Ellagic acid
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| Names | |
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| IUPAC name
2,3,7,8-Tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione
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| Other names
4,4′,5,5′,6,6′-Hexahydroxydiphenic acid 2,6,2′,6′-dilactone
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| Identifiers | |
476-66-4  |
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| ChEBI | CHEBI:4775 |
| ChEMBL | ChEMBL6246 |
| ChemSpider | 4445149 |
| DrugBank | DB08468 |
| Jmol 3D model | Interactive image |
| KEGG | C10788 |
| PubChem | 5281855 |
| UNII | 19YRN3ZS9P |
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| Properties | |
| C14H6O8 | |
| Molar mass | 302.197 g/mol |
| Density | 1.67 g/cm3 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables. The antiproliferative and antioxidant properties of ellagic acid have prompted research into its potential health benefits. Ellagic acid is the dilactone of hexahydroxydiphenic acid.
Contents
Metabolism
Biosynthesis
Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin[1] and geraniin.[2]:208
Biodegradation
Urolithins are microflora human metabolites of dietary ellagic acid derivatives[3]
History
Ellagic acid was first discovered by chemist Henri Braconnot in 1831.[4]:20 Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905.[4]:20 He also suggested its formation from galloyl-glycine by Penicillium in 1915.[5] Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide.[4]:20 [6]
Natural occurrences
Ellagic acid is found in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur).[7]
The macrophyte Myriophyllum spicatum produces ellagic acid.[8]
Ellagic acid can be found in the medicinal mushroom Phellinus linteus.[9]
In food
The highest levels of ellagic acid are found in blackberries, cranberries, pecans, pomegranates, raspberries, strawberries, walnuts, wolfberries, and grapes.[10] It is also found in peach[11] and other plant foods.
Medicinal claims and research
Ellagic acid has antiproliferative and antioxidant properties in a number of in vitro and small-animal models.[12][13] The antiproliferative properties of ellagic acid may be due to its ability to directly inhibit the DNA binding of certain carcinogens, including nitrosamines[14][15] and polycyclic aromatic hydrocarbons.[16] As with other polyphenol antioxidants, ellagic acid has a chemoprotective effect in cellular models by reducing oxidative stress.[10]
Ellagic acid has been marketed as a dietary supplement with a range of claimed benefits against cancer, heart disease, and other medical problems. Ellagic acid has been identified by the U.S. Food and Drug Administration as a "Fake Cancer Cure Consumers Should Avoid".[17] A number of U.S.-based sellers of dietary supplements have received Warning Letters from the Food and Drug Administration for promoting ellagic acid with claims that violate the Federal Food, Drug, and Cosmetic Act.[18][19]
Urolithins, such as urolithin A, are microflora human metabolites of dietary ellagic acid derivatives that are under study as anti-cancer agents.[20] Claims that ellagic acid can treat or prevent cancer in humans have not been proven.[21]
See also
References
- ↑ Ascacio-Valdés JA et al. (2011) Review: Ellagitannins: Biosynthesis, biodegradation and biological properties Journal of Medicinal Plants Research Vol. 5(19):4696-4703
- ↑ David S. Seigler Plant Secondary Metabolism. Springer, 1998.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 4.0 4.1 4.2 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Löwe, Zeitschrift für Chemie, 1868, 4, 603
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.[dead link]
- ↑ 10.0 10.1 Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Postharvest sensory and phenolic characterization of ‘Elegant Lady’ and ‘Carson’ peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal Of Agricultural Research, 71(3), July–September 2011, pages 445-451 (article)
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 187 Fake Cancer 'Cures' Consumers Should Avoid, from the U.S. Food and Drug Administration. Accessed June 17, 2008.
- ↑ Warning Letter sent to Millennium Health by the United States Food and Drug Administration, dated May 21, 2008.
- ↑ Warning Letter sent to Kenton Campbell at Prime Health Direct, Ltd. by the United States Food and Drug Administration dated July 2, 2007.
- ↑ Davis CD, Milner JA. Gastrointestinal microflora, food components and colon cancer prevention. J Nutr Biochem. 2009 Oct;20(10):743-52. doi: 10.1016/j.jnutbio.2009.06.001. PMID 19716282
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
External links
- A Food-Based Approach to the Prevention of Gastrointestinal Tract Cancers - video lecture dedicated mainly to ellagic acid. Read by Dr. Gary D. Stoner from the Ohio State University Comprehensive Cancer Center.
- Polyphenols as cancer chemopreventive agents, J. Cell Biochem Suppl. 1995'22:169-80
