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

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, anti fungal, estrogenic, neurosurgical, etc.

commercial importance, no review on Gardenia Introduction species has so far been published. The genus Gardenia belongs to the family Rubiaceae and has more than 80 species spread Biological Activity among tropical and subtropical regions of the World. Gardenia species are used medicinally in The plants of Gardenia genus have high medicinal various ways. Gardeniae Fructus, the fruit of G. value and hence are of commercial importance. Some jasminoides is an important crude drug and has been exotic species are grown in gardens. Several used in China and Japan and reported to have Gardenia species yield timber which is used as laxative, anti-inflammatory, antipyretic, diuretic, substitute of boxwood. The destructive distillation of antihepatitis, cholagolic and hemostatic effects3.4 . The wood 1 of Gardenia Lucida yields charcoal, 30.1, fruit extract decreased cholesterol level in serum of 5 pyroligeneous acid, 39.5; tar, 10.8; pitch and losses, rats . The flowers of G. jasminoides are used in 1.3; acid, 5.4; ester, 4.6; acetone, 3.8, and methanol, Chinese folk medicine for birth control6• The eth yl 1.2 per cent. Gardenia species play important role as acetate extract of flowers showed significant effects 2 a fragrance modifier. The recent perfumes containing on terminating early pregnancy in rats6• In Malaya, its 1 Gardenia and its components are Vent Vert, Charlie, leaves are frequently used in poultices • Root of the 1 Michelle, Adolfo, etc. The fresh flowers of G. plant is used in dyspepsia and nervous disorders • jasminoides on maceration with petroleum and G. erubescens is a local medicinal plant found di stillation of the extract yield about 0.07 per cent of in Nigeria, its methanolic crude extract and saponins a cl ear yellowish essential oil. The oil contains benzyl separated from it showed sedative, analgesic, acetate, styrene acetate, linalool, linalyl acetate, hypotensive and diuretic effects in vivo on rats, mi ce terpeneol and methyl anthranilate. The fragrance is 7 1 and cats . Water decoctions of the aerial parts are mainly due to styrene acetate • The leaf buds and the used locally in Northern Nigeria as a multipurpose young shoots of G. gummifera and G. Lucida yield a remedy, particularly for the treatment of gonorrhoea, resinous exudation, commercially known as Dikamali abdominal disorders, loss of apetite and insomnia8·9. gum or Cumbi gum containing resin , 89.9; steam volatile oil, 0.1; and plant impurites, I 0.0 per cent. The resinous exudates of G. gummifera and G. The acid, iodine and saponin values for the resin were Lucida exhibit antispasmodi c, expectorant, carmi 87 .I , 80.8 and 172.3, respectively. It has a pi gment, native, diaphoreti c and anthelmintic effects. It is gardenin (5-hydroxy-3, 6, 8, 3', 4', 5'-hexameth oxy given to children in nervous disorders and di arrhoea 1 fl avone, 1, 1.4 per cent), which can be obtained by due to dentition • It is also used to clean foul ul cers. A 1 digesti ng the resin with hot alcohol • It may be decoction of the resin is used in fever. The resin is mentioned that despite hi gh medi cin al an d 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 xanthomicrol (2), and the last was reported for the wounds'. Ether extract of the leaves of G. Lu cida first time (Parmar, V.S., personal comunnication). showed antibiotic activity against Staphylococcus As a part of the ongoing research programme, a 10 aureus and Escherichia coli , and leaves of the plant few of the highly oxygenated flavones were screened are used in cutaneous disease''· for various biological activities and gardenin B (14) A preparation from roots of G. turgida is used exhibited antiinvasive activity, without any by the Santals (an Indian tribe) as a remedy for histological signs of cytotoxicity in MCF-7 and HBL- indigestion in children. Crushed roots form a lather 100 cells and also showed antiviral activity against 19 with water, which is applied in headache' . Fruits of Encepehalomyocarditis virus (EMV) in vitro . the species are used in affections of mammary glands. Gardenin A and B were compared for their ability to Saponin isolated from G. turgida decreased the modulate cytochrome P-450 dependent mixed formation of, and inhibited the spasmogenic effects of function oxidases (MFO) and gardenin B was more the slow reacting substance anaphylaxis in sensitised effective in stimulation of MFO activity (Parmar et guinea pigs. The use of saponin as antiasthmatic drug al., unpublished resu lts). A few of these flavones 12 has also been reported • were also active against the Natural killer cells (NK cell s) (Parmar, V.S., personal comunnication). Flavonoids

