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Article

Controlled Production of Zearalenone-Glucopyranoside Standards with Cunninghamella Strains Using Sulphate-Depleted Media

1
Wageningen Food Safety Research, Wageningen University and Research, Akkermaalsbos 2, 6708 WB Wageningen, The Netherlands
2
Innosieve Diagnostics BV, Nieuwe Kanaal 7A, 6709 PA Wageningen, The Netherlands
3
Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708 WE Wageningen, The Netherlands
*
Author to whom correspondence should be addressed.
Received: 1 May 2021 / Revised: 17 May 2021 / Accepted: 17 May 2021 / Published: 21 May 2021
(This article belongs to the Special Issue Metabolism of Mycotoxins by Animals and Microbes)
In recent years, conjugated mycotoxins have gained increasing interest in food safety, as their hydrolysis in human and animal intestines leads to an increase in toxicity. For the production of zearalenone (ZEN) glycosides reference standards, we applied Cunninghamellaelegans and Cunninghamella echinulata fungal strains. A sulphate-depleted medium was designed for the preferred production of ZEN glycosides. Both Cunninghamella strains were able to produce zearalenone-14-β-D-glucopyranoside (Z14G), zearalenone-16-β-D-glucopyranoside (Z16G) and zearalenone-14-sulphate (Z14S). In a rich medium, Cunninghamellaelegans preferably produced Z14S, while Cunninghamellaechinulata preferably produced Z14G. In the sulphate-depleted medium a dramatic change was observed for Cunninghamellaelegans, showing preferred production of Z14G and Z16G. From 2 mg of ZEN in sulphate-depleted medium, 1.94 mg of Z14G and 0.45 mg of Z16G were produced. Following preparative Liquid Chromatography-Mass Spectrometry (LC-MS) purification, both fractions were submitted to 1H and 13C NMR and High-Resolution Mass Spectrometry (HRMS). These analyses confirmed that the purified fractions were indeed Z14G and Z16G. In conclusion, the presented research shows that a single Cunninghamella strain can be an effective and efficient tool for the controlled biotransformation of ZEN glycosides and other ZEN metabolites. Additionally, the biotransformation method was extended to zearalanone, β-zearalenol and other mycotoxins. View Full-Text
Keywords: modified mycotoxins; zearalenone; zearalanone; β-zearalenol; conjugated; masked; fungi; Cunninghamella; biotransformation modified mycotoxins; zearalenone; zearalanone; β-zearalenol; conjugated; masked; fungi; Cunninghamella; biotransformation
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MDPI and ACS Style

Peters, J.; Ash, E.; Gerssen, A.; Van Dam, R.; Franssen, M.C.R.; Nielen, M.W.F. Controlled Production of Zearalenone-Glucopyranoside Standards with Cunninghamella Strains Using Sulphate-Depleted Media. Toxins 2021, 13, 366. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13060366

AMA Style

Peters J, Ash E, Gerssen A, Van Dam R, Franssen MCR, Nielen MWF. Controlled Production of Zearalenone-Glucopyranoside Standards with Cunninghamella Strains Using Sulphate-Depleted Media. Toxins. 2021; 13(6):366. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13060366

Chicago/Turabian Style

Peters, Jeroen, Edward Ash, Arjen Gerssen, Ruud Van Dam, Maurice C.R. Franssen, and Michel W.F. Nielen 2021. "Controlled Production of Zearalenone-Glucopyranoside Standards with Cunninghamella Strains Using Sulphate-Depleted Media" Toxins 13, no. 6: 366. https://0-doi-org.brum.beds.ac.uk/10.3390/toxins13060366

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