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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

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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.
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