Ellagic acid
| Ellagic acid | |
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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 | |
| CAS number | 476-66-4  |
| PubChem | 5281855 |
| ChemSpider | 4445149 |
| UNII | 19YRN3ZS9P |
| DrugBank | DB08468 |
| KEGG | C10788 |
| ChEBI | CHEBI:4775 |
| ChEMBL | CHEMBL6246 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C14H6O8 |
| Molar mass | 302.197 g/mol |
| Exact mass | 302.006267 |
| Density | 1.67 g/cm³ |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables including blackberries, raspberries, strawberries, cranberries, walnuts, pecans, pomegranates, wolfberry and other plant foods. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption.
Ellagic acid is the dilactone of hexahydroxydiphenic acid.
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[edit] History
Ellagic acid was first discovery made by chemist Michel Eugène Chevreul in oak galls and was more closely examined by Henri Braconnot in 1831. Nierenstein prepared this substance from algarobilla and certain other fruits. Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid.[1]
[edit] Natural occurrence
Plants produce ellagic acid and convert it to a form of tannin known as ellagitannins.[citation needed] These are glucosides which are readily hydrolyzed by water to regenerate ellagic acid when the plants are eaten. The highest levels of ellagic acid are found in strawberries, raspberries, cranberries, and grapes.[2] It is also found in peach.[3]
Ellagic acid can be found in the mushroom Phellinus linteus.[4]
[edit] Proposed health benefits
Ellagic acid has antiproliferative and antioxidant properties in a number of in vitro and small-animal models.[5][6] The antiproliferative properties of ellagic acid are due to its ability to directly inhibit the DNA binding of certain carcinogens, including nitrosamines[7][8] and polycyclic aromatic hydrocarbons.[9] As with other polyphenol antioxidants, ellagic acid has a chemoprotective effect in cellular models by reducing oxidative stress.[2] However, one study found it to be antagonistic with catechins, such as those found in tea.[10]
These properties have generated interest in potential human health benefits from the consumption of ellagic acid. However, very little study of these proposed benefits has been reported as of 2010. A small randomized controlled trial involving 19 patients with carotid artery stenosis found that pomegranate juice, which is high in ellagic acid, appeared to reduce blood pressure and carotid artery wall thickness.[11] A 2005 controlled study of 48 patients undergoing chemotherapy for prostate cancer found that ellagic acid supplementation reduced the rate of chemotherapy-associated neutropenia (though there were no cases of severe neutropenia in either the ellagic acid or control group). Ellagic acid supplementation did not improve overall or progression-free survival of patients with prostate cancer in this trial.[12]
Despite the very preliminary state of evidence supporting health benefits in humans, 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".[13] 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.[14][15]
[edit] References
- ^ [1]
- ^ a b D. A. Vattem and K. Shetty (2005). "Biological Function of Ellagic Acid: A Review". Journal of Food Biochemistry 29 (3): 234–266. doi:10.1111/j.1745-4514.2005.00031.x.
- ^ 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)
- ^ Lee YS, Kang YH, Jung JY, et al. (October 2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus" ([dead link]). Biological & Pharmaceutical Bulletin 31 (10): 1968–72. doi:10.1248/bpb.31.1968. PMID 18827365. http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/31.1968?from=PubMed.
- ^ Seeram NP, Adams LS, Henning SM, et al. (June 2005). "In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice". J. Nutr. Biochem. 16 (6): 360–7. doi:10.1016/j.jnutbio.2005.01.006. PMID 15936648.
- ^ Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW (March 1999). "p53/p21(WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells". Cancer Lett. 136 (2): 215–21. doi:10.1016/S0304-3835(98)00323-1. PMID 10355751. http://linkinghub.elsevier.com/retrieve/pii/S0304-3835(98)00323-1.
- ^ Madal, Shivappurkar, Galati, and Stoner (1988). "Inhibition of N-nitrosobenzymethylamine metabolism and DNA binding in cultured rat esophagus by ellagic acid". Carcinogenesis 9 (7): 1313–1316. doi:10.1093/carcin/9.7.1313. PMID 3383347.
- ^ Mandal and Stoner; Stoner, GD (1990). "Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid". Carcinogenesis 11 (1): 55–61. doi:10.1093/carcin/11.1.55. PMID 2295128.
- ^ Teel, Babcock, Dixit, and Stoner (1986). "Ellagic acid toxicity and interaction with benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol in human bronchial epithelial cells". Cell Biol. Toxicol. 2 (1): 53–62. doi:10.1007/BF00117707. PMID 3267445.
- ^ Anne S. Meyer, Marina Heinonen, Edwin N. Frankel (January 1998). "Antioxidant interactions of catechin, cyanidin, caffeic acid, quercetin, and ellagic acid on human LDL oxidation". Food Chemistry 61 (1-2): 71–75. doi:10.1016/S0308-8146(97)00100-3.
- ^ Aviram M, Rosenblat M, Gaitini D, et al. (June 2004). "Pomegranate juice consumption for 3 years by patients with carotid artery stenosis reduces common carotid intima-media thickness, blood pressure and LDL oxidation". Clin Nutr 23 (3): 423–33. doi:10.1016/j.clnu.2003.10.002. PMID 15158307.
- ^ Falsaperla M, Morgia G, Tartarone A, Ardito R, Romano G (April 2005). "Support ellagic acid therapy in patients with hormone refractory prostate cancer (HRPC) on standard chemotherapy using vinorelbine and estramustine phosphate". Eur. Urol. 47 (4): 449–54; discussion 454–5. doi:10.1016/j.eururo.2004.12.001. PMID 15774240.
- ^ 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.
[edit] 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
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