So far thirty three flavonoids have been isolated Table 1- Flavonoids from Gard enia species from Gardenia species, most are highly oxygenated Compound Plant//Component flavones and only two are flavanones (Table I ). Of Accrosin (3) Dikamali gum20 various Gardenia species, mainly two, viz., G. Apigenin (4) Dikama/i gum20 and G. are quite rich in flavonoids 1 gummifera Lucida 7,4'-Dihydroxytlavone (5) G. sootepen.1·ii and account for seventeen flavones (> 50 per cent of 5,3'-Dihydroxy-3,6, 7 ,4',5 ' G . .fosbergi/3 total). Interestingly all of these lack a substituent at pentametho xytlavone (6) the C-3 position. 5 ,5'-Dihydrox y-3,6, 7,3 ',4' G. cramerii22 Gunatilaka et al. 13 isolated flavonoids 6, 8, 10, pentamethoxytlavone (7) 22 21, 32 from two Sri Lankan species G. fosbergii and 5,4'- Di hydrox y-3,6, 7,8- G. fosbergi/'· letramethoxytlavone (8) G. cramerii in which the C-3 position is oxygenated. 5 ,5'-Di hydrox y-6, 7 ,2' ,3 ' G. cramerii22 Thus the compounds isolated from the above species lelramelhoxytlavone (9) G. fosbergii 22 are of chemotaxonomic significance and presence of 1 5 ,4'-Di hydroxy-3 ,6, 7- G . .fosbergi/- oxidising enzymes was also indicated. Gardenin was trimethoxyflavone ( I 0) the first flavonoid isolated way back in 1877 from thi s 3',4'-Dihydroxywogonin ( II ) Dikamali gum23 14 20 23 genus • The structure assigned to it earlier as 5- 3',4'-Dimethoxywogonin ( 12) Dikamali gum · 15 16 14 20 24 hydroxy-3,6,8,3',4',5'-hexamethoxyflavone (1) · was Gardenin A ( 13) Dikamali gum ' · revised by Rao and Venkataraman 17 on the basis of its G. lucida25 NMR and mass spectra as 5-hydroxy-6,7,8,3',4',5' G. turgida26 20 24 hexamethoxyflavone (13) which is now known as Garclenin 8 (14) Dikamali gum · 5 gardenin A. Miller et a/. 18 examined five Fijian G. /ucidc/ 26 Gardenia species, viz., G. gordonii, G. grievi, G. G. turgida Gard en inC ( 15 ) 25 hillii, G. storckii and G. taitensis. The bud exudates G. lucida Garden in D ( 16) G. lucida25 of these species had a less complex flavonoid profile Garden in E ( 17) Dikamali gum20 as compared to that of Asian Gardmia gum exudates G. lucidc/' which are reported to contain several polyoxygenated G. lllrgida2r, flavonoids. Gardenin-A-5-0-• -D G. j7orida27 Due to its high commercial and medicinal glucopyranoside ( 18) importance and high flavonoid content, the 5- Hydroxy-7 ,4'-dimethoxyllavanone G. erubesceni 'i phytochemical examination of Dikamali gum was ( 19) 8 undertaken to isolate highly oxygenated flavones, 5-Hydroxy-7,4'-climethoxyllavone G. em bescen/ (20) viz., gardenin A, gardenin B, gardenin E and PARMAR eta/.: CONSTITUENTS OF GARDENIA SPECIES 895

