LL-Z1272alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae.
A novel metabolite, LL-Z1272alpha epoxide, structurally related to ascochlorin, was isolated from the cultured mycelium of Ascochyta viciae J-29, a mutant derived from A. viciae Libert. The structure was elucidated on the basis of spectroscopic data. The epoxide is proposed to be enzymatically formed from LL-Z1272alpha and is a precursor of ascochlorin, an antiviral and antitumor antibiotic. The conversion of the epoxide to ascochlorin by cyclization of its farnesyl chain to a cyclohexanone ring is similar to that of squalene 2, 3-oxide to sterols. Unlike ascochlorin, the new metabolite had no growth inhibitory activity against Candida albicans in the paper-disc agar diffusion assay.
Hosono
Kuniaki
K
Department of Applied Biological Science, College of Bioresource Sciences, Nihon University, Kameino, Fujisawa, Japan. khosono@brs.nihon-u.ac.jp
Ogihara
Jun
J
Ohdake
Takamichi
T
Masuda
Setsuko
S
D000475:Alkenes / Q000737:chemistry / Q000378:metabolism*; D001203:Ascomycota / Q000145:classification / Q000235:genetics / Q000254:growth & development / Q000378:metabolism*; D001547:Benzaldehydes / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D002176:Candida albicans / Q000187:drug effects / Q000254:growth & development; D002627:Chemistry, Physical; D003470:Culture Media; D004852:Epoxy Compounds / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests / Q000379:methods; D009154:Mutation; D010636:Phenols / Q000737:chemistry / Q000378:metabolism*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism
D000475:Alkenes; D001547:Benzaldehydes; D003470:Culture Media; D004852:Epoxy Compounds; C545192:LL 21272alpha epoxide; D010636:Phenols; D012717:Sesquiterpenes; C415745:ascochlorin