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{{Short description|Naturally occurring amino acid}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443733003
| Watchedfields = changed
⚫ | ImageFileL1 = Ergothioneine.png
⚫ | verifiedrevid = 443735061
| ImageSizeL1 = 125px
⚫ | ImageFileL1 = Ergothioneine.svg
| ImageFileR1 = Ergothioneine ball and stick.png | ImageFileR1 = Ergothioneine ball and stick.png
| ImageSizeR1 = 125px
| ImageFile2 = Ergothioneine 3D.png | ImageFile2 = Ergothioneine 3D.png
| ImageSize2 = 150px | ImageSize2 = 150px
|IUPACName=3-(2-sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate | PIN=(2''S'')-3-(2-Sulfanylidene-2,3-dihydro-1''H''-imidazol-4-yl)-2-(trimethylazaniumyl)propanoate
|OtherNames=<small>L</small>-Ergothioneine | OtherNames=<small>L</small>-Ergothioneine; (+)-Ergothioneine; Thiasine; Sympectothion; Ergothionine; Erythrothioneine; Thiolhistidinebetaine
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4508619 | ChemSpiderID = 4508619
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C05570
| InChI = 1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1 | InChI = 1/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
| InChIKey = SSISHJJTAXXQAX-ZETCQYMHBA | InChIKey = SSISHJJTAXXQAX-ZETCQYMHBA
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SSISHJJTAXXQAX-ZETCQYMHSA-N | StdInChIKey = SSISHJJTAXXQAX-ZETCQYMHSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=497-30-3 | CASNo=497-30-3
| PubChem = 5351619
| UNII_Ref = {{fdacite|correct|FDA}} | PubChem = 5351619
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = BDZ3DQM98W | UNII = BDZ3DQM98W
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
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}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>9</sub>H<sub>15</sub>N<sub>3</sub>O<sub>2</sub>S | Formula=C<sub>9</sub>H<sub>15</sub>N<sub>3</sub>O<sub>2</sub>S
| MolarMass=229.30 g/mol | MolarMass=229.30 g/mol
| Appearance= | Appearance= white solid
| Density= | Density=
| MeltingPtC= 275 to 277
| MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
}} }}


'''Ergothioneine''' is a naturally occurring ] and is a thiourea derivative of histidine, containing a ] atom in the ] ring. This compound is made in rather few organisms, notably ] and filamentous fungi.<ref name=Fahey>{{cite journal |author=Fahey RC |title=Novel thiols of prokaryotes |journal=Annu. Rev. Microbiol. |volume=55 |issue= |pages=333–56 |year=2001 |pmid=11544359 |doi=10.1146/annurev.micro.55.1.333}}</ref> Ergothioneine was discovered in 1909 and named after the ] fungus from which it was first purified, with its structure being determined later, in 1911.<ref name=Mann/> This amino acid has ] properties, but its chemistry differs from conventional sulfur-containing antioxidants such as ] or ]. '''Ergothioneine''' is a naturally occurring ] and is a ] derivative of ], containing a ] atom on the ] ring.<ref name="pubchem">{{cite web |title=Ergothioneine |url=https://pubchem.ncbi.nlm.nih.gov/compound/5351619 |publisher=PubChem, National Center for Biotechnology Information, US National Library of Medicine |access-date=7 November 2019 |date=2 November 2019}}</ref> This compound occurs in relatively few organisms, notably ], ], and certain ].<ref name=Fahey>{{cite journal | vauthors = Fahey RC | title = Novel thiols of prokaryotes | journal = Annual Review of Microbiology | volume = 55 | pages = 333–56 | year = 2001 | pmid = 11544359 | doi = 10.1146/annurev.micro.55.1.333 }}</ref><ref>{{Cite journal | vauthors = Pfeiffer C, Bauer T, Surek B, Schömig E, Gründemann D | year = 2011 | title = Cyanobacteria produce high levels of ergothioneine | journal = Food Chemistry | volume = 129 | issue = 4 | pages = 1766–1769 | doi = 10.1016/j.foodchem.2011.06.047 }}</ref> Ergothioneine was discovered by ] in 1909 and named after the ] fungus from which it was first purified,<ref>{{ cite journal | last=Tanret | first=C. | author-link=Charles Joseph Tanret | date=1909 | title=Sur une base nouvelle retirée du seigle ergoté : l'ergothioneine | language=French | journal=Comptes rendus hebdomadaires des séances de l'Académie des sciences | volume=149 | page=222-224 | url=https://www.biodiversitylibrary.org/page/7138439 }}</ref> with its structure being determined in 1911.<ref>{{ cite journal | last1=Barger| first1=G. | author1-link=George Barger | last2=Erwins | first2=A.J. | date=1911 | title=The constitution of ergothioneine : a betaine related to histidine | journal=Journal of the Chemical Society, Transactions | volume=99 | pages=2336–2341 | doi=10.1039/CT9119902336 | url=https://archive.org/details/sim_journal-of-the-chemical-society-transactions_1911_99_part-ii/page/2336/mode/1up }}</ref><ref name=Mann/>


