| Gardenia jasminoides Ellis is a shrub or tree plant of the genus of Gardenia in Rubiaceae, widely distributed throughout the central and southern China. Its fruit is used as a traditional Chinese medicine for its diuretic and detoxification effects. In recent chemical and pharmacological studies, a number of iridoid glucosides, crocin, terpenoids, flavones, quinic acid, polysaccharides and volatile oil components have been isolated from the fruit of G. jasminoides and reported as ant-inflammatory, analgesic, protecting liver, cholagogic function, oxidation resistance, and inhibiting tumor.In our investigation for compounds with transgenic Alzheimer’s disease fly model, 68 compounds were isolated from the 60% ethanol extract of the fruit of G. jasminoides through various chromatographic techniques. The structures of 63 compounds were established on the basis of their physico-chemical properties and spectroscopic analysis as 6"-O-trans-sinapoylgenipin gentiobioside (1)*, 6"-O-trans-p-coumaroylgenipin gentiobioside (2)*,6"-O-trans-cinnamoylgenipin gentiobioside (3)*,6’-O-trans-p-coumaroylgeniposide (4)*, 6’-O-trans-p-coumaroylgeniposidic acid (5)*,10-O-trans-sinapoylgeniposide (6)*, 6’-O-trans-sinapoylgeniposide (7),10-O-succinoylgeniposide (8)*, 6’-O-acetylgeniposide (9)*,10-O-acetylgeniposide (10), geniposide (11), genipin (12), (1R,7R,10S)-11-0-β-D-glucopyranosyl-4-guaien-3-one (13)*, (1R,7R,10S)-7-hydroxy-11-O-β-D-glucopyranosyl-4-guaien-3-one(14)*, 10-(6-O-trans-sinapoylglucopyranosyl) gardendiol (15)*, 11-(6-O-trans-sinapoylglucopyranosyl) gardendiol (16)*, jasminoside J (17)*, jasminoside K (18)*,6’-O-trans-sinapoyljasminoside B (19)*, 6’-O-trans-sinapoyljasminoside L (20)*, jasminoside M (21)*, jasminoside C (22), 6’-O-trans-sinapoyljasminoside A (23),6’-O-trans-sinapoyljasminoside C (24), jasminol E (25),jasminoside N (26)*, jasminoside O (27)*, jasminoside P (28)*, sacranoside B (29), trans-crocetin (30), trans-crocetin mono(β-D-glucopyranosyl) ester (31),trans-crocetin mono(β-D-gentiobiosyl) ester (32),trans-crocetin (β-D-glucopyranosyl)-(β-D-gentiobiosyl) ester (33),trans-crocetin di(β-D-gentiobiosyl) ester (34), 13cis-crocetin di(β-D-gentiobiosyl) ester (35), gardenianan A (36)*, syringaresinol (37), pinoresinol (38), syringaresinol-4-O-β-D-glucopyranoside (39), lariciresinol (40), alangilignoside D (41), lyoniresinol (42), lyoniresinol-9-O-β-D-glucopyranoside (43), balanophonin (44), glycosmisic acid (45), ficusal (46), ceplignan (47), rutin (48), quercetin 3-O-β-D-glucopyranoside (49), quercetin (50), kaemferol (51),5,7,3’,5’-tetrahydroxy-4’-methoxyflavone (52), 3,5-di-O-caffeoylquinic acid (53),4-O-sinapoyl-5-O-caffeoylquinic acid (54), 3,4-di-O-caffeoylquinic methyl ester (55),4,5-di-O-caffeoylquinic methyl ester (56), vanillic acid 4-O-β-D-(6’-O-trans-sinapoyl)glucopyranoside (57), syringaldehyde (58), 3,4,5-trimethoxybenzyl alcohol (59), cis-2,4-dihydroxy-5-methoxy-cinnamic acid (60),trans-caffeic acid (61), trans-p-coumaric acid (62), trans-sinapic acid (63). Among them,21 compounds (1-6,8-9,13-21,26-28,36) were new compounds,2 compounds (25,60) were new natural products, and 17 compounds (29,37-41,44-47, 52,54,56,58-59,62-63) were isolated from the Gardenia genus for the first time.Their biological activities of the isolated compounds were evaluated by using a transgenic fly AD model. The results showed that 12 compounds (4,7-12,14-16,30, 34) could improve the short-term memory capacity to varying degrees, suggesting that these compounds may have a potential antagonism effects against Alzheimer’s disease. Compared with control groups, most of iridoids and crocin showed potent activity, suggesting that they could be active components of G jasminoides. |
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