Study on the uptake and deglycosylation of the masked forms of zearalenone in human intestinal Caco-2 cells.
This study investigated for the first time the intestinal transfer of two modified forms of zearalenone (ZEN), zearalenone-14-glucoside (ZEN14Glc) and zearalenone-16-glucoside (ZEN16Glc), using polarized monolayers of Caco-2 cells. The cells were apically exposed to 40 μM of ZEN14Glc, ZEN16Glc and ZEN, separately. Results showed that, after apical administration, ZEN14Glc and ZEN16Glc can be detected in cellular extracts indicating uptake by intestinal cells. Moreover, the glucosylated forms were cleaved to release ZEN, with a different cleavage ability for the two conjugated isomers. In particular, ZEN16Glc seems to be less prone to deglycosylation compared to ZEN14Glc, probably on account of an increased steric hindrance. We could show that human cytosolic β-glucosidase is able to cleave ZEN14Glc liberating ZEN, but is unable to cleave ZEN16Glc.All metabolites could cross the cell membrane and be detected in the apical compartment, while ZEN was also found in the basolateral compartment together with the modified mycotoxin form.
Department of Food Science, University of Parma, Via Parco Area delle Scienze 49/A, 43124 Parma, Italy.
Martina
M
Cirlini
Department of Biomedical, Biotechnological and Translational Science - S.Bi.Bi.T, Via Gramsci 14, 43125 Parma, Italy.
Amelia
A
Barilli
Department of Food Science, University of Parma, Via Parco Area delle Scienze 49/A, 43124 Parma, Italy.
Gianni
G
Galaverna
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Str. 24, 3430 Tulln, Austria.
Herbert
H
Michlmayr
Department of Applied Genetics and Cell Biology, University of Natural Resources and Life Sciences, Vienna (BOKU), Konrad-Lorenz-Str. 24, 3430 Tulln, Austria.
Gerhard
G
Adam
Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department of Agrobiotechnology (IFA-Tulln), BOKU, Konrad-Lorenz-Str. 20, 3430 Tulln, Austria.
Franz
F
Berthiller
Department of Food Science, University of Parma, Via Parco Area delle Scienze 49/A, 43124 Parma, Italy. Electronic address: chiara.dallasta@unipr.it.
Chiara
C
Dall'Asta
D018938:Caco-2 Cells; D002470:Cell Survival / Q000187:drug effects*; D002851:Chromatography, High Pressure Liquid; D004968:Estrogens, Non-Steroidal / Q000737:chemistry / Q000494:pharmacology*; D006031:Glycosylation; D006801:Humans; D007413:Intestinal Mucosa / Q000378:metabolism*; D007422:Intestines / Q000187:drug effects; D053719:Tandem Mass Spectrometry; D015025:Zearalenone / Q000737:chemistry* / Q000494:pharmacology*; D001617:beta-Glucosidase / Q000378:metabolism*
D004968:Estrogens, Non-Steroidal; D015025:Zearalenone; C424266:GBA3 protein, human; D001617:beta-Glucosidase
Enzymatic cleavage; Masked mycotoxins; Modified mycotoxins; Small intestine; Zearalenone glucoside