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. [Figure not available: see fulltext.].

Identification of acetylated derivatives of zearalenone as novel plant metabolites by high-resolution mass spectrometry / Righetti, Laura; Dellafiora, Luca; Cavanna, Daniele; Rolli, Enrico; Galaverna, Gianni; Bruni, Renato; Suman, Michele; Dall’Asta, Chiara. - In: ANALYTICAL AND BIOANALYTICAL CHEMISTRY. - ISSN 1618-2642. - 410:22(2018), pp. 5583-5592. [10.1007/s00216-018-1066-y]

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

Righetti, Laura;Dellafiora, Luca;Cavanna, Daniele;Rolli, Enrico;Galaverna, Gianni;Bruni, Renato;Dall’Asta, Chiara
2018

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. [Figure not available: see fulltext.].
Identification of acetylated derivatives of zearalenone as novel plant metabolites by high-resolution mass spectrometry / Righetti, Laura; Dellafiora, Luca; Cavanna, Daniele; Rolli, Enrico; Galaverna, Gianni; Bruni, Renato; Suman, Michele; Dall’Asta, Chiara. - In: ANALYTICAL AND BIOANALYTICAL CHEMISTRY. - ISSN 1618-2642. - 410:22(2018), pp. 5583-5592. [10.1007/s00216-018-1066-y]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2849148
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 3
  • ???jsp.display-item.citation.isi??? 3
social impact