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Issue 11, 2010
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Abiesatrines A–J: anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

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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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Publication details

The article was received on 02 Feb 2010, accepted on 23 Mar 2010 and first published on 07 Apr 2010


Article type: Paper
DOI: 10.1039/C001885F
Citation: Org. Biomol. Chem., 2010,8, 2609-2616
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    Abiesatrines A–J: anti-inflammatory and antitumor triterpenoids from Abies georgei Orr

    X. Yang, S. Li, L. Wu, Y. Li, L. Feng, Y. Shen, J. Tian, J. Tang, N. Wang, Y. Liu and W. Zhang, Org. Biomol. Chem., 2010, 8, 2609
    DOI: 10.1039/C001885F

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