Prenylation and Backbone Structure of Flavonoids and Isoflavonoids from Licorice and Hop Influence Their Phase i and II Metabolism

Milou G.M. Van De Schans, Toine F.H. Bovee, Geert M. Stoopen, Marlies Lorist, Harry Gruppen, Jean Paul Vincken*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

9 Citations (Scopus)

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-MSn. 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.

Original languageEnglish
Pages (from-to)10628-10640
JournalJournal of Agricultural and Food Chemistry
Volume63
Issue number49
DOIs
Publication statusPublished - 16 Dec 2015

Keywords

  • glucuronidation
  • hydroxylation
  • phytoestrogens
  • prenylated flavonoids
  • prenylated isoflavonoids
  • sulfation

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