Estrogenicity of novel phase I and phase II metabolites of zearalenone and cis-zearalenone.
Zearalenone and its cis-isomer, cis-zearalenone, are nonsteroidal mycotoxins that elicit an estrogenic response upon binding to the estrogen receptor. This study compares the estrogenicity of eleven congeners including novel metabolites as 15-OH-zearalenone, zearalenone-14-sulfate, α-cis-zearalenol and β-cis-zearalenol using the E-Screen assay. Overall, a change in the configuration from trans to cis retains significant estrogenic activity. In contrast, alterations of the aromatic moiety including hydroxylation and sulfation showed a markedly decreased estrogenicity when compared to zearalenone.
Department of Analytical Chemistry, Reference Materials, Federal Institute for Materials Research and Testing (BAM), 12489, Berlin, Germany.
Sarah S
SS
Drzymala
Institute of Medical Biotechnology, Department of Biotechnology, Technische Universität Berlin, 13355, Berlin, Germany.
Jennifer
J
Binder
Department of Analytical Chemistry, Reference Materials, Federal Institute for Materials Research and Testing (BAM), 12489, Berlin, Germany.
Antje
A
Brodehl
Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor Str. 2, 12489, Berlin, Germany.
Martin
M
Penkert
Institute of Medical Biotechnology, Department of Biotechnology, Technische Universität Berlin, 13355, Berlin, Germany.
Mark
M
Rosowski
Institute of Bioanalytics, Department of Biotechnology, Technische Universität Berlin, 13355, Berlin, Germany.
Leif-Alexander
LA
Garbe
Department of Analytical Chemistry, Reference Materials, Federal Institute for Materials Research and Testing (BAM), 12489, Berlin, Germany. Electronic address: matthias.koch@bam.de.
Matthias
M
Koch
D045744:Cell Line, Tumor; D004967:Estrogens / Q000378:metabolism*; D006801:Humans; D015025:Zearalenone / Q000378:metabolism*
D004967:Estrogens; D015025:Zearalenone
E-screen assay; Estrogenicity; Isomerization; MCF-7; Mycotoxin; Zearalenone