Cyclodextrins can entrap zearalenone-14-glucoside: Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer

Zelma Faisal, Eszter Fliszár-Nyúl, Luca Dellafiora, Gianni Galaverna, Chiara Dall’Asta, Beáta Lemli, S. Kunsági-Máté, Lajos Szente, Miklós Poór

Research output: Contribution to journalArticle

1 Citation (Scopus)

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).

Original languageEnglish
Article number354
JournalBiomolecules
Volume9
Issue number8
DOIs
Publication statusPublished - Aug 1 2019

Fingerprint

Zearalenone
Mycotoxins
Glucosides
Cyclodextrins
Polymers
Fluorescence
cyclodextrin polymer
Molecular modeling
Fluorescence Spectrometry
Fluorescence spectroscopy
Fusarium
Metabolites
Oligosaccharides
Binders

Keywords

  • Cyclodextrin bead polymer
  • Cyclodextrins
  • Fluorescence spectroscopy
  • Host–guest interaction
  • Masked mycotoxin
  • Mycotoxin binder
  • Toxin removal
  • Zearalenone-14-glucoside

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

Cite this

Faisal, Z., Fliszár-Nyúl, E., Dellafiora, L., Galaverna, G., Dall’Asta, C., Lemli, B., ... Poór, M. (2019). Cyclodextrins can entrap zearalenone-14-glucoside: Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer. Biomolecules, 9(8), [354]. https://doi.org/10.3390/biom9080354

Cyclodextrins can entrap zearalenone-14-glucoside : Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer. / Faisal, Zelma; Fliszár-Nyúl, Eszter; Dellafiora, Luca; Galaverna, Gianni; Dall’Asta, Chiara; Lemli, Beáta; Kunsági-Máté, S.; Szente, Lajos; Poór, Miklós.

In: Biomolecules, Vol. 9, No. 8, 354, 01.08.2019.

Research output: Contribution to journalArticle

Faisal, Z, Fliszár-Nyúl, E, Dellafiora, L, Galaverna, G, Dall’Asta, C, Lemli, B, Kunsági-Máté, S, Szente, L & Poór, M 2019, 'Cyclodextrins can entrap zearalenone-14-glucoside: Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer', Biomolecules, vol. 9, no. 8, 354. https://doi.org/10.3390/biom9080354
Faisal, Zelma ; Fliszár-Nyúl, Eszter ; Dellafiora, Luca ; Galaverna, Gianni ; Dall’Asta, Chiara ; Lemli, Beáta ; Kunsági-Máté, S. ; Szente, Lajos ; Poór, Miklós. / Cyclodextrins can entrap zearalenone-14-glucoside : Interaction of the masked mycotoxin with cyclodextrins and cyclodextrin bead polymer. In: Biomolecules. 2019 ; Vol. 9, No. 8.
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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).",
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AU - Galaverna, Gianni

AU - Dall’Asta, Chiara

AU - Lemli, Beáta

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AU - Poór, Miklós

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