LL-Z1272 alpha epoxide, a precursor of ascochlorin produced by a mutant of Ascochyta viciae

A novel metabolite, LL-Z1272 alpha 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 form...

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Bibliographic Details
Published inJournal of antibiotics Vol. 62; no. 10; pp. 571 - 574
Main Authors Hosono, Kuniaki, Ogihara, Jun, Ohdake, Takamichi, Masuda, Setsuko
Format Journal Article
LanguageEnglish
Published TOKYO Japan Antibiotics Research Assoc 01.10.2009
Subjects
Biotechnology & Applied Microbiology
Immunology
Life Sciences & Biomedicine
Microbiology
Pharmacology & Pharmacy
Science & Technology
fungal metabolite
ANTIBIOTICS
METABOLITES
prenylphenol antibiotic
ASCOFURANONE
PROPERTY
RATS
MICE
CYLINDROCLADIUM
ascochlorin precursor
LL-Z1272 alpha epoxide
ANTITUMOR
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Summary:A novel metabolite, LL-Z1272 alpha 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-Z1272 alpha 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. The Journal of Antibiotics (2009) 62, 571-574; doi:10.1038/ja.2009.80; published online 14 August 2009
ISSN:0021-8820
1881-1469
DOI:10.1038/ja.2009.80