In humans, ergothioneine is acquired exclusively through the diet and accumulates in ]s, ], liver, kidney, ], and eyes.<ref name="cheah">{{Cite journal |last1=Cheah |first1=Irwin K. |last2=Halliwell |first2=Barry |date=2021-01-26 |title=Ergothioneine, recent developments |journal=Redox Biology |volume=42 |pages=101868 |doi=10.1016/j.redox.2021.101868 |issn=2213-2317 |pmc=8113028 |pmid=33558182}}</ref> Although the effect of ergothioneine '']'' is under preliminary research, its ] is unknown.<ref name=cheah/> Ergothioneine is sold as a ].<ref name=efsa/>
Although ergothioneine cannot be made in human cells, it is present in some tissues at high levels as it is absorbed from the diet.<ref>{{cite journal |author=Melville DB, Otken CC, Kovalenko V |title=On the origin of animal ergothioneine |journal=J. Biol. Chem. |volume=216 |issue=1 |pages=325–31 |year=1955 |month=September |pmid=13252032 |doi= |url=http://www.jbc.org/cgi/reprint/216/1/325}}</ref> In humans ergothioneine is taken up from the gut and concentrated in some tissues by a specific transporter called ETT (gene symbol ]). However, even today, one hundred years after its discovery, precisely what ergothioneine does in the human body remains a mystery.<ref name=Schomig/><ref name=Taubert/>


⚫ == Metabolism and sources ==
==Chemistry==
⚫ Ergothioneine has been found in bacteria, plants, and animals, sometimes at ] levels.<ref name="Schomig">{{cite journal | vauthors = Ey J, Schömig E, Taubert D | title = Dietary sources and antioxidant effects of ergothioneine | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 16 | pages = 6466–74 | date = August 2007 | pmid = 17616140 | doi = 10.1021/jf071328f }}</ref> Foods found to contain ergothioneine include ], ], ], ], and ], with the highest levels in ] and ]s.<ref name=Schomig/><ref>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}}</ref> 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 ]s, ], ],<ref name=Mann>{{cite journal | vauthors = Mann T, Leone E | title = Studies on the metabolism of semen. VIII. Ergothioneine as a normal constituent of boar seminal plasma; purification and crystallization; site of formation and function | journal = The Biochemical Journal | volume = 53 | issue = 1 | pages = 140–8 | date = January 1953 | pmid = 13032046 | pmc = 1198115 | doi = 10.1042/bj0530140 }}</ref> and ].<ref name=":6">{{cite journal | vauthors = Markova NG, Karaman-Jurukovska N, Dong KK, Damaghi N, Smiles KA, Yarosh DB | title = Skin cells and tissue are capable of using L-ergothioneine as an integral component of their antioxidant defense system | journal = Free Radical Biology & Medicine | volume = 46 | issue = 8 | pages = 1168–76 | date = April 2009 | pmid = 19439218 | doi = 10.1016/j.freeradbiomed.2009.01.021 }}</ref>
Ergothioneine is a ] derivative of the ] of ] and contains a sulfur atom bonded to the 2-position of the imidazole ring. This compound is unusual since the sulfur atom is most stable in solution in the ] form, rather than the ].<ref>{{cite journal |author=Hartman PE |title=Ergothioneine as antioxidant |journal=Meth. Enzymol. |volume=186 |issue= |pages=310–8 |year=1990 |pmid=2172707 |doi=10.1016/0076-6879(90)86124-E}}</ref> This makes ergothioneine much less reactive than thiols such as ] towards alkylating agents like ]s, and also prevents the compound from ] in air.<ref name=Schomig/> However, ergothioneine can be slowly oxidized over several days to the ] form in acidic solutions.<ref>{{cite journal |author=Heath H, Toennies G |title=The preparation and properties of ergothioneine disulphide |journal=Biochem. J. |volume=68 |issue=2 |pages=204–10 |year=1958 |month=February |pmid=13522601 |pmc=1200325 |url=http://www.biochemj.org/bj/068/0204/0680204.pdf}}</ref> If ergothioneine does become oxidized, the disulfide is a very strong oxidizing agent, so this will in turn rapidly oxidize other thiols in the cell such as glutathione.<ref>{{cite journal |author=Hand CE, Taylor NJ, Honek JF |title=Ab initio studies of the properties of intracellular thiols ergothioneine and ovothiol |journal=Bioorg. Med. Chem. Lett. |volume=15 |issue=5 |pages=1357–60 |year=2005 |month=March |pmid=15713386 |doi=10.1016/j.bmcl.2005.01.014}}</ref>


