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Toxins 2015, 7(8), 3112-3126; doi:10.3390/toxins7083112

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

1
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Straße 24, 3430 Tulln, Austria
2
Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln), University of Natural Resources and Life Sciences, Vienna (BOKU) Konrad-Lorenz-Straße 20, 3430 Tulln, Austria
3
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria
4
Christian Doppler Laboratory for Mycotoxin Metabolism, Konrad-Lorenz-Straße 20, 3430 Tulln, Austria
These authors contributed equally to this work.
Current Affiliation: Department of Food Chemistry and Toxicology, University of Vienna, Währinger Str. 38, 1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Academic Editor: Ana Calvo
Received: 24 June 2015 / Revised: 24 July 2015 / Accepted: 4 August 2015 / Published: 12 August 2015
(This article belongs to the Section Mycotoxins)
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Abstract

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. View Full-Text
Keywords: carboxylesterase; Fusarium; 3-acetyl-deoxynivalenol; 15-acetyl-deoxynivalenol; 3,15-diacetyl-deoxynivalenol; masked mycotoxins; chemotype carboxylesterase; Fusarium; 3-acetyl-deoxynivalenol; 15-acetyl-deoxynivalenol; 3,15-diacetyl-deoxynivalenol; masked mycotoxins; chemotype
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Schmeitzl, C.; Warth, B.; Fruhmann, P.; Michlmayr, H.; Malachová, A.; Berthiller, F.; Schuhmacher, R.; Krska, R.; Adam, G. 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 2015, 7, 3112-3126.

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