Interaction of glucoside and sulfate metabolites of alternariol and alternariol-9-monomethylether with cyclodextrins: Extraction of the masked/modified derivatives with beta-cyclodextrin bead polymer

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Alternariol (AOH) and alternariol-9-monomethylether (AME) are emerging mycotoxins produced by Alternaria molds. Besides the parent mycotoxins, the presence of their modified/masked derivatives – including alternariol-3-sulfate (AS), alternariol-9-monomethylether-3-sulfate (AMS), alternariol-3-glucoside (AG), and alternariol-9-monomethylether-3-glucoside (AMG) – has also been reported as contaminants in certain foodstuffs. Previous studies demonstrated that AOH forms highly stable complex with sugammadex (K = 4.8 × 104 L/mol) [1], and AOH can be effectively extracted from aqueous solutions (and from wine samples) by insoluble (but water-swellable) beta-cyclodextrin bead polymer (BBP) [2,3]. In addition, some cyclodextrins proved to be protective vs. AOH-induced toxicity in cell experiments and in zebrafish embryos [1].

In recent studies, the interaction of sugammadex and BBP was examined with AS, AG, AME, AMS, and AMG [4,5]. Sulfate (AS, AMS) and glucoside (AG, AMG) metabolites formed moderately stable complexes with sugammadex (K ≈ 103 L/mol), and the binding constant of AME-sugammadex complex (K = 1.1 × 104 L/mol) was also lower compared to AOH-sugammadex. However, BBP successfully extracted AS, AMS, and AME from aqueous solution, causing approximately 95% decrease in the toxin content. Nevertheless, the polymer was less effective in the removal of AG and AMG, resulting in approximately 85% and 75% decreases in the toxin content, respectively [4,5].

These observations are in agreement with the previous results demonstrated that BBP can very effectively extract zearalenone [6] and zearalenone-14-sulfate [7] from aqueous matrices, while the polymer was less successful in the removal of zearalenone-14-glucoside [8]. Regarding glucoside derivatives, the presence of the bulky, hydrophilic substituent may interfere with the accommodation of the guest molecule in the apolar cyclodextrin cavity.  

The above-listed observations demonstrate that BBP can strongly decrease the levels of methyl (AME) and sulfate (AS, AMS) derivatives of AOH in aqueous solutions, and the polymer can also reduce the concentrations of glucoside (AG, AMG) metabolites. These data underline that cyclodextrin technology may be suitable for the development of new mycotoxin binders, which can be considered in analytical extraction and/or in the removal of certain mycotoxins and their masked/modified derivatives from contaminated beverages.


[1] Fliszár-Nyúl E., Bock I., Csepregi R., Szente L., Szabó I., Csenki Z., Poór M., Testing the protective effects of cyclodextrins vs. alternariol-induced acute toxicity in HeLa cells and in zebrafish embryos. Environmental Toxicology and Pharmacology 95 (2022) 103965.

[2] Fliszár-Nyúl E., Lemli B., Kunsági-Máté S., Szente L., Poór M., Interactions of mycotoxin alternariol with cyclodextrins and its removal from aqueous solution by beta-cyclodextrin bead polymer. Biomolecules 9 (2019) 428.

[3] Fliszár-Nyúl E., Szabó Á., Szente L., Poór M., Extraction of mycotoxin alternariol from red wine and from tomato juice with beta-cyclodextrin bead polymer. Journal of Molecular Liquids 319 (2020) 114180.

[4] Lemli B., Vilmányi P., Fliszár-Nyúl E., Zsidó B.Z., Hetényi C., Szente L., Poór M., Testing serum albumins and cyclodextrins as potential binders of the mycotoxin metabolites alternariol-3-sulfate, alternariol-9-monomethylether, and alternariol-9-monomethylether-3-sulfate. International Journal of Molecular Sciences 23 (2022) 14353.

[5] Poór M., Lemli B., Vilmányi P., Dombi Á., Nagymihály Z., Both E.B., Lambert N., Czömpöly T., Szente L., Probing serum albumins and cyclodextrins as binders of the mycotoxin metabolites alternariol-3-glucoside, alternariol-9-monomethylether-3-glucoside, and zearalenone-14-glucuronide. Metabolites 13 (2023) 446.

[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 10 (2018) 216.

[7] Faisal Z., Fliszár-Nyúl E., Dellafiora L., Galaverna G., Dall’Asta C., Lemli B., Kunsági-Máté S., Szente L., Poór M., Interaction of zearalenone-14-sulfate with cyclodextrins and the removal of the modified mycotoxin from aqueous solution by beta-cyclodextrin bead polymer. Journal of Molecular Liquids 310 (2020) 113236.

[8] 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 9 (2019) 354.

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