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Cited by 261

The DOI matches its Crossref record; 3 of the 3 references it cites were found in a registry or an index.

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

Larrosa, Mar, González-Sarrías, Antonio, García-Conesa, María Teresa, Tomás-Barberán, Francisco A., Espín, Juan Carlos·2006·Journal of Agricultural and Food Chemistry
DOI 10.1021/jf0527403
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Abstract

Urolithins 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 alpha- and beta-estrogen receptors. Both urolithins A and B showed estrogenic activity in a dose-dependent manner even at high concentrations (40 microM), 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-beta-estradiol in a dose-dependent manner) than the other phytoestrogens. The IC(50) values for the ERalpha and ERbeta binding assays were 0.4 and 0.75 microM for urolithin A; 20 and 11 microM 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".

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Metadata

Authors
Larrosa, M., González-Sarrías, A., García-Conesa, M. T., Tomás-Barberán, F. A., & Espín, J. C.
Venue
Journal of Agricultural and Food Chemistry
Publisher
American Chemical Society (ACS)
Published
2006-02-11
Volume
54
Issue
5
Pages
1611-1620
ISSN
  • 0021-8561 (ISSN-L)
  • 1520-5118
DOI
10.1021/jf0527403
OpenAlex
W1963837940
Cited by
261
References
3
FWCI
5.88
Type
journal article
Language
en
Open access
closed

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