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Novel oxidative metabolites of the mycoestrogen zearalenone in vitro

2007; Wiley; Volume: 51; Issue: 7 Linguagem: Inglês

10.1002/mnfr.200600295

1613-4133

Erika Pfeiffer, Anja Heyting, Manfred Metzler,

Plant Toxicity and Pharmacological Properties

Abstract The estrogenic mycotoxin zearalenone (ZEN) is known to get metabolized to the α‐and β‐isomers of zearalenol, but no hydroxylation products of ZEN have yet been reported as metabolites in animals or humans. We have therefore incubated ZEN with microsomes from rat liver in the presence of a nicotinamide adenine dinucleotide phosphate (reduced form) (NADPH)‐regenerating system and analyzed the extracted metabolites with HPLC and GC‐MS after trimethylsilylation. A total of 17 in vitro metabolites were observed. The two major metabolites were tentatively identified as monohydroxylated ZEN with the newly introduced hydroxyl group localized in the aliphatic macrocyclic ring. According to the GC‐MS analysis, other six monohydroxylation products of ZEN were formed as minor metabolites, together with α‐and β‐zearalenol and monohydroxylated zearalenols. Thus, ZEN has a considerable propensity for undergoing metabolic hydroxylation reactions in vitro , and the in vivo formation and biological properties of such oxidative metabolites should now be studied.