TY - JOUR
T1 - Identification of acetylated derivatives of zearalenone as novel plant metabolites by high-resolution mass spectrometry
AU - Righetti, L.
AU - Dellafiora, Luca
AU - Cavanna, Daniele
AU - Rolli, Enrico
AU - Galaverna, Gianni
AU - Bruni, Renato
AU - Suman, Michele
AU - Dall’Asta, Chiara
PY - 2018/9/1
Y1 - 2018/9/1
N2 - 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.].
AB - 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.].
KW - Acetylation
KW - Food safety
KW - Masked mycotoxins
KW - Plant biotransformation
U2 - 10.1007/s00216-018-1066-y
DO - 10.1007/s00216-018-1066-y
M3 - Article
C2 - 29707753
AN - SCOPUS:85046097937
SN - 1618-2642
VL - 410
SP - 5583
EP - 5592
JO - Analytical and Bioanalytical Chemistry
JF - Analytical and Bioanalytical Chemistry
IS - 22
ER -