期刊
ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 5, 页码 953-960出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01475c
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资金
- Career Development Support Plan for Young and Middle-Aged Teachers in Shenyang Pharmaceutical University [ZQN2018006]
- Project of Innovation Team Foundation [LT2015027]
- Program for Major Scientific and Medical Technology Problems of China Medicine Education Association in 2020 [2020KTS003]
Three pairs of highly modified spirocyclohexenone neolignans, along with a pair of biogenetically related enantiomers, were isolated from Crataegus pinnatifida. One of the compounds exhibited cytotoxicity against Hep3B cells by inducing cell apoptosis.
(+/-)-Pinnatifidaones A-C (1-3), three enantiomeric pairs of highly modified spirocyclohexenone neolignans, along with a pair of biogenetically related enantiomers (+/-)-pinnatifidaones D (4), were isolated from Crataegus pinnatifida. Pinnatifidaones A (1) and B (2) share an unprecedented 5/6/6 tricyclic ring system with a rare 2-oxaspiro[4.5]deca-6-en-8-one motif, while 3 features a unique 2-oxaspiro[4.5]deca-6-en-8-one 5/5/6/6 tetracyclic framework. Their structures including absolute configurations were established by spectroscopic analysis, X-ray diffraction, and application of Snatzke's method, as well as NMR and ECD calculations. Moreover, (+)-3 possessed cytotoxicity against Hep3B cells by inducing cell apoptosis.
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