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Toxins 2018, 10(3), 104; https://doi.org/10.3390/toxins10030104

Biosynthesis and Characterization of Zearalenone-14-Sulfate, Zearalenone-14-Glucoside and Zearalenone-16-Glucoside Using Common Fungal Strains

1
Department Analytical Chemistry, Reference Materials, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter-Str. 11, 12489 Berlin, Germany
2
Department Materials and the Environment, Bundesanstalt für Materialforschung und-prüfung (BAM), Unter den Eichen 87, 12205 Berlin, Germany
3
Institute of Food Chemistry, Hamburg School of Food Science, University of Hamburg, Grindelallee 117, 20146 Hamburg, Germany
4
German Federal Institute for Risk Assessment (BfR), Max-Dohrn-Str. 8-10, 10589 Berlin, Germany
*
Author to whom correspondence should be addressed.
Received: 29 January 2018 / Revised: 23 February 2018 / Accepted: 24 February 2018 / Published: 1 March 2018
(This article belongs to the Special Issue Recent Advances in Fusarium Research)
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Abstract

Zearalenone (ZEN) and its phase II sulfate and glucoside metabolites have been detected in food and feed commodities. After consumption, the conjugates can be hydrolyzed by the human intestinal microbiota leading to liberation of ZEN that implies an underestimation of the true ZEN exposure. To include ZEN conjugates in routine analysis, reliable standards are needed, which are currently not available. Thus, the aim of the present study was to develop a facilitated biosynthesis of ZEN-14-sulfate, ZEN-14-glucoside and ZEN-16-glucoside. A metabolite screening was conducted by adding ZEN to liquid fungi cultures of known ZEN conjugating Aspergillus and Rhizopus strains. Cultivation conditions and ZEN incubation time were varied. All media samples were analyzed for metabolite formation by HPLC-MS/MS. In addition, a consecutive biosynthesis was developed by using Fusarium graminearum for ZEN biosynthesis with subsequent conjugation of the toxin by utilizing Aspergillus and Rhizopus species. ZEN-14-sulfate (yield: 49%) is exclusively formed by Aspergillus oryzae. ZEN-14-glucoside (yield: 67%) and ZEN-16-glucoside (yield: 39%) are formed by Rhizopus oryzae and Rhizopus oligosporus, respectively. Purities of ≥73% ZEN-14-sulfate, ≥82% ZEN-14-glucoside and ≥50% ZEN-16-glucoside were obtained by 1H-NMR. In total, under optimized cultivation conditions, fungi can be easily utilized for a targeted and regioselective synthesis of ZEN conjugates. View Full-Text
Keywords: mycotoxin; zearalenone; conjugate; biosynthesis; Fusarium; Aspergillus; Rhizopus mycotoxin; zearalenone; conjugate; biosynthesis; Fusarium; Aspergillus; Rhizopus
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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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Borzekowski, A.; Drewitz, T.; Keller, J.; Pfeifer, D.; Kunte, H.-J.; Koch, M.; Rohn, S.; Maul, R. Biosynthesis and Characterization of Zearalenone-14-Sulfate, Zearalenone-14-Glucoside and Zearalenone-16-Glucoside Using Common Fungal Strains. Toxins 2018, 10, 104.

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