Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. II. Physicochemical properties and structural elucidation

J Antibiot (Tokyo). 1996 Jul;49(7):635-8. doi: 10.7164/antibiotics.49.635.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Cyclohexanones / chemistry
  • Epoxy Compounds / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Sesquiterpenes / chemistry*
  • Sporothrix / metabolism*

Substances

  • Anti-Bacterial Agents
  • Cyclohexanones
  • Epoxy Compounds
  • Sesquiterpenes
  • chlovalicin