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

Ling Ding, Jan Muenich, Helmar Goerls, Armin Maier, Heinz-Herbert Fiebig, Wen-Han Lin, Christian Hertweck

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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 IC50 = 10.13 µM) compared to compound 1 (geometric mean IC50 > 30 µM), with antitumor potency being generally less pronounced. Xiamycin represents one of the first examples of indolosesquiterpenes isolated from prokaryotes. 
Original languageEnglish
JournalBioorganic & Medicinal Chemistry Letters
Volume20
Issue number22
Pages (from-to)6685-6687
Number of pages3
ISSN0960-894X
DOIs
Publication statusPublished - 2010
Externally publishedYes

Keywords

  • Endophytes
  • HIV
  • Indolosesquiterpene
  • Natural Products
  • Streptomyces

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