Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships

Free Radical Biology and Medicine

Volumn 22, Issue 5, 1997, Pages 749-760

  Cao, Guohua ^a,b   Sofic, Emin ^a   Prior, Ronald L ^a,c  

^a U S DEPARTMENT OF AGRICULTURE   (United States)

^b UNIVERSITY OF CONNECTICUT   (United States)

^c AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

Antioxidant; Flavanone; Flavone; Flavonoid; Free radicals; Isoflavone; Prooxidant

Indexed keywords

FLAVANONE; FLAVONE DERIVATIVE; FLAVONOID; FREE RADICAL; ISOFLAVONE; OXYGEN RADICAL;

ANTIOXIDANT ACTIVITY; ARTICLE; OXIDATIVE STRESS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; COPPER; FLAVONOIDS; FREE RADICALS; HYDROXYL RADICAL; OXIDANTS; PEROXIDES; PHYCOERYTHRIN; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031020195     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(96)00351-6     Document Type: Article

References (62)

1. Das D. K. Naturally occurring flavonoids: Structure, chemistry, and high-performance liquid chromatography methods for separation and characterization. Methods Enzymol. 234:1994;410-420.
2. Terao J., Piskula M., Yao Q. Protective effect of epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch. Biochem. Biophys. 308:1994;278-284.
3. Deschner E. E., Ruperto J., Wong G., Newmark H. L. Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis. 12:1991;1193-1196.
4. Elangovan V., Sekar N., Govindasamy S. Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis. Cancer Lett. 87:1994;107-113.
5. Brown J. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat. Res. 75:1980;243-277.
6. Tzeng S. H., Ko W. C., Ko F. N., Teng C. M. Inhibition of platelet aggregation by some flavonoids. Thromb. Res. 64:1991;91-100.
7. Rump A. F., Schussler M., Acar D., Cordes A., Ratke R., Theisohn M., Rosen R., Klaus W., Fricke U. Effects of different inotropes with antioxidant properties on acute regional myocardial ischemia in isolated rabbit hearts. Gen. Pharmacol. 26:1995;603-611.
8. Gil B., Sanz M. J., Terencio M. C., Ferrándiz M. L., Bustos G., Payá M., Gunasegaran R., Alcaraz M. J. Effects of flavonoids on Naja naja and human recombinant synovial phospholipases A2 and inflammatory responses in mice. Life Sci. 54:1994;333-338.
9. Ferrándiz M. L., Alcaraz M. J. Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents Actions. 32:1991;283-288.
10. Middleton E. Jr., Kandaswami C. Effects of flavonoids on immune and inflammatory cell functions. Biochem. Pharmacol. 43:1992;1167-1179.
11. Laughton M. J., Evans P. J., Moroney M. A., Hoult J. R. C., Halliwell B. Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic dietary additives: Relationship to antioxidant activity and to iron ion-reducing ability. Biochem. Pharmacol. 42:1991;1673-1681.
12. Hoult J. R. S., Moroney M. A., Payá M. Action of flavonoids and coumarins on lipoxygenase and cyclooxygenase. Methods Enzymol. 234:1994;443-455.
13. Siess M. H., Leclerc J., Canivenc-Lavier M. C., Rat P., Suschetet M. Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol. Appl. Pharmacol. 130:1995;73-78.
14. Cotelle N., Bernier J. L., Catteau J. P., Pommery J., Wallet J. C., Gaydou E. M. Antioxidant properties of hydroxy-flavones. Free Radic. Biol. Med. 20:1996;35-43.
15. Hodnick W. F., Duval D. L., Pardini R. S. Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids. Biochem. Pharmacol. 47:1994;573-580.
16. Cushman M., Nagarathnam D., Burg D. L., Geahlen R. L. Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues. J. Med. Chem. 34:1991;798-806.
17. Jinsart W., Ternai B., Polya G. M. Inhibition of wheat embryo calcium-dependent protein kinase and avian myosin light chain kinase by flavonoids and related compounds. Biol. Chem. Hoppe-Seyler. 372:1991;819-827.
18. Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants: Determination of radical-scavenging efficiencies. Methods Enzymol. 186:1990;343-355.
19. Rice-Evans C. A., Miller N. J., Bolwell P. G., Bramley P. M., Pridham J. B. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radic. Res. 22:1995;375-383.
20. Nakayama T., Yamada M., Osawa T., Kawakishi S. Suppression of active oxygen-induced cytotoxicity by flavonoids. Biochem. Pharmacol. 45:1993;265-267.
21. -/̇016/ . Free Radic. Biol. Med. 11:1991;1-8.
22. g ) quenching. J. Photochem. Photobiol. B: Biol. 19:1993;205-215.
23. Rapta P., Mišik V., Staško A., Vrábel I. Redox intermediates of flavonoids and caffeic acid esters from propolis: An EPR spectroscopy and cyclic voltammetry study. Free Radic. Biol. Med. 18:1995;901-908.
24. Saija A., Scalese M., Lanza M., Marzullo D., Bonina F., Castelli F. Flavonoids as antioxidant agents: Importance of their interaction with biomembranes. Free Radic. Biol. Med. 19:1995;481-486.
25. Manach C., Morand C., Texier O., Favier M. L., Agullo G., Demigné C., Régérat F., Rémésy C. Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin. J. Nutr. 125:1995;1911-1922.
26. Morel I., Lescoat G., Cillard P., Cillard J. Role of flavonoids and iron chelation in antioxidant action. Methods Enzymol. 243:1994;437-443.
27. Morel I., Lescoat G., Cogrel P., Sergent O., Pasdeloup N., Brissot P., Cillard P., Cillard J. Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures. Biochem. Pharmacol. 45:1993;13-19.
28. Takahama U. Inhibition of lipoxygenase-dependent lipid peroxidation by quercetin: Mechanism of antioxidative function. Phytochemistry. 24:1985;1443-1446.
29. Popp R., Schimmer O. Induction of sister-chromatid exchanges (SCE), polyploidy, and micronuclei by plant flavonoids in human lymphocyte cultures. A comparative study of 19 flavonoids. Mutat. Res. 246:1991;205-213.
30. Sahu S. C., Gray G. C. Interactions of flavonoids, trace metals, and oxygen: Nuclear DNA damage and lipid peroxidation induced by myricetin. Cancer Lett. 70:1993;73-79.
31. Sahu S. C., Gray G. C. Kaempferol-induced nuclear DNA damage and lipid peroxidation. Cancer Lett. 85:1994;159-164.
32. Rahman A., Fazal F., Greensill J., Ainley K., Parish J. H., Hadi S. M. Strand scission in DNA induced by dietary flavonoids: Role of Cu(I) and oxygen free radicals and biological consequence of scission. Mol. Cell. Biochem. 111:1992;3-9.
33. Ahmad M. S., Fazal F., Rahman A., Hadi S. M., Parish J. H. Activities of flavonoids for the cleavage of DNA in the presence of Cu(II): Correlation with generation of active oxygen species. Carcinogenesis. 13:1992;605-608.
34. Hanasaki Y., Ogawa S., Fukui S. The correlation between active oxygen scavenging and antioxidative effects of flavonoids. Free Radic. Biol. Med. 16:1994;845-850.
35. Cao G., Verdon C., Wu A. H. B., Wang H., Prior R. L. Automated oxygen radical absorbance capacity assay using the COBAS FARA II. Clin. Chem. 41:1995;1738-1744.
36. Cao G., Alessio H. M., Cutler R. G. Oxygen-radical absorbance capacity assay for antioxidants. Free Radic. Biol. Med. 14:1993;303-311.
37. Wayner D. D. M., Burton G. W., Ingold K. U., Locke S. Quantitative measurement of the total, peroxyl radical-trapping antioxidant capacity of human blood plasma by controlled peroxidation. FEBS Lett. 187:1985;33-37.
38. Glazer A. N. Phycoerythrin fluorescence-based assay for reactive oxygen species. Methods Enzymol. 186:1990;161-168.
39. Whitehead T. P., Thorpe G. H. G., Maxwell S. R. J. Enhanced chemiluminescent assay for antioxidant capacity in biological fluids. Anal. Chim. Acta. 266:1992;265-277.
40. Miller N. J., Rice-Evans C., Davies M. J., Gopinathan V., Milner A. A novel method for measuring antioxidant capacity and its application to monitoring the antioxidant status in premature neonates. Clin. Sci. 84:1993;407-412.
