Structural aspects of the inhibitory effect of glabridin on LDL oxidation

Free Radical Biology and Medicine

Volumn 24, Issue 9, 1998, Pages 1419-1429

  Belinky, Paula A ^a,b   Aviram, Michael ^b   Mahmood, Saeed ^a   Vaya, Jacob ^a  

^a MIGAL GALILEE TECHNOLOGY CENTER   (Israel)

^b RAMBAM MEDICAL CENTER   (Israel)

Author keywords

Chelating ability; Free radicals; Glabridin; LDL oxidation; Lsoflavan; Peak potential; Radical scavenging capacity

Indexed keywords

GLABRIDIN; LOW DENSITY LIPOPROTEIN;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CHELATION; ELECTRON TRANSPORT; GLYCYRRHIZA; HUMAN; LIPOPROTEIN METABOLISM; MOUSE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL;

ANIMALS; ANTIOXIDANTS; BEPRIDIL; CELL LINE; COPPER; FREE RADICAL SCAVENGERS; HUMANS; IRON CHELATING AGENTS; LIPOPROTEINS, LDL; MACROPHAGES; MICE; OXIDATION-REDUCTION; PHENOLS; PICRATES; POTENTIOMETRY;

ANIMALIA; GLYCYRRHIZA; GLYCYRRHIZA GLABRA;

EID: 0031839964     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(98)00006-9     Document Type: Article

References (54)

1. Hertog M. G. L., Hollman P. C. H., Katan M. B., Kromhout D. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr. Cancer. 20:1993;21-29.
2. Harborne J. B. Nature, distribution and function of plant flavonoids. Cody B., Middleton E., Harborne J. B. Plant flavonoids in biology and medicine. 1986;15-24 Alan Liss, New York.
3. Havsteen B. Flavonoids, a class of natural products of high pharmacological potency. Biochem. Pharmacol. 32:1983;1141-1148.
4. Das D. K. Naturally occurring flavonoids Structure, chemistry, and high-performance liquid chromatography methods for separation and characterization . Methods Enzymol. 234:1994;410-420.
5. Rice-Evans C. A., Miller N. J., Paganda G. Structure-antioxidant activity relationships of flavonoids and phenolics acids. Free Radic. Biol Med. 20:1996;933-956.
6. Cao G., Sofic E., Prior R. L. Antioxidant and prooxidant behavior of flavonoids structure-activity relationships . Free Radic. Biol. Med. 22:1997;749-760.
7. 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.
8. Jovanovic S. V., Steenken S., Tosic M., Marjanovic B., Simic M. G. Flavonoids as antioxidants. J. Am. Chem. Soc. 116:1994;4846-4852.
9. Cody V., Middleton E., Harborne J. B. Plant flavonoids in biology and medicine - biochemical, pharmacological and structure-activity relationships. 1986;Alan Liss, New York.
10. Cody V., Middleton E., Harborne J. B., Beretz A. Plant flavonoids in biology and medicine II - biochemical, cellular and medicinal properties. 1986;Alan Liss, New York.
11. Das N. P. Flavonoids in biology and medicine III - Current issues in flavonoids research. 1990;Singapore University Press, Singapore.
12. Rump A. F., Schussler M., Acar D., Cordes A., Ratke R., Theisohn M., Rosen R., Klaus W., Friecke U. Effects of different inotropes with antioxidant properties on acute regional myocardial ischemia in isolated rabbit hearts. Gen. Pharmacol. 26:1995;603-611.
13. Tzeng S. H., Ko F. N., Teng C. M. Inhibition of platelet aggregation by some flavonoids. Thromb. Res. 64:1991;91-100.
14. 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.
15. Elangovan V., Sekar N., Govindasamy S. Chemoprotective potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorogenesis. Cancer Lett. 87:1994;107-113.
16. Brown J. A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds. Mutat. Res. 75:1980;243-277.
17. 2 and inflammatory responses in mice. Life Sci. 54:1994;333-338.
18. Ferrandiz M. L., Alcaraz M. J. Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents Actions. 32:1991;283-288.
19. Middleton E. Jr, Kandaswami C. Effects of flavonoids on immune and inflammatory cell functions. Biochem. Pharmacol. 43:1992;1167-1179.
20. 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.
21. 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-reducing ability . Biochem. Pharmacol. 42:1991;1673-1681.
22. Siess M. H., Leclerc J., Canivenc-Lavier M. C., Rat P., Suschetet M. Heterogeneous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicol. Appl. Pharmacol. 130:1995;73-78.
23. 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.
24. 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.
25. Cusham 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.
26. Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants Determination of radical-scavenging efficiencies . Methods Enzymol. 186:1990;343-355.
27. 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.
28. Briviba K., Sies H. Nonenzymatic antioxidant defense systems. Frei B. Natural antioxidