Abstract
The xenoestrogenic mycotoxin zearalenone is a common food contaminant produced by Fusarium strains. The modified mycotoxin zearalenone-14-sulfate (Z14S) is formed in both fungi and mammals during the biotransformation of zearalenone. Cyclodextrins (CD) are cyclic oligosaccharides which can form host-guest type complexes with some mycotoxins, including zearalenone, zearalenols, and zearalenone-14-glucoside. As a result of the complex formation, the fluorescence signal of these mycotoxins strongly increases. Furthermore, CD polymers seem to be suitable for the extraction of some mycotoxins from aqueous solutions and beverages. In this study, the interaction of Z14S with CDs and soluble CD polymers was examined with fluorescence spectroscopy and molecular modeling. Furthermore, the removal of Z14S from aqueous solution by β-CD bead polymer (BBP) was also tested. Our results demonstrate the formation of stable Z14S-CD complexes (K = 0.1 to 5.0 × 104 L/mol). Dimethyl-β-CD (DIMEB) produced the most stable complexes with Z14S at pH 5.0 and 7.4. At pH 10.0, the binding constant of Z14S-DIMEB complex decreased and quaternary ammonium-β-CD showed similar affinity toward the mycotoxin than DIMEB. In addition, Z14S was successfully removed from aqueous solutions by BBP. Considering the above-listed observations, besides the parent mycotoxins, some of their modified/masked derivatives can also interact with CDs.
Highlights
Zearalenone is a toxic secondary metabolite of Fusarium species, which frequently contaminate grains and other commodities [1,2]
Mycotoxin conjugates produced by plants are designated as masked mycotoxins, while other compounds formed by structural modification of the parent mycotoxins are referred to modified mycotoxins [5,6]
Despite the fact that modified mycotoxins commonly appear in grains and in other commodities, we have only limited information regarding their interactions with CDs
Summary
Zearalenone is a toxic secondary metabolite of Fusarium species, which frequently contaminate grains (especially maize) and other commodities (e.g., fruits, meat, pastry, and beverages) [1,2]. Zearalenone is highly biotransformed by mammals, plants, and fungi, during which reduced (zearalenols, zearalanone, and zearalanols) and conjugated metabolites are formed [4,5]. Mycotoxin conjugates produced by plants are designated as masked mycotoxins, while other compounds formed by structural modification of the parent mycotoxins are referred to modified mycotoxins [5,6]. Zearalenone-14-sulfate (Z14S; termed as zearalenone-4sulfate; Fig. 1) is produced by different strains (e.g., Aspergillus oryzae, Fusarium and Rhizopus species) as a fungal metabolite or by sulfotransferase (SULT) enzyme during the phase II metabolism of zearalenone in mammals [4,5]. The sulfate conjugation results in less toxic derivatives, due to the increased hydrophilicity of the metabolite formed. We need to consider Z14S as a toxic compound to zearalenone, and should take into consideration during the health risk assessment of the exposure [5]
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