5-Hydrox y-3 ,6, 7,3 ',4' ,5' G. fosbergii'-1 hexamethoxy flavone (21) 5-Hydroxy-6, 7,3 ',4' ,5' G. cramerii12 pentamethoxyflavone (22) G. fosbergii/.1. 22 5-Hydroxy-7,3',4' G. erubescen.1.2x trimethoxyflavanone (23) 0 4'-Hydroxywogonin (24) Dikamali gum211 3-0-Methylkaempferol (25) G. gordonii18 1 R,=Re=H; Rs=OH; R2=R3=R4=Rs=R7=Rg=OCH3 G. grievi18 2 R,=R2=R4=Rs=H; R3=Rs=OH; R7=Re=Rg=OCH3 G. hillii'8 3 R1=R4=Rs=H; R2=Rs=Re=OH; R3=R7=R9=0CH3 G. storckii'x 4 R1=R2=R4=Rs=R7= Rg=H; R3=R6=R8=0H 211 24 5 R1=R2=R4=Rs=Rs=R7=Rg=H; R3=Re=OH Nevadensin (26) Dikamali gum ' 6 R, =Rg=H; R2=Rs=OH; R3=R =Rs=R7=R =0CH 5 ,6, 7 ,4'-Tetrahydroxy-3 ,3 ',5' G. fosbergii 13 4 8 3 7 R,=Rg=H; R4=Rs=OH; R2=R3=Rs=R =Re=OCH trimethoxyflavone (27) 7 3 8 R1=R2=R4=H ; R3=Rs=OH; Rs=R7=Re=R =0CH 5,7 ,3',4'-Tetrahydroxy-6,8- Dikamali gum 2 ~ 9 3 9 R3=Rs=Rg=H; R4=Rs=OH; R,=R2=~1=Re=OCH 3 dimethoxyflavone (28) 311 10 R1=R2=R4=Rg=H; R3=Rs=OH; R5=R7=Re=OCH3 5,7 ,3',5'-Tetrahydrox y-8,4' Dikamali gum 11 R1=R4=Rs=R1=H; R2=R3=Rs=Re=OH; R9=0CH3 dimethoxyflavone (29) 12 R1=R4=Rs=R7=H; Rs=Re=OH; R2=R3=R9=0CH3 5,7 ,4'-Trihydroxy-3,6- G. gordonii'8 13 R,=Rs=H ; Rs=OH; R2=R3=R4=R 7=Re=R9=0CH3 dimethoxytlavone (30) G. grievi'x 14 R1=R2=R4=Rs=H ; Rs=OH; R3=R7=R8=Rg=OCH3 G. hiflii1x 15 R1 =Rs=H; R2=Rs=OH; R3=R4=R7=Re=R9=0CH3 G. storckii'8 16 R1=R4=Rs=H; R2=Rs=OH; R3=R7=R8=R9=0CH3 G. taitensis'8 17 R,=Rs=H; R2=R4=Rs=OH; R3=R 7=Re=Rg=OCH3 5,7 ,4'-Trihydroxy-6,8- Dikamali gum211 18 R,=Rs=H; R2=R3=R4=Rs=R7=Rg=OCH3; R6=0-glucopyranosyl dimethoxyflavone (3 1) 20 R1=R2=R4=Rs=R7=Rg=H; R6=0H; R3=Re=OCH3 5,3',5'-Trihydroxy-3,6,7,4' G. cramerii12 21 R,=Rg=H; Rs=OH; R2=R3=R4=Rs=R7=R8=0CH3 G. fosbergii /.1. 22 tetramethoxyflavone (32) 22 R1=Rs=Rg=H ; Rs=OH; R2=R3=R4=R7=R8=0CH3 23 3',4',5'-Trihydroxywogonin (33) Dikamali gum 24 R1=R2=R4=Rs=R7=H; R3=Rs=R8=0H; R9=0CH3 211 24 3',4',5'-Trimethoxywogonin (34) Dikamali gum • 25 R1=R2=R4=R7=R 9=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=R 8=0H; R2=R4=R5=0CH3 Iridoids 28 R,=R4=Rs=H; R2=R3=R6=R8=0H; R7=R9=0CH3 29 R1=Rs=R7=H; R2=R4=Rs=R 8=0H; R3=R9=0CH3 The iridoid glucosides are a group of naturally 30 R1=R2=R4=Rg=H ; R3=R6=R8=0H; R5=R7=0CH3 occurring compounds characterised by the 31 R1=R2=R4=R 5=H; R3=R6=R8=0H; R7=R9=0CH3 cyclopentano pyran ring system. In most of the 32 R,=Rg=H; R2=R4=R6=0H; R3=R5=R7=R8=0CH3 33 R1=Rs=R1=H; R2=R3=R4=Rs= R =0H; R =0CH compounds, a ~-glucosyloxy group is present on C-1 8 9 3 34 R1=Rs=R1=H ; Rs=Re=OH ; R2=R3=R 4=R9=0CH and a double bond between C-3 and C-4 giving rise to 3 the characteristic enol ether. Several names were applied to this group of compounds and fin ally iridoid 1 glucosides was selected as suggested by Briggs et aP •

