The metabolic fate of deoxynivalenol and its acetylated derivatives in a wheat suspension culture: Identification and detection of DON-15-O-glucoside, 15-acetyl-DON-3-O-glucoside and 15-acetyl-DON-3-sulfate

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Abstract

© 2015 by the authors; licensee MDPI, Basel, Switzerland.Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives.

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Schmeitzl, C., Warth, B., Fruhmann, P., Michlmayr, H., Malachová, A., Berthiller, F., … Adam, G. (2015). The metabolic fate of deoxynivalenol and its acetylated derivatives in a wheat suspension culture: Identification and detection of DON-15-O-glucoside, 15-acetyl-DON-3-O-glucoside and 15-acetyl-DON-3-sulfate. Toxins, 7(8), 3112–3126. https://doi.org/10.3390/toxins7083112

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