title: Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. II. Physicochemical properties and structural elucidation.
abstract: A new growth inhibitor of IL-6 responsive MH60 cells, chlovalicin (MW; 332, C16H25O5Cl), was found in cultures of Sporothrix sp. FO-4649, together with a known sesquiterpene, ovalicin. The structure of chlovalicin was elucidated by spectroscopic methods. Chlovalicin possesses a chlorinated methylene moiety at the C-1 position, and it corresponds to halogenated products derived from the epoxide ring attached to the C-1 position of ovalicin. The absolute configuration of chlovalicin was clarified as 1S, 2R, 3S, 1'S, 2'R by chemical transformation from ovalicin.
authors.affiliation: Kitasato Institute, Kitasato University, Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Takamatsu
authors.forename: Y P
authors.initials: YP
authors.lastname: Kim
authors.forename: T
authors.initials: T
authors.lastname: Komiya
authors.forename: T
authors.initials: T
authors.lastname: Sunazuka
authors.forename: M
authors.initials: M
authors.lastname: Hayashi
authors.forename: H
authors.initials: H
authors.lastname: Tanaka
authors.forename: K
authors.initials: K
authors.lastname: Komiyama
authors.forename: S
authors.initials: S
authors.lastname: Omura
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry*; D013175:Sporothrix / Q000378:metabolism*
chemical_list: D000900:Anti-Bacterial Agents; D003512:Cyclohexanones; D004852:Epoxy Compounds; D012717:Sesquiterpenes; C101438:chlovalicin