Iridoids are not commonly found in Gardellio 0 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 Rs iridoids have been isolated are G. augusta and G. R4 0 lutea. Probably due to the presence of iridoid s'' th e 19 R1=R3=Rs=H ; R =0H; R =R =0CH fruits of G. jasminoides are used as an anti 4 2 6 3 23 R1=R2=Rs=OCH 3; R3=R 5=H ; R4=0H inflammatory and tranqiuilizer and hold an important 4 position in Chinese medicine. Cerbinal (36), a a/. , reported that genipin (42) and geniposide (44) pseudoazulene iridoid is a potent antifungal induced bile secretion, inhibited both spontaneous 13 compound against Puccina fungi· . Iridoid glycoside, contraction and pliocarpine induced contraction of rat gcmpm (42) showed choleretic activity. Harada et stomach. Geniposide has also been used as a 896 J SCIIND RES VOL 59 NOVEMBER 2000

35 R1=J3 -D-Gic; R2=CH3; R3=H ; R4=Ac 48 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=R 4=H Tabl e 2- lrid oids from Gardeni a species 44 R =J3-D-Gic; Rr CH3; R3=R4=H 1 Compo und Plant/Component 45 R1=J3-D-Gic; Rr R3=R4=H 15 Acetyl geniposide (35) G. jasminoides · .M 46 R1=J3-D-Gic; R2=CH3; R3=a-OH; R4=H Cerbinal (3 6) G. jasminoides33 50 R1=J3-D-Gic; R2=CH3; R3=!3-0 H; R4=H Cho leretic geniposidic acid G. j asminoide/7 aglycon (37) 6"-p-Coumaroyl geni pin G. jasminoides fruir1x genti obioside (38) Deacety l aspelu rosidi c ac id (39) G. j asminoides35 Gardenoside (40) G. j asminoides35. 3Y. 4o. 41 . 42 G. j asminoides fruit43 35 44 40 R1=0H; R2=CH20H Gardoside (41 ) G. j asminoides · 35 39 2 47 R1=CH20H; RrOH Genipin (42) G. jasminoides · .4 43 45 G. jasminoides fruit · Genipin genti obioside (43) G. jasminoides35· 39' 4~ HD C CH3 COOH 47 Geniposide (44) G. augusta CH20H I G. jasm ilw ide/1"1 ~"141' 4243.411. ,.).5/ll/ HO~ O CH3 G. lu/ea52 HO OH 51 49 G. sooletJensis · 35 41 42 Geniposidic aci d (45) G. jasminoides · ' Methyl deacetyl G. j asminoides35· 39 as pelurosid ate (46) G. jasminoides fruit 43 G. soolepensis53 Monotro pein methyl ester (47) G. j asminoides fmi t43 Pent a acetyl geniposide (48) G. jasminoides34 36 Picrocrocinic acid (49) G. jasminoides36 Scanclos ide meth yl ester (50) G. jasminoides35· 44 G. jasminoides fru i t ~ -1 ,,{Q'' G. .1·oo 1epensis53 Shanzhi side (5 1) G. jasminoide/5· 39· 54 R4 O- J3 -D-Gic Tarennoside (52) G. jasminoide/1 ~~~~~~------~~~ ~~~------41 R1=CH3; R2=H ; R3= J3-0H; R4==CH2 51 R1=H ; R2=J3- 0H; R3= H; R•=a.-CH 3; J3-0H Terpenoids and Steroids purgative\ and its pentaacetate is biologicall y acti ve A number of steroids and terpenoids have been as an antitumor agent against C-6 glioma cell s in isolated from Gardenia species (Table 3). Oleanolic 34 cu lture . acid 3-0-glucoside (75) showed high molluscicidal PARMAR et al.: CONSTITUENTS OF GARDENIA SPECIES 897

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.

