Estrogenicity of novel phase I and phase II metabolites of zearalenone and cis-zearalenone. (October 2015)

• Record Type: Journal Article
• Authors: Drzymala, Sarah S.; Binder, Jennifer; Brodehl, Antje; Penkert, Martin; Rosowski, Mark; Garbe, Leif-Alexander; Koch, Matthias
• Is Part Of: Toxicon. Volume 105(2015)
• Page Start: 10
• Page End: 12
• Publication Date: 2015-10
• Subjects: Zearalenone -- Mycotoxin -- MCF-7 -- E-screen assay -- Estrogenicity -- Isomerization; COMT catechol-O-methyltransferase -- EC50 half maximal effective concentration -- ER estrogen receptor -- RAL resorcylic acid lactone -- ZAL zearalanol -- ZEL zearalenol -- ZEN zearalenone; Toxins -- Periodicals; Venom -- Periodicals; 615.9
• DOI: 10.1016/j.toxicon.2015.08.027
• Languages: English
• ISSNs: 0041-0101

Abstract

Abstract: 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. Graphical abstract: Highlights: First assessment of estrogenicity of α- and β-cis-ZEL, 15-OH-ZEN, and ZEN-14-sulfate. α-cis-ZEL shows even elevated estrogenicity compared to its parent compound cis-ZEN. Modifications on the aromatic moiety generally decrease estrogenic activity. Change from trans to cis configuration does not have a major impact on estrogenicity.