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.<ref>{{Cite journal | title = The uptake of ergothioneine from the soil into the latex of Hevea brasiliensis | year = 1968 | journal = Phytochemistry | pages = 1999–2000 | volume = 7 | vauthors = Audley BS, Tan CH | doi = 10.1016/S0031-9422(00)90759-3 | issue = 11| bibcode = 1968PChem...7.1999A }}</ref> Biosynthesis has been detected in ], such as '']'' and certain fungi, such as '']''.<ref name=Fahey/>
⚫ ==Metabolism and sources==
⚫ Ergothioneine has been found in bacteria, plants and animals, sometimes at ] levels.<ref name=Schomig/> Foods rich in ergothioneine include ], ], ], ] and ], with the highest levels in ] and ]s.<ref name=Schomig/> 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 ]s, ] and ],<ref name=Mann>{{cite journal |author=Mann T, Leone E |title=Studies on the metabolism of semen. VIII. Ergothioneine as a normal constituent of boar seminal plasma; purification and crystallization; site of formation and function |journal=Biochem. J. |volume=53 |issue=1 |pages=140–8 |year=1953 |month=January |pmid=13032046 |pmc=1198115 }}</ref> and it is also present in the ].<ref>{{cite journal |author=Markova NG, Karaman-Jurukovska N, Dong KK, Damaghi N, Smiles KA, Yarosh DB. |title=Skin cells and tissue are capable of using l-ergothioneine as an integral component of their antioxidant defense system |journal=Free Radic Biol Med. |volume=46 |issue=8 |pages=1168–76 |year=2009 |month=April |doi=10.1016/j.freeradbiomed.2009.01.021 |pmid=19439218}}</ref>


