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.