Ellagic acid

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Ellagic acid
Ellagic acid.svg
Ellagic acid 3D spacefill.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 Yes check.svgY
    Key: AFSDNFLWKVMVRB-UHFFFAOYSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
UV visible spectrum of ellagic acid Std Acide ellagique UV.PNG
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

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 molecular 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

Biosynthesis

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

Biodegradation

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

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

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

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 sourceEllagic acid [15]
Fruits (mg/100g fresh weight)
Yellow raspberries1900
Cloudberries 315.1
Raspberries270
Pomegranate269.9 [16]
Blackberries 150
Rose hip 109.6
Black raspberries 90
Strawberries77.6
Boysenberries 70
Strawberry jam24.5
Nuts (mg/100g fresh weight)
Walnuts59
Pecans33
Beverages (mg/L)
Pomegranate juice811.1 [16]
Cognac 31–55
Oak-aged red wine 33
Whiskey 1.2
Seeds (mg/g)
Boysenberries30
Red raspberries8.7
Black raspberries6.7
Mango 1.2

Research and health claims

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

References

  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. 1 2 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. 1 2 3 Grasser, Georg; Enna, F. G. A. (1922). Synthetic Tannins. Read Books. p.  20. ISBN   9781406773019.{{cite book}}: ISBN / Date incompatibility (help)
  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. 1 2 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. Archived from the original on September 8, 2019. Retrieved December 2, 2021.
  18. 1 2 3 "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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