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Zearalenone‐malonyl‐glucosides as phase II metabolites in plant cell suspension cultures
Author(s) -
Kohn Beate N.,
Bunzel Mirko
Publication year - 2021
Publication title -
cereal chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.558
H-Index - 100
eISSN - 1943-3638
pISSN - 0009-0352
DOI - 10.1002/cche.10273
Subject(s) - zearalenone , chemistry , mycotoxin , glucoside , nuclear magnetic resonance spectroscopy , chromatography , stereochemistry , biochemistry , food science , medicine , alternative medicine , pathology
Background and objectives Conjugation of mycotoxins in the phase II metabolism of plants results in modified mycotoxins such as glucosides and malonyl‐glucosides. However, malonyl‐glucosides have not yet been completely elucidated for zearalenone (ZEN). Thus, the aim of this study was to produce and isolate malonyl‐glucosides of ZEN for an unambiguous identification by NMR spectroscopy. Findings Zearalenone was incubated in plant cell suspension cultures of wheat, soy, and tobacco, and phase II metabolites were analyzed by using LC‐DAD‐MS, ‐HRMS, and NMR spectroscopy. Four main metabolites of ZEN were detected in the cell extracts and identified as two glucosides (attached in positions 14 and 16) and their 6´‐malonyl derivatives. Conclusions Zearalenone‐malonyl‐glucosides should be incorporated in future analyses of modified mycotoxins because of their potential relevance for food and feed safety. Significance and novelty For the first time, the structures of the two malonyl‐glucosides of ZEN were unambiguously identified by NMR spectroscopy after preparative isolation as 14‐ O ‐(6’‐ O ‐malonyl‐β‐ D ‐glucopyranosyl)ZEN and 16‐ O ‐(6’‐ O ‐malonyl‐β‐ D ‐glucopyranosyl)ZEN.