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Ellagic acid

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Ellagic acid
Skeletal formula of ellagic acid
Space-filling model of the ellagic acid molecule
Names
Preferred IUPAC name
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione
Other names
4,4′,5,5′,6,6′-Hexahydroxydiphenic acid 2,6,2′,6′-dilactone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.827 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H checkY
    Key: AFSDNFLWKVMVRB-UHFFFAOYSA-N checkY
  • InChI=1/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H
    Key: AFSDNFLWKVMVRB-UHFFFAOYAQ
  • O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O
Properties
C14H6O8
Molar mass 302.197 g/mol
Density 1.67 g/cm3
Melting point >360 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
UV visible spectrum of ellagic acid

Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.

Name

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The name comes from the French term acide ellagique, from the word galle spelled backward[1] because it can be obtained from noix de galle (galls), and to distinguish it from acide gallique (gallic acid). The molecule structure resembles to that of two gallic acid molecules being assembled "head to tail" and bound together by a C–C bond (as in biphenyl, or in diphenic acid) and two lactone links (cyclic carboxylic esters).

Metabolism

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Biosynthesis

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

Biodegradation

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Urolithins are gut flora human metabolites of dietary ellagic acid derivatives.[3][4] Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolithins.[4]

History

[edit]

Ellagic acid was first discovered by chemist Henri Braconnot in 1831.[5] Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905.[5] He also suggested its formation from galloyl-glycine by Penicillium in 1915.[6] Julius Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide.[5][7]

Natural occurrences

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Ellagic acid is found in edible nuts.[8] It is also found in oak species such as the North American white oak (Quercus alba) and European red oak (Quercus robur).[9]

The macrophyte Myriophyllum spicatum produces ellagic acid.[10]

Ellagic acid can be found in the medicinal mushroom Phellinus linteus.[11]

In food

[edit]

The highest levels of ellagic acid are found in raw chestnuts, walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages.[12] It is also found in peaches[13] and pomegranates.[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/100g fresh weight)
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

Research and health claims

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Ellagic acid has been marketed as a dietary supplement with various claimed benefits against cancer, heart disease, and other diseases. In the 21st century, numerous U.S.-based supplement companies received FDA warning letters for promoting ellagic acid with false anti-disease claims that violate the Federal Food, Drug, and Cosmetic Act.[17][18][19] Ellagic acid has been identified by the FDA as a "fake cancer 'cure'".[18] There is no scientific evidence to support the claims that ellagic acid can treat or prevent cancer.[18]

See also

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References

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  1. ^ Littré, Émile. "ellagique". Dictionnaire de la langue française.
  2. ^ Seigler, David S. (December 31, 1998). Plant Secondary Metabolism. Springer Science & Business Media. p. 208. ISBN 978-0-412-01981-4.
  3. ^ Larrosa, M.; González Sarrías, A.; García Conesa, M. T.; Tomás Barberán, F. A.; Espín, J. C. (2006). "Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities". Journal of Agricultural and Food Chemistry. 54 (5): 1611–1620. Bibcode:2006JAFC...54.1611L. doi:10.1021/jf0527403. PMID 16506809.
  4. ^ a b Luca SV, Macovei I, Bujor A, Trifan A (2020). "Bioactivity of dietary polyphenols: The role of metabolites". Critical Reviews in Food Science and Nutrition. 60 (4): 626–659. doi:10.1080/10408398.2018.1546669. PMID 30614249. S2CID 58651581.
  5. ^ a b c Grasser, Georg; Enna, F. G. A. (1922). Synthetic Tannins. Read Books. p. 20. ISBN 9781406773019.
  6. ^ Nierenstein, M. (1915). "The Formation of Ellagic Acid from Galloyl-Glycine by Penicillium". The Biochemical Journal. 9 (2): 240–244. doi:10.1042/bj0090240. PMC 1258574. PMID 16742368.
  7. ^ Löwe, Julius (1868). "Über die Bildung von Ellagsäure aus Gallussäure" [On the synthesis of ellagic acid from gallic acid]. Zeitschrift für Chemie. 4: 603.
  8. ^ Bodoira, Romina; Maestri, Damián (2020). "Phenolic Compounds from Nuts: Extraction, Chemical Profiles, and Bioactivity". Journal of Agricultural and Food Chemistry. 68 (4): 927–942. Bibcode:2020JAFC...68..927B. doi:10.1021/acs.jafc.9b07160. PMID 31910006.
  9. ^ Mämmelä, P.; Savolainen, H.; Lindroos, L.; Kangas, J.; Vartiainen, T. (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.
  10. ^ Nakai, S. (2000). "Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa". Water Research. 34 (11): 3026–3032. Bibcode:2000WatRe..34.3026N. doi:10.1016/S0043-1354(00)00039-7.
  11. ^ Lee, Y.-S.; Kang, Y.-H.; Jung, J.-Y.; Lee, S.; Ohuchi, K.; Shin, K.-H.; Kang, I.-J.; Park, J.-H.; Shin, H.-K.; Lim, S.-S. (2008). "Protein glycation inhibitors from the fruiting body of Phellinus linteus". Biological and Pharmaceutical Bulletin. 31 (10): 1968–1972. doi:10.1248/bpb.31.1968. PMID 18827365.
  12. ^ Vattem, D. A.; Shetty, K. (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.
  13. ^ Infante, R.; Contador, L.; Rubio, P.; Aros, D.; Peña Neira, Á. (2011). "Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches" (PDF). Chilean Journal of Agricultural Research. 71 (3): 445–451. doi:10.4067/S0718-58392011000300016.
  14. ^ Usta, C.; Özdemir, S.; Schiariti, M.; Puddu, P. E. (November 2013). "The pharmacological use of ellagic acid-rich pomegranate fruit". International Journal of Food Sciences and Nutrition. 64 (7): 907–913. doi:10.3109/09637486.2013.798268. PMID 23700985. S2CID 10798834.
  15. ^ Landete, J.M. (2011). "Ellagitannins, ellagic acid and their derived metabolites: A review about source, metabolism, functions and health". Food Research International. 44 (5): 1150–1160. doi:10.1016/j.foodres.2011.04.027.
  16. ^ a b García-Villalba, Rocío; Espín, Juan Carlos; Tomás-Barberán, Francisco A. (2016). "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: 162–175. doi:10.1016/j.chroma.2015.08.044. PMID 26341594.
  17. ^ Miriam R. Burbach (May 12, 2017). "Warning letter:VitaPurity Corporation". US Food and Drug Administration. Retrieved December 2, 2021.
  18. ^ a b c "187 Fake Cancer 'Cures' Consumers Should Avoid". U.S. Food and Drug Administration. Archived from the original on May 2, 2017. Retrieved June 17, 2008.
  19. ^ "FDA Cracks Down On Unproved Cancer Cures". CBS News. June 17, 2008. Archived from the original on June 29, 2018. Retrieved February 16, 2021.
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