Urolithin
Urolithins are microflora metabolites of dietary ellagic acid derivatives, such as ellagitannins.[1] 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.[2] During intestinal metabolism by bacteria, ellagitannins and punicalagins are converted to urolithins, which have unknown biological activity in vivo.[medical citation needed]
Ellagitannins exhibit low bioavailability and are transformed in the gut to ellagic acid and its microbiota metabolites.[medical citation needed] Urolithins are found in plasma mostly as glucuronides at low concentrations.[3] 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.[medical citation needed][4]
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
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- v
- t
- e
- Diphenolic acid : Hexahydroxydiphenic acid (HHDP)
- Triphenolic acids : Nonahydroxytriphenic acid
- Sanguisorbic acid
- Valoneic acid
- Tetraphenolic acids : Isoterchebulic acid
- Terchebulinic acid
- Ellagic acid
- Gallagic acid
- Gallagic acid dilactone
- Luteic acid
- Sanguisorbic acid dilactone
- Valoneic acid dilactone
- Acetonyl geraniin
- Alnusiin
- Bicornin
- Carlesiin
- Casuarictin
- Emblicanin A and B
- Euscaphinin
- Galloyl pedunculagin
- Grandinin
- Helioscopinin B
- Jolkinin
- Lagerstannin A, B and C
- Macranganin
- Myrobalanitannin
- Nupharin A, B, C, D, E and F
- Pedunculagin
- Punicalagin
- Punigluconin
- Phyllanemblinin A, B, C, D, E and F
- Punicalin
- Roburin E
- Rugosin E
- Sanguiin H-5
- Stenophyllanin A, B and C
- Strictinin
- Tellimagrandin I and II
- Teracatain
- Terchebulin
- Terflavin A and B
- Tergallic acid
- Tergallic acid dilactone
C-glycosidic ellagitannins |
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Dehydroellagitannins (molecules with dehydrohexahydroxydiphenic acid (DHHDP) |
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Transformed ellagitannins |
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- Dimers
- Agrimoniin
- Cornusiin E (dimer of tellimagrandin II)
- Lambertianin A and B
- Nobotanin B
- Roburin A, B, C and D
- Sanguiin H-6
- Trimers
- Lambertianin C
- Raspberry ellagitannin
- Tetramers
- Lambertianin D
- Nobotanin S
- Pentamer
- Melastoflorin A
- Flavono-ellagitannins (hybrid type)
- Urolithins (metabolites)
- Pomegranate ellagitannins