An uncommon redox behavior sheds light on the cellular antioxidant properties of ergothioneine

Free Radical Biology and Medicine

Volumn 79, Issue , 2015, Pages 228-236

  Servillo, Luigi ^a   Castaldo, Domenico ^b   Casale, Rosario ^a   D'Onofrio, Nunzia ^a   Giovane, Alfonso ^a   Cautela, Domenico ^b   Balestrieri, Maria Luisa ^a  

^a SECOND UNIVERSITY OF NAPLES   (Italy)

^b Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA   (Italy)

Author keywords

Ergothioneine; Ergothioneine sulfonic acid; Free radicals; Hercynine; Neutrophils; Oxidative burst; Oxidative stress

Indexed keywords

HYDROGEN PEROXIDE; HYPOCHLORITE; PEROXYNITRITE; PHORBOL 13 ACETATE 12 MYRISTATE; THIONEINE; ANTIOXIDANT;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; NEUTROPHIL; OXIDATION; PRIORITY JOURNAL; REDOX BEHAVIOR; RESPIRATORY BURST; DRUG EFFECTS; OXIDATION REDUCTION REACTION;

ANTIOXIDANTS; ERGOTHIONEINE; HUMANS; NEUTROPHILS; OXIDATION-REDUCTION;

EID: 84920849496     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2014.11.017     Document Type: Article

References (34)

