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Abiesatrines A–J: anti-inflammatory and antitumor triterpenoids from Abies georgei Orr†
Su-Mei Li,Liang Wu,Yong-Li Li,Lin Feng,Yun-Heng Shen,Jun-Mian Tian,Jian Tang,Ning Wang,Yonghong Liu,Wei-Dong Zhang
Organic & Biomolecular Chemistry Pub Date : 04/07/2010 00:00:00 , DOI:10.1039/C001885F
Abstract

A novel spiro-lanostane (abiesatrine A, 1) was isolated from the aerial parts of Abies georgei together with 9 new (abiesatrines B–J, 2–10) and 10 known triterpenes (11–20). The new structures were established by the extensive analysis of their spectroscopic data. The configuration of 1, featuring a unique spirolactone formed by C-13 and C-23 via oxygen-bridge, was confirmed by X-ray crystallography, and its biopathway was tentatively proposed. Among these isolates, compound 16 showed the strongest inhibitory activity against LPS-induced NO production in RAW264.7 macrophages (IC50 = 8.9 μg mL−1). While compounds 1 and 20 exhibited potent anti-proliferative effects on QGY-7703 cells with IC50 values of 9.3 and 7.6 μg mL−1, respectively. Preliminary structure–activity relationship (SAR) investigations defined structural feature of the 24Z-olefinic bond key to the lanostane and cycloartane pharmacophore.

Graphical abstract: Abiesatrines A–J: anti-inflammatory and antitumor triterpenoids from Abies georgei Orr
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