Dietary sources and antioxidant effects of ergothioneine

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 16, 2007, Pages 6466-6474

  Ey, Janine ^a   Schömig, Edgar ^a   Taubert, Dirk ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Antioxidant effects; Ergothioneine; Food; Glutathione; OCTN1; Thiol

Indexed keywords

ANTIOXIDANT; THIONEINE;

AGARICALES; ANIMAL; ARTICLE; BEAN; CHEMISTRY; DIET; FOOD ANALYSIS; HUMAN; MEAT; OAT;

AGARICALES; ANIMALS; ANTIOXIDANTS; AVENA SATIVA; DIET; ERGOTHIONEINE; FOOD ANALYSIS; HUMANS; MEAT; PHASEOLUS;

BASIDIOMYCOTA;

EID: 34548016273     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf071328f     Document Type: Article

References (48)

1. Grundemann, D.; Harlfinger, S.; Golz, S.; Geerts, A.; Lazar, A.; Berkels, R.; Jung, N.; Rubbert, A.; Schomig, E. Discovery of the ergothioneine transporter. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 5256-5261.
2. Tokuhiro, S.; Yamada, R.; Chang, X.; Suzuki, A.; Kochi, Y.; Sawada, T.; Suzuki, M.; Nagasaki, M.; Ohtsuki, M.; Ono, M.; Furukawa, H.; Nagashima, M.; Yoshino, S.; Mabuchi, A.; Sekine, A.; Saito, S.; Takahashi, A.; Tsunoda, T.; Nakamura, Y.; Yamamoto, K. An intronic SNP in a RUNX1 binding site of SLC22A4, encoding an organic cation transporter, is associated with rheumatoid arthritis. Nat. Genet. 2003, 35, 341-348.
3. Yamada, R.; Tokuhiro, S.; Chang, X.; Yamamoto, K. SLC22A4 and RUNX1: identification of RA susceptible genes. J. Mol. Med. 2004, 82, 558-564.
4. Peltekova, V. D.; Wintle, R. F.; Rubin, L. A.; Amos, C. I.; Huang, Q.; Gu, X.; Newman, B.; Van Oene, M.; Cescon, D.; Greenberg, G.; Griffiths, A. M.; St George-Hyslop, P. H.; Siminovitch, K. A. Functional variants of OCTN cation transporter genes are associated with Crohn disease. Nat. Genet. 2004, 36, 471-475.
5. Torek, H. P.; Glas, J.; Tonenchi, L.; Lohse, P.; Muller-Myhsok, B.; Limbersky, O.; Neugebauer, C.; Schnitzler, F.; Seiderer, J.; Tillack, C.; Brand, S.; Bruennler, G.; Jagiello, P.; Epplen, J. T.; Griga, T.; Klein, W.; Schiemann, U.; Folwaczny, M.; Ochsenkuehn, T.; Folwaczny, C. Polymorphisms in the DLG5 and OCTN cation transporter genes in Crohn's disease. Gut 2005, 54, 1421-1427.
6. Taubert, D.; Grimberg, G.; Jung, N.; Rubbert, A.; Schomig, E. Functional role of the 503F variant of the organic cation transporter OCTN1 in Crohn's disease. Gut 2005, 54, 1505-1506.
7. Taubert, D.; Lazar, A.; Grimberg, G.; Jung, N.; Rubbert, A.; Delank, K. S.; Perniok, A.; Erdmann, E.; Schomig, E. Association of rheumatoid arthritis with ergothioneine levels in red blood cells: a case control study. J. Rheumatol. 2006, 33, 2139-2145.
8. Genghof, D. S. Biosynthesis of ergothioneine and hercynine by fungi and Actinomycetales. J. Bacteriol. 1970, 103, 475-478.
9. Melville, D. B.; Eich, S.; Ludwig, M. L. The biosynthesis of ergothioneine. J. Biol. Chem. 1957, 224, 871-877.
10. Dubost, N. J.; Beelman, R. B.; Peterson, D.; Royse, D. J. Identification and quantification of ergothioneine in cultivated mushrooms by liquid chromatography-mass spectrometry. Int. J. Med. Mushrooms 2006, 8, 215-222.
11. Melville, D. B.; Eich, S. The occurrence of ergothioneine in plant material. J. Biol. Chem. 1956, 218, 647-651.
12. Brummel, M. C.; Stegink, L. D. Ergothioneine (ERT) in foods and human erythrocytes (RBC). FASEB J. 1993, 7, A741.
