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.[12] Biosynthesis has been detected in Actinomycetota, such as Mycobacterium smegmatis and certain fungi, such as Neurospora crassa.[2]
Ergothioneine is a thiourea derivative of the betaine of histidine and contains a sulfur atom bonded to the 2-position of the imidazole ring.[19] Typical of thioureas, ergothioneine is less reactive than typical thiols such as glutathione towards alkylating agents like maleimides. It also resists oxidation by air.[9] However, ergothioneine can be slowly oxidized over several days to the disulfide form in acidic solutions.[20]
Ergothioneine derivativesedit
Various derivatives of ergothioneine have been reported in the literature, such as S-methyl-ergothioneine[21] or selenium-containing selenoneine.[22]
Preliminary researchedit
Although potential effects of ergothioneine are under preliminary research, its physiological role in vivo has not been determined.[1][7]
Safe intake levelsedit
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.[8]
^ ab"Ergothioneine". PubChem, National Center for Biotechnology Information, US National Library of Medicine. 2 November 2019. Retrieved 7 November 2019.
^ abFahey RC (2001). "Novel thiols of prokaryotes". Annual Review of Microbiology. 55: 333–56. doi:10.1146/annurev.micro.55.1.333. PMID 11544359.
^Pfeiffer C, Bauer T, Surek B, Schömig E, Gründemann D (2011). "Cyanobacteria produce high levels of ergothioneine". Food Chemistry. 129 (4): 1766–1769. doi:10.1016/j.foodchem.2011.06.047.
^Tanret, C. (1909). "Sur une base nouvelle retirée du seigle ergoté : l'ergothioneine". Comptes rendus hebdomadaires des séances de l'Académie des sciences (in French). 149: 222-224.
^Barger, G.; Erwins, A.J. (1911). "The constitution of ergothioneine : a betaine related to histidine". Journal of the Chemical Society. Transactions. 99: 2336–2341.
^ abMann T, Leone E (January 1953). "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. doi:10.1042/bj0530140. PMC1198115. PMID 13032046.
^ abTurck D, Bresson JL, Burlingame B, Dean T, Fairweather-Tait S, Heinonen M, et al. (November 2017). "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. doi:10.2903/j.efsa.2017.5060. PMC7010164. PMID 32625352.
^ abcdEy J, Schömig E, Taubert D (August 2007). "Dietary sources and antioxidant effects of ergothioneine". Journal of Agricultural and Food Chemistry. 55 (16): 6466–74. doi:10.1021/jf071328f. PMID 17616140.
^Kalač P. Edible Mushrooms. Chapter 4 - Health-Stimulating Compounds and Effects. pp 137-153. Academic Press, 2016. ISBN 9780128044551 doi:10.1016/B978-0-12-804455-1.00004-7
^Markova NG, Karaman-Jurukovska N, Dong KK, Damaghi N, Smiles KA, Yarosh DB (April 2009). "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. doi:10.1016/j.freeradbiomed.2009.01.021. PMID 19439218.
^Audley BS, Tan CH (1968). "The uptake of ergothioneine from the soil into the latex of Hevea brasiliensis". Phytochemistry. 7 (11): 1999–2000. doi:10.1016/S0031-9422(00)90759-3.
^Melville DB, Ludwig ML, Inamine E, Rachele JR (May 1959). "Transmethylation in the biosynthesis of ergothionelne". The Journal of Biological Chemistry. 234 (5): 1195–8. doi:10.1016/S0021-9258(18)98157-3. PMID 13654346.[permanent dead link]
^Seebeck FP (May 2010). "In vitro reconstitution of Mycobacterial ergothioneine biosynthesis". Journal of the American Chemical Society. 132 (19): 6632–3. doi:10.1021/ja101721e. PMID 20420449.
^Bello MH, Barrera-Perez V, Morin D, Epstein L (February 2012). "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. doi:10.1016/j.fgb.2011.12.007. PMID 22209968.
^Pluskal T, Ueno M, Yanagida M (2014). "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. Bibcode:2014PLoSO...997774P. doi:10.1371/journal.pone.0097774. PMC4020840. PMID 24828577.
^Genghof DS (August 1970). "Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales". Journal of Bacteriology. 103 (2): 475–8. doi:10.1128/JB.103.2.475-478.1970. PMC248105. PMID 5432011.
^Genghof DS, Inamine E, Kovalenko V, Melville DB (November 1956). "Ergothioneine in microorganisms". The Journal of Biological Chemistry. 223 (1): 9–17. doi:10.1016/S0021-9258(18)65113-0. PMID 13376573.[permanent dead link]
^Hartman PE (1990). "[32] Ergothioneine as antioxidant". Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants. Methods in Enzymology. Vol. 186. pp. 310–8. doi:10.1016/0076-6879(90)86124-E. ISBN 978-0-12-182087-9. PMID 2172707.
^Heath H, Toennies G (February 1958). "The preparation and properties of ergothioneine disulphide". The Biochemical Journal. 68 (2): 204–10. doi:10.1042/bj0680204. PMC1200325. PMID 13522601.
^Asmus KD, Bensasson RV, Bernier JL, Houssin R, Land EJ (April 1996). "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. doi:10.1042/bj3150625. PMC1217242. PMID 8615839.
^Yamashita Y, Yamashita M (June 2010). "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. doi:10.1074/jbc.C110.106377. PMC2881734. PMID 20388714.