Dellafiora Luca, Ruotolo Roberta, Perotti Alessio, Cirlini Martina, Galaverna Gianni, Cozzini Pietro, Buschini Annamaria, Dall'Asta Chiara
Department of Food and Drug, University of Parma, Viale delle Scienze 95/A, 43124, Parma, Italy.
Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Viale delle Scienze 11/A, 43124, Parma, Italy.
Food Chem Toxicol. 2017 Oct;108(Pt A):257-266. doi: 10.1016/j.fct.2017.07.062. Epub 2017 Aug 12.
The mycotoxin zearalenone may contaminate food and feed worldwide upon infections by Fusarium spp. of plants and raw materials intended for human and animal consumption. Currently, contamination by zearalenone and congeners pose concern for health due to xenoestrogenic effects. However, while zearalenone and the main reduced metabolites are well-known xenoestrogens, some plant metabolites that may enter the food chain have been observed aside. Among them, zearalenone-14-glucoside may be abundant in the edible parts of infected plants, thereby entering significantly the human diet and animal feeding. On the basis of previous works, the lack of xenoestrogenicity for this compound per se was taken for granted, while neglecting the direct proof of estrogenic activity and considering the hydrolysis as a possible source of estrogenically active metabolites. The present work investigated the xenoestrogenicity of zearalenone-14-glucoside, in comparison to zearalenone, deepening the underlying molecular mechanisms through an integrated in vitro/in silico approach. On the basis of our results, zearalenone-14-glucoside effectively stimulated a xenoestrogenic response in cells, but such stimulus can be entirely attributable to the hydrolysis phenomenon, as the glycosylated form turned out to be unable to effectively bind and activate the estrogens receptors.
霉菌毒素玉米赤霉烯酮可能会在全球范围内污染食品和饲料，这是由于植物以及供人类和动物食用的原材料受到镰刀菌属感染所致。目前，玉米赤霉烯酮及其同系物的污染因其外源性雌激素效应而引发了对健康问题的关注。然而，虽然玉米赤霉烯酮及其主要的还原代谢产物是众所周知的外源性雌激素，但也观察到一些可能进入食物链的植物代谢产物。其中，玉米赤霉烯酮 -14-葡萄糖苷在受感染植物的可食用部分中可能含量丰富，从而大量进入人类饮食和动物饲料中。基于以往的研究，人们理所当然地认为这种化合物本身缺乏外源性雌激素活性，却忽略了雌激素活性的直接证据，并且将水解视为雌激素活性代谢产物的一个可能来源。本研究通过体外/计算机模拟相结合的方法，与玉米赤霉烯酮相比，研究了玉米赤霉烯酮 -14-葡萄糖苷的外源性雌激素活性，并深入探讨了其潜在的分子机制。根据我们的研究结果，玉米赤霉烯酮 -14-葡萄糖苷能有效刺激细胞产生外源性雌激素反应，但这种刺激完全归因于水解现象，因为糖基化形式无法有效结合并激活雌激素受体。