13. Hartman, P. E. Ergothioneine as antioxidant. Methods Enzymol. 1990, 186, 310-318.
14. Akanmu, D.; Cecchini, R.; Aruoma, O. I.; Halliwell, B. The antioxidant action of ergothioneine. Arch. Biochem. Biophys. 1991, 288, 10-16.
15. Asmus, K. D.; Bensasson, R. V.; Bernier, J. L.; Houssin, R.; Land, E. J. One-electron oxidation of ergothioneine and analogues investigated by pulse radiolysis: redox reaction involving ergothioneine and vitamin C. Biochem. J. 1996, 315, 625-629.
16. Aruoma, O. I.; Whiteman, M.; England, T. G.; Halliwell, B. Antioxidant action of ergothioneine: assessment of its ability to scavenge peroxynitrite. Biochem. Biophys. Res. Commun. 1997, 231, 389-391.
17. Aruoma, O. I.; Spencer, J. P.; Mahmood, N. Protection against oxidative damage and cell death by the natural antioxidant ergothioneine. Food Chem. Toxicol. 1999, 37, 1043-1053.
18. Guijarro, M. V.; Indart, A.; Aruoma, O. I.; Viana, M.; Bonet, B. Effects of ergothioneine on diabetic embryopathy in pregnant rats. Food Chem. Toxicol. 2002, 40, 1751-1755.
19. Rahman, I.; Gilmour, P. S.; Jimenez, L. A.; Biswas, S. K.; Antonicelli, F.; Aruoma, O. I. Ergothioneine inhibits oxidative stress- and TNF-alpha-induced NF-kappa B activation and interleukin-8 release in alveolar epithelial cells. Biochem. Biophys. Res. Commun. 2003, 302, 860-864.
20. Deiana, M.; Rosa, A.; Casu, V.; Piga, R.; Assunta Dessi, M.; Aruoma, O. I. L-ergothioneine modulates oxidative damage in the kidney and liver of rats in vivo: studies upon the profile of polyunsaturated fatty acids. Clin. Nutr. 2004, 23, 183-193.
21. Jang, J. H.; Aruoma, O. I.; Jen, L. S.; Chung, H. Y.; Surh, Y. J. Ergothioneine rescues PC12 cells from beta-amyloid-induced apoptotic death. Free Radical Biol. Med. 2004, 36, 288-299.
22. Jacob, C. A scent of therapy: pharmacological implications of natural products containing redox-active sulfur atoms. Nat. Prod. Rep. 2006, 23, 851-863.
23. Colognato, R.; Laurenza, I.; Fontana, I.; Coppede, F.; Siciliano, G.; Coecke, S.; Aruoma, O. I.; Benzi, L.; Migliore, L. Modulation of hydrogen peroxide-induced DNA damage, MAPKs activation and cell death in PC12 by ergothioneine. Clin. Nutr. 2006, 25, 135-145.
24. 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. An in vitro study on the free radical scavenging capacity of ergothioneine: comparison with reduced glutathione, uric acid and trolox. Biomed. Pharmacother. 2006, 60, 453-457.
25. Taubert, D.; Harlfinger, S.; Henkes, L.; Berkels, R.; Schomig, E. Influence of processing parameters on acrylamide formation during frying of potatoes. J. Agric. Food Chem. 2004, 52, 2735-2739.
26. Taubert, D.; Grimberg, G.; Stenzel, W.; Schomig, E. Identification of the endogenous key substrates of the human organic cation transporter OCT2 and their implication in function of dopaminergic neurons. PLoS ONE 2007, 2, e385.
27. Piga, R.; Saito, Y.; Yoshida, Y.; Niki, E. Cytotoxic effects of various stressors on PC12 cells: involvement of oxidative stress and effect of antioxidants. Neurotoxicology 2007, 28, 67-75.
28. Park, J. E.; Yang, J. H.; Yoon, S. J.; Lee, J. H.; Yang, E. S.; Park, J. W. Lipid peroxidation-mediated cytotoxicity and DNA damage in U937 cells. Biochimie 2002, 84, 1199-1205.
29. Kinter, M.; Roberts, R. J. Glutathione consumption and glutathione peroxidase inactivation in fibroblast cell lines by 4-hydroxy-2-nonenal. Free Radical Biol. Med. 1996, 21, 457-462.
