Enzymatic Synthesis of Modified <i>Alternaria</i> Mycotoxins Using a Whole-Cell Biotransformation System

Reference standards for <i>Alternaria</i> mycotoxins are rarely available, especially the modified mycotoxins alternariol-3-glucoside (AOH-3-G), alternariol-9-glucoside (AOH-9-G), and alternariol monomethylether-3-glucoside (AME-3-G). To obtain these three glucosides as analytical standa...

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Bibliographic Details
Main Authors: Sophie Scheibenzuber, Thomas Hoffmann, Isabelle Effenberger, Wilfried Schwab, Stefan Asam, Michael Rychlik
Format: Article
Language:English
Published: MDPI AG 2020-04-01
Series:Toxins
Subjects:
Online Access:https://www.mdpi.com/2072-6651/12/4/264
Description
Summary:Reference standards for <i>Alternaria</i> mycotoxins are rarely available, especially the modified mycotoxins alternariol-3-glucoside (AOH-3-G), alternariol-9-glucoside (AOH-9-G), and alternariol monomethylether-3-glucoside (AME-3-G). To obtain these three glucosides as analytical standards for method development and method validation, alternariol and alternariol monomethylether were enzymatically glycosylated in a whole-cell biotransformation system using a glycosyltransferase from strawberry (<i>Fragaria x ananassa</i>), namely UGT71A44, expressed in <i>Escherichia coli</i> (<i>E. coli)</i>. The formed glucosides were isolated, purified, and structurally characterized. The exact amount of the isolated compounds was determined using high-performance liquid chromatography with UV-detection (HPLC-UV) and quantitative nuclear resonance spectroscopy (qNMR). This method has proved to be highly effective with biotransformation rates of 58% for AOH-3-G, 5% for AOH-9-G, and 24% for AME-3-G.
ISSN:2072-6651