Mannitol hexabenzoate Nonacosane

Oleic acid

Palmitic acid

Pentacosanol

Phencthyl benzoate (96)

G. lutea52

G. lucidaw

G. turgidax2

G. jlorida'~3

G. gtmuniferafi5

G. latifolic/8

G. lucida'~4

G. jasminoide/' · 72

G. pomodorax5

G. turgida2r,. sr,

G. sootepensis53

G. vogelil5

G. turgidaxr.

G. jasminoide/1

G. sootepensi/1

G. lucidaw

G. turgida81

G. Iucida w

G. lutea52

G. soo1epensis21

G. turgida'~2

G. sootepensi/ 1

G. tahitensi/"

Polysaccharides (GPS4, GPS5)

Quinidc (97) and G. jasminoidel7

G. sootepensis xx

G. sootepensi.r13

G. tahitensi/0

G. lucida00

Quinide's dimer

Squalenol Stearic acid

G. turgidax2

Triacontane G. sootepensii 1

98 G. sootepensii 1

Mixture of long chain (C?YC?,;) esters Dikamali gum8Y

Mixture of c21 -c33 long chain alkenes G. tahitensi/0

and alcohols

Conclusion

The survey of phytochemical investigations on Gardenia species has revealed a wide variety of chemical constituents produced by them, important classes among them are flavonoids, iridoids, terpenoids and steroids. Out of a total of 115 compounds isolated from Gardenia sp., 33 are flavonoids, 18 iridoids and 31 steroids and terpenoids. The present review pinpoints the active components besides finding out new structural leads

78 R= H 79 R = P-D-glucopyranosyl (t-- 4)

0-n-L-rhamnopyranosyl

R20,,,,,, .. ~COOH r .,,~OH

R30

84 R1=R2=H; R3= caffeoyl

88 R1=H; R2=R3= caffeoyl

OH

89 R1=R2= glutaroyl; R2=R3= caffeoyl 90 R1=R3"' caffeoyl ; R2= glutaroyl

900 J SCI IND RES VOL 59 NOVEMBER 2000

OH ¢roc,, H3co:x:::r:t

H3co ~ o o

80

HO _.- 9 91

CH:!CH=CH2

92

Ht?o~o ~ OH~

HO OH 0 HC=CH-{CO}-OCH,-{CH2)24-CH3

CHJ-(CH2)4-CH;z-CH=CH-CH2-CH2-CH;z-(CO)-CH2·(CH2)4·COOH

94 82

93

Ht?o~o OH ~-0 HO~~O~ _

HO OH ..----· \__/

~ ""=:, COOR1

85 R,=R2=H 86 R1-=H; R2=gantiobiose 87 R1=R2= gentiobiose 97

fo r future drugs. It is be lieved that thi s updated review would he lp fellow researchers in locating the info rmation in Gardenia sp .

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