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Zearalenone-malonyl-glucosides as phase II metabolites in plant cell suspension cultures

Kohn, B. N.; Bunzel, M.

Abstract:
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.

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Verlagsausgabe §
DOI: 10.5445/IR/1000118218
Veröffentlicht am 14.10.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Angewandte Biowissenschaften (IAB)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 0009-0352, 1943-3638
KITopen-ID: 1000118218
Erschienen in Cereal chemistry
Verlag American Association of Cereal Chemists
Nachgewiesen in Scopus
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