A spectroelectrochemical and chemical study on oxidation of 7,8-dihydroxy-4-methylcoumarin (DHMC) and some related compounds in aprotic medium

Biochimie

Volumn 92, Issue 9, 2010, Pages 1123-1129

  Petrucci, Rita ^a   Saso, Luciano ^a   Kumar, Vineet ^b,c   Prasad, Ashok K ^b   Malhotra, Sanjay V ^c   Parmar, Virinder S ^b   Marrosu, Giancarlo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF DELHI   (India)

^c SAIC FREDERICK INC   (United States)

Author keywords

Antioxidants; Polyphenols oxidation; Radical anions; Semiquinones; Spectroelectrochemistry

Indexed keywords

7,8 DIACETOXY 4 METHYLCOUMARIN; 7,8 HYDROXY 4 METHYLCOUMARIN; ACETONITRILE; COUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; ELECTROLYSIS; OXIDATION; ULTRAVIOLET RADIATION;

ACETONITRILES; BENZOQUINONES; COUMARINS; ELECTROCHEMISTRY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77955843272     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2010.06.008     Document Type: Article

References (52)

1. Halliwell B., Cross C.E. Oxygen-derived species: their relation to human disease and environmental stress. Environ. Health Perspect. 1994, 102(10):5-12.
2. Jenner P., Olanow C.W. Oxidative stress and the pathogenesis of Parkinson's disease. Neurology 1996, 47:161-170.
3. McKenzie S.J., Baker M.S., Buffinton G.D., Doe W.F. Evidence of oxidant-induced injury to epithelial cells during inflammatory bowel deseasa. J. Clin. Invest. 1996, 98:136-141.
4. Heinecke J.W. Mechanism of oxidative damage of low density lipoprotein in human atherosclerosis. Curr. Opin. Lipidol. 1997, 8:268-274.
5. J.W. Heinecke, Oxidants and antioxidants in the pathogenesis of atherosclerosis: implications for the oxidized low density lipoprotein hypothesis, Atherosclerosis 141(1998) 1-15.
6. Hawkins C.L., Davies M.J. Hypochlorite-induced damage to proteins: formation of nitrogen-centred radicals from lysine residues and their role in protein fragmentation. Biochem. J. 1998, 332:617-625.
7. C.L. Hawkins, M.J. Davies, Hypochlorite-induced oxidation of proteins in plasma: formation of chloramines and nitrogen-centred radicals and their role in protein fragmentation, Biochem. J. 340(1999) 539-548.
8. Blackburn A.C., Doe W.F., Buffinton G.D. Protein carbonyl formation on mucosal proteins in vitro and in dextran sulfate-induced colitis. Free Radic. Biol. Med. 1999, 27:262-270.
9. Hazell L.J., Davies M.J., Stocker R. Secondary radicals derived from chloramines of apolipoprotein B-100 contribute to HOCl-induced lipid peroxidation of low-density lipoproteins. Biochem. J. 1999, 339:489-495.
10. Betteridge D.J. What is oxidative stress?. Metabolism 2000, 49:3-8.
11. Podrez E.A., Abou-Soud H.M., Hazen S.L. Myeloperoxidase-generated oxidants and atherosclerosis. Free Radic. Biol. Med. 2000, 28:1717-1725.
12. Babior B.M. Phagocytes and oxidative stress. Am. J. Med. 2000, 109:33-44.
13. Smith M.A., Rottkamp C.A., Nunomura A., Raina A.K., Perry G. Oxidative stress in Alzheimer's disease. Biochim. Biophys. Acta 2000, 1502:139-144.
14. Noguchi N., Nakada A., Itoh Y., Watanabe A., Niki E. Formation of active oxygen species and lipid peroxidation induced by hypochlorite. Arch. Biochem. Biophys. 2002, 397:440-447.
15. Kandaswami C., Middleton E. Free radical scavenging and antioxidant activity of plant flavonoids. Adv. Exp. Med. Biol. 1994, 366:351-376.
