Quantitative structure-activity relationship analysis of phenolic antioxidants

Free Radical Biology and Medicine

Volumn 26, Issue 3-4, 1999, Pages 285-294

  Lien, Eric J ^a   Ren, Shijun ^a   Bui, Huynh Hoa ^a   Wang, Rubin ^b  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b SHANDONG UNIVERSITY SCHOOL OF MEDICINE   (China)

Author keywords

Antioxidants; E(homo); E(lumo); Flavonoids; Free radical; Heat of formation; One electron redox potential; Phenols; Quantitative structure activity relationship (QSAR); TEAC; Vitamin E derivatives

Indexed keywords

ALPHA TOCOPHEROL DERIVATIVE; ANTIOXIDANT; FLAVONOID; PHENOL DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; OXIDATION REDUCTION POTENTIAL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTIOXIDANTS; CHEMISTRY, PHYSICAL; LINEAR MODELS; LOGISTIC MODELS; OXIDATION-REDUCTION; PHENOLS; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN E;

EID: 0032953597     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00190-7     Document Type: Article

References (33)

1. Rice-Evans C.A., Diplock A.T. Current status of antioxidant therapy. Free Radic. Biol. Med. 15:1993;77-96.
2. Cadenas E., Packer L. Handbook of antioxidants. 1996;Marcel Dekker, Inc, New York.
3. Rice-Evans C.A., Packer L. Flavonoids in health and disease. 1998;Marcel Dekker, Inc, New York.
4. Steenken S., Neta P. One-electron redox potentials of phenols. Hydroxy and aminophenols and related compounds of biological interest. J. Phys. Chem. 86:1982;3661-3667.
5. Jovanovic S.V., Tosic M., Simic M.G. Use of the Hammet correlation and σ+ for calculation of one-electron redox potentials of antioxidants. J. Phys. Chem. 95:1991;10824-10827.
6. Shertzer H.G., Tabor M.W., Hogan I.T.D., Brown S.J., Sainsburg M. Molecular modeling parameters predict antioxidant efficacy of 3-indolyl compounds. Arch. Toxicol. 70:1996;830-834.
7. van Acker S.A.B.E., de Groot M.J., van den Berg D., Tromp M.N.J.L., den Kelder G.D., van der Vijgh W.J.F., Bast A. A quantum chemical explanation of the antioxidant activity of flavonoids. Chem. Res. Toxicol. 9:1996;1305-1312.
8. Cao G., Sofic E., Prior R.L. Antioxidant and prooxidant behavior of flavonoids Structure-activity relationships . Free Radi. Biol. Med. 22:1997;749-760.
9. Burton G.W., Le Page Y., Gabe E.J., Ingold K.U. Antioxidant activity of vitamin E and related phenols. Importance of stereoelectronic factors. J. Am. Chem. Soc. 102:1980;7791-7792.
10. Burton G.W., Doba T., Gabe E.J., Hughes L., Lee F.L., Prasad L., Ingold K.U. Autoxidation of biological molecules. 4. Maximizing the antioxidant activity of phenols. J. Am. Chem. Soc. 107:1985;7053-7056.
11. Doba T., Burton G.W., Ingold K.U. EPR spectra of some α-tocopherol model compounds. Polar and conformational effects and their relation to antioxidant activities. J. Am. Chem. Soc. 105:1983;6505-6506.
12. Burton G.W., Hughes L., Ingold K.U. Antioxidant activity of phenols related to vitamin E. Are there chain-breaking antioxidants better than α-tocopherol? J. Am. Chem. Soc. 105:1983;5950-5951.
13. Janero D.R., Cohen N., Burghardt B., Schaer B.H. Novel 6-hydroxychroman-2-carbonitrile inhibitors of membrane peroxidative injury. Biochem. Pharmacol. 40:1990;551-558.
14. Mukai K., Fukuda K., Ajima K., Ishizu K. A kinetic study of reactions of tocopherol with a substituted phenoxyl radical. J. Org. Chem. 53:1988;430-432.
15. Burkey T.J., Castelhano A.L., Griller D., Lossing F.P. Heats of formation and ionization potentials of some α-aminoalkyl radicals. J. Am. Chem. Soc. 105:1983;4701-4703.
16. van Acker S.A.B.E., Koymans L.M.H., Bast A. Molecular pharmacology of vitamin E Structural aspects of antioxidant activity . Free Radi. Biol. Med. 15:1993;311-328.
17. Hypercube, Inc. HyperChem for Window, Version 5.0, publication HC 50-00-02-00, 419 Phillip St. Waterloo, Ontario, Canada, 1996.
18. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107:1985;3902-3909.
19. th St., Suite 204, Claremont, CA 91711, 1998.
20. Jovanovic S.V., Steenken S., Simic M.G., Hara Y. Antioxidant properties of flavonoids: Reduction potentials and electron transfer reductions of flavonoid radicals. Rice-Evans C.A., Packers L. Flavonoids in health and disease. 1998;137-161 Marcel Dekker, Inc, New York.
21. Lind J., Shen X., Eriksen T.E., Merenyi G. The one-electron reduction potential of 4-substituted phenoxyl radicals in water. J. Am. Chem. Soc. 112:1990;479-482.
22. Bordwell F.G., Cheng J.P. Substituent effects on the stabilities of phenoxyl radicals and the acidities of phenoxyl radical cations. J. Am. Chem. Soc. 113:1991;1736-1743.
23. Matsushita S. Antioxidant studies in retrospect. Hayaishi O., Niki E., Kondo M., Yoshikawa T. Medical biochemical and chemical aspects of free radicals. Vol. 1:1988;327-334 Elsevier, New York.
24. Bunyan J., McHale D., Green J., Marcinkiewicz S. Biological potencies of ε- and ζ1-tocopherol and 5-methyltocol. Brit. J. Nutr. 15:1961;253-257.
25. Weiser H., Vecchi M. Stereoisomers of α-tocopheryl acetate. II. Biopotencies of all eight stereoisomers, individually or in mixtures, as determined by rat resorption-gestation tests. Internat. J. Vit. Nutr. Res. 52:1982;351-370.
26. Lien E.J. Chirality and drug targeting Pros and cons . J. Drug Targeting. 2:1995;527-532.
27. Das A., Wang J.H., Lien E.J. Carcinogenicity, mutagenicity and cancer preventing activities of flavonoids A structure-system-activity relationship (SSAR) analysis . Prog. Drug Res. 42:1994;13-166.
28. Harborne J.B., Mabry T.J., Mabry H. The flavonoids. 1975;Chapman and Hall Ltd, London.
29. Lien L.L., Lien E.J. Hormone therapy and phytoestrogens. J. Clin. Pharm. Ther. 21:1996;101-111.
30. Lien E.J., Das A., Lien L.L. Immunopharmacological and biochemical bases of Chinese herbal medicine. Prog. Drug Res. 46:1996;263-280.
31. Rice-Evans C.A., Miller N.J. Structure-antioxidant activity relationships of flavonoids and isoflavonoids. Rice-Evans C.A., Packers L. Flavonoids in health and disease. 1998;199-219 Marcel Dekker, Inc, New York.
32. Childs R.E., Bardsley W.G. The steady-state kinetics of peroxidase with 2,2′-azino-di-(3-ethyl-benzthiazoline-6-sulphonic acid) as chromogen. Biochem. J. 145:1975;93-103.
33. Chen Z.Y., Chan P.T., Ho K.Y., Fung K.P., Wang J. Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups. Chem. Phys. Lipids. 79:1996;157-163.