41. Halliwell B., Gutteridge J. M. C. The definition and measurement of antioxidants in biological systems. Free Radic. Biol. Med. 18:1995;125-126.
42. Grisham M. B. Reactive metabolites of oxygen and nitrogen in biology and medicine. 1992;10 R. G. Landes Company, Austin, TX.
43. Pieri C., Marra M., Moroni F., Recchioni R., Marcheselli F. Melatonin: A peroxyl radical scavenger more effective than vitamin E. Life Sci. 55:1994;271-276.
44. Yoshida Y., Tsuchiya J., Niki E. Interaction of alpha-tocopherol with copper and its effect on lipid peroxidation. Biochem. Biophys. Acta. 1200:1994;85-92.
45. Iwatsuki M., Niki E., Stone D., Darley-Usmar V. M. Alpha-tocopherol mediated peroxidation in the copper (II) and metmyoglobin induced oxidation of human low density lipoprotein: The influence of lipid hydroperoxides. FEBS Lett. 360:1995;271-276.
46. Cao G., Cutler R. G. High concentrations of antioxidants may not improve defense against oxidative stress. Arch. Gerontol. Geriatr. 17:1993;189-201.
47. Parthasarathy S., Wieland E., Steinberg D. A role for endothelial cell lipoxygenase in the oxidative modification of low density lipoprotein. Proc. Natl. Acad. Sci. USA. 86:1989;1046-1050.
48. 2 plus Cu,Zn-superoxide dismutase reflects the activity of free copper released from the oxidatively damaged enzyme. J. Biol. Chem. 267:1992;25371-25377.
49. Rice-Evans C. A., Miller N. J., Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20:1996;933-956.
50. Hodnick W. F., Kung F. S., Roettger W. J., Bohmont C. W., Pardini R. S. Inhibition of mitochondrial respiration NADH-oxidase (NADH-coenzyme Q oxidoreductase) enzyme system by flavonoids: A structure-activity study. Biochem. Pharmacol. 36:1987;2873-2874.
51. Bohmont C., Aaronson L. M., Mann K., Pardini R. S. Inhibition of mitochondrial NADH oxidase, succinoxidase, and ATPase by naturally occurring flavonoids. J. Nat. Prod. 50:1987;427-433.
52. Decharneux T., Dubois F., Beauloye C., Coninck S. W. D., Wattiaux R. Effect of various flavonoids on lysosomes subjected to an oxidative or an osmotic stress. Biochem. Pharmacol. 44:1992;1243-1248.
53. Limasset B., Doucen C., Dore J., Ojasoo T., Damon M., Paulet A. C. Effects of flavonoids on the release of reactive oxygen species by stimulated human neutrophils: Multivative analysis of structure-activity relationships (SAR). Biochem. Pharmacol. 46:1993;1257-1271.
54. Ioku K., Tsushida T., Takei Y., Nakatani N., Terao J. Antioxidative activity of quercetin and quercetin monoglucosides in solution and phospholipid bilayers. Biochim. Biophys. Acta. 1234:1995;99-104.
55. Igile G. O., Oleszek W., Jurzyst M., Burda S., Fafunso M., Fasanmade A. A. Flavonoids from Vernonia amygdalina and the antioxidant activities. J. Agric. Food Chem. 42:1994;2445-2448.
56. Zhu B. T., Ezell E. L., Liehr J. G. Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. J. Biol. Chem. 269:1994;292-299.
57. 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.
58. Beach D. C., Giroux E. Inhibition of lipid peroxidation promoted by iron (III) and ascorbate. Arch. Biochem. Biophys. 297:1992;258-264.
59. Maiorino M., Zamburlini A., Roveri A., Ursini F. Prooxidant role of vitamin E in copper induced lipid peroxidation. FEBS Lett. 330:1993;174-176.
60. Hertog M. G. L., Feskens E. J. M., Hollman P. C. H., Katan M. B., Kromhout D. Dietary antioxidant flavonoids and the risk of coronary heart disease: The Zutohen Elderly Study. Lancet. 342:1993;1007-1011.
61. Renaud S., De Lorgeril J. M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet. 339:1992;1523-1526.
62. Whitehead T. P., Robinson D., Allaway S., Syms J., Hale A. Effect of red wine ingestion on the antioxidant capacity of serum. Clin. Chem. 41:1995;32-35.