Reduction of hypervalent states of myoglobin and hemoglobin to their ferrous forms by thymoquinone: The role of GSH, NADH and NADPH

Biochimica et Biophysica Acta - General Subjects

Volumn 1780, Issue 4, 2008, Pages 627-637

  Khalife, K H ^a   Lupidi, G ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Dihydrothymoquinone Nigella sativa L.; Ferryl hemoglobin; Glutathione; Met hemoglobin; Oxidative damage; redox regulation; Thymoquinone

Indexed keywords

FERROUS ION; GLUTATHIONE; HEMOGLOBIN; METHEMOGLOBIN; METMYOGLOBIN; MYOGLOBIN; OXYHEMOGLOBIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; THYMOQUINONE;

ANTIOXIDANT ACTIVITY; CONTROLLED STUDY; DRUG EFFECT; DRUG SCREENING; HUMAN; HUMAN CELL; LIPID PEROXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW;

BENZOQUINONES; ERYTHROCYTES; GLUTATHIONE; HEMOGLOBIN A; HEMOGLOBINS; HUMANS; METMYOGLOBIN; MODELS, CHEMICAL; MYOGLOBIN; NAD; NADP; OXIDATION-REDUCTION; OXYHEMOGLOBINS; SPECTROPHOTOMETRY;

NIGELLA SATIVA;

EID: 40949150246     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2007.12.006     Document Type: Review

References (60)

