Urolithin A

Chemical compound From Wikipedia, the free encyclopedia

Urolithin A is a metabolite compound resulting from the transformation of ellagitannins by the gut bacteria.[1] It belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. Its precursors – ellagic acids and ellagitannins – are ubiquitous in nature, including edible plants, such as pomegranates, strawberries, raspberries, walnuts, and others.[2]

Quick facts Names, Identifiers ...
Urolithin A
Chemical structure of urolithin A
Names
Preferred IUPAC name
3,8-Dihydroxy-6H-dibenzo[b,d]pyran-6-one
Other names
Uro-A
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • 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
  • Oc1ccc2c3ccc(O)cc3OC(=O)c2c1
Properties
C13H8O4
Molar mass 228.203 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Urolithin A is not known to be found in any food source. Its bioavailability mostly depends on individual microbiota composition, as only some bacteria are able to convert ellagitannins into urolithins.[3]

Chemistry

Urolithin A belongs to the class of organic compounds known as benzo-coumarins or dibenzo-α-pyrones. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Biochemistry and metabolism

Pomegranate fruits, walnuts, and raspberries are sources of ellagitannins.[4][5][6] Ellagitannins are hydrolyzed in the gut to release ellagic acid, which is further processed by the gut microflora into urolithins through the loss of one of its two lactones and by successive removal of hydroxyl groups.[7]

While studies have shown that Gordonibacter urolithinfaciens and Gordonibacter pamelaeae play a role in the conversion of ellagic acids and ellagitannins into urolithin A, the microorganisms responsible for the complete transformation into the final urolithins are still unknown.[3] The efficiency of the conversion of ellagitannins into urolithin A significantly varies in humans, and some individuals do not show any conversion.[8]

When synthesized and absorbed in the intestines, urolithin A enters the systemic circulation where it becomes available to tissues throughout the body where it is further subjected to additional chemical transformations (including glucuronidation, methylation, sulfation, or a combination of them) within the enterocytes and hepatocytes.[9] Urolithin A and its derivatives - urolithin A glucuronide and urolithin A sulfate being most abundant - release into the circulation, before being excreted in the urine.[10]

Safety

In vivo studies did not determine any toxicity or specific adverse effects following dietary intake of urolithin A.[11] Safety studies in elderly humans indicated urolithin A was well tolerated.[12] In 2018, the US Food and Drug Administration listed urolithin A as a safe ingredient for food products having content in the range of 250 mg to one gram per serving.[13]

Research

In preliminary human studies, urolithin A appears to be well-tolerated with mild side effects.[14]

Dietary sources

Urolithin A is not known to be found in any food but rather forms as the result of transformation of ellagic acids and ellagitannins by the gut microflora in humans.[citation needed] Sources of ellagitannins are: pomegranates, nuts, some berries (raspberries, strawberries, blackberries, cloudberries), tea, muscadine grapes, many tropical fruits, and oak-aged wines (table below).

The conversion of the ellagic acids into urolithin A depends on individual microflora composition and can vary significantly.[8][15]

More information Dietary source, Ellagic Acid ...
Dietary source Ellagic Acid[16]
Fruits (mg/100g fresh weight)
Blackberries 150
Black raspberries 90
Boysenberries 70
Cloudberries 315.1
Pomegranate 269.9[17]
Raspberries 270
Rose hip 109.6
Strawberries 77.6
Strawberry jam 24.5
Yellow raspberries 1900
Nuts (mg/g)
Pecans 33
Walnuts 59
Beverages (mg/L)
Pomegranate juice 811.1[17]
Cognac 31-55
Oak-aged red wine 33
Whiskey 1.2
Seeds (mg/g)
Black raspberries 6.7
Red raspberries 8.7
Boysenberries 30
Mango 1.2
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See also

References

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