Chemistry:Urolithin A
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| Preferred IUPAC name
3,8-Dihydroxy-6H-dibenzo[b,d]pyran-6-one | |
| Other names
Uro-A
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
| Infobox references | |
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]
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 or 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 or dietary supplement products having content in the range of 250 mg to one gram per serving.[13]
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][14]
| Dietary source | Ellagic Acid[15] |
|---|---|
| Fruits (mg/100g fresh weight) | |
| Blackberries | 150 |
| Black raspberries | 90 |
| Boysenberries | 70 |
| Cloudberries | 315.1 |
| Pomegranate | 269.9[16] |
| 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[16] |
| 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 |
See also
References
- ↑ "Metabolic fate of ellagitannins: implications for health, and research perspectives for innovative functional foods". Critical Reviews in Food Science and Nutrition 54 (12): 1584–98. 2014-12-02. doi:10.1080/10408398.2011.644643. PMID 24580560.
- ↑ "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): 227–35. January 2005. doi:10.1021/jf049144d. PMID 15656654.
- ↑ 3.0 3.1 "Isolation of Human Intestinal Bacteria Capable of Producing the Bioactive Metabolite Isourolithin A from Ellagic Acid". Frontiers in Microbiology 8: 1521. 2017. doi:10.3389/fmicb.2017.01521. PMID 28824607.
- ↑ "Pomegranate as a functional food and nutraceutical source". Annual Review of Food Science and Technology 2 (1): 181–201. 2011-02-28. doi:10.1146/annurev-food-030810-153709. PMID 22129380.
- ↑ "Health benefits of walnut polyphenols: An exploration beyond their lipid profile". Critical Reviews in Food Science and Nutrition 57 (16): 3373–3383. November 2017. doi:10.1080/10408398.2015.1126218. PMID 26713565.
- ↑ "New insights into the bioavailability of red raspberry anthocyanins and ellagitannins". Free Radical Biology & Medicine 89: 758–69. December 2015. doi:10.1016/j.freeradbiomed.2015.10.400. PMID 26475039. http://eprints.gla.ac.uk/114297/1/114297.pdf.
- ↑ "Biological significance of urolithins, the gut microbial ellagic Acid-derived metabolites: the evidence so far". Evidence-Based Complementary and Alternative Medicine 2013: 270418. 2013. doi:10.1155/2013/270418. PMID 23781257.
- ↑ 8.0 8.1 "Urolithins, the rescue of "old" metabolites to understand a "new" concept: Metabotypes as a nexus among phenolic metabolism, microbiota dysbiosis, and host health status". Molecular Nutrition & Food Research 61 (1): n/a. January 2017. doi:10.1002/mnfr.201500901. PMID 27158799.
- ↑ "Urolithins are the main urinary microbial-derived phenolic metabolites discriminating a moderate consumption of nuts in free-living subjects with diagnosed metabolic syndrome". Journal of Agricultural and Food Chemistry 60 (36): 8930–40. September 2012. doi:10.1021/jf301509w. PMID 22631214.
- ↑ "Strawberry processing does not affect the production and urinary excretion of urolithins, ellagic acid metabolites, in humans". Journal of Agricultural and Food Chemistry 60 (23): 5749–54. June 2012. doi:10.1021/jf203641r. PMID 22126674.
- ↑ "Safety assessment of Urolithin A, a metabolite produced by the human gut microbiota upon dietary intake of plant derived ellagitannins and ellagic acid". Food and Chemical Toxicology 108 (Pt A): 289–297. October 2017. doi:10.1016/j.fct.2017.07.050. PMID 28757461.
- ↑ "Orally administered urolithin A is safe and modulates muscle and mitochondrial biomarkers in elderly". Innovation in Aging 1 (suppl_1): 1223–1224. 2017-07-01. doi:10.1093/geroni/igx004.4446.
- ↑ "FDA GRAS notice GRN No. 791: urolithin A". US Food and Drug Administration. 20 December 2018. https://www.cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=GRASNotices&id=791.
- ↑ "The human gut microbial ecology associated with overweight and obesity determines ellagic acid metabolism". Food & Function 7 (4): 1769–74. April 2016. doi:10.1039/c5fo01100k. PMID 26597167.
- ↑ "Ellagitannins, ellagic acid and their derived metabolites: A review about source, metabolism, functions and health". Food Research International 44 (5): 1150–1160. 2011. doi:10.1016/j.foodres.2011.04.027.
- ↑ 16.0 16.1 "Chromatographic and spectroscopic characterization of urolithins for their determination in biological samples after the intake of foods containing ellagitannins and ellagic acid". Journal of Chromatography A 1428: 162–75. January 2016. doi:10.1016/j.chroma.2015.08.044. PMID 26341594.
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