Urolithin

Urolithins are microflora human metabolites of dietary ellagic acid derivatives[1] such as ellagitannins. They are produced in the human gut, and found in the urine in the form of urolithin B glucuronide after absorption of ellagitannins-containing food such as pomegranate,[2] strawberries, red raspberries, walnuts or oak-aged red wine.[3]

Chemical structure of urolithin A.

During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity in vivo in humans.[2][4] Urolithins metabolites of pomegranate juice ellagitannins localize specifically in the prostate gland, colon, and intestinal tissues of mice.[5]

Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites. Urolithins are found in plasma mostly as glucuronides at low concentrations.[6]

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.[7]

Urolithin M7 has also been synthetized from 2-hydroxy-4-methoxybenzaldehyde using the inverse electron-demand Diels–Alder reaction.[8]

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

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. 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.
  3. Cerdá, Begoña; Tomás-Barberán, Francisco A.; Espín, Juan Carlos (2005). "Metabolism of Antioxidant and Chemopreventive Ellagitannins from Strawberries, Raspberries, Walnuts, and Oak-Aged Wine in Humans: Identification of Biomarkers and Individual Variability". Journal of Agricultural and Food Chemistry. 53 (2): 227–235. doi:10.1021/jf049144d. PMID 15656654.
  4. 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.
  5. Seeram, N. P.; Aronson, W. J.; Zhang, Y; Henning, S. M.; Moro, A; Lee, R. P.; Sartippour, M; Harris, D. M.; Rettig, M; Suchard, M. A.; Pantuck, A. J.; Belldegrun, A; Heber, D (2007). "Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and localize to the mouse prostate gland". Journal of Agricultural and Food Chemistry. 55 (19): 7732–7. doi:10.1021/jf071303g. PMID 17722872.
  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. PMID 22648625.
  7. García-Villalba, Rocío; Beltrán, David; Espín, Juan Carlos; Selma, María Victoria; Tomás-Barberán, Francisco A. (2013). "Time Course Production of Urolithins from Ellagic Acid by Human Gut Microbiota". Journal of Agricultural and Food Chemistry. 61 (37): 8797–8806. doi:10.1021/jf402498b. PMID 23984796.
  8. Bodwell, Graham; Pottie, Ian; Nandaluru, Penchal (2011). "An Inverse Electron-Demand Diels-Alder-Based Total Synthesis of Urolithin M7". Synlett. 2011 (15): 2245–2247. doi:10.1055/s-0030-1261203.
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