4.7 Article

Two new sesquiterpenoids and anti-HIV principles from the root bark of Zanthoxylum ailanthoides

Journal

BIOORGANIC & MEDICINAL CHEMISTRY
Volume 13, Issue 21, Pages 5915-5920

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2005.07.050

Keywords

Zanthoxylum ailanthoides; rutaceae; root bark; sesquiterpene; 10 beta-methoxymuurolan-4-en-3-one; 10 alpha-methoxycadinan-4-en-3-one; anti-HIV activity; secarine; gamma-fagarine; (+)-tembamide

Funding

  1. NIAID NIH HHS [AI-33066] Funding Source: Medline

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Two new sesquiterpenes, 10 beta-methoxymuurolan-4-en-3-one (1) and 10 alpha-methoxycadinan-4-en-3-one (2), were isolated from the root bark of Zanthoxylum ailanthoides. The structures of I and 2 were elucidated from spectroscopic data. Sixty-seven compounds obtained from the root bark of the same plant were evaluated for inhibition of HIV replication in H9 lymphocyte cells, and 14 compounds demonstrated significant activity. Among them, decarine, gamma-fagarine, and (+)-tembamide were the most potent anti-HIV compounds, with EC50 values of < 0.1 mu g/mL and TI values of > 226, > 231, and > 215, respectively, (c) 2005 Elsevier Ltd. All rights reserved.

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