30. Gille, L.; Nohl, H. Analyses of the molecular mechanism of adriamycin-induced cardiotoxicity. Free Radical Biol. Med. 1997, 23, 775-782.
31. Lloyd, D.; Harris, J. C.; Maroulis, S.; Mitchell, A.; Hughes, M. N.; Wadley, R. B.; Edwards, M. R. Nitrosative stress induced cytotoxicity in Giardia intestinalis. J. Appl. Microbiol. 2003, 95, 576-583.
32. Heath, H.; Wildy, J. Biosynthesis of ergothioneine by Claviceps purpurea. 3. The incorporation of labelled histidine. Biochem. J. 1958, 68, 407-410.
33. Heath, H.; Wildy, J. The biosynthesis of ergothioneine and histidine by Claviceps purpurea. I. The incorporation of [2-14C]-acetate. Biochem. J. 1956, 64, 612-620.
34. Fahey, R. C.; Newton, G. L.; Dorian, R.; Kosower, E. M. Analysis of biological thiols: derivatization with monobromotrimethylammoniobimane and characterization by electrophoresis and chromatography. Anal. Biochem. 1980, 107, 1-10.
35. Melville, D. B. L-ergothioneine. Vitam. Horm. (Leipzig) 1958, 17, 155-204.
36. Hand, C. E.; Honek, J. F. Biological chemistry of naturally occurring thiols of microbial and marine origin. J. Nat. Prod. 2005, 68, 293-308.
37. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. BLASTX 2.2.16 [accessed Mar-25-2007]. Nucleic Acids Res. 1997, 25, 3389-3402.
38. Demirkol, O.; Adams, C.; Ercal, N. Biologically important thiols in various vegetables and fruits. J. Agric. Food Chem. 2004, 52, 8151-8154.
39. Collin-Hansen, C.; Andersen, R. A.; Steinnes, E. Molecular defense systems are expressed in the king bolete (Boletus edulis) growing near metal smelters. Mycologia 2005, 97, 973-983.
40. Kobayashi, D.; Aizawa, S.; Maeda, T.; Tsuboi, I.; Yabuuchi, H.; Nezu, J.; Tsuji, A.; Tamai, I. Expression of organic cation transporter OCTN1 in hematopoietic cells during erythroid differentiation. Exp. Hematol. 2004, 32, 1156-1162.
41. Shires, T. K.; Brummel, M. C.; Pulido, J. S.; Stegink, L. D. Ergothioneine distribution in bovine and porcine ocular tissues. Comp. Biochem. Physiol., C 1997, 117, 117-120.
42. Hayeshi, R.; Mukanganyama, S.; Hazra, B.; Abegaz, B.; Hasler, J. The interaction of selected natural products with human recombinant glutathione transferases. Phytother. Res. 2004, 18, 877-883.
43. Cargnoni, A.; Bernocchi, P.; Ceconi, C.; Curello, S.; Ferrari, R. In vitro administration of ergothioneine failed to protect isolated ischaemic and reperfused rabbit heart. Biochim. Biophys. Acta 1995, 1270, 173-178.
44. Pedersen, J. Z.; Steinkuhler, C.; Weser, U.; Rotilio, G. Copper-glutathione complexes under physiological conditions in solution different from solid state coordination. Biometals 1996, 9, 3-9.
45. Freedman, J. H.; Ciriolo, M. R.; Peisach, J. The role of glutathione in copper metabolism and toxicity. J. Biol. Chem. 1989, 264, 5598-5605.
46. Hanlon, D. P. Interaction of ergothioneine with metal ions and metalloenzymes. J. Med. Chem. 1971, 14, 1084-1087.
47. Stockert, R. J.; Grushoff, P. S.; Morell, A. G.; Bentley, G. E.; O'Brien, H. A.; Scheinberg, I. H.; Sternlieb, I. Transport and intracellular distribution of copper in a human hepatoblastoma cell line, HepG2. Hepatology 1986, 6, 60-64.
48. Reglinski, J.; Hoey, S.; Smith, W. E.; Sturrock, R. D. Cellular response to oxidative stress at sulfhydryl group receptor sites on the erythrocyte membrane. J. Biol. Chem. 1988, 263, 12360-12366.