Bioactive iridoid glucosides from the fruit of Gardenia jasminoides.
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 Abeta transgenic drosophila model showed that compounds 4 and 6-12 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.
Yu
Yang
Y
Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
Xie
Zuo-Lei
ZL
Gao
Hao
H
Ma
Wei-Wei
WW
Dai
Yi
Y
Wang
Ying
Y
Zhong
Yi
Y
Yao
Xin-Sheng
XS
D000544:Alzheimer Disease / Q000188:drug therapy; D000818:Animals; D030801:Animals, Genetically Modified; D004195:Disease Models, Animal; D004330:Drosophila; D005638:Fruit / Q000737:chemistry; D032062:Gardenia / Q000737:chemistry*; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008570:Memory, Short-Term / Q000187:drug effects*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D039823:Iridoids; C007835:geniposide