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UDP-Glucosyltransferases from Rice, Brachypodium, and Barley: Substrate Specificities and Synthesis of Type A and B Trichothecene-3-O-β-d-glucosides

Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna, (BOKU), Konrad Lorenz Str. 24, 3430 Tulln, Austria
Department of Food Chemistry and Toxicology, University of Vienna, Währinger Str. 38, 1090 Vienna, Austria
Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), BOKU, Konrad Lorenz Str. 20, 3430 Tulln, Austria
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, 1060 Vienna, Austria
CEST Kompetenzzentrum für elektrochemische Oberflächentechnologie GmbH, Viktor-Kaplan-Str. 2, 2700 Wiener Neustadt, Austria
Department of Chemistry and Biochemistry, Mendel University in Brno, Zemědělská 1, 613 00 Brno, Czech Republic
Romerlabs Division Holding GmbH, Technopark 1, 3430 Tulln, Austria
Biotechnology in Plant Production, IFA-Tulln, BOKU, Konrad Lorenz Str. 20, 3430 Tulln, Austria
Author to whom correspondence should be addressed.
Toxins 2018, 10(3), 111;
Received: 7 February 2018 / Revised: 28 February 2018 / Accepted: 1 March 2018 / Published: 6 March 2018
(This article belongs to the Section Mycotoxins)
PDF [831 KB, uploaded 8 March 2018]


Trichothecene toxins are confirmed or suspected virulence factors of various plant-pathogenic Fusarium species. Plants can detoxify these to a variable extent by glucosylation, a reaction catalyzed by UDP-glucosyltransferases (UGTs). Due to the unavailability of analytical standards for many trichothecene-glucoconjugates, information on such compounds is limited. Here, the previously identified deoxynivalenol-conjugating UGTs HvUGT13248 (barley), OsUGT79 (rice) and Bradi5g03300 (Brachypodium), were expressed in E. coli, affinity purified, and characterized towards their abilities to glucosylate the most relevant type A and B trichothecenes. HvUGT13248, which prefers nivalenol over deoxynivalenol, is also able to conjugate C-4 acetylated trichothecenes (e.g., T-2 toxin) to some degree while OsUGT79 and Bradi5g03300 are completely inactive with C-4 acetylated derivatives. The type A trichothecenes HT-2 toxin and T-2 triol are the kinetically preferred substrates in the case of HvUGT13248 and Bradi5g03300. We glucosylated several trichothecenes with OsUGT79 (HT-2 toxin, T-2 triol) and HvUGT13248 (T-2 toxin, neosolaniol, 4,15-diacetoxyscirpenol, fusarenon X) in the preparative scale. NMR analysis of the purified glucosides showed that exclusively β-D-glucosides were formed regio-selectively at position C-3-OH of the trichothecenes. These synthesized standards can be used to investigate the occurrence and toxicological properties of these modified mycotoxins. View Full-Text
Keywords: Fusarium head blight; phase II detoxification; masked mycotoxin; NMR; cereals Fusarium head blight; phase II detoxification; masked mycotoxin; NMR; cereals

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Michlmayr, H.; Varga, E.; Malachová, A.; Fruhmann, P.; Piątkowska, M.; Hametner, C.; Šofrová, J.; Jaunecker, G.; Häubl, G.; Lemmens, M.; Berthiller, F.; Adam, G. UDP-Glucosyltransferases from Rice, Brachypodium, and Barley: Substrate Specificities and Synthesis of Type A and B Trichothecene-3-O-β-d-glucosides. Toxins 2018, 10, 111.

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