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Identification of acetylated derivatives of zearalenone as novel plant metabolites by high-resolution mass spectrometry

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Abstract

Zearalenone (ZEN) major biotransformation pathways described so far are based on glycosylation and sulfation, although acetylation of trichothecenes has been reported as well. We investigated herein the ZEN acetylation metabolism route in micropropagated durum wheat leaf, artificially contaminated with ZEN. We report the first experimental evidence of the formation of novel ZEN acetylated forms in wheat, attached both to the aglycone backbone as well as on the glucose moiety. Thanks to the advantages provided by high-resolution mass spectrometry, identification and structure annotation of 20 metabolites was achieved. In addition, a preliminary assessment of the toxicity of the annotated metabolites was performed in silico focusing on the toxicodynamic of ZEN group toxicity. All the metabolites showed a worse fitting within the estrogen receptor pocket in comparison with ZEN. Nevertheless, possible hydrolysis to the respective parent compounds (i.e., ZEN) may raise concern from the health perspective because these are well-known xenoestrogens. These results further enrich the biotransformation profile of ZEN, providing a helpful reference for assessing the risks to animals and humans.

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Acknowledgements

The authors acknowledge with gratitude Mr. Dante Catellani from Advanced Laboratory Research (Barilla G.R. F.lli SpA) for his technical assistance.

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Authors and Affiliations

  1. Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124, Parma, Italy

    Laura Righetti, Luca Dellafiora, Daniele Cavanna, Gianni Galaverna, Renato Bruni & Chiara Dall’Asta

  2. Barilla G.R. F.lli SpA, Advanced Laboratory Research, Via Mantova 166, 43122, Parma, Italy

    Daniele Cavanna & Michele Suman

  3. Deparment of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Via Università 12, 43121, Parma, Italy

    Enrico Rolli

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  1. Laura Righetti
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  2. Luca Dellafiora
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  3. Daniele Cavanna
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  5. Gianni Galaverna
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  8. Chiara Dall’Asta
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Correspondence to Chiara Dall’Asta.

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Conflict of interest

Michele Suman is employee of Barilla G.R. F.lli SpA. Daniele Cavanna has received a PhD grant by Barilla G.R. F.lli SpA. All the other authors declare that they have no conflict of interest.

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Published in the topical collection Food Safety Analysis with guest editor Steven J. Lehotay.

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Righetti, L., Dellafiora, L., Cavanna, D. et al. Identification of acetylated derivatives of zearalenone as novel plant metabolites by high-resolution mass spectrometry. Anal Bioanal Chem 410, 5583–5592 (2018). https://doi.org/10.1007/s00216-018-1066-y

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  • DOI: https://doi.org/10.1007/s00216-018-1066-y

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