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Chemical Compound Review

Thioneine     3-(2-sulfanylidene-1,3- dihydroimidazol-4...

Synonyms: Ergothionine, Sympectothion, l-Thioneine, AC1MHTWO, NSC 7175, ...
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Disease relevance of ERGOTHIONEINE


High impact information on ERGOTHIONEINE

  • Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death [6].
  • Ergothioneine (ESH) is a low-molecular-mass thiol present in millimolar concentrations in a limited number of tissues, including erythrocytes, kidney, seminal fluid and liver; however, its biological function is still unclear [7].
  • We have investigated, via pulse radiolysis, the one-electron oxidation of ergothioneine, a molecule with antioxidant properties which is detected at millimolar concentrations in certain tissues and fluids subject to oxidative stress, including erythrocytes and plasma [8].
  • In the presence of vitamin C, the oxidized form of ergothioneine is repaired by a rapid reduction (k = 6.3 x 10(8) M(-1).s(-1)) producing ascorbyl radicals [8].
  • Ergothioneine was observed not to take part in any chemical reactions with arsenicals in free solution or in intact erythrocytes, and we conclude that ergothioneine may still be used as an internal intensity reference in 1H SEFT NMR spectra, bearing in mind the above physical factors [9].

Chemical compound and disease context of ERGOTHIONEINE


Biological context of ERGOTHIONEINE


Anatomical context of ERGOTHIONEINE


Associations of ERGOTHIONEINE with other chemical compounds


Gene context of ERGOTHIONEINE


Analytical, diagnostic and therapeutic context of ERGOTHIONEINE


  1. Effects of ergothioneine, cysteine, and glutathione on nitrosation of secondary amines under physiologic conditions. Kunisaki, N., Hayashi, M. J. Natl. Cancer Inst. (1980) [Pubmed]
  2. Novel thiols of prokaryotes. Fahey, R.C. Annu. Rev. Microbiol. (2001) [Pubmed]
  3. Detection of ferryl myoglobin in the isolated ischemic rat heart. Arduini, A., Eddy, L., Hochstein, P. Free Radic. Biol. Med. (1990) [Pubmed]
  4. Low-molecular-weight thiols in streptomycetes and their potential role as antioxidants. Newton, G.L., Fahey, R.C., Cohen, G., Aharonowitz, Y. J. Bacteriol. (1993) [Pubmed]
  5. Ergothioneine treatment protects neurons against N-methyl-D-aspartate excitotoxicity in an in vivo rat retinal model. Moncaster, J.A., Walsh, D.T., Gentleman, S.M., Jen, L.S., Aruoma, O.I. Neurosci. Lett. (2002) [Pubmed]
  6. Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death. Jang, J.H., Aruoma, O.I., Jen, L.S., Chung, H.Y., Surh, Y.J. Free Radic. Biol. Med. (2004) [Pubmed]
  7. Role of ergothioneine on S-nitrosoglutathione catabolism. Misiti, F., Castagnola, M., Zuppi, C., Giardina, B., Messana, I. Biochem. J. (2001) [Pubmed]
  8. One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C. Asmus, K.D., Bensasson, R.V., Bernier, J.L., Houssin, R., Land, E.J. Biochem. J. (1996) [Pubmed]
  9. Stability and nonreactivity of ergothioneine in human erythrocytes studied by 1H NMR. Rae, C.D., Sweeney, K.J., Kuchel, P.W. Magnetic resonance in medicine : official journal of the Society of Magnetic Resonance in Medicine / Society of Magnetic Resonance in Medicine. (1993) [Pubmed]
  10. Interception of some direct-acting mutagens by ergothioneine. Hartman, Z., Hartman, P.E. Environ. Mol. Mutagen. (1987) [Pubmed]
  11. Characteristics of Mycoplasma strains isolated from stallion semen. Zgórniak-Nowosielska, I., Kosiniak, K., Slagowska, A. Arch. Immunol. Ther. Exp. (Warsz.) (1985) [Pubmed]
  12. Modulation of hydrogen peroxide-induced DNA damage, MAPKs activation and cell death in PC12 by ergothioneine. Colognato, R., Laurenza, I., Fontana, I., Coppedé, F., Siciliano, G., Coecke, S., Aruoma, O.I., Benzi, L., Migliore, L. Clinical nutrition (Edinburgh, Scotland) (2006) [Pubmed]
