Interaction of α- and β-zearalenols with β-cyclodextrins.

Miklós Poór,Lajos Szente,Afshin Zand,Sándor Kunsági-Máté,Beáta Lemli

doi:10.3390/molecules22111910

Miklós Poór, Lajos Szente + Show 3 more

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https://doi.org/10.3390/molecules22111910

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Abstract

Zearalenone (ZEN) is a mycotoxin produced by Fusarium fungi. ZEN primarily contaminates different cereals, and exerts a strong xenoestrogenic effect in animals and humans. ZEN is a fluorescent mycotoxin, although molecular interactions and microenvironmental changes significantly modify its spectral properties. During biotransformation, ZEN is converted into α-zearalenol (α-ZOL) and β-zearalenol (β-ZOL), the toxic metabolites of ZEN, which mimick the effect of estrogen. Cyclodextrins (CDs) are host molecules, and have been studied extensively; they can form stable complexes with several mycotoxins, including ZEN. However, information is limited regarding the interactions of CDs with ZOLs. Therefore, we studied the interactions of α- and β-ZOLs with native and six chemically modified β-CDs by fluorescence spectroscopy. Fluorescence enhancement during complex formation, as well as binding constants, were determined. To understand ZOL-CD interactions better, molecular modeling studies were also carried out. Both mycotoxin derivatives formed the most stable complexes with methylated and sulfobutylated CD-derivatives; however, the CD complexes of α-ZOL were significantly stronger than those of β-ZOL. The data presented here indicate which of the chemically modified β-CDs appear more suitable as fluorescence enhancers or as potential mycotoxin binders.

Highlights

Zearalenone (ZEN; Figure 1) is a mycotoxin produced by Fusarium species [1]
The external surface of cyclodextrins is hydrophilic, whereas their interior is hydrophobic, First, fluorescence excitation and emission spectraorofmolecules α- and β-ZOLs were examined under making it possible to accommodate lipophilic structures within this internal cavity different environmental conditions
The results show that the formation of β-ZOL–SBBCD complex requires much higher activation energy than the formation of the five other complexes (Table 5)

Summary

Introduction

Zearalenone (ZEN; Figure 1) is a mycotoxin produced by Fusarium species [1]. ZEN commonly contaminates a variety of different cereals, including maize, wheat, rye, sorghum, and barley.it appears in nuts, spices, milk, edible oils, beer, and drinking water [1,2,3].The wide occurrence of ZEN is associated with its high thermal stability, which makes its elimination from foodstuffs or animal feed difficult [4]. Zearalenone (ZEN; Figure 1) is a mycotoxin produced by Fusarium species [1]. ZEN commonly contaminates a variety of different cereals, including maize, wheat, rye, sorghum, and barley. It appears in nuts, spices, milk, edible oils, beer, and drinking water [1,2,3]. ZEN expresses a strong estrogenic effect in animals and humans; it has been classified as an endocrine disruptor molecule [7]. Its extensive biotransformation gives rise to its reduced metabolites, α-zearalenol (α-ZOL) and β-zearalenol (β-ZOL; Figure 1), which (along with ZEN) are, in turn, conjugated with glucuronic acid [1,8]. In addition to the liver, some other tissues are able

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