title: Prenylation and Backbone Structure of Flavonoids and Isoflavonoids from Licorice and Hop Influence Their Phase I and II Metabolism.
abstract: In vitro liver metabolism of 11 prenylated flavonoids and isoflavonoids was investigated by determining their phase I glucuronyl and sulfate metabolites using pork liver preparations. One hundred metabolites were annotated using RP-UHPLC-ESI-MS(n). A mass spectrometry-based data interpretation guideline was proposed for the tentative annotation of the position of hydroxyl groups, considering its relevance for estrogenic activity. To relate structure to metabolism, compounds were classified on the basis of three criteria: backbone structure (isoflavene, isoflavan, or flavanone), number of prenyl groups (0, 1, or 2), and prenyl configuration (chain or pyran). Glucuronidation was most extensive for isoflavenes and for unprenylated compounds (yield of 90-100%). Pyran and chain prenylation gave more complex hydroxylation patterns with 4 or more than 6 hydroxyl isomers, respectively, as compared to unprenylated compounds (only 1 hydroxyl isomer). Moreover, the number of hydroxyl isomers also increased with the number of prenyl groups.
authors.affiliation: Laboratory of Food Chemistry, Wageningen University , 6700 AA Wageningen, The Netherlands.
authors.forename: Milou G M
authors.initials: MG
authors.lastname: van de Schans
authors.affiliation: Business Unit of Toxicology and Bioassays, RIKILT-Institute of Food Safety , 6700 AE Wageningen, The Netherlands.
authors.forename: Toine F H
authors.initials: TF
authors.lastname: Bovee
authors.affiliation: Business Unit of Toxicology and Bioassays, RIKILT-Institute of Food Safety , 6700 AE Wageningen, The Netherlands.
authors.forename: Geert M
authors.initials: GM
authors.lastname: Stoopen
authors.affiliation: Laboratory of Food Chemistry, Wageningen University , 6700 AA Wageningen, The Netherlands.
authors.forename: Marlies
authors.initials: M
authors.lastname: Lorist
authors.affiliation: Laboratory of Food Chemistry, Wageningen University , 6700 AA Wageningen, The Netherlands.
authors.forename: Harry
authors.initials: H
authors.lastname: Gruppen
authors.affiliation: Laboratory of Food Chemistry, Wageningen University , 6700 AA Wageningen, The Netherlands.
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Vincken
mesh_terms: D005419:Flavonoids / Q000737:chemistry* / Q000378:metabolism*; D020719:Glucuronides / Q000737:chemistry; D006035:Glycyrrhiza / Q000737:chemistry*; D027582:Humulus / Q000737:chemistry*; D007536:Isomerism; D008099:Liver / Q000378:metabolism*; D050216:Metabolic Detoxication, Phase I; D050217:Metabolic Detoxication, Phase II; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D054876:Prenylation; D013329:Structure-Activity Relationship
chemical_list: D005419:Flavonoids; D020719:Glucuronides; D010936:Plant Extracts
keywords: glucuronidation; hydroxylation; phytoestrogens; prenylated flavonoids; prenylated isoflavonoids; sulfation