Xiamycin, a pentacyclic indolosesquiterpene with selective anti-HIV activity from a bacterial mangrove endophyte

被引：156

作者：

Ding, Ling ^{[1
]}

Muenich, Jan ^{[2
]}

Goerls, Helmar ^{[3
]}

Maier, Armin ^{[4
]}

Fiebig, Heinz-Herbert ^{[4
]}

Lin, Wen-Han ^{[5
]}

Hertweck, Christian ^{[1
]}

机构：

[1] HKI, Leibniz Inst Nat Prod Res & Infect Biol, D-07745 Jena, Germany

[2] Univ Hosp Ulm, Inst Mol Virol, D-89081 Ulm, Germany

[3] Univ Jena, Inst Inorgan & Analyt Chem, D-07743 Jena, Germany

[4] Oncotest GmbH, D-79108 Freiburg, Germany

[5] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 22期

关键词：

Indolosesquiterpene; Natural products; HIV; Endophytes; Streptomyces; STREPTOMYCES-GRISEUS SUBSP; SOUTH CHINA SEA; BRUGUIERA-GYMNORRHIZA; NATURAL-PRODUCTS; DERIVATIVES; METABOLITES; SUAVEOLENS; ANNONACEAE;

D O I：

10.1016/j.bmcl.2010.09.010

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel pentacyclic indolosesquiterpene, named xiamycin (1), and its methyl ester (2) have been obtained from Streptomyces sp. GT2002/1503, an endophyte from the mangrove plant Bruguiera gymnorrhiza. The structures were established by 1D and 2D NMR, MS, and X-ray crystallography, and the absolute configuration of 1 was elucidated by the modified Mosher method. Compound 1 exhibits selective anti-HIV activity; it specifically blocks R5 but has no effects on X4 tropic HIV-1 infection. In a panel of cytotoxicity assays, compound 2 showed to be more potent (geometric mean IC(50) = 10.13 mu M) compared to compound 1 (geometric mean IC(50) > 30 mu M), with antitumor potency being generally less pronounced. Xiamycin represents one of the first examples of indolosesquiterpenes isolated from prokaryotes. (C) 2010 Published by Elsevier Ltd.

引用

页码：6685 / 6687

页数：3

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