title: Simultaneous preparation of α/β-zearalenol glucosides and glucuronides.
abstract: An improved and reproducible procedure for the preparation of four different glycosides of the mycotoxins α- and β-zearalenol (α,β-ZEL), both metabolites of the Fusarium toxin zearalenone (ZEN), is reported. These conjugated or masked mycotoxins are formed during phase II metabolism in plants (glucosides) or animals and humans (glucuronides). Improved regioselective Königs-Knorr glucuronidation was applied to ZEN followed by reduction of the keto group of the mycotoxin, leading to α- and β-configuration of ZEL and also to a partial reduction of the glucuronic acid methyl ester to obtain the corresponding glucosides. After deprotection of the sugar moiety, α- and β-zearalenol-14-β,D-glucuronide as well as the corresponding glucosides were isolated at once using preparative HPLC. The reduction step was studied under different reaction conditions to finally develop an optimized and also tunable procedure for the first simultaneous preparation of both, glucosides and glucuronides of a xenobiotic substance in reasonable amounts to be used as reference materials for bioanalytical and toxicological investigations.
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna 1060, Austria. hannes.mikula@tuwien.ac.at
authors.forename: Hannes
authors.initials: H
authors.lastname: Mikula
authors.forename: Julia
authors.initials: J
authors.lastname: Weber
authors.forename: Stefan
authors.initials: S
authors.lastname: Lexmüller
authors.forename: Gerlinde
authors.initials: G
authors.lastname: Bichl
authors.forename: Heidi
authors.initials: H
authors.lastname: Schwartz
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Varga
authors.forename: Franz
authors.initials: F
authors.lastname: Berthiller
authors.forename: Christian
authors.initials: C
authors.lastname: Hametner
authors.forename: Rudolf
authors.initials: R
authors.lastname: Krska
authors.forename: Johannes
authors.initials: J
authors.lastname: Fröhlich
mesh_terms: D060326:Chemistry Techniques, Synthetic; D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry*; D020719:Glucuronides / Q000138:chemical synthesis / Q000737:chemistry*; D015029:Zeranol / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D005960:Glucosides; D020719:Glucuronides; C029659:zearalenol; D015029:Zeranol