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

Literature Information

Publication Date 2010-04-07
DOI 10.1039/C001885F
Impact Factor 3.876
Authors

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


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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