title: Xiamycin, a pentacyclic indolosesquiterpene with selective anti-HIV activity from a bacterial mangrove endophyte.
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 IC(50)=10.13 μM) compared to compound 1 (geometric mean IC(50) >30 μM), with antitumor potency being generally less pronounced. Xiamycin represents one of the first examples of indolosesquiterpenes isolated from prokaryotes.
authors.affiliation: Leibniz Institute for Natural Product Research and Infection Biology, HKI, Beutenbergstr. 11a, 07745 Jena, Germany.
authors.forename: Ling
authors.initials: L
authors.lastname: Ding
authors.forename: Jan
authors.initials: J
authors.lastname: Münch
authors.forename: Helmar
authors.initials: H
authors.lastname: Goerls
authors.forename: Armin
authors.initials: A
authors.lastname: Maier
authors.forename: Heinz-Herbert
authors.initials: HH
authors.lastname: Fiebig
authors.forename: Wen-Han
authors.initials: WH
authors.lastname: Lin
authors.forename: Christian
authors.initials: C
authors.lastname: Hertweck
mesh_terms: D019380:Anti-HIV Agents / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D043982:Rhizophoraceae / Q000737:chemistry*; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D019380:Anti-HIV Agents; D012717:Sesquiterpenes; C556785:xiamycin