Ergothioneine

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Ergothioneine
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Names
IUPAC name
3-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)-2-(trimethylazaniumyl)propanoate
Other names
L-Ergothioneine; (+)-Ergothioneine; Thiasine; Sympectothion; Ergothionine; Erythrothioneine; Thiolhistidinebetaine
Identifiers
497-30-3 YesY
ChEBI CHEBI:4828 YesY
ChemSpider 4508619 YesY
Jmol 3D model Interactive image
Interactive image
KEGG C05570 N
PubChem 5351619
UNII BDZ3DQM98W YesY
  • InChI=1S/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 YesY
    Key: SSISHJJTAXXQAX-ZETCQYMHSA-N YesY
  • 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
    Key: SSISHJJTAXXQAX-ZETCQYMHBA
  • C[N+](C)(C)C(CC1=CNC(=S)N1)C(=O)[O-]
  • S=C1N\C(=C/N1)C[C@@H](C([O-])=O)[N+](C)(C)C
Properties
C9H15N3O2S
Molar mass 229.30 g/mol
Appearance white solid
Melting point 275 to 277 °C (527 to 531 °F; 548 to 550 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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

In vitro assays, as well as in vivo animal models, are used in basic research to identify its potential biological properties.[4][5][6][7]

In humans, ergothioneine is acquired exclusively through the diet and accumulates in erythrocytes, bone marrow, liver, kidney, seminal fluid and the eyes.[4] Ergothioneine requires a specific transporter, ETT, also known as OCTN1 (gene symbol SLC22A4), to enter cells.[4][8] ETT expression has been confirmed in human and animal cell lines and its functional ability to transport ergothioneine has been confirmed in vivo.[4][5][5][9][10][11][12][13] Although the effect of ergothioneine in vivo is an active area of research, its physiological role in humans is undetermined.[4]

Metabolism and sources

Ergothioneine has been found in bacteria, plants and animals, sometimes at millimolar levels.[14] Foods found to contain ergothioneine include liver, kidney, black beans, kidney bean and oat bran, with the highest levels in bolete and oyster mushrooms.[14] 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 and semen,[3] and it is also present in the skin.[15]

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.[16] Biosynthesis has been detected in Actinobacteria, such as Mycobacterium smegmatis and certain fungi, such as Neurospora crassa.[1]

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.[14][17] The biosynthetic genes of ergothioneine have been described in Mycobacterium smegmatis,[18] Neurospora crassa,[19] and Schizosaccharomyces pombe.[20]

Other species of bacteria, such as Bacillus subtilis, Escherichia coli, Proteus vulgaris and Streptococcus, as well as fungi in the Saccharomycotina cannot make ergothioneine.[21][22]

Chemistry

Ergothioneine is a thiourea derivative of the betaine of histidine 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 thione form, rather than the sulfhydryl, as is the case for the structurally related ovothiol.[6] This makes ergothioneine much less reactive than thiols such as glutathione towards alkylating agents like maleimides, and also prevents the compound from oxidizing in air.[14] However, ergothioneine can be slowly oxidized over several days to the disulfide form in acidic solutions.[23] 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.[24]

Ergothioneine derivatives

Various derivatives of ergothioneine have been reported in the literature, such as S-methyl-ergothioneine[25] or selenium-containing selenoneine.[26]

Preliminary research

Ergothioneine has antioxidant properties in vitro.[1][27] Under laboratory conditions, it scavenges hydroxyl radicals and hypochlorous acid, inhibits production of oxidants by metal ions,[28][29] and may participate in metal ion transport and regulation of metalloenzymes.[29]

Although potential effects of ergothioneine are under preliminary research, its physiological role in vivo is unknown.[4]

See also

References

  1. ↑ 1.0 1.1 1.2 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 5.2 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ 14.0 14.1 14.2 14.3 Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  28. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  29. ↑ 29.0 29.1 Lua error in package.lua at line 80: module 'strict' not found.

External links

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