Ellagic acid

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Ellagic acid
Ellagic acid
Identifiers
CAS number 476-66-4 YesY
PubChem 5281855
ChemSpider 4445149 YesY
UNII 19YRN3ZS9P YesY
DrugBank DB08468
KEGG C10788 YesY
ChEBI CHEBI:4775 YesY
ChEMBL CHEMBL6246 YesY
Jmol-3D images Image 1
Properties
Molecular formula C14H6O8
Molar mass 302.197 g/mol
Density 1.67 g/cm³
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
UV visible spectrum of ellagic acid

Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables. 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.

Metabolism[edit]

Biosynthesis[edit]

Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin[1] and geraniin.[2]:208

Biodegradation[edit]

Urolithins are microflora human metabolites of dietary ellagic acid derivatives[3]

History[edit]

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[edit]

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[edit]

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.

Research into potential medicinal uses[edit]

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]

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.[17] 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.[18]

Despite there being only a 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".[19] 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.[20][21]

Urolithins, such as urolithin A, are microflora human metabolites of dietary ellagic acid derivatives that are under study as anti-cancer agents.[22]

References[edit]

  1. ^ Ascacio-Valdés JA et al. (2011) Review: Ellagitannins: Biosynthesis, biodegradation and biological properties Journal of Medicinal Plants Research Vol. 5(19):4696-4703
  2. ^ David S. Seigler Plant Secondary Metabolism. Springer, 1998.
  3. ^ 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): 1611–20. doi:10.1021/jf0527403. PMID 16506809. 
  4. ^ a b c Grasser, Georg (1922). Synthetic Tannins. F. G. A. Enna. ISBN 9781406773019. 
  5. ^ Nierenstein, M (1915). "The Formation of Ellagic Acid from Galloyl-Glycine by Penicillium". The Biochemical journal 9 (2): 240–4. PMC 1258574. PMID 16742368. 
  6. ^ Löwe, Zeitschrift für Chemie, 1868, 4, 603
  7. ^ Mämmelä, Pirjo; Savolainen, Heikki; Lindroos, Lasse; Kangas, Juhani; Vartiainen, Terttu (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626. 
  8. ^ Nakai, S (2000). "Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa". Water Research 34 (11): 3026. doi:10.1016/S0043-1354(00)00039-7. 
  9. ^ Lee YS, Kang YH, Jung JY et al. (October 2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological & Pharmaceutical Bulletin 31 (10): 1968–72. doi:10.1248/bpb.31.1968. PMID 18827365. [dead link]
  10. ^ 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. 
  11. ^ 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)
  12. ^ 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. 
  13. ^ 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. 
  14. ^ 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. 
  15. ^ 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. 
  16. ^ 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. 
  17. ^ 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. 
  18. ^ 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. 
  19. ^ 187 Fake Cancer 'Cures' Consumers Should Avoid, from the U.S. Food and Drug Administration. Accessed June 17, 2008.
  20. ^ Warning Letter sent to Millennium Health by the United States Food and Drug Administration, dated May 21, 2008.
  21. ^ Warning Letter sent to Kenton Campbell at Prime Health Direct, Ltd. by the United States Food and Drug Administration dated July 2, 2007.
  22. ^ 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

External links[edit]