Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. II. Physicochemical properties and structural elucidation.
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.
Takamatsu
S
S
Kitasato Institute, Kitasato University, Tokyo, Japan.
Kim
Y P
YP
Komiya
T
T
Sunazuka
T
T
Hayashi
M
M
Tanaka
H
H
Komiyama
K
K
Omura
S
S
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*
D000900:Anti-Bacterial Agents; D003512:Cyclohexanones; D004852:Epoxy Compounds; D012717:Sesquiterpenes; C101438:chlovalicin