Ellagic acid

Name

The name comes from the French term acide ellagique, from the word galle spelled backward 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.

Biodegradation

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

History

Ellagic acid was first discovered by chemist Henri Braconnot in 1831. Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905. Julius Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide.

Natural occurrences

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

The macrophyte Myriophyllum spicatum produces ellagic acid.

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

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. It is also found in peaches and pomegranates.

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

References

References

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8. (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A.
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11. (2005). "Biological Function of Ellagic Acid: A Review". Journal of Food Biochemistry.
12. (2011). "Postharvest sensory and phenolic characterization of 'Elegant Lady' and 'Carson' peaches". Chilean Journal of Agricultural Research.
13. (November 2013). "The pharmacological use of ellagic acid-rich pomegranate fruit". International Journal of Food Sciences and Nutrition.
14. Landete, J.M.. (2011). "Ellagitannins, ellagic acid and their derived metabolites: A review about source, metabolism, functions and health". Food Research International.
15. (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.
16. (May 12, 2017). "Warning letter:VitaPurity Corporation". US Food and Drug Administration.
17. "187 Fake Cancer 'Cures' Consumers Should Avoid". U.S. [[Food and Drug Administration]].
18. (June 17, 2008). "FDA Cracks Down On Unproved Cancer Cures". CBS News.