Indole alkaloids from Gelsemium elegans.

Abstract:

:Five previously undescribed monoterpenoid indole alkaloids were isolated from the roots of Gelsemium elegans. Their structures with absolute configurations were elucidated by HRESIMS, X-ray diffraction, ECD spectra, and molecular modeling. 19,20-Epoxyhumantenine is a humantenine-type alkaloid with an epoxypropyl group at the C-20 position, (4R)-19-oxo-gelsevirine N4-oxide is a gelsemine-related alkaloid, and gelsedethenine is a gelsedine-type alkaloid with a butenyl group at the C-20 position. Moreover, 10,11-dimethoxy-N1-demethoxy-gelsemamide is an open-loop indole alkaloid and 11-demethoxy-gelsemazonamide is an aromatic azo-linked dimeric indole alkaloid. Among the five alkaloids, (4R)-19-oxo-gelsevirine N4-oxide and 10,11-dimethoxy-N1-demethoxy-gelsemamide exhibited significant inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells, with IC50 values of 6.18 ± 1.07 and 12.2 ± 1.02 μM, respectively.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Sun MX,Cui Y,Li Y,Meng WQ,Xu QQ,Zhao J,Lu JC,Xiao K

doi

10.1016/j.phytochem.2019.03.016

subject

Has Abstract

pub_date

2019-06-01 00:00:00

pages

232-240

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(19)30096-2

journal_volume

162

pub_type

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