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Urolithins, Ellagic Acid-Derived Metabolites Produced by Human Colonic Microflora, Exhibit Estrogenic and Antiestrogenic Activities

AuthorsLarrosa, Mar ; González-Sarrías, Antonio ; García-Conesa, María Teresa ; Tomás Barberán, Francisco ; Espín de Gea, Juan Carlos
KeywordsBreast cancer
Hydroxy-6H-dibenzo[b,d]pyran-6-one derivative
Estrogen receptor
Issue Date11-Feb-2006
PublisherAmerican Chemical Society
CitationJournal of Agricultural and Food Chemistry 54(5): 1611-1620 (2006)
AbstractUrolithins A and B (hydroxy-6H-dibenzo[b,d]pyran-6-one derivatives) are colonic microflora metabolites recently proposed as biomarkers of human exposure to dietary ellagic acid derivatives. Molecular models suggest that urolithins could display estrogenic and/or antiestrogenic activity. To this purpose, both urolithins and other known phytoestrogens (genistein, daidzein, resveratrol, and enterolactone) were assayed to evaluate the capacity to induce cell proliferation on the estrogen-sensitive human breast cancer MCF-7 cells as well as the ability to bind to α- and β-estrogen receptors. Both urolithins A and B showed estrogenic activity in a dose-dependent manner even at high concentrations (40 μM), without antiproliferative or toxic effects, whereas the other phytoestrogens inhibited cell proliferation at high concentrations. Overall, urolithins showed weaker estrogenic activity than the other phytoestrogens. However, both urolithins displayed slightly higher antiestrogenic activity (antagonized the growth promotion effect of 17-β-estradiol in a dose-dependent manner) than the other phytoestrogens. The IC50 values for the ERα and ERβ binding assays were 0.4 and 0.75 μM for urolithin A; 20 and 11 μM for urolithin B; 3 and 0.02 for genistein; and 2.3 and 1 for daidzein, respectively; no binding was detected for resveratrol and enterolactone. Urolithins A and B entered into MCF-7 cells and were metabolized to yield mainly urolithin-sulfate derivatives. These results, together with previous studies regarding absorption and metabolism of dietary ellagitannins and ellagic acid in humans, suggest that the gut microflora metabolites urolithins are potential endocrine-disrupting molecules, which could resemble other described “enterophytoestrogens” (microflora-derived metabolites with estrogenic/antiestrogenic activity). Further research is warranted to evaluate the possible role of ellagitannins and ellagic acid as dietary “pro-phytoestrogens”.
Description10 pages, 8 figures, 1 table.
Publisher version (URL)http://dx.doi.org/10.1021/jf0527403
Appears in Collections:(CEBAS) Artículos
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