Cyclodextrins can entrap the masked mycotoxin zearalenone-14-glucoside

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Mycotoxins are toxic secondary metabolites of filamentous fungi. Zearalenone is a xenoestrogenic mycotoxin produced by Fusarium species. Plants commonly form less toxic hydrophilic conjugates from mycotoxins; these are called as “masked mycotoxins”, due to their challenging analytical determination. Zearalenone-14-glucoside (Z14G) is one of the most dominant masked mycotoxin produced from zearalenone. Z14G exerts lower toxicity than zearalenone; however, zearalenone is formed after its deglycosylation in the gastrointestinal tract. As a recent study highlighted, cyclodextrins (CDs) can entrap Z14G and insoluble beta-CD bead polymer successfully decrease the Z14G content of aqueous solutions [1]. Previous studies reported the significant interactions of CDs with zearalenone and zearalenols [2-5]. The complex formation with CDs results in the strong increase in the fluorescence signal of these mycotoxins. Furthermore, it was also demonstrated that insoluble beta-CD bead polymer can effectively remove zearalenone from aqueous buffers and from spiked corn beer samples [6]. Despite the previous observations regarding zearalenone and zearalenols, it was not obvious that CDs can accommodate Z14G because the masked mycotoxin possesses a large hydrophilic glucose part. In a recent study, the interaction of Z14G with beta- and gamma-CDs (native as well as methyl and hydroxypropyl derivatives) was tested [1]. Z14G formed the most stable complexes with gamma-CDs under acidic and close to neutral conditions (K ≈ 10^3 L/mol), during which the fluorescence signal of Z14G considerably increased. In addition, insoluble beta-CD bead polymer strongly reduced the Z14G content of aqueous solutions [1]. Based on these observations, CD technology may be a promising tool to develop mycotoxin binders which can remove both parent mycotoxins and some of their metabolites (e.g., masked mycotoxins) from aqueous solutions (including beverages).

References: [1] Faisal Z, Fliszár-Nyúl E, Dellafiora L, Galaverna G, Dall’Asta C, Lemli B, Kunsági-Máté S, Szente L, Poór M, Cyclodextrins can entrap zearalenone-14-glucoside: Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer. Biomolecules 2019, 9, E354. (;

[2] Dall’Asta C, Faccini A, Galaverna G, Corradini R, Dossena A, Marchelli R, Complexation of the mycotoxin zearalenone with b-cyclodextrin: study of the interaction and first promising applications, Mycotoxin Res. 2008, 24, 14-18. (;

[3] Dall’Asta C, Faccini A, Galaverna G, Corradini R, Dossena A, Marchelli R, Complexation of zearalenone and zearalenols with native and modified b-cyclodextrins, J. Incl. Phenom. Macrocycl. Chem. 2009, 64, 331–340. (;

[4] Poór M, Kunsági-Máté S, Sali N, Kőszegi T, Szente L, Peles-Lemli B, Interactions of zearalenone with native and chemically modified cyclodextrins and their potential utilization. J. Photochem. Photobiol. B 2015, 151, 63-68. (;

[5] Poór M, Zand A, Szente L, Lemli B, Kunsági-Máté S, Interaction of α- and β-zearalenols with β-cyclodextrins. Molecules 2017, 22, E1910. (;

[6] Poór M, Faisal Z, Zand A, Bencsik T, Lemli B, Kunsági-Máté S, Szente L, Removal of zearalenone and zearalenols from aqueous solutions using insoluble beta-cyclodextrin bead polymer. Toxins 2018, 10, E216. (

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