Ergothioneine Explained

Ergothioneine is a naturally occurring amino acid and is a thiourea derivative of histidine, containing a sulfur atom on the imidazole ring.[1] This compound occurs in relatively few organisms, notably actinomycetota, cyanobacteria, and certain fungi.[2] [3] Ergothioneine was discovered by Charles Tanret in 1909 and named after the ergot fungus from which it was first purified,[4] with its structure being determined in 1911.[5]

In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid, and eyes.[6] Although the effect of ergothioneine in vivo is under preliminary research, its physiological role in humans is unknown.[6] Ergothioneine is sold as a dietary supplement.

Metabolism and sources

Ergothioneine has been found in bacteria, plants, and animals, sometimes at millimolar levels.[7] Foods found to contain ergothioneine include liver, kidney, black beans, kidney bean, and oat bran, with the highest levels in bolete and oyster mushrooms.[7] [8] Levels can be variable, even within species and some tissues can contain much more than others. In the human body, the largest amounts of ergothioneine are found in erythrocytes, eye lens, semen,[9] and skin.[10]

Although many species contain ergothioneine, only a few make it; the others absorb it from their diet or, in the case of plants, from their environment.[11] Biosynthesis has been detected in Actinomycetota, such as Mycobacterium smegmatis and certain fungi, such as Neurospora crassa.[2]

The metabolic pathway to produce ergothioneine starts with the methylation of histidine to produce histidine betaine (hercynine). The sulfur atom is then incorporated from cysteine.[7] [12] The biosynthetic genes of ergothioneine have been described in Mycobacterium smegmatis,[13] Neurospora crassa,[14] and Schizosaccharomyces pombe.[15]

Other species of bacteria, such as Bacillus subtilis, Escherichia coli, Proteus vulgaris, and Streptococcus, as well as fungi in the Saccharomycotina cannot make ergothioneine.[16] [17]

Structure

Ergothioneine is a thiourea derivative of the betaine of histidine and contains a sulfur atom bonded to the 2-position of the imidazole ring.[18] Typical of thioureas, ergothioneine is less reactive than typical thiols such as glutathione towards alkylating agents like maleimides. It also resists oxidation by air. However, ergothioneine can be slowly oxidized over several days to the disulfide form in acidic solutions.[19]

Ergothioneine derivatives

Various derivatives of ergothioneine have been reported in the literature, such as S-methyl-ergothioneine[20] or selenium-containing selenoneine.[21]

Preliminary research

Although potential effects of ergothioneine are under preliminary research, its physiological role in vivo has not been determined.[1] [6]

Safe intake levels

The Panel on Dietetic Products for the European Food Safety Authority reported safe daily limits of 2.82 mg/kg of body weight for infants, 3.39 mg/kg for small children, and 1.31 mg/kg for adults, including pregnant and breastfeeding women.[22]

