钩吻中的吲哚生物碱。

Indole alkaloids from Gelsemium elegans.

机构信息

Lab of Toxicology and Pharmacology, Faculty of Naval Medicine, Second Military Medical University, Shanghai, 200433, China.

Lab of Toxicology and Pharmacology, Faculty of Naval Medicine, Second Military Medical University, Shanghai, 200433, China; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, 110016, China.

出版信息

Phytochemistry. 2019 Jun;162:232-240. doi: 10.1016/j.phytochem.2019.03.016. Epub 2019 Apr 4.

DOI:10.1016/j.phytochem.2019.03.016

PMID:30953910

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 N-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-N-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 N-oxide and 10,11-dimethoxy-N-demethoxy-gelsemamide exhibited significant inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophage cells, with IC values of 6.18 ± 1.07 and 12.2 ± 1.02 μM, respectively.

摘要

从钩吻根部分离得到了 5 种以前未描述的单萜吲哚生物碱。通过高分辨质谱、X 射线衍射、ECD 光谱和分子建模确定了它们的结构和绝对构型。19,20-环氧胡蔓藤碱是一种胡蔓藤碱型生物碱，在 C-20 位有一个环氧丙基；（4R）-19-氧代钩吻绿宁 N-氧化物是一种钩吻绿宁相关的生物碱；钩吻斯定碱是一种 C-20 位有丁烯基的钩吻斯定型生物碱。此外，10,11-二甲氧基-N-去甲氧基钩吻酰胺是一种开环吲哚生物碱，11-去甲氧基钩吻沙林酰胺是一种芳基偶氮连接的二聚吲哚生物碱。在这 5 种生物碱中，（4R）-19-氧代钩吻绿宁 N-氧化物和 10,11-二甲氧基-N-去甲氧基钩吻酰胺对脂多糖诱导的 RAW 264.7 巨噬细胞中一氧化氮的产生有显著的抑制作用，IC 值分别为 6.18±1.07 和 12.2±1.02 μM。