1. Grisham M.B., Gaginella T.S., von Ritter C., Tamai H., Be R.M., and Granger D.N. Effects of neutrophil-derived oxidants on intestinal permeability, electrolyte transport, and epithelial cell viability. Inflammation 14 (1990) 531-542
2. Misra H.P., and Fridovich I. The generation of superoxide radical during the autoxidation of hemoglobin. J. Biol. Chem 247 (1972) 6960-6962.
3. Giulivi C., Hochstein P., and Davies K.J.A. Hydrogen peroxide production by red blood cells. Free Radical Biol. Med. 16 (1994) 123-129
4. Juliano L., Violi F., Pedersen J.Z., Pratico D., Rotilio G., and Balsano F. Free radical-mediated platelet activation by hemoglobin released from red blood cells. Arch. Biochem. Biophys. 299 (1992) 220-224
5. Kindt J.T., Woods A., Martin B.M., Cotter R.J., and Osawa Y. Covalent alteration of the prosthetic heme of human hemoglobin by BrCCl3. Cross-linking of heme to cysteine residue 93. J. Biol. Chem. 267 (1992) 8739-8743
6. Faivre B., Menu P., Labrude P., and Vigneron C. Hemoglobin autoxidation/oxidation mechanisms and methemoglobin prevention or reduction processes in the blood stream. Literature review and outline of autoxidation reaction. Art. Cells Blood Subs. Immob. Biotech. 26 (1998) 17-26
7. Alayash A.I. Hemoglobin-based blood substitutes: oxygen carriers, pressor agents, or oxidants?. Nat. Biotechnol. 17 (1999) 545-549
8. Everse J., and Hsia N. The toxicities of native and modified hemoglobins. Free Radical Biol. Med. 22 (1997) 1075-1099
9. 2. J. Biol. Chem. 267 (1992) 8827-8833
10. Giulivi C., and Cadenas E. Ferrylmyoglobin: formation and chemical reactivity toward electron-donating compounds. Methods Enzymol. 233 (1994) 189-202
11. Giulivi C., and Davies K.J.A. A novel antioxidant role for hemoglobin. J Biol Chem 265 (1990) 19453-19460.
12. Gunther M.R. Probing the free radicals formed in the metmyoglobin-hydrogen peroxide reaction. Free Radic. Biol Med. 36 11 (2004 Jun 1) 1345-1354
13. Jørgensen L.V., and Skibsted L.H. Flavonoids deactivation of ferrylmyoglobin in relation to ease of oxidation as determined by cyclic voltammetry. Free Radic. Res. 28 (1998) 335-351
14. Yusa K., and Shikama K. Oxidation of oxymyoglobin to metmyoglobin with hydrogen peroxide: involvement of ferryl intermediate. Biochemistry 26 21 (1987 Oct 20) 6684-6688.
15. Harel S., and Kanner J. The generation of ferryl or hydroxyl radicals during interaction of hemoproteins with hydrogen peroxide. Free Radic. Res. Commun. 5 1 (1988) 21-33.
16. Laurie McLeod L., and Abdu Alaysh I. Detection of a ferrylhemoglobin intermediate in an endothelial cell model after hypoxia-reoxygenation. Am. J. Physiol. Heart Circ. Physiol. 277 (1999) 92-99
17. Balagopalakrishna C., Manoharan P.T., Abugo O.O., and Rifkind J.M. Production of superoxide from hemoglobin-bound oxygen under hypoxic conditions. Biochemistry 35 20 (1996 May 21) 6393-6398.
18. Rifkind J.M., Zhang L., Levy A., and Manoharan P.T. The hypoxic stress on erythrocytes associated with superoxide formation. Free Radic. Res Commun. 12-13 Pt 2 (1991) 645-652
19. 2 and 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonate) as substrates. J. Agric Food Chem. 51 19 (2003 Sep 10) 5815-5823
20. Moore K.P., Holt S.G., Patel R.P., Svistunenko D.A., Zackert W., Goodier D., Reeder B.J., Clozel M., Anand R., Cooper C.E., Morrow J.D., Wilson M.T., Darley-Usmar V., and Roberts L.J. A causative role for redox cycling of myoglobin and its inhibition by alkalinisation in the pathogenesis and treatment of rhabdomyolysis-induced renal failure. J. Biol. Chem. 273 (1998) 31731-31737
21. Grisham M.B., and Everse J. In: Everse J., Everse K.E., and Grisham M.B. (Eds). Peroxidises in Chemistry and Biology (1991), CRC Press, Boca Raton, FL 335-344
22. Carlsen C.U., Kröger-Ohlsen M., Bellio R., and Skibsted L.H. Protein binding in deactivation of ferrylmyoglobin by chlorogenate and ascorbate. J. Agric. Food Chem 48 (2000) 204-212
23. Romero F., Ordonez I., Arduini A., and Cadenas E. The reactivity of thiols and disulphides with different redox states of myoglobin. J. Biol. Chem. 267 (1992) 1680-1688.
24. Gunther M.R. Glutathione-dependent reduction of peroxides during ferryl- and met-myoglobin interconversion: a potential protective mechanism in muscle. Free Radic Biol Med. 6 5 (1989) 473-478.
25. Giulivi C., and Cadenas E. Inhibition of protein radical reaction ferrylmyoglobin by the water-soluble analog of vitamin E, trolox C. Arch. Biophys Biochem. 303 (1993) 152-158.
26. Hu M., and Skibsted L.H. Kinetics of reduction of ferrylmyoglobin by (-)-epigallocatechin gallate and green tea extract. J. Agric. Food Chem. 50 (2002) 2998-3003.
27. al-Ghamdi M.S. The anti-inflammatory, analgesic and antipyretic activity of Nigella sativa. J. E. Thnopharmacol 76 (2001) 45-48.
28. El Gazzar M., El Mezayen R., Marecki J.C., Nicolls M.R., Canastar A., and Dreskin S.C. Anti-inflammatory effect of thymoquinone in a mouse model of allergic lung inflammation. Int Immunopharmacol 6 7 (2006 Jul) 1135-1142.
29. Gali-Muhtasib H., Roessner A., and Schneider-Stock R. Thymoquinone: a promising anti-cancer drug from natural sources. Int. J. Biochem Cell Biol. 38 8 (2006) 1249-1253 Review
30. Al-Majed A.A., Al-Omar F.A., and Nagi M.N. Neuroprotective effects of thymoquinone against transient forebrain ischemia in the rat hippocampus. Eur. J. Pharmacol. 543 1-3 (2006 Aug 14) 40-47
