# Urolithin

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{{short description|Group of chemical compounds}}
{{MCN|date=January 2025}}
[[File:Urolithin A.svg|thumb|Chemical structure of [urolithin A](/source/urolithin_A).]]
'''Urolithins''' are [microflora](/source/Microbiota) [metabolite](/source/metabolite)s of dietary [ellagic acid](/source/ellagic_acid) derivatives, such as [ellagitannins](/source/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](/source/Gastrointestinal_tract), and found in the [urine](/source/urine) in the form of urolithin B glucuronide after absorption of ellagitannins-containing foods, such as [pomegranate](/source/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 [punicalagin](/source/punicalagin)s are converted to urolithins, which have unknown [biological activity](/source/biological_activity) ''in vivo''.{{medcn|date=February 2022}}

Ellagitannins exhibit low [bioavailability](/source/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 [glucuronide](/source/glucuronide)s 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](/source/gut_microbiome) [enterotype](/source/enterotype). Individuals producing urolithins show a much higher abundance of the ''[Clostridium leptum](/source/Clostridium_leptum)'' group of Firmicutes phylum than ''[Bacteroides](/source/Bacteroides)'' or ''[Prevotella](/source/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](/source/Urolithin_A) (3,8-Dihydroxyurolithin)
* [Urolithin A glucuronide](/source/Urolithin_A_glucuronide)
* [Urolithin B](/source/Urolithin_B) (3-Hydroxyurolithin)
* [urolithin B glucuronide](/source/urolithin_B_glucuronide)
* [Urolithin D](/source/Urolithin_D) (3,4,8,9-Tetrahydroxyurolithin)
catabolic intermediates:
* [Urolithin M-5](/source/Urolithin_M-5)
* [Urolithin M-6](/source/Urolithin_M-6)
* [Urolithin M-7](/source/Urolithin_M-7)
* [Urolithin C](/source/Urolithin_C) ([3,8,9-Trihydroxy urolithin](/source/3%2C8%2C9-Trihydroxy_urolithin))
* [Urolithin E](/source/Urolithin_E) ([2,3,8,10-Tetrahydroxy urolithin](/source/2%2C3%2C8%2C10-Tetrahydroxy_urolithin))

== See also ==
* [Pomegranate ellagitannin](/source/Pomegranate_ellagitannin)s

== References ==
{{reflist}}

{{Ellagitannin}}

Category:Benzochromenes
Category:Coumarins
Category:Phenolic human metabolites

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Adapted from the Wikipedia article [Urolithin](https://en.wikipedia.org/wiki/Urolithin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Urolithin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.