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Issue 28, 2014
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Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes

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Abstract

Methylthiodeoxynivalenol (MTD), a novel derivative of the trichothecene mycotoxin deoxynivalenol (DON), was prepared by applying a reliable procedure for the formal Michael addition of methanethiol to the conjugated double bond of DON. Structure elucidation revealed the preferred formation of the hemiketal form of MTD by intramolecular cyclisation between C8 and C15. Computational investigations showed a negative total reaction energy for the hemiketalisation step and its decrease in comparison with theoretical model compounds. Therefore, this structural behaviour seems to be a general characteristic of thia-Michael adducts of type B trichothecenes. MTD was shown to be less inhibitory for a reticulocyte lysate based in vitro translation system than the parent compound DON, which supports the hypothesis that trichothecenes are detoxified through thia-adduct formation during xenobiotic metabolism.

Graphical abstract: Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes

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Publication details

The article was received on 27 Feb 2014, accepted on 20 May 2014 and first published on 20 May 2014


Article type: Paper
DOI: 10.1039/C4OB00458B
Citation: Org. Biomol. Chem., 2014,12, 5144-5150
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    Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes

    P. Fruhmann, T. Weigl-Pollack, H. Mikula, G. Wiesenberger, G. Adam, E. Varga, F. Berthiller, R. Krska, C. Hametner and J. Fröhlich, Org. Biomol. Chem., 2014, 12, 5144
    DOI: 10.1039/C4OB00458B

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