乌药根状茎中的倍半萜内酯

Sesquiterpene lactones from the root tubers of Lindera aggregata.

作者信息

Gan Li-She, Zheng Yun-Liang, Mo Jian-Xia, Liu Xin, Li Xin-Hua, Zhou Chang-Xin

机构信息

Institute of Modern Chinese Medicine (IMCM), College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, People's Republic of China.

出版信息

J Nat Prod. 2009 Aug;72(8):1497-501. doi: 10.1021/np900354q.

DOI:10.1021/np900354q

PMID:19639966

Abstract

Phytochemical investigation of the root tubers of Lindera aggregata resulted in the isolation of five new sesquiterpene lactones, linderagalactones A-E (1-5), along with eight known sesquiterpenoids, 3-eudesmene-1beta,11-diol, hydroxylindestenolide, strychnistenolide, hydroxyisogermafurenolide, atractylenolide III, linderane, neolinderalactone, and linderalactone. The structures and relative configurations of 1-5 were determined by spectroscopic methods, especially HRESIMS and 2D NMR techniques. The absolute configurations of 1-4 were defined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Linderagalactone A (1) is a halogenated sesquiterpene lactone possessing a unique rearranged carbon skeleton. Linderagalactone E (5), linderane, hydroxylindestenolide, and linderalactone showed hepatoprotective activity against H2O2-induced oxidative damages on HepG2 cells with EC(50) values of 67.5, 167.0, 42.4, and 98.0 microM, respectively.

摘要

对乌药块根进行植物化学研究，从中分离出5个新的倍半萜内酯，即乌药半乳糖内酯A - E（1 - 5），以及8个已知的倍半萜类化合物，3 - 桉叶烯 - 1β，11 - 二醇、羟基乌药内酯、马钱子内酯、羟基异吉马呋喃内酯、苍术内酯III、乌药烷、新乌药内酯和乌药内酯。通过光谱方法，尤其是高分辨电喷雾电离质谱（HRESIMS）和二维核磁共振（2D NMR）技术确定了1 - 5的结构和相对构型。通过比较量子化学含时密度泛函理论（TDDFT）计算的和实验的电子圆二色谱（ECD）光谱确定了1 - 4的绝对构型。乌药半乳糖内酯A（1）是一种具有独特重排碳骨架的卤代倍半萜内酯。乌药半乳糖内酯E（5）、乌药烷、羟基乌药内酯和乌药内酯对H2O2诱导的HepG2细胞氧化损伤具有肝保护活性，其半数有效浓度（EC50）值分别为67.5、167.0、42.4和98.0微摩尔。