HO Table3- Steroids and terpenoids from Gardenia species Compound Plant/Component o.-Amyrin (53) G. turgida 2~ ~-Amyrin (54) G. Lucida~ 0 R, G. Lutea52 3-epi-~-Amyrin (55) G. imperialil'' 01 ~-Amyrin acetate (56) G. imperialis Cycloartadienone (57) G. gordonil-62 G. ltiflc-62 G. storckii02 0 Cycloartenone (58) G. gordonic-6 2 G. grievet2 G. hilll-62 57 R,=CH2-CH=CH-CH=C.(CH3)2; R2=CH3 G. storckit-62 58 R,=CH2-CH2-CH7CH=C.(CH3)2; R2=CH3 2 59 R,=CH2-CH2-(CO)-CH=C.(CH3)2; R2=CH3 9, 19-Cyclolanost-24-ene-3,23-dione G. gordonil 60 R,=CH2-CHT(CO)-CH2-CH(CH3)2; R2=CH3 (59) 2 61 R,=CH2-CHTCHT(CO)-CH(CH3)2; R2=CH3 G. hilll' 2 72 R,=CH2-CHT(CO)-CH=C.(CH3)2; R2=H G. storckic.fJ 9, 19-Cyclolanostane-3,23-dione (60) G. taitensil'2 9, 19-Cyclolanostane-3,24-dione (61) G. gordonic.fJ2 G. g rievel2 G. hillt2 G. storckit2 3o., 19o.-Dihydroxy-olean-12-ene-28- G. latifolia63 oic acid (62) Erubescenone (63) G. erubescenl>4 0 Erythrodiol (64) G. g wmnifera~5 Gardendiol (65) G. jasminoidesw Gardenic acid G. jasminoidei' Gardenolic acid (66) G. jasminoidel'· tSO 5 Gardenone (67) G. jasminoides Y Gypsogenic acid (68) G. turgida67 actiVIty against Bulinus truncatus and Biomphalaria Hederagenin (69) G. latifolia68 67 pfeifferi52 • ~-Sitosteroi (78) and ursolic acid (81) (3 ~-23-Dihydroxyolean-12-ene-28-oic G. turgida inhibited arachidonic acid-induced platelet acid) 5 aggregation in decreasing order of potency5 . ~ Hydroxycitronellal G. jasminoide/'Y Sitosterol and ursolic acid inhibited platelet activating 1 9-~-Hydroxyerythrodiol (70) G. gummiferc/' 0 factor induced aggregation while only the former Linalool (7 1) G. tahitensi/ 2 inhibited ADP-induced platelet aggregation. Ursolic 4-Nor-9, 19-cyclolanost-24-ene-3,23- G. ga rdonic.fJ 1 dione (72) acid (@25-100 mg kg- ) exhibited a concentration 55 G. hilliM dependant anti-inflammatory effect . ~ - Sitosterol has G. storckil.fJ2 been reported to possess estrogenic activity and to Oleanolic acid (73) G. erubescens''4 stimulate uterine tissue; it also serves as plant steroid G. latifolicP 56 58 precursor for cortisone production - . Most terpenes G. sootepensis21 26 67 isolated from the genus Gardenia are triterpenoids. G. turg ida · 898 J SCI IND RES VOL 59 NOVEMBER 2000

Oleanolic acid acetate (74) G. erubescen/'4 Miscellaneous Compounds G. jasminoide/1 Besides the above mentioned group of Oleanolic acid 3-0-glucoside (75) G. lutea52 compounds, several acids, alkanes, esters and Oleanonic aldehyde (76) G. gwnmifercl5 glycosides have been isolated from Gardenia species. Spinosic acid (77) G. fatifolia6x 65 Crocetin (85) and crocin (87) are the yellow pigments ~- s itoste rol (78) G. gummifera isolated from G. jasminoides. The demand for crocin G. jasminoides72 as a natural material for yellow colouration in food G. latifolianx stuffs is increasing. Crocin is an important colouring G. Lucida60 agent in a wide variety of foods in Japan. The acids G. lutea 51 83, 84, 88 and 90 are found to be lipoxygenase G. sootepensii'· 53 26 inhibitors and compound 88 has been found to be the · G. turgida n? 38 73 most potent inhibitor . ~-Sitosterol-3 - 0-~-D -g lu copy r a nos yl G. lucida ( 1-4)-0-a L-rhamno-pyranoside (79) D-Mannitol, isolated from a number of Stigmasterol (80) G. erubescens64 Gardenia species (Table 4), is quite a valuable G. jasminoides 71 compound as it is used in medicaments for the G. lutea51 prevention of renal failure and in neuro surgical Styrolaceta~e G. jasminoideiy activity. D-Mannitol was shown to have dialating Ursolic acid (8 1) G. erubescens64 effects on vascular smooth muscle in the cerebral 74 micro circulation .