16. Rice-Evans C.A., Miller N.J. Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 1996, 24:790-795.
17. Rice-Evans C.A., Nicholas J.M., Paganga G. Antioxidant properties of phenolic compounds. Trends Plant Sci. 1997, 2:152-159.
18. Chen J.H., Ho C.T. Antioxidant activity of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45:2374-2378.
19. De Groot H., Rauen U. Tissue injury by reactive oxygen species and the protective effects of flavonoids. Fundam. Clin. Pharmacol. 1998, 12:249-255.
20. Youdim K.A., Shukitt-Hale B., MacKinnon S., Kalt W., Joseph J.A. Polyphenolics enhance red blood cell resistance to oxidative stress: in vitro and in vivo. Biochim. Biophys. Acta 2000, 1523:117-122.
21. Son S., Lewis B.A. Free radical scavenging and antioxidative activity of caffeic acid amide and ester analogues: structure-activity relationship. J. Agric. Food Chem. 2002, 50:468-472.
22. Firuzi O., Giansanti L., Vento R., Seibert C., Petrucci R., Marrosu G., Agostino R., Saso L. Hypochlorite scavenging activity of hydroxycinnamic acids evaluated by a rapid microplate method based on the measurement of chloramines. J. Pharm. Pharmacol. 2003, 55:1021-1027.
23. Firuzi O., Mladěnka P., Petrucci R., Marrosu G., Saso L. Hypochlorite scavenging activity of flavonoids. J. Pharm. Pharmacol. 2004, 56:801-807.
24. Takeda S., Aburada M. The choleretic mechanism of coumarin compounds and phenolic compounds. J. Pharmacobio-dyn. 1981, 4:724-734.
25. Deana A.A., Stokker G.E., Schultz E.M., Smith R.L., Cragoe E.J., Russo H.F., Watson L.S. 2-(Aminomethyl)phenols, a new class of saluretic agents. 5. Fused-ring analogues. J. Med. Chem. 1983, 26:580-585.
26. Hoult J.R.S., Paya M. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen. Pharmacol. 1996, 27:713-722.
27. Raj H.G., Gupta S., Biswas G., Singh S., Singh A., Jha A., Bisht K.S., Sharma S.K., Jain S.C., Parmar V.S. Chemoprevention of carcinogen-DNA binding: the relative role of different oxygenated substituents on 4-methylcoumarins in the inhibition of aflatoxin B1-DNA binding in vitro. Bioorg. Med. Chem. 1996, 4:2225-2228.
28. Raj H.G., Parmar V.S., Jain S.C., Goel S., Poonam, Malhotra S., Singh A., Olsen C.E., Wengel J. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: dioxygenated 4-methylcoumarins as superb antioxidant and radical scavenging agents. Bioorg. Med. Chem. 1998, 6:833-839.
29. Liu Z.Q., Yu W., Liu Z.L. Antioxidative and prooxidative effects of coumarin derivatives on free radical initiated and photosensitized peroxidation of human low-density lipoprotein. Chem. Phys. Lipids 1999, 103:125-135.
30. Parmar V.S., Sharma S.K., Foti M.C., Shakya G., Prasad A.K., Nicolosi G., Bovicelli P., Ghosh B., Raj H.G., Rastogi R.C. Biopolyphenolics as antioxidants: studies under an Indo-italian CSIR-CNR project. Pure App. Chem. 2005, 77:91-101.
31. Sharma S.D., Rajor H.K., Chopra S., Sharma R.K. Studies on structure activity relationship of some dihydroxy-4-methylcoumarin antioxidants based on their interaction with Fe(III) and ADP. BioMetals 2005, 18:143-154.
32. Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radic. Biol. Med. 1996, 20:933-956.
33. Kaneko T., Baba N., Matsuo M. Protection of coumarins against linoleic acid hydroperoxide-induced cytotoxicity. Chem.-Biol. Interact. 2003, 142:239-254.
