Cyclodextrins Can Entrap Zearalenone-14-Glucoside: Interaction of the Masked Mycotoxin with Cyclodextrins and Cyclodextrin Bead Polymer

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).

Interactions of zearalanone, α-zearalanol, β-zearalanol, zearalenone-14-sulfate, and zearalenone-14-glucoside with serum albumin

“…I 0 and I are the fluorescence emission signal of albumin in the absence and presence of mycotoxins, respectively. Z14S and Z14G exert fluorescence; their excitation and emission spectra, under different environmental conditions, have been reported previously (Faisal et al 2019 , 2020 ). Under the applied circumstances, the emission signals of Z14S and Z14G did not interfere with the evaluation of fluorescence studies (e.g., the emission maxima of albumins and warfarin-HSA complex).…”

Interactions of Mycotoxin Alternariol with Cyclodextrins and Its Removal from Aqueous Solution by Beta-Cyclodextrin Bead Polymer

“…Furthermore, CDs can also entrap the masked mycotoxin zearalenone-14- O -β-D-glucoside. BBP significantly reduced the zearalenone-14- O -β-D-glucoside content of aqueous solution [55]. Despite AOH-BCD complex showed similar binding constant in the pH range tested (pH 3.0–10.0; see in Section 3.3 and Section 3.6), BBP proved to be a less effective mycotoxin binder at pH 10.0 compared to other conditions examined (pH 3.0–7.4).…”

Peering into the Kaleidoscope of Cyclodextrins

“…In another work, HPBCD inclusion is used to sharply increase the antioxidant power of idebenone, an analogue of coenzyme Q10 [ 7 ]. Cyclodextrins can also help keep food safe from contamination with mycotoxins by contributing to their detection and entrapment, as reported by Faisal et al [ 8 ] and Fliszár-Nyúl et al [ 9 ].…”