54 R=OH; R1=H 55 R=H; R 1=0H 56 R=OCOCH3; R,=H

HO OHC CH3 68

H 62 R=R,=~-oH ; R2=H ~" OH n R=R1= ~- H ; R2=H 71

R 73 R,=R2=H 74 R,=-COCHJ, R2=H 70 R=OH 75 R 1=H, R2=0-glucos1de 76 PARMAR eta/.: CONSTITUENTS OF GARDENIA SPECIES 899

7 Table 4- Miscellaneous Compounds from Gardenia Species Polysaccharides (GPS4, GPS5) G. jasminoidel Compounds Plant/Component Quinidc (97) and G. sootepensis xx Benzyl acetate G. jasminoidesm Quinide's dimer G. sootepensi.r13 5 0 Bornyi-6-0-~-D-xylopyranosyi-~-D G. jasminoide/ Squalenol G. tahitensi/ glucopyranoside (82) Stearic acid G. lucida00 3-0-Caffeoyl-4-0-sinapoyi-quinic acid G. jasminoides G. turgidax2 38 70 1 (83) fruit · Triacontane G. sootepensii Chlorogenic acid (84) G. jasminoides 98 G. sootepensii 1 38 8 fruit Mixture of long chain (C?YC?,;) esters Dikamali gum Y 77 0 Crocef6n (85) G. grandiflora Mixture of c21 -c33 long chain alkenes G. tahitensi/ G. jasminoide.r11 18 and alcohols Crocetin mono (~-gentiobiosyl) (86) G. jasminoide.1.7x 48 50 Conclusion Crocin (87) G. jasminoides · · 51. 77 The survey of phytochemical investigations on 3,4-Di-0-caffeoylquinic acid (88) G. jasminoides Gardenia species has revealed a wide variety of 38 fruit chemical constituents produced by them, important 3,4-Di -caffeoyl-5 -(3-hydroxy-3- G. jasminoides 7 classes among them are flavonoids, iridoids, methyl)glutaroyl quinic acid (89) fruit Y terpenoids and steroids. Out of a total of 115 3,5-Di-0-caffeoyl-4-0-(3-hydroxy-3- G. jasminoides methyl-) glutaroylquinic acid (90) fruir'x compounds isolated from Gardenia sp., 33 are 6,7-Dimethylacsculetin (9 1) G. jasminoides flavonoids, 18 iridoids and 31 steroids and 4 45 fruit -'· terpenoids. The present review pinpoints the active Eugenol (92) G. jasminoidesm components besides finding out new structural leads Heneicosane G. sootepen.si/1 Heptacosanol G. sootepensii 1 Hexaacetyl D-mannitol G. turgida26 Hexacosyl-p-coumarate (93) Dika/imali gum80 cis-3-Hexenyl benzoate G. tahitensi/'' 7-Keto-octadec-cis-1 1- enoic acid (94) G. lucidast (R)-Li nalyl-6-0-a-L-arabinopyranosyl- G. jasminoide/5 ~-D-glucopyranoside (95) Linoleic acid G. lutea52 78 R= H Linolenic acid G. lucidaw 79 R =P-D-glucopyranosyl (t-- 4) G. turgidax2 0-n-L-rhamnopyranosyl D-Mannitol G. jlo rida'~3 G. gtmuniferafi5 G. latifolic/8 G. lu c ida'~4 72 G. jasminoide/'· OH G. pomodora x5 G. turgida2r,. sr, G. sootepensis53 G. vogelil5 D-Mannitol hexabenzoate G. turgidaxr. Nonacosane G. jasminoide/1 G. sootepensi/1 Oleic ac id G. lucidaw G. turgida81 R20,,,,,, .. ~COOH Palmitic acid G. Iucida w r .,,~OH 52 G. lutea R30 G. soo1epensis21 84 R1=R2=H ; R3= caffeoyl G. turg ida'~2 88 R1=H; R2=R 3= caffeoyl 1 Pentacosanol G. sootepensi/ 89 R1=R2= glutaroyl; R2=R3= caffeoyl Phencthyl ben zoate (96) G. tahitensi/" 90 R1=R3"' caffeoyl; R2= glutaroyl 900 J SCI IND RES VOL 59 NOVEMBER 2000

OH H3 co:x:::r:t ¢roc,, H3 co ~ o o 91

80 CH:!CH=CH2 92

Ht?o~o ~ O H~HO _.- CHJ-(CH2)4-CH;z-CH=CH-CH2-CH2-CH;z- (CO)-CH2·(CH2)4·COOH HO OH 0 HC=CH-{CO}-OCH,-{CH2)24-CH3 9 94 93 82

Ht?o~o OH ~-0 HO ~~O~ _ HO OH ..----· \__/

~ ""=:, COOR1

85 R,=R2=H 86 R1-=H; R2=gantiobiose 87 R1=R 2= gentiobiose 97

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