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

• Published in: Toxins 2021-05, Vol.13 (6), p.366
• Main Authors: Peters, Jeroen, Ash, Edward, Gerssen, Arjen, Van Dam, Ruud, Franssen, Maurice C R, Nielen, Michel W F
• Format: Article
• Language: English
• Subjects: Biotransformation; Chromatography, Liquid; conjugated; Cunninghamella; Cunninghamella - chemistry; Cunninghamella - metabolism; Cunninghamella echinulata; Cunninghamella elegans; Depletion; Food safety; Fungi; Glycosides; Glycosides - biosynthesis; Intestine; Liquid chromatography; Magnetic Resonance Spectroscopy; masked; Mass Spectrometry; Mass spectroscopy; Metabolites; modified mycotoxins; Mycotoxins; NMR; Nuclear magnetic resonance; Retention; Spectroscopy; Sulfates; Toxicity; Worms; zearalanone; Zearalenone; Zearalenone - chemistry; Zearalenone - metabolism; β-zearalenol
• ISSN: 2072-6651; 2072-6651
• DOI: 10.3390/toxins13060366

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 and fungal strains. A sulphate-depleted medium was designed for the preferred production of ZEN glycosides. Both 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, preferably produced Z14S, while preferably produced Z14G. In the sulphate-depleted medium a dramatic change was observed for , 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 H and C 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 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.