The ] to produce ergothioneine starts with the ] of ] to produce histidine betaine (hercynine). The sulfur atom is then incorporated from cysteine.<ref name=Schomig/><ref>{{cite journal | vauthors = Melville DB, Ludwig ML, Inamine E, Rachele JR | title = Transmethylation in the biosynthesis of ergothionelne | journal = The Journal of Biological Chemistry | volume = 234 | issue = 5 | pages = 1195–8 | date = May 1959 | doi = 10.1016/S0021-9258(18)98157-3 | pmid = 13654346 | url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13654346 | doi-access = free }}{{Dead link|date=March 2022 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> The biosynthetic genes of ergothioneine have been described in '']'',<ref>{{cite journal | vauthors = Seebeck FP | title = In vitro reconstitution of Mycobacterial ergothioneine biosynthesis | journal = Journal of the American Chemical Society | volume = 132 | issue = 19 | pages = 6632–3 | date = May 2010 | pmid = 20420449 | doi = 10.1021/ja101721e }}</ref> '']'',<ref>{{cite journal | vauthors = Bello MH, Barrera-Perez V, Morin D, Epstein L | title = 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 | journal = Fungal Genetics and Biology | volume = 49 | issue = 2 | pages = 160–72 | date = February 2012 | pmid = 22209968 | doi = 10.1016/j.fgb.2011.12.007 }}</ref> and '']''.<ref>{{cite journal | vauthors = Pluskal T, Ueno M, Yanagida M | title = Genetic and metabolomic dissection of the ergothioneine and selenoneine biosynthetic pathway in the fission yeast, S. pombe, and construction of an overproduction system | journal = PLOS ONE | volume = 9 | issue = 5 | pages = e97774 | year = 2014 | pmid = 24828577 | pmc = 4020840 | doi = 10.1371/journal.pone.0097774 | bibcode = 2014PLoSO...997774P | doi-access = free }}</ref>
Although many species contain ergothioneine, only a few can make it, the others absorb it from their diet or, in the case of plants, from their environment.<ref>{{Cite journal | title = The uptake of ergothioneine from the soil into the latex of Hevea brasiliensis | year = 1968 | journal = Phytochemistry | pages = 1999–2000 | volume = 7 | last1 = Audley | first1 = B.S. | last2 = Tan | first2 = C.H. | doi = 10.1016/S0031-9422(00)90759-3}}</ref> Biosynthesis has been detected in ], such as '']'' and filamentous fungi, such as '']''.<ref name=Fahey/> Although the exact ] is not clear, it is known that the imidazole ring is supplied by ], which is then ] to produce histidine betaine, and then the sulfur atom incorporated from cysteine.<ref name=Schomig/><ref>{{cite journal |author=MELVILLE DB, LUDWIG ML, INAMINE E, RACHELE JR |title=Transmethylation in the biosynthesis of ergothioneine |journal=J. Biol. Chem. |volume=234 |issue=5 |pages=1195–8 |year=1959 |month=May |pmid=13654346 |doi= |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13654346}}</ref> Other species of bacteria, such as '']'', '']'', '']'' and '']'', as well as fungi belonging to the groups ] and ], cannot make ergothioneine.<ref>{{cite journal |author=Genghof DS |title=Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales |journal=J. Bacteriol. |volume=103 |issue=2 |pages=475–8 |date=1 August 1970|pmid=5432011 |pmc=248105 |url=http://jb.asm.org/cgi/pmidlookup?view=long&pmid=5432011 }}</ref><ref>{{cite journal |author=Genghof DS, Inamine E, Kovalenko V, Melville DB |title=Ergothioneine in microorganisms |journal=J. Biol. Chem. |volume=223 |issue=1 |pages=9–17 |year=1956 |month=November |pmid=13376573 |doi= |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13376573}}</ref>


Other species of bacteria, such as '']'', '']'', '']'', and '']'', as well as fungi in the ] cannot make ergothioneine.<ref>{{cite journal | vauthors = Genghof DS | title = Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales | journal = Journal of Bacteriology | volume = 103 | issue = 2 | pages = 475–8 | date = August 1970 | pmid = 5432011 | pmc = 248105 | doi = 10.1128/JB.103.2.475-478.1970 }}</ref><ref>{{cite journal | vauthors = Genghof DS, Inamine E, Kovalenko V, Melville DB | title = Ergothioneine in microorganisms | journal = The Journal of Biological Chemistry | volume = 223 | issue = 1 | pages = 9–17 | date = November 1956 | doi = 10.1016/S0021-9258(18)65113-0 | pmid = 13376573 | url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13376573 | doi-access = free }}{{Dead link|date=March 2022 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
==Possible functions==
Despite its unusual chemistry, ergothioneine does still have ] properties.<ref name=Fahey/><ref>{{cite journal |author=Hand CE, Honek JF |title=Biological chemistry of naturally occurring thiols of microbial and marine origin |journal=J. Nat. Prod. |volume=68 |issue=2 |pages=293–308 |year=2005 |month=February |pmid=15730267 |doi=10.1021/np049685x}}</ref> It is a good scavenger of ]s and ], and can inhibit the production of oxidants by metal ions.<ref>{{cite journal |author=Akanmu D, Cecchini R, Aruoma OI, Halliwell B |title=The antioxidant action of ergothioneine |journal=Arch. Biochem. Biophys. |volume=288 |issue=1 |pages=10–6 |year=1991 |month=July |pmid=1654816 |doi=10.1016/0003-9861(91)90158-F }}</ref> On the other hand, since these antioxidant properties were measured in simple cell-free systems, their relevance to the actual function of ergothioneine in the body has been questioned.<ref name=Schomig/> Another possibility is that ergothioneine is important in protecting cells against the nitrosative stress produced by ] such as ].<ref name=Misiti>{{cite journal |author=Misiti F, Castagnola M, Zuppi C, Giardina B, Messana I |title=Role of ergothioneine on S-nitrosoglutathione catabolism |journal=Biochem. J. |volume=356 |issue=Pt 3 |pages=799–804 |year=2001 |month=June |pmid=11389687 |pmc=1221906 |url=http://www.biochemj.org/bj/356/0799/bj3560799.htm |doi=10.1042/0264-6021:3560799}}</ref> However, it might also be involved in metal ion transport and the regulation of ]s.<ref name=Misiti/>


