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Hydroxylation and dimerization of zearalenone: comparison of chemical, enzymatic and electrochemical oxidation methods

  • Investigations of the metabolic pathway of mycotoxins by microsomal techniques are often laborious, causing an increasing demand for easy and rapid simulation methods. Thus, the non-microsomal oxidation technique of electrochemistry coupled online to mass spectrometry (EC/MS) was applied to simulate phase I biotransformation of the Fusarium mycotoxin zearalenone (ZEA). The obtained transformation products were identified by high resolution mass spectrometry (FT-ICR) and HPLC-MS/MS. Transformation products (TPs) from EC/MS were compared to those of other oxidative methods such as Fenton-like and Ce(IV) reactions and metabolites derived from in vitro assays (human and rat liver microsomes). Electrochemical oxidization of ZEA was achieved by applying a potential between 0 and 2,500 mV vs. Pd/H2 using a flow-through cell with a boron-doped diamond working electrode. Several mono-hydroxylated TPs were generated by EC/MS and Fenton-like reaction, which could also be found in microsomal inInvestigations of the metabolic pathway of mycotoxins by microsomal techniques are often laborious, causing an increasing demand for easy and rapid simulation methods. Thus, the non-microsomal oxidation technique of electrochemistry coupled online to mass spectrometry (EC/MS) was applied to simulate phase I biotransformation of the Fusarium mycotoxin zearalenone (ZEA). The obtained transformation products were identified by high resolution mass spectrometry (FT-ICR) and HPLC-MS/MS. Transformation products (TPs) from EC/MS were compared to those of other oxidative methods such as Fenton-like and Ce(IV) reactions and metabolites derived from in vitro assays (human and rat liver microsomes). Electrochemical oxidization of ZEA was achieved by applying a potential between 0 and 2,500 mV vs. Pd/H2 using a flow-through cell with a boron-doped diamond working electrode. Several mono-hydroxylated TPs were generated by EC/MS and Fenton-like reaction, which could also be found in microsomal in vitro assays. EC and Ce(IV) led to the formation of structurally different ZEA dimers and dimeric quinones probably connected over covalent biaryl C-C and C-O-C bonds. Although the dimerization of phenolic compounds is often observed in natural processes, ZEA dimers have not yet been reported. This is the first report on the formation of stable ZEA dimers and their related quinones. The tested non-microsomal methods, in particular EC/MS, could be useful in order to predict the biotransformation products of mycotoxins, even in cases where one to one simulation is not always feasible.zeige mehrzeige weniger

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Metadaten
Autor*innen:Julia Keller, H. Haase, Matthias KochORCiD
Dokumenttyp:Zeitschriftenartikel
Veröffentlichungsform:Verlagsliteratur
Sprache:Englisch
Titel des übergeordneten Werkes (Englisch):World Mycotoxin Journal
Jahr der Erstveröffentlichung:2017
Verlag:Wageningen Academic Publishers
Jahrgang/Band:10
Ausgabe/Heft:4
Erste Seite:297
Letzte Seite:307
DDC-Klassifikation:Naturwissenschaften und Mathematik / Chemie / Analytische Chemie
Technik, Medizin, angewandte Wissenschaften / Ingenieurwissenschaften / Sanitär- und Kommunaltechnik; Umwelttechnik
Freie Schlagwörter:Dimer; Electrochemistry; Zearalenone
DOI:10.3920/WMJ2017.2213
ISSN:1875-0710
ISSN:1875-0796
Verfügbarkeit des Dokuments:Datei im Netzwerk der BAM verfügbar ("Closed Access")
Datum der Freischaltung:12.12.2017
Referierte Publikation:Ja
Datum der Eintragung als referierte Publikation:12.12.2017
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