Protective effect of rutin (vitamin p) against heme oxidation: A quantum mechanical approach

Computational and Theoretical Chemistry

Volumn 996, Issue , 2012, Pages 28-36

  Ghiasi, Mina ^a   Azadnia, Afsaneh ^a   Arabieh, Masoud ^b   Zahedi, Mansour ^b  

^a ALZAHRA UNIVERSITY   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Heme; Intermolecular interaction; QM calculation; Rutin

Indexed keywords

EID: 84865414131     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.07.009     Document Type: Article

References (40)

1. Misra H.P., Fridovich I. The generation of superoxide anion during the autooxidation of haemoglobin. J. Biol. Chem. 1972, 247:6960-6962.
2. Thornalley P., Stern A., Bannister J. A mechanism for primaquine mediated oxidation of NADPH in red blood cells. Biochem. Pharmacol. 1983, 32:3571-3575.
3. 2 formation, or gluthathion turnover. Biochem. Pharmacol. 1982, 31:2409-2414.
4. Carrel R.W., Winterbourn C.C., Rachmilevitz E.A. Activated oxygen and haemolysis. Br. J. Haematol. 1975, 30:259-264.
5. Giulivi C., Davies K.J.A. Hydrogen peroxide-mediated ferrylhemoglobin generation in vitro and in red blood cells. Method. Enzymol. 1994, 231:490-496.
6. Winterbourn C.C. Oxidative reactions of hemoglobin. Method. Enzymol. 1990, 186:256-272.
7. Scott M.D., van den Berg J., Repka T., Rouyer-Fessard Ph, Hebbel R.P., Beuzard Y., Lubin B.H. Effect of excess of α-hemoglobin chains in cellular and membrance oxidation in model β-thalassemic erythrocytes. J. Clin. Invest. 1993, 91:1706-1712.
8. Hebbel R.P., Eaton J.W., Balasingam M., Steinberg M.H. Spontaneous oxygen radical generation by sickle erythrocytes. J. Clin. Invest. 1982, 70:1253-1259.
9. Winterbourn C.C., Benatti U., de Flora A. Contributions of superoxide, hydrogen peroxide and transition metal ions to auto-oxidation of favism inducing pyrimidine aglycone, divicine, and its reactions with haemoglobin. Biochem. Pharmacol. 1986, 35:2009-2015.
10. Grinberg L.N., Shalev O., Goldfarb A., Rachmilewitz E.A. Primaquine-induced superoxide production by β-thalassemic red blood cells. Biochim. Biophys. Acta 1992, 1139:248-250.
11. Aron P.M. A Kennedy, Flavan-3-ols: nature, occurrence and biological activity. J. Mol. Nutr. Food Res. 2008, 52:79-104.
12. Halliwell B. Dietary polyphenols: good, bad, or indifferent for your health?. Cardiovasc. Res. 2007, 73:341-347.
13. Manach C., Mazur A., Scalbert A. Polyphenols and prevention of cardiovascular diseases. Curr. Opin. Lipidol. 2005, 16:77-84.
14. Chen Y.T., Zheng R.L., Jia Z.J., Ju Y. Flavonoids as superoxide scavengers and antioxidants. Free. Radical. Bio. Med. 1990, 9:19-21.
15. Cotelle N. Role of flavonoids in oxidative stress. Top. Med. Chem. 2001, 1:569-590.
16. Heim K.E., Tagliaferro A.R., Bobilya D.J. Flavonoid antioxidants: chemistry, metabolism and structure activity relationships. J. Nutr. Biochem. 2002, 13:572-584.
17. Bors W., Heller W., Michel C.H., Saran M. Flavonoids as antioxidants: determination of radical scavenging efficiencies. Method. Enzymol. 1990, 186:343-355.
18. Casley-Smith J.R., Morgan R.G., Pillar N.B. Treatment of Lymphedema of the Arms and Legs with 5,6-Benzo-[alpha]-pyrone Engl. N. J. Med. 1993, 329:1158-1163.
19. Robak J., Gryglewski R. Flavonoids are scavengersof superoxide anion. Biochem. Pharmacol. 1988, 37:837-841.
20. Afanas'ev I., Dorozhko A., Brodski A., Kostyuk V., Potapovitch A. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochem. Pharmacol. 1989, 38:1763-1769.
21. Grinberg L.N., Rachmilewitz E.A., Newmark H. Protective effects of rutin against hemoglobin oxidation. Biochem. Pharmacol. 1994, 48:643-649.
22. Gebicka L., Banasik E. Flavonoids as reductants of ferryl hemoglobin. Acta. Biochim. Pol. 2009, 56:509-513.
23. ghiasi M., Heravi M.M. Quantum mechanical study of antioxidative ability and antioxidative mechanism of rutin (vitamin P) in solution. Carbohyd. Res. 2011, 346:739-744.
24. Gaussian 1998 (Revision-B), M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C.V. Ghonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.
25. Becke A.D. A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 1993, 98:1372-1377.
26. Lee C., Yang W., Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1998, 37:785-789.
27. Carpenter J.E., Weinhold F. Analysis of geometry of the hydroxymethyl radicals by the " different hybrids for different spins" natural bond orbital procedure. J. Mol. Struct.: Theochem. 1988, 169:41-62.
28. Cowan J.A. Inorganic Biochemistry: An introduction 1993, VHC Publishers, New York.
29. Silva J.J.R.F., Williams R.J.P. The Inorganic Chemistry of Life 1993, Charendon Press, New York.
30. Harris D.L., Loew G.H. Determinants of the spin state of the resting state of cytochrome P450cam. J. Am. Chem. Soc. 1993, 115:5799-5802.
31. Harris D.L., Loew G.H. Determinants of the spin state of the resting state of cytochrome P450cam. J. Am. Chem. Soc. 1993, 115:8775-8779.
32. cam complexes. J. Phys. Chem. B. 2005, 109:1268-1280.
33. 5 on the interaction between cytochrome P450 2B4 and P450 reductase. J. Inorg. Biochem. 2003, 97:265-275.
34. Urano Y., Higuchi T., Hirobe M., Nagano T. Pronounced axial thiolate ligand effect on the reactivity of high-valent oxo-iron porphyrin intermediate. J. Am. Chem. Soc. 1997, 119:12008-12009.
35. Szabo A., Ostlund N.S. Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory 1982, Dover Publication, New York.
36. Leopoldini M., Pitarch I.P., Russo N., Toscano M. Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study. J. Phys. Chem. A. 2004, 108:92-96.
37. Parkinson C.P., Mayer P.M., Radom L. An assessment of theoretical procedures for the calculation of reliable radical stabilization energies. J. Chem. Soc., Perk. Trans. 1999, 211:2305-2313.
38. Wan C., Cui M., Song F., Liu Z., Liu S. A study of the non-covalent interaction between flavonoids and DNA triplexes by electrospray ionization mass spectrometry. Int. J. Mass Spectrom. 2009, 283:48-55.
39. Ray A., Kumar G.S., Das S., Maiti M. Spectroscopic studies on the interaction of aristololactam-β-d-Glucoside with DNA and RNA double and triple helices: a comparative study. Biochemistry 1999, 38:6239-6247.
40. Chowdhury A.R., Sharma S., Mandal S., Goswami A., Mukhopadhyay S., Majumder H.K. Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase. Biochem. J. 2002, 366:653-661.