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Toxins 2018, 10(3), 111; https://doi.org/10.3390/toxins10030111

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

1
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna, (BOKU), Konrad Lorenz Str. 24, 3430 Tulln, Austria
2
Department of Food Chemistry and Toxicology, University of Vienna, Währinger Str. 38, 1090 Vienna, Austria
3
Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), BOKU, Konrad Lorenz Str. 20, 3430 Tulln, Austria
4
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, 1060 Vienna, Austria
5
CEST Kompetenzzentrum für elektrochemische Oberflächentechnologie GmbH, Viktor-Kaplan-Str. 2, 2700 Wiener Neustadt, Austria
6
Department of Chemistry and Biochemistry, Mendel University in Brno, Zemědělská 1, 613 00 Brno, Czech Republic
7
Romerlabs Division Holding GmbH, Technopark 1, 3430 Tulln, Austria
8
Biotechnology in Plant Production, IFA-Tulln, BOKU, Konrad Lorenz Str. 20, 3430 Tulln, Austria
*
Author to whom correspondence should be addressed.
Received: 7 February 2018 / Revised: 28 February 2018 / Accepted: 1 March 2018 / Published: 6 March 2018
(This article belongs to the Section Mycotoxins)
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Abstract

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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