Secondary metabolites of Fusarium species: apotrichothecene derivatives

Two epimers (3 alpha -OH, 3 beta -OH) of 3,13-dihydroxy-11-epiapotrichothec-9-ene have been isolated from liquid cultures of Fusarium species. These epimers are common minor metabolites of Fusarium crookwellense, Fusarium culmorum, Fusarium graminearum , and Fusarium sporotrichioides , the ratio of...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1989-05, Vol.37 (3), p.699-705
Main Authors: Greenhalgh, Roy, Fielder, David A, Morrison, Lisa A, Charland, Jean Pierre, Blackwell, Barbara A, Savard, Marc E, ApSimon, John W
Format: Article
Language:English
Subjects:
Biological and medical sciences
Food industries
Food toxicology
Fundamental and applied biological sciences. Psychology
FUSARIUM
Medical sciences
METABOLITE
METABOLITES
METABOLITOS
Plant poisons toxicology
TOXICIDAD
TOXICITE
TOXICITY
Toxicology
TRICHOTHECENE
TRICHOTHECENES
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Summary:Two epimers (3 alpha -OH, 3 beta -OH) of 3,13-dihydroxy-11-epiapotrichothec-9-ene have been isolated from liquid cultures of Fusarium species. These epimers are common minor metabolites of Fusarium crookwellense, Fusarium culmorum, Fusarium graminearum , and Fusarium sporotrichioides , the ratio of the epimers being species dependent. The absolute configuration of the 3 alpha -OH epimer was determined by X-ray crystallography and shown to have a trans A/B ring system with H-11 in the beta -configuration as opposed to the cis A/B ring system of the trichothecenes. Both epimers readily undergo oxidation. The 3 alpha -OH epimer is involved in a unique rearrangement to form a ketal, 3,11-epoxy-13-hydroxyapotrichothec-9-ene, a compound also detected in the crude extracts of F. culmorum and F. sporotrichioides fermentations. The mass and NMR spectral data of these compounds and their epoxy derivatives are discussed.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00087a026