Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system

Free Radical Biology and Medicine

Volumn 24, Issue 9, 1998, Pages 1355-1363

  Arora, Arti ^a   Nair, Muraleedharan G ^b   Strasburg, Gale M ^a  

^a Michigan State University   (United States)

^b Bioactive Natural Products and Phytoceuticals   (United States)

Author keywords

Antioxidants; Diphenylhexatriene propionic acid; Flavonoids; Fluorescence spectroscopy; Free Radicals; Lipid peroxidation; Liposomes; TBHQ

Indexed keywords

ANTIOXIDANT; FLAVONOID; FREE RADICAL; LIPOSOME;

ANTIOXIDANT ACTIVITY; ARTICLE; ISCHEMIC HEART DISEASE; LIPID PEROXIDATION; OXIDATIVE STRESS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AMIDINES; ANTIOXIDANTS; COUMARINS; FERRIC COMPOUNDS; FERROUS COMPOUNDS; FLAVONOIDS; HYDROQUINONES; LIPID PEROXIDATION; LIPOSOMES; OXIDANTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031864258     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(97)00458-9     Document Type: Article

References (27)

1. Kühnau J. The flavonoids. A class of semi-essential food components: their role in human nutrition. Wld. Rev. Nutr. Diet. 24:1976;117-191.
2. Renaud S., De Lorgeril M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet. 339:1992;1523-1526.
3. Frankel E. N., Kanner J., German J. B., Parks E., Kinsella J. E. Inhibition of oxidation of low-density lipoprotein by phenolic substances in red wine. Lancet. 341:1993;454-457.
4. Pace-Asciak C. R., Hahn S., Diamandis E. P., Soleas G., Goldberg D. M. The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis implications for protection against coronary heart disease . Clin. Chim. Acta. 235:1995;207-219.
5. Fuhrman B., Lavy A., Aviram M. Consumption of red wine with meals reduces the susceptibility of human plasma and low-density lipoprotein to lipid peroxidation. Am. J. Clin. Nutr. 61:1995;549-554.
6. Cotelle N., Bernier J. L., Henichart J. P., Catteau J. P., Gaydou E., Wallet J. C. Scavenger and antioxidant properties of ten synthetic flavones. Free Radic. Biol. Med. 13:1992;211-219.
7. 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.
8. Heilmann J., Merfort I., Weiss M. Radical scavenger activity of different 3′,4′-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescence. Planta Med. 61:1995;435-438.
9. Montensinos M. C., Ubeda A., Terencio M. C., Paya M., Alcaraz M. J. Antioxidant profile of mono- and dihydroxylated flavone derivatives in free radical generating systems. Z. Naturforsch. 50c:1995;552-560.
10. Afanas'ev I. B., Dorozhko A. I., Brodskii A. V., Kostyuk V. A., Potapovitch A. I. Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation. Biochem. Pharmacol. 38:1989;1763-1769.
11. 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.
12. Laughton M. J., Evans P. J., Moroney M. A., Hoult J. R. S., Halliwell B. Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolic dietary additives. Biochem. Pharmacol. 42:1991;1673-1681.
13. Thompson M., Williams C. R. Stability of flavonoid complexes of copper (II) and flavonoid antioxidant activity. Anal. Chim. Acta. 85:1976;375-381.
14. Van Acker S. A. B. E., Van den Berg D.-J., Tromp M. N. J. L., Griffioen D. H., Van Bennekom W. P., Van der Vijgh W. J. F., Bast A. Structural aspects of antioxidant activity of flavonoids. Free Radic. Biol. Med. 20:1996;331-342.
15. Morel I., Lescoat G., Cillard P., Cillard J. Role of flavonoids and iron chelation in antioxidant action. Meth. Enzymol. 234:1994;437-443.
16. Hollman P. C. H., de Vries J. H. M., van Leeuwen S. D., Mengelers M. J. B., Katan M. B. Absorption of dietary quercetin glycosides and quercetin in healthy ileostomy volunteers. Am. J. Clin. Nutr. 62:1995;1276-1282.
17. Hollman P. C. H., Hertog M. G. L., Katan M. B. Role of dietary flavonoids in protection against cancer and coronary disease. Biochem. Soc. Trans. 24:1996;785-789.
18. MacDonald R. C., MacDonald R. I., Menco B. P. M., Takeshita K., Subbarao N. K., Hu L. Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim. Biophys. Acta. 1061:1991;297-303.
19. Arora A., Strasburg G. M. Development and validation of fluorescence spectroscopic assays to evaluate antioxidant efficacy. Application to metal chelators. J. Am. Oil Chem. Soc. 74:1997;1031-1040.
20. van Acker S. A. B. E., de Groot M. J., van den Berg D.-J., Tromp M. N. J. L., den Kelder G. D.-O., 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.
21. Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants Determination of radical-scavenging efficiencies . Meth. Enzymol. 186:1990;343-355.
22. 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.
23. Rice-Evans C. A., Miller N. J. Antioxidant activities of flavonoids as bioactive components of food. Biochem. Soc. Trans. 24:1996;790-795.
24. 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.
25. Roginsky V. A., Barsukova T. K., Remosova A. A., Bors W. Moderate antioxidative efficiencies of flavonoids during peroxidation of methyl linoleate in homogenous and micellar solutions. J. Am Oil Chem. Soc. 73:1996;777-786.
26. Mayouf A. M., Lemmetyinen H. Oxidation-reduction reaction of photoinduced benzyl radicals in water para substituent effect . J. Photochem. Photobiol. A:Chem. 73:1993;205-211.
27. Jovanovic S. V., Steenken S., Tosic M., Maryanovic B., Simic M. G. Flavonoids as antioxidants. J. Am. Chem. Soc. 116:1994;4846-4851.