== Structure ==
Ergothioneine is transported into human cells by a specific transporter called ETT (gene symbol ]).<ref>{{cite journal | author=Gründemann D, Harlfinger S, Golz S, ''et al.'' |title=Discovery of the ergothioneine transporter. |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=102 |issue= 14 |pages= 5256–61 |year= 2005 |pmid= 15795384 |doi= 10.1073/pnas.0408624102 | pmc=555966 }}</ref><ref>{{cite journal |author=Nakamura T, Yoshida K, Yabuuchi H, Maeda T, Tamai I |title=Functional characterization of ergothioneine transport by rat organic cation/carnitine transporter Octn1 (slc22a4) |journal=Biol. Pharm. Bull. |volume=31 |issue=8 |pages=1580–4 |year=2008 |month=August |pmid=18670092 |doi= 10.1248/bpb.31.1580|url=http://joi.jlc.jst.go.jp/JST.JSTAGE/bpb/31.1580?from=PubMed |format= &ndash; <sup></sup>}} {{dead link|date=April 2009}}</ref> Mutants of this transporter are associated with the autoimmune disorders ] and ].<ref name=Schomig>{{cite journal |author=Ey J, Schömig E, Taubert D |title=Dietary sources and antioxidant effects of ergothioneine |journal=J. Agric. Food Chem. |volume=55 |issue=16 |pages=6466–74 |year=2007 |month=August |pmid=17616140 |doi=10.1021/jf071328f}}</ref> Surprisingly, these mutant transporters are not impaired and instead can transport ergothioneine more efficiently than the normal forms of these proteins.<ref name=Taubert>{{cite journal |author=Taubert D, Grimberg G, Jung N, Rubbert A, Schömig E |title=Functional role of the 503F variant of the organic cation transporter OCTN1 in Crohn's disease |journal=Gut |volume=54 |issue=10 |pages=1505–6 |year=2005 |month=October |pmid=16162962 |pmc=1774715 |doi=10.1136/gut.2005.076083}}</ref> This may also relate to the fact that higher blood ergothioneine levels have been associated with rheumatoid arthritis.<ref>{{cite journal |author=Taubert D, Lazar A, Grimberg G, ''et al'' |title=Association of rheumatoid arthritis with ergothioneine levels in red blood cells: a case control study |journal=J. Rheumatol. |volume=33 |issue=11 |pages=2139–45 |year=2006 |month=November |pmid=17086603 |url=http://www.jrheum.org/cgi/pmidlookup?view=long&pmid=17086603}}</ref> Since the function of ergothioneine in human ] remains unknown, whether these findings point to a direct role for this amino acid in human disease is unclear.<ref name=Schomig/>
Ergothioneine is a ] derivative of the ] of ] and contains a sulfur atom bonded to the 2-position of the imidazole ring.<ref name=":2">{{cite book|author = Hartman PE| title=Oxygen Radicals in Biological Systems Part B: Oxygen Radicals and Antioxidants | chapter=&#91;32&#93; Ergothioneine as antioxidant |series = Methods in Enzymology |volume = 186|pages = |year = 1990|pmid = 2172707|doi = 10.1016/0076-6879(90)86124-E |isbn = 978-0-12-182087-9|chapter-url = https://archive.org/details/oxygenradicalsin0000unse/page/310}}</ref> Typical of thioureas, ergothioneine is less reactive than typical thiols such as ] towards ]s like ]s. It also resists ] by air.<ref name="Schomig" /> However, ergothioneine can be slowly oxidized over several days to the ] form in acidic solutions.<ref name=":3">{{cite journal | vauthors = Heath H, Toennies G | title = The preparation and properties of ergothioneine disulphide | journal = The Biochemical Journal | volume = 68 | issue = 2 | pages = 204–10 | date = February 1958 | pmid = 13522601 | pmc = 1200325 | doi = 10.1042/bj0680204 }}</ref>


