{{short description|Group of chemical compounds}} {{MCN|date=January 2025}} [[File:Urolithin A.svg|thumb|Chemical structure of urolithin A.]] '''Urolithins''' are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins.<ref>{{Cite journal |last1=Larrosa |first1=M |last2=González-Sarrías |first2=A |last3=García-Conesa |first3=MT |last4=Tomás-Barberán |first4=FA |last5=Espín |first5=JC |year=2006 |title=Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=5 |pages=1611–1620 |doi=10.1021/jf0527403 |pmid=16506809}}</ref> They are produced in the gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as pomegranate.<ref name="Bialonska">{{Cite journal |vauthors=Bialonska D, Kasimsetty SG, Khan SI, Ferreira D |date=11 November 2009 |title=Urolithins, intestinal microbial metabolites of Pomegranate ellagitannins, exhibit potent antioxidant activity in a cell-based assay |journal=J Agric Food Chem |volume=57 |issue=21 |pages=10181–6 |doi=10.1021/jf9025794 |pmid=19824638}}</ref> During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity ''in vivo''.{{medcn|date=February 2022}}
Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites.{{medcn|date=February 2022}} Urolithins are found in plasma mostly as glucuronides at low concentrations.<ref>{{Cite journal |last1=Giménez-Bastida |first1=Juan A. |last2=González-Sarrías |first2=Antonio |last3=Larrosa |first3=Mar |last4=Tomás-Barberán |first4=Francisco |last5=Espín |first5=Juan C. |last6=García-Conesa |first6=María-Teresa |year=2012 |title=Ellagitannin metabolites, urolithin a glucuronide and its aglycone urolithin A, ameliorate TNF-α-induced inflammation and associated molecular markers in human aortic endothelial cells |journal=Molecular Nutrition & Food Research |volume=56 |issue=5 |pages=784–796 |doi=10.1002/mnfr.201100677 |pmid=22648625|hdl=10261/375590 |hdl-access=free }}</ref> Urolithins production is dependent on the gut microbiome enterotype. Individuals producing urolithins show a much higher abundance of the ''Clostridium leptum'' group of Firmicutes phylum than ''Bacteroides'' or ''Prevotella''.{{medcn|date=February 2022}}<ref>{{Cite journal |last1=García-Villalba |first1=Rocío |last2=Beltrán |first2=David |last3=Espín |first3=Juan Carlos |last4=Selma |first4=María Victoria |last5=Tomás-Barberán |first5=Francisco A. |year=2013 |title=Time Course Production of Urolithins from Ellagic Acid by Human Gut Microbiota |journal=Journal of Agricultural and Food Chemistry |volume=61 |issue=37 |pages=8797–8806 |doi=10.1021/jf402498b |pmid=23984796}}</ref>
== Known molecules == * Urolithin A (3,8-Dihydroxyurolithin) * Urolithin A glucuronide * Urolithin B (3-Hydroxyurolithin) * urolithin B glucuronide * Urolithin D (3,4,8,9-Tetrahydroxyurolithin) catabolic intermediates: * Urolithin M-5 * Urolithin M-6 * Urolithin M-7 * Urolithin C (3,8,9-Trihydroxy urolithin) * Urolithin E (2,3,8,10-Tetrahydroxy urolithin)
== See also == * Pomegranate ellagitannins
== References == {{reflist}}
{{Ellagitannin}}
Category:Benzochromenes Category:Coumarins Category:Phenolic human metabolites