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.

中文翻译：

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高分辨率质谱鉴定玉米赤霉烯酮的乙酰化衍生物作为新型植物代谢产物

迄今为止描述的玉米赤霉烯酮（ZEN）主要生物转化途径均基于糖基化和硫酸化，尽管也已经报道了毛果霉素的乙酰化。我们在这里研究了人工繁殖的ZEN污染的硬粒硬质小麦叶片中的ZEN乙酰化代谢途径。我们报道了小麦中新的ZEN乙酰化形式的形成的第一个实验证据，既附着在糖苷配基主链上，又附着在葡萄糖部分上。由于高分辨率质谱法提供的优势，实现了20种代谢物的鉴定和结构注释。另外，对注释的代谢物的毒性的初步评估是在计算机上进行的，重点是ZEN组毒性的毒性动力学。与ZEN相比，所有代谢物在雌激素受体袋中的拟合都较差。然而，从健康的角度看，可能水解为相应的母体化合物（即ZEN）可能引起关注，因为它们是众所周知的异种雌激素。这些结果进一步丰富了ZEN的生物转化谱，为评估对动物和人类的风险提供了有用的参考。