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

Clemens Schmeitzl³  Benedikt Warth¹  Philipp Fruhmann²  Herbert Michlmayr³  Alexandra Malachová¹  Franz Berthiller¹  Rainer Schuhmacher¹  Rudolf Krska¹  Gerhard Adam³ 

[1] 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; E-Mails:;Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria; E-Mail:;Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Straße 24, 3430 Tulln, Austria; E-Mails:

关键词: carboxylesterase;    Fusarium;    3-acetyl-deoxynivalenol;    15-acetyl-deoxynivalenol;    3;    15-diacetyl-deoxynivalenol;    masked mycotoxins;    chemotype;   

DOI  :  10.3390/toxins7083112

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.