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Bioactive Iridoid Glucosides from the Fruit of Gardenia jasminoides

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journal contribution
posted on 28.08.2009, 00:00 by Yang Yu, Zuo-lei Xie, Hao Gao, Wei-wei Ma, Yi Dai, Ying Wang, Yi Zhong, Xin-sheng Yao
Seven new iridoid glucosides, 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-succinoylgeniposide (6), and 6′-O-acetylgeniposide (7), two new monoterpenoids, 11-(6-O-trans-sinapoylglucopyranosyl)gardendiol (8) and 10-(6-O-trans-sinapoylglucopyranosyl)gardendiol (9), and three known ones, 6′-O-trans-sinapoylgeniposide (10), geniposide (11), and 10-O-acetylgeniposide (12), were isolated from the fruit of Gardenia jasminoides. The structures of these compounds were elucidated on the basis of 1D and 2D NMR spectra analyses. Furthermore, short-term memory assays on an Aβ transgenic drosophila model showed that compounds 4 and 612 can improve the short-term memory capacity to varying degrees, with compounds 4 and 7 being the most active ones, suggesting that these compounds may have a potential antagonism effect against Alzheimer’s disease.