Ellagic acid explained

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 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

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 urolintins.

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 oak species such as the North American white oak (Quercus alba) and European red oak (Quercus robur).[8]

The macrophyte Myriophyllum spicatum produces ellagic acid.[9]

Ellagic acid can be found in the medicinal mushroom Phellinus linteus.[10]

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.[11] It is also found in peaches[12] and pomegranates.[13]

Dietary sourceEllagic acid[14]
Fruits (mg/100g fresh weight)
Blackberries150
Black raspberries90
Boysenberries70
Cloudberries315.1
Pomegranate269.9[15]
Raspberries270
Rose hip109.6
Strawberries 77.6
Strawberry jam24.5
Yellow raspberries1900
Nuts (mg/100g fresh weight)
Pecans33
Walnuts59
Beverages (mg/L)
Pomegranate juice811.1
Cognac31–55
Oak-aged red wine33
Whiskey1.2
Seeds (mg/g)
Black raspberries6.7
Red raspberries8.7
Boysenberries30
Mango1.2

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.[16] [17] [18] Ellagic acid has been identified by the FDA as a "fake cancer 'cure'".[17] There is no scientific evidence to support the claims that ellagic acid can treat or prevent cancer.[17]

See also

Notes and References

  1. Web site: ellagique . Littré . Émile . Dictionnaire de la langue française.
  2. Book: Seigler, David S. . Plant Secondary Metabolism . December 31, 1998 . Springer Science & Business Media . 978-0-412-01981-4 . 208.
  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 . 10.1021/jf0527403 . 16506809.
  4. Luca SV, Macovei I, Bujor A, Trifan A . Bioactivity of dietary polyphenols: The role of metabolites . . 60 . 4 . 626–659 . 2020 . 10.1080/10408398.2018.1546669 . 30614249. 58651581 .
  5. Book: Grasser . Georg . Synthetic Tannins . Enna . F. G. A. . 1922 . 9781406773019 . 20. Read Books .
  6. Nierenstein . M. . 1915 . The Formation of Ellagic Acid from Galloyl-Glycine by Penicillium . The Biochemical Journal . 9 . 2 . 240–244 . 10.1042/bj0090240 . 1258574 . 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. 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 . 10.1016/S0021-9673(00)00624-5 . 10999626.
  9. Nakai . S. . 2000 . Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa . Water Research . 34 . 11 . 3026–3032 . 10.1016/S0043-1354(00)00039-7. 2000WatRe..34.3026N .
  10. 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 . 10.1248/bpb.31.1968 . 18827365 . free.
  11. Vattem . D. A. . Shetty . K. . 2005 . Biological Function of Ellagic Acid: A Review . Journal of Food Biochemistry . 29 . 3 . 234–266 . 10.1111/j.1745-4514.2005.00031.x.
  12. Infante . R. . Contador . L. . Rubio . P. . Aros . D. . Peña Neira . Á. . 2011 . Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches . Chilean Journal of Agricultural Research . 71 . 3 . 445–451 . 10.4067/S0718-58392011000300016. free .
  13. 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 . 10.3109/09637486.2013.798268 . 23700985. 10798834 .
  14. 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 . 10.1016/j.foodres.2011.04.027.
  15. 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 . 10.1016/j.chroma.2015.08.044 . 26341594.
  16. Web site: Miriam R. Burbach . Warning letter:VitaPurity Corporation . US Food and Drug Administration . December 2, 2021 . May 12, 2017.
  17. Web site: 187 Fake Cancer 'Cures' Consumers Should Avoid . . https://web.archive.org/web/20170502034227/https://www.fda.gov/drugs/guidancecomplianceregulatoryinformation/enforcementactivitiesbyfda/ucm171057.htm . May 2, 2017 . June 17, 2008.
  18. News: June 17, 2008. FDA Cracks Down On Unproved Cancer Cures. CBS News. live. February 16, 2021. https://web.archive.org/web/20180629181344/https://www.cbsnews.com/news/fda-cracks-down-on-unproved-cancer-cures/. June 29, 2018.

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