Abstract
Zearalenone (ZEN) is a Fusarium-derived xenoestrogenic mycotoxin. In plants, zearalenone-14-O-β-d-glucoside (Z14G) is the major conjugated metabolite of ZEN, and is a masked mycotoxin. Masked mycotoxins are plant-modified derivatives, which are not routinely screened in food and feed samples. Cyclodextrins (CDs) are cyclic oligosaccharides built up from D-glucopyranose units. CDs can form stable host–guest type complexes with lipophilic molecules (e.g., with some mycotoxins). In this study, the interaction of Z14G with native and chemically modified β- and γ-CDs was examined employing fluorescence spectroscopy and molecular modeling. Furthermore, the removal of Z14G from aqueous solution by insoluble β-CD bead polymer (BBP) was also tested. Our results demonstrate that Z14G forms the most stable complexes with γ-CDs under acidic and neutral conditions (K ≈ 103 L/mol). Among the CDs tested, randomly methylated γ-CD induced the highest increase in the fluorescence of Z14G (7.1-fold) and formed the most stable complexes with the mycotoxin (K = 2 × 103 L/mol). Furthermore, BBP considerably reduced the Z14G content of aqueous solution. Based on these observations, CD technology seems a promising tool to improve the fluorescence analytical detection of Z14G and to discover new mycotoxin binders which can also remove masked mycotoxins (e.g., Z14G).
Highlights
Mycotoxins are toxic secondary metabolites of filamentous fungi, occurring in several food products [1]
Zearalenone (ZEN) is a Fusarium-derived mycotoxin; it appears in cereals, beer, milk, spices, etc. [3,4]
Plants possess detoxification system, which protects them from harmful xenobiotics, including mycotoxins [10,11,12]
Summary
Mycotoxins are toxic secondary metabolites of filamentous fungi, occurring in several food products (e.g., cereals, meat, fruits, and numerous beverages) [1]. Due to the consumption of contaminated food, mycotoxin exposure induces health problems in both animals and humans [2]. Zearalenone (ZEN) is a Fusarium-derived mycotoxin; it appears in cereals (e.g., in maize), beer, milk, spices, etc. Despite its non-steroidal structure, ZEN can cause reproductive disorders in animals and humans, due to its xenoestrogenic effect [5,6,7]. Plants possess detoxification system, which protects them from harmful xenobiotics, including mycotoxins [10,11,12]. The formation of hydrophilic conjugates of mycotoxins is a common detoxification process in plants [11,12], such as the glucose conjugation of ZEN, from which zearalenone-14-O-β-d-glucoside is the main product
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