34. Firuzi O., Lacanna A., Petrucci R., Marrosu G., Saso L. Evaluation of the antioxidant activity of flavonoids by " ferric reducing antioxidant power" assay and cyclic voltammetry. Biochim. Biophys. Acta 2005, 1721:174-184.
35. Raj H.G., Parmar V.S., Jain S.C., Goel S., Singh A., Gupta K., Rohil V., Tyagi Y.K., Jha H.N., Olsen C.E., Wengel J. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part II: mechanism-based inhibition of rat liver microsome-mediated aflatoxin B1-DNA binding by the candidate antimutagen 7,8-diacetoxy-4-methylcoumarin. Bioorg. Med. Chem. 1998, 6:1895-1904.
36. Raj H.G., Parmar V.S., Jain S.C., Goel S., Singh A., Tyagi Y.K., Jha H.N., Olsen C.E., Wengel J. Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part IV: hyperbolic activation of rat liver microsomal NADPH-cytocorme C reductase by the novel acetylator 7,8-diacetoxy-4-methylcoumarin. Bioorg. Med. Chem. 1999, 7:369-373.
37. Kuhn R., Hammer I. Active lead dioxide for the preparation of sensitive quinones. Chem. Ber. 1950, 83:413-414.
38. Kumar S., Singh B.K., Kalra N., Kumar V., Kumar A., Prasad A.K., Raj H.G., Parmar V.S., Ghosh B. Novel thiocoumarins as inhibitors of TNF-α induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation. Bioorg. Med. Chem. 2005, 13:1605-1613.
39. Pechmann H.V., Duisberg C. Substituted coumarins. Chem. Ber. 1893, 16:2119.
40. Parmar V.S., Singh S., Boll P.M. Carbon-13 nuclear magnetic resonance spectroscopy of 4-methylcoumarins (4-methyl-2H-1-benzopyran-2-ones). Mag. Res. Chem. 1988, 26(5):430-433.
41. Chakravarti Duhkhaharan Synthesis of coumarins from phenols and β-ketonic esters. III. Use of various condensing agents. J. Indian Chem. Soc. 1935, 12:536-539.
42. Parmar V.S., Singh S., Rathore J.S. Synthesis of some new 4-methylcoumarins. J. Indian Chem. Soc. 1987, 64:254-257.
43. Parmar V.S., Bisht K.S., Jain R., Singh S., Sharma S.K., Gupta S., Malhotra S., Tyagi O.D., Vardhan A. Synthesis, antimicrobial and antiviral activities of novel polyphenolic compounds. Indian J. Chem. 1996, 35B:220-232.
44. Andruzzi R., Trazza A., Greci L., Marchetti L. Electrochemical and ESR study on the reduction mechanism of some indoxyl derivatives in DMF. Ann. Chim. (Rome, Italy) 1979, 69:583-596.
45. Sawyer D.T., Sobkowiak A., Roberts J.L. Electrochemistry for Chemists 1995, John Wiley & Sons, Inc., New York, p. 442. second ed.
46. Adams R.N. Electrochemistry at Solid Electrodes 1969, Marcel Dekker, New York, p. 244.
47. Parker V.D. The anodic oxidation of hydroquinone in acetonitrile: on the question of a possible one elctron intermediate. Electrochim. Acta 1973, 18:519-524.
48. Parker V.D., Eberson L. On the anodic oxidation of hydroquinone in acetonitrile. Chem. Commun. 1970, 1289.
49. 0 and superoxide anion. Could ubiquinones mimic superoxide dismutase (SOD)?. Res. Chem. Intermed. 2000, 26:269-282.
50. Ross S.D., Finkelstein M., Rudd E.J. Organic Chemistry, a Series of Monographs 1975, vol. 32:271. Academic Press, Inc., New York. A.T. Blomquist, H.H. Wasserman (Eds.).
51. Petrucci R., Astolfi P., Greci L., Firuzi O., Saso L., Marrosu G. A spectroelectrochemical and chemical study on oxidation of hydroxycinnamic acids in aprotic medium. Electrochim. Acta 2007, 52:2461-2470.
52. Litwinienko G., Ingold K.U. Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc. Chem. Res. 2007, 40:222-230.