1. Fahey, R. C. Novel thiols of prokaryotes. Annu. Rev. Microbiol. 55:333-356; 2001.
2. Kaneko, I.; Takeuchi, Y.; Yamaoka, Y.; Tanaka, Y.; Fukuda, T.; Fukumori, Y.; Mayumi, T.; Hama, T. Quantitative determination of ergothioneine in plasma and tissues by TLC densitometry. Chem. Pharm. Bull. 28:3093-3097; 1980.
3. Gründemann, D.; Harlfinger, S.; Golz, S.; Geerts, A.; Lazar, A.; Berkels, R.; Jung, N.; Rubbert, A.; Schömig, E. Discovery of the ergothioneine transporter. Proc. Natl. Acad. Sci. USA 102:5256-5261; 2005.
4. 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. 32:1156-1162; 2004.
5. Chevion, M.; Berenshtein, E.; Stadtman, E. R. Human studies related to protein oxidation: protein carbonyl content as a marker of damage. Free Radic. Res 33 (Suppl):S99-108; 2000.
6. Kato, Y.; Kubo, Y.; Iwata, D.; Kato, S.; Sudo, T.; Sugiura, T.; Kagaya, T.; Wakayama, T.; Hirayama, A.; Sugimoto, M.; Sugihara, K.; Kaneko, S.; Soga, T.; Asano, M.; Tomita, M.; Matsui, T.; Wada, M.; Tsuji, A. Gene knockout and metabolome analysis of carnitine/organic cation transporter OCTN1. Pharm. Res. 27:832-840; 2010.
7. Cheah, I. K.; Halliwell, B. Ergothioneine: antioxidant potential, physiological function and role in disease. Biochim. Biophys. Acta 1822:784-793; 2012.
8. Hartman, P. E.; Hartman, Z.; Ault, K. T. Scavenging of singlet molecular oxygen by imidazole compounds: high and sustained activities of carboxy terminal histidine dipeptides and exceptional activity of imidazole-4-acetic acid. Photochem. Photobiol. 51:59-66; 1990.
9. Dahl, T. A.; Midden, W. R.; Hartman, P. E. Some prevalent biomolecules as defenses against singlet oxygen damage. Photochem. Photobiol. 47:357-362; 1988.
10. Hans, J. S. Effects of various chemical compounds on spontaneous and hydrogen peroxide-induced reversion in strain TA104 of Salmonella typhimurium. Mutat. Res. 22:77-84; 1992.
11. Akanmu, D.; Cecchini, R.; Aruoma, O. I.; Halliwell, B. The antioxidant action of L-ergothioneine. Arch. Biochem. Biophys. 288:10-16; 1991.
12. 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. 231:389-391; 1997.
13. Kunisaki, N.; Hayashi, M. Effects of ergothioneine, cysteine, and glutathione on nitrosation of secondary amines under physiologic conditions. J. Natl. Cancer Inst. 65:791-794; 1980.
14. Puppo, A.; Halliwell, B. Formation of hydroxyl radicals in biological systems: does myoglobin stimulate hydroxyl radical formation from hydrogen peroxide? Free Radic. Res. Commun 4:415-422; 1988.
15. Puppo, A.; Halliwell, B. Formation of hydroxyl radicals from hydrogen peroxide in the presence of iron: is haemoglobin a biological Fenton reagent? Biochem. J. 249:185-190; 1988.
16. Potor, L.; Bányai, E.; Becs, G.; Soares, M. P.; Balla, G.; Balla, J.; Jeney, V. Atherogenesis may involve the prooxidant and proinflammatory effects of ferryl hemoglobin. Oxid. Med. Cell. Longevity 2013:676425; 2013.
17. Arduini, A.; Eddy, L.; Hochstein, P. Detection of ferryl myoglobin in the isolated ischemic rat heart. Free Radic. Biol. Med. 9: 511-513; 1990.
18. Arduini, A.; Eddy, L.; Hochstein, P. The reduction of ferryl myoglobin by ergothioneine: a novel function for ergothioneine. Arch. Biochem. Biophys. 281:41-43; 1990.
19. Arduini, A.; Mancinelli, G.; Radatti, G. L.; Hochstein, P.; Cadenas, E. Possible mechanism of inhibition of nitrite-induced oxidation of oxyhemoglobin by L-ergothioneine and uric acid. Arch. Biochem. Biophys. 294:398-402; 1992.
20. Hand, C. E.; Taylor, N. J.; Honek, J. F. Ab initio studies of the properties of intracellular thiols ergothioneine and ovothiol. Bioorg. Med. Chem. Lett. 15:1357-1360; 2005.
21. Morris, J. C. The acid ionization constant of HOCl from 5 to 35 degrees. J. Phys. Chem. 70:3798-3805; 1966.
22. Beckman, J. S.; Chen, J.; Ischiropoulos, H.; Crow, J. P. Oxidative chemistry of peroxynitrite. Methods Enzymol. 233:229-240; 1994.
23. Heath, H.; Toennies, G. The preparation and properties of ergothioneine disulfide. Biochem. J. 68:204-210; 1958.
24. Chen, F. M. F.; Benoiton, N. L. A new method of quaternizing amines and its use in amino acid and peptide chemistry. Can. J. Chem. 54:3310-3311; 1976.
25. 6-trimethyl-L-lysine dioxalate in gram amounts. Biochem. Cell Biol. 64:182-183; 1986.
26. Misiti, F.; Castagnola, M.; Zuppi, C.; Giardina, B.; Messana, I. Role of ergothioneine on S-nitrosoglutathione catabolism. Biochem. J. 356:799-804; 2001.
27. Lo Conte, M.; Carrol, K. S. The chemistry of thiol oxidation and detection. In: Jakob, U., Reichmann, D., editors. Oxidative Stress and Redox Regulation. Heidelberg: Springer; 2013. p. 1-42.
28. Hofmann, K., editor. The Chemistry of Heterocyclic Compounds, Imidazole and Its Derivatives. New York: Wiley Intersci.; 1953.
29. Peskin, A. V.; Winterbourn, C. C. Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine and ascorbate. Free Radic. Biol. Med. 30:572-579; 2001.
30. Paul, B. D.; Snyder, S. H. The unusual amino acid L-ergothioneine is a physiologic cytoprotectant. Cell Death Differ. 17:1134-1140; 2010.
31. Kawano, H.; Otani, M.; Takeyama, K.; Kawai, Y.; Mayumi, T.; Hama, T. Studies on ergothioneine. VI. Distribution and fluctuations of ergothioneine in rats. Chem. Pharm. Bull. 30:1760-1765; 1982.
32. 35S-labelled 2-thiolhistidine and ergothioneine in the rat. Biochem. J. 54:689-694; 1953.
33. Heath, H.; Rimington, C.; Glover, T.; Mann, T.; Leone, E. Studies using radioactive sulphur on ergothioneine formation in the pig. Biochem. J. 54:606-611; 1953.
34. Grigat, S.; Harlfinger, S.; Pal, S.; Striebinger, R.; Golz, S.; Geerts, A.; Lazar, A.; Schömig, E.; Gründemann, D. Probing the substrate specificity of the ergothioneine transporter with methimazole, hercynine, and organic cations. Biochem. Pharmacol. 74:309-316; 2007.