==Ergothioneine derivatives==
⚫ ==See also==

*]
Various derivatives of ergothioneine have been reported in the literature, such as ''S''-methyl-ergothioneine<ref>{{cite journal | vauthors = Asmus KD, Bensasson RV, Bernier JL, Houssin R, Land EJ | title = One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C | journal = The Biochemical Journal | volume = 315 | issue = 2 | pages = 625–9 | date = April 1996 | pmid = 8615839 | pmc = 1217242 | doi = 10.1042/bj3150625 }}</ref> or ]-containing ].<ref>{{cite journal | vauthors = Yamashita Y, Yamashita M | title = Identification of a novel selenium-containing compound, selenoneine, as the predominant chemical form of organic selenium in the blood of bluefin tuna | journal = The Journal of Biological Chemistry | volume = 285 | issue = 24 | pages = 18134–8 | date = June 2010 | pmid = 20388714 | pmc = 2881734 | doi = 10.1074/jbc.C110.106377 | doi-access = free }}</ref>

== Characteristics ==

* '''] Antioxidant:''' Ergothioneine is an adaptogenic antioxidant that preferentially accumulates in cells and tissues exposed to oxidative stress and damage. The organic cation transporter OCTN1 (now known as SLC22A4, a transporter protein with 551 amino acids and three glycosylation sites) in the human body can transport ergothioneine to where it is needed.<ref>{{Cite journal |last=Halliwell |first=Barry |last2=Cheah |first2=Irwin K. |last3=Tang |first3=Richard M. Y. |date=October 2018 |title=Ergothioneine – a diet‐derived antioxidant with therapeutic potential |url=https://febs.onlinelibrary.wiley.com/doi/10.1002/1873-3468.13123 |journal=FEBS Letters |language=en |volume=592 |issue=20 |pages=3357–3366 |doi=10.1002/1873-3468.13123 |issn=0014-5793}}</ref>
* '''Regenerative Pathway:''' The human body has a regenerative pathway for ergothioneine. When ergothioneine combines with glutathione, it can regenerate, allowing it to react with singlet oxygen in a cyclical manner, achieving a more comprehensive and lasting antioxidant effect.
* '''Slow Excretion:''' Ergothioneine is excreted very slowly in the body, allowing it to be highly retained in the tissues and red blood cells of humans and other animals, thereby maximizing its effectiveness.
* '''Stable Form:''' Ergothioneine mainly exists in the form of thione, which has ideal thermal stability and pH stability.

==Preliminary research==

Although potential effects of ergothioneine are under preliminary research, its physiological role ''in vivo'' has not been determined.<ref name=pubchem/><ref name=cheah/>

==Safe intake levels==
The Panel on Dietetic Products for the ] reported safe daily limits of 2.82&nbsp;mg/kg of body weight for infants, 3.39&nbsp;mg/kg for small children, and 1.31&nbsp;mg/kg for adults, including pregnant and breastfeeding women.<ref name="efsa">{{cite journal | vauthors = 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 | display-authors = 6 | title = 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 | journal = EFSA Journal | volume = 15 | issue = 11 | pages = e05060 | date = November 2017 | pmid = 32625352 | doi = 10.2903/j.efsa.2017.5060 | pmc = 7010164 | doi-access = free }}</ref>

⚫ == See also ==
*] *]
*] *]
*] *]


==References== == References ==
{{Reflist|2}} {{Reflist}}


==External links== == External links ==
* Human Metabolome Database * Human Metabolome Database
* KEGG Compound * KEGG Compound
* OXIS INTERNATIONAL
* TETRAHEDRON


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