Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 498472
Title Prenylation and Backbone Structure of Flavonoids and Isoflavonoids from Licorice and Hop Influence Their Phase i and II Metabolism
Author(s) De Schans, Milou G.M. Van; Bovee, Toine F.H.; Stoopen, Geert M.; Lorist, Marlies; Gruppen, Harry; Vincken, Jean Paul
Source Journal of Agricultural and Food Chemistry 63 (2015)49. - ISSN 0021-8561 - p. 10628 - 10640.
DOI https://doi.org/10.1021/acs.jafc.5b04703
Department(s) Food Chemistry Group
RIKILT - Business unit Dierbehandelingsmiddelen
Rikilt B&T Toxicologie en Effectanalyse
RIKILT - BU Toxicology Bioassays & Novel Foods
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2015
Keyword(s) glucuronidation - hydroxylation - phytoestrogens - prenylated flavonoids - prenylated isoflavonoids - sulfation
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.

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