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Mucroniferanines A–G, Isoquinoline Alkaloids from Corydalis mucronifera

Author:
Zhang, Jun, Zhang, Qing-Ying, Tu, Peng-Fei, Xu, Fu-Chun, Liang, Hong
Source:
Journal of natural products 2018 v.81 no.2 pp. 364-370
ISSN:
1520-6025
Subject:
Corydalis, X-radiation, acetylcholinesterase, enantiomers, enzyme inhibition, inhibitory concentration 50, isoquinoline alkaloids, moieties, spectral analysis, stereoisomerism
Abstract:
Five pairs of isoquinoline alkaloid enantiomers, mucroniferanines A–E (1–5), two inseparable epimeric pairs, mucroniferanines F and G (6, 7), and 10 known isoquinoline alkaloids (8–17) were obtained from Corydalis mucronifera. The structures were characterized using spectroscopic data analysis, and the absolute configurations were established by ECD and X-ray data analysis. The new compounds except for 3 possess a rare 9-methyl group in the isoquinoline alkaloids, and compounds 2 and 3 possess rare benzo[1,2-d:3,4-d]bis[1,3]dioxole moieties. It is the first report of stereoisomerism involving the 9-methyl phthalideisoquinoline alkaloids. Compounds (−)-4, 6, and 7 exhibited acetylcholinesterase inhibitory activities with IC₅₀ values of 28.3, 12.2, and 11.3 μM, respectively.
Agid:
6043068