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.
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.
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Straße 24, 3430 Tulln, Austria. clemens.schmeitzl@boku.ac.at.
Clemens
C
Schmeitzl
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. benedikt.warth@univie.ac.at.
Benedikt
B
Warth
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria. philipp.fruhmann@tuwien.ac.at.
Philipp
P
Fruhmann
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Straße 24, 3430 Tulln, Austria. herbert.michlmayr@boku.ac.at.
Herbert
H
Michlmayr
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. alexandra.malachova@boku.ac.at.|Christian Doppler Laboratory for Mycotoxin Metabolism, Konrad-Lorenz-Straße 20, 3430 Tulln, Austria. alexandra.malachova@boku.ac.at.
Alexandra
A
Malachová
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. franz.berthiller@boku.ac.at.|Christian Doppler Laboratory for Mycotoxin Metabolism, Konrad-Lorenz-Straße 20, 3430 Tulln, Austria. franz.berthiller@boku.ac.at.
Franz
F
Berthiller
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. rainer.schuhmacher@boku.ac.at.
Rainer
R
Schuhmacher
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. rudolf.krska@boku.ac.at.
Rudolf
R
Krska
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Straße 24, 3430 Tulln, Austria. gerhard.adam@boku.ac.at.
Gerhard
G
Adam
D000107:Acetylation; D005960:Glucosides / Q000378:metabolism*; D013431:Sulfates / Q000378:metabolism*; D014255:Trichothecenes / Q000494:pharmacology*; D014908:Triticum / Q000378:metabolism*
D005960:Glucosides; D013431:Sulfates; D014255:Trichothecenes; C007262:deoxynivalenol
15-acetyl-deoxynivalenol; 3,15-diacetyl-deoxynivalenol; 3-acetyl-deoxynivalenol; Fusarium; carboxylesterase; chemotype; masked mycotoxins