Urolithin A

Urolithin A

Names
IUPAC name 3,8-dihydroxybenzo[c]chromen-6-one
Other names Uro-A
Identifiers
CAS Number	1143-70-0
ChemSpider	4589709
Jmol interactive 3D	Image
PubChem	5488186
InChI InChI=1S/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H Key: RIUPLDUFZCXCHM-UHFFFAOYSA-N InChI=1/C13H8O4/c14-7-1-3-9-10-4-2-8(15)6-12(10)17-13(16)11(9)5-7/h1-6,14-15H Key: RIUPLDUFZCXCHM-UHFFFAOYAT
SMILES Oc1ccc2c3ccc(O)cc3OC(=O)c2c1
Properties
Chemical formula	C13H8O4
Molar mass	228.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Urolithin A is an urolithin, a type of microflora human metabolite of dietary ellagic acid derivatives,^[1][2] such as ellagitannins.^[3]

During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity in vivo.^[4][5]

Urolithin A glucuronide is found in plasma at low concentrations.^[6]

See also

• Urolithins

References

1. Larrosa, M; González-Sarrías, A; García-Conesa, MT; Tomás-Barberán, FA; Espín, JC (2006). "Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities". Journal of Agricultural and Food Chemistry 54 (5): 1611–1620. doi:10.1021/jf0527403. PMID 16506809.
2. Vicinanza, Roberto; Zhang, Yanjun; Henning, Susanne M.; Heber, David (2013). "Pomegranate Juice Metabolites, Ellagic Acid and Urolithin A, Synergistically Inhibit Androgen-Independent Prostate Cancer Cell Growth via Distinct Effects on Cell Cycle Control and Apoptosis". Evidence-Based Complementary and Alternative Medicine 2013: 1. doi:10.1155/2013/247504.
3. Cerdá, Begoña; Periago, Paula; Espín, Juan Carlos; Tomás-Barberán, Francisco A. (2005). "Identification of Urolithin a as a Metabolite Produced by Human Colon Microflora from Ellagic Acid and Related Compounds". Journal of Agricultural and Food Chemistry 53 (14): 5571–5576. doi:10.1021/jf050384i. PMID 15998116.
4. Bialonska D, Kasimsetty SG, Khan SI, Ferreira D (11 November 2009). "Urolithins, intestinal microbial metabolites of Pomegranate ellagitannins, exhibit potent antioxidant activity in a cell-based assay". J Agric Food Chem 57 (21): 10181–6. doi:10.1021/jf9025794. PMID 19824638.
5. Larrosa M, González-Sarrías A, Yáñez-Gascón MJ, Selma MV, Azorín-Ortuño M, Toti S, Tomás-Barberán F, Dolara P, Espín JC (19 July 2009). "Anti-inflammatory properties of a pomegranate extract and its metabolite urolithin-A in a colitis rat model and the effect of colon inflammation on phenolic metabolism". J Nutr Biochem 21 (8): 717–25. doi:10.1016/j.jnutbio.2009.04.012. PMID 19616930.
6. Giménez-Bastida, Juan A.; González-Sarrías, Antonio; Larrosa, Mar; Tomás-Barberán, Francisco; Espín, Juan C.; García-Conesa, María-Teresa (2012). "Ellagitannin metabolites, urolithin a glucuronide and its aglycone urolithin A, ameliorate TNF-α-induced inflammation and associated molecular markers in human aortic endothelial cells". Molecular Nutrition & Food Research 56 (5): 784–796. doi:10.1002/mnfr.201100677.

External links

• Urolithin A at Phenol-Explorer.eu
• Urolithin A at the Human Metabolome Database