31. El-Tahir K.E., Ashour M.M., and Al-Harbi M.M. The cardiovascular actions of volatile oil of the black seeds (Nigella sativa) in guinea-pigs: elucidation of the mechanism(s) of action. Gen Pharmacol 24 (1993) 1123-1131
32. Fararh K.M., Shimizu Y., Shiina T., Nikami H., Ghanem M.M., and Takewaki T. Thymoquinone reduces hepatic glucose production in diabetic hamsters. Res. Vet. Sci. 79 3 (2005 Dec) 219-223
33. El-Dakhakhny M., Mady N., Lembert N., and Ammon H.P. The hypoglycemic effect of Nigella sativa oil is mediated by extrapancreatic actions. Planta Med. 68 5 (2002 May) 465-466
34. El-Saleh S.C., Al-Sagair O.A., and Al-Khalaf M.I. Thymoquinone and Nigella sativa oil protection against methionine-induced hyperhomocysteinemia in rats. Int. J. Cardiol. 93 1 (Jan 2004) 19-23
35. Badary O.A., Abdel-Naim A.B., Abdel-Wahab M.H., and Hamada F.M. The influence of thymoquinone on doxorubicin-induced hyperlipidemic nephropathy in rats. Toxicology 143 3 (Mar 7 2000) 219-226
36. Khalife K.H., and Lupidi G. Non enzymatic reduction of thymoquinone in physiological conditions. Free Rad. Res. 41 2 (2007) 153-161
37. Buffinton G., Mira D., Galaris D., Hochstein P., and Cadenas E. Reduction of ferryl- and metmyoglobin to ferrous myoglobin by menadione-glutathione conjugate. Spectrophotometric studies under aerobic and anaerobic conditions. Chem-Biol. Interactions 66 (1988) 205-222
38. Mordente A., Martorana G.E., Minotti G., and Giardina B. Antioxidant properties of 2,3-dimethoxy-5-methyl-6-(10-hydroxydecyl)-1,4-benzoquinone (Idebenone). Chem. Res Toxicol. 11 1 (1998) 54-63
39. Smith L.I., and Tess R.W. Dithymoquinone. J. Am. Chem. Soc. 66 (1944) 1323-1325.
40. El-Alfy T.S., El-Fattatry H.M., and Toama M.A. Isolation and structure assignment of an antimicrobial principle from the volatile oil of Nigella sativa L seeds. Pharmazie 30 (1975) 109-111.
41. Williams R.P., and Tsay K.Y. A convenient chromatographic method for the preparation of human hemoglobin. Anal. Biochem. 54 (1973) 137-145.
42. Di Iorio E.E. Preparation of derivatives of ferrous and ferric hemoglobin. Methods Enzymology 76 (1981) 57-72.
43. Sanchez-Moreno C. Methods used to evaluate the free radical scavenging activity in foods and biological systems. Food Sci. Technol. Int. 44 (2002) 743-745
44. Winterbourn C.C., French J.K., and Claridge R.F.C. The reaction of menadione with hemoglobin. Biochem. J. 179 (1979) 665-673.
45. *. J. Biol. Chem. vol. 277 8 (2002) 6104-6110
46. Kanner J., and Harel S. Initiation of membrane lipid peroxidation by activated metmyoglobin and methemoglobin. Arch Biochem Biophys 237 2 (1985 Mar) 314-321
47. Hua D.H., Lou K., Battina S.K., Zhao H., Perchellet E.M., Wang Y., and Perchellet J.P. Syntheses, molecular targets and antitumor activities of novel triptycene bisquinones and 1,4-anthracenedione analogs. Anticancer Agents Med. Chem. 6 4 (2006 Jul) 303-318 Review
48. Jones W.P., Lobo-Echeverri T., Mi Q., Chai H., Lee D., Soejarto D.D., Cordell G.A., Pezzuto J.M., Swanson S.M., and Kinghorn A.D. Antitumour activity of 3-chlorodeoxylapachol, a naphthoquinone from Avicennia germinans collected from an experimental plot in southern Florida. J. Pharm. Pharmacol. 57 9 (2005 Sep) 1101-1108.
49. Galaris D., Sevanian Cadenas E., and Hochstein P. Ferrylmyoglobin-catalyzed linoleic acid peroxidation. Arch. Biochem.Biophys 281 (1990) 163-169.
50. Mordente A., Martorana G.E., Miggiano D., Pelitti T., Littarru B.G.P., and Santini S.A. Free radical production by activated heme proteins: protective effect of coenzyme Q. Molec. Aspects Med. 15 (1994) 109-115.
51. Jorgensen K., and Skibsted L.H. Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antoxidative activity. Z. Lebensm. Unters Forsch 196 5 (May 1993) 423-4239
52. Ames B.N., Cathcart R., Schwiers E., and Hochstein P. Uric acid provides an antioxidant defence in humans against oxidant- and radical-caused aging and cancer: a hypothesis. Proc. Natl. Acad. Sci. U. S. A. 78 11 (1981 Nov) 6858-6862.
53. 2. Arch. Biochem. Biophys. 262 1 (Apr 1988) 221-231
54. Giulivi C., Romero F., and Cardens E. The interaction of trolox C, a water soluble vitamin E analog with ferrylmyoglobin. Reduction of the oxoferryl moiety. Arch. Biochem. Biophys. 299 (1992) 302-312.
55. Jaffé E.R., and Hultquist D.E. Cytochrome b5 reductase deficiency and enzymopenic hereditary methemoglobinaemia. In: Stanbury J.B., Wyngaarden J.B., and Fredrickson D.G. (Eds). The Metabolic and Molecular Bases of Inherited Disease (1995), New York, McGraw-Hill 2269-2280
56. Wright R.O., Lewander W.J., and Woolf A.D. Methemoglobinaemia: etiology, pharmacology, and clinical management. Ann. Emerg. Med. 34 (1999) 646-656
57. El Mezayen R., El Gazzar M., Nicolls M.R., Marecki J.C., Dreskin S.C., and Nomiyama H. Effect of thymoquinone on cyclooxygenase expression and prostaglandin production in a mouse model of allergic airway inflammation. Immunol. Lett. 106 1 (Jul 15 2006) 72-81
58. Sayed-Ahmed M.M., and Nagi M.N. Thymoquinone supplementation prevents the development of gentamicin-induced acute renal toxicity in rats. Clin. Exp. Pharmacol. Physiol. 34 5-6 (May-Jun 2007) 399-405
59. Khattab M.M., and Nagi M.N. Thymoquinone supplementation attenuates hypertension and renal damage in nitric oxide deficient hypertensive rats. Phytother. Res. 21 5 (May 2007) 410-414
60. Badary O.A., Abd-Ellah M.F., El-Mahdy M.A., Salama S.A., and Hamada F.M. Anticlastogenic activity of thymoquinone against benzo(a)pyrene in mice. Food Chem. Toxicol. 45 (2007) 88-92