  13. Ergothioneine inhibits oxidative stress- and TNF-alpha-induced NF-kappa B activation and interleukin-8 release in alveolar epithelial cells. Rahman, I., Gilmour, P.S., Jimenez, L.A., Biswas, S.K., Antonicelli, F., Aruoma, O.I. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  14. In search of a physiological function for L-ergothioneine--II. Brummel, M.C. Med. Hypotheses (1989) [Pubmed]
  15. The interaction of selected natural products with human recombinant glutathione transferases. Hayeshi, R., Mukanganyama, S., Hazra, B., Abegaz, B., Hasler, J. Phytotherapy research : PTR. (2004) [Pubmed]
  16. Protection against oxidative damage and cell death by the natural antioxidant ergothioneine. Aruoma, O.I., Spencer, J.P., Mahmood, N. Food Chem. Toxicol. (1999) [Pubmed]
  17. beta-Hydroxyergothioneine, a new ergothioneine derivative from the mushroom Lyophyllum connatum, and its protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes. Kimura, C., Nukina, M., Igarashi, K., Sugawara, Y. Biosci. Biotechnol. Biochem. (2005) [Pubmed]
  18. Biochemistry of stallion semen. Mann, T. J. Reprod. Fertil. Suppl. (1975) [Pubmed]
  19. L-ergothioneine modulates oxidative damage in the kidney and liver of rats in vivo: studies upon the profile of polyunsaturated fatty acids. Deiana, M., Rosa, A., Casu, V., Piga, R., Assunta Dessì, M., Aruoma, O.I. Clinical nutrition (Edinburgh, Scotland) (2004) [Pubmed]
  20. Comparative (13)C and (31)P NMR studies of the ligand exchange reactions of auranofin with ergothionine, imidazolidine-2-thione and diazinane-2-thione. Isab, A.A., Ahmad, S. J. Inorg. Biochem. (2002) [Pubmed]
  21. The 13C NMR study of the binding of gold(I) thiomalate with ergothionine in aqueous solution. Isab, A.A. J. Inorg. Biochem. (1992) [Pubmed]
  22. An in vitro study on the free radical scavenging capacity of ergothioneine: comparison with reduced glutathione, uric acid and trolox. Franzoni, F., Colognato, R., Galetta, F., Laurenza, I., Barsotti, M., Di Stefano, R., Bocchetti, R., Regoli, F., Carpi, A., Balbarini, A., Migliore, L., Santoro, G. Biomed. Pharmacother. (2006) [Pubmed]
  23. Association of rheumatoid arthritis with ergothioneine levels in red blood cells: a case control study. Taubert, D., Lazar, A., Grimberg, G., Jung, N., Rubbert, A., Delank, K.S., Perniok, A., Erdmann, E., Sch??mig, E. J. Rheumatol. (2006) [Pubmed]
  24. L-Ergothioneine scavenges superoxide and singlet oxygen and suppresses TNF-alpha and MMP-1 expression in UV-irradiated human dermal fibroblasts. Obayashi, K., Kurihara, K., Okano, Y., Masaki, H., Yarosh, D.B. Journal of cosmetic science. (2005) [Pubmed]
  25. The reduction of ferryl myoglobin by ergothioneine: a novel function for ergothioneine. Arduini, A., Eddy, L., Hochstein, P. Arch. Biochem. Biophys. (1990) [Pubmed]
  26. Ergothioneine as antioxidant. Hartman, P.E. Meth. Enzymol. (1990) [Pubmed]
  27. Ergothioneine distribution in bovine and porcine ocular tissues. Shires, T.K., Brummel, M.C., Pulido, J.S., Stegink, L.D. Comp. Biochem. Physiol. C, Pharmacol. Toxicol. Endocrinol. (1997) [Pubmed]
  28. Determination of ergothioneine in red blood cells by high-performance liquid chromatography. Muda, M., Pelizzoni, F., Sello, G., Mussini, E. J. Chromatogr. (1988) [Pubmed]
  29. Clinical analysis in intact erythrocytes using 1H spin echo NMR. Reglinski, J., Smith, W.E., Wilson, R., Buchanan, L.M., McKillop, J.H., Thomson, J.A., Brzeski, M., Marabani, M., Sturrock, R.D. Clin. Chim. Acta (1991) [Pubmed]
  30. In vitro administration of ergothioneine failed to protect isolated ischaemic and reperfused rabbit heart. Cargnoni, A., Bernocchi, P., Ceconi, C., Curello, S., Ferrari, R. Biochim. Biophys. Acta (1995) [Pubmed]
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