See also

External links

Notes and References

  1. Web site: Ergothioneine . PubChem, National Center for Biotechnology Information, US National Library of Medicine . 7 November 2019 . 2 November 2019.
  2. Fahey RC . Novel thiols of prokaryotes . Annual Review of Microbiology . 55 . 333–56 . 2001 . 11544359 . 10.1146/annurev.micro.55.1.333 .
  3. Pfeiffer C, Bauer T, Surek B, Schömig E, Gründemann D . 2011 . Cyanobacteria produce high levels of ergothioneine . Food Chemistry . 129 . 4 . 1766–1769 . 10.1016/j.foodchem.2011.06.047 .
  4. Tanret . C. . Charles Joseph Tanret . 1909 . Sur une base nouvelle retirée du seigle ergoté : l'ergothioneine . French . Comptes rendus hebdomadaires des séances de l'Académie des sciences . 149 . 222-224 .
  5. Barger. G. . George Barger . Erwins . A.J. . 1911 . The constitution of ergothioneine : a betaine related to histidine . Journal of the Chemical Society, Transactions . 99 . 2336–2341 . 10.1039/CT9119902336 .
  6. Cheah . Irwin K. . Halliwell . Barry . 2021-01-26 . Ergothioneine, recent developments . Redox Biology . 42 . 101868 . 10.1016/j.redox.2021.101868 . 2213-2317 . 8113028 . 33558182.
  7. Ey J, Schömig E, Taubert D . Dietary sources and antioxidant effects of ergothioneine . Journal of Agricultural and Food Chemistry . 55 . 16 . 6466–74 . August 2007 . 17616140 . 10.1021/jf071328f .
  8. Kalač P. Edible Mushrooms. Chapter 4 - Health-Stimulating Compounds and Effects. pp 137-153. Academic Press, 2016.
  9. Mann T, Leone E . Studies on the metabolism of semen. VIII. Ergothioneine as a normal constituent of boar seminal plasma; purification and crystallization; site of formation and function . The Biochemical Journal . 53 . 1 . 140–8 . January 1953 . 13032046 . 1198115 . 10.1042/bj0530140 .
  10. Markova NG, Karaman-Jurukovska N, Dong KK, Damaghi N, Smiles KA, Yarosh DB . Skin cells and tissue are capable of using L-ergothioneine as an integral component of their antioxidant defense system . Free Radical Biology & Medicine . 46 . 8 . 1168–76 . April 2009 . 19439218 . 10.1016/j.freeradbiomed.2009.01.021 .
  11. The uptake of ergothioneine from the soil into the latex of Hevea brasiliensis . 1968 . Phytochemistry . 1999–2000 . 7 . Audley BS, Tan CH . 10.1016/S0031-9422(00)90759-3 . 11. 1968PChem...7.1999A .
  12. Melville DB, Ludwig ML, Inamine E, Rachele JR . Transmethylation in the biosynthesis of ergothionelne . The Journal of Biological Chemistry . 234 . 5 . 1195–8 . May 1959 . 10.1016/S0021-9258(18)98157-3 . 13654346 . free .
  13. Seebeck FP . In vitro reconstitution of Mycobacterial ergothioneine biosynthesis . Journal of the American Chemical Society . 132 . 19 . 6632–3 . May 2010 . 20420449 . 10.1021/ja101721e .
  14. Bello MH, Barrera-Perez V, Morin D, Epstein L . The Neurospora crassa mutant NcΔEgt-1 identifies an ergothioneine biosynthetic gene and demonstrates that ergothioneine enhances conidial survival and protects against peroxide toxicity during conidial germination . Fungal Genetics and Biology . 49 . 2 . 160–72 . February 2012 . 22209968 . 10.1016/j.fgb.2011.12.007 .
  15. Pluskal T, Ueno M, Yanagida M . Genetic and metabolomic dissection of the ergothioneine and selenoneine biosynthetic pathway in the fission yeast, S. pombe, and construction of an overproduction system . PLOS ONE . 9 . 5 . e97774 . 2014 . 24828577 . 4020840 . 10.1371/journal.pone.0097774 . 2014PLoSO...997774P . free .
  16. Genghof DS . Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales . Journal of Bacteriology . 103 . 2 . 475–8 . August 1970 . 5432011 . 248105 . 10.1128/JB.103.2.475-478.1970 .
  17. Genghof DS, Inamine E, Kovalenko V, Melville DB . Ergothioneine in microorganisms . The Journal of Biological Chemistry . 223 . 1 . 9–17 . November 1956 . 10.1016/S0021-9258(18)65113-0 . 13376573 . free .
  18. Book: Hartman PE. Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants . [32] Ergothioneine as antioxidant . Methods in Enzymology . 186. 310–8. 1990. 2172707. 10.1016/0076-6879(90)86124-E . 978-0-12-182087-9. https://archive.org/details/oxygenradicalsin0000unse/page/310.
  19. Heath H, Toennies G . The preparation and properties of ergothioneine disulphide . The Biochemical Journal . 68 . 2 . 204–10 . February 1958 . 13522601 . 1200325 . 10.1042/bj0680204 .
  20. Asmus KD, Bensasson RV, Bernier JL, Houssin R, Land EJ . One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C . The Biochemical Journal . 315 . 2 . 625–9 . April 1996 . 8615839 . 1217242 . 10.1042/bj3150625 .
  21. Yamashita Y, Yamashita M . Identification of a novel selenium-containing compound, selenoneine, as the predominant chemical form of organic selenium in the blood of bluefin tuna . The Journal of Biological Chemistry . 285 . 24 . 18134–8 . June 2010 . 20388714 . 2881734 . 10.1074/jbc.C110.106377 . free .
  22. Turck D, Bresson JL, Burlingame B, Dean T, Fairweather-Tait S, Heinonen M, Hirsch-Ernst KI, Mangelsdorf I, McArdle HJ, Naska A, Neuhäuser-Berthold M, Nowicka G, Pentieva K, Sanz Y, Siani A, Sjödin A, Stern M, Tomé D, Vinceti M, Willatts P, Engel KH, Marchelli R, Pöting A, Poulsen M, Schlatter JR, Ackerl R, van Loveren H . 6 . Statement on the safety of synthetic l-ergothioneine as a novel food - supplementary dietary exposure and safety assessment for infants and young children, pregnant and breastfeeding women . EFSA Journal . 15 . 11 . e05060 . November 2017 . 32625352 . 10.2903/j.efsa.2017.5060 . 7010164 . free .

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