Identification of the naturally occurring isomer of zearalenol produced by Fusarium roseum 'Gibbosum' in rice culture
| Autor: | W M Hagler, J. C. Behrens, Chester J. Mirocha, S V Pathre |
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| Rok vydání: | 1979 |
| Předmět: |
Fusarium
Chemical Phenomena Stereochemistry Metabolite Stereoisomerism Applied Microbiology and Biotechnology chemistry.chemical_compound Zeranol Animals Bioassay Zearalenone Ecology biology Uterus Diastereomer Oryza Resorcinols biology.organism_classification Culture Media Rats Chemistry chemistry Mass spectrum Female Research Article Food Science Biotechnology |
| Zdroj: | Applied and Environmental Microbiology. 37:849-853 |
| ISSN: | 1098-5336 0099-2240 |
| Popis: | One diastereomer of trans-zearalenol [2,4-dihydroxy-6-(6,10-dihydroxy-trans-1-undecenyl)-benzoic acid-mu-lactone] was isolated from cultures of Fusarium roseum 'Gibbosum.' This strongly estrogenic metabolite was identified by analysis of its mass spectrum and its behavior in thin-layer, high-pressure liquid and gas-liquid chromatographic systems. The concentration of zearalenol in cultures was 563 mu g/g, or 7% of the 8,000-mu g/g zearalenone content, while the two diastereomers of 8'-hydroxyzearalenone each occurred at 3% of the zearalenone level. Of the two possible diastereomers of zearalenol, the one occurring in cultures was identical to the low-melting-point (171 degrees C) isomer (alpha) obtained by synthesis. In the rat uterus bioassay, the alpha zearalenol isomer was three times more estrogenic than zearalenone while the beta isomer was equal in activity in zearalenone. The two diastereomers of zearalenol can be distinguished from each other by the intensity of the m/e+ 302 fragment of the mass spectrum of the pure underivatized compound. |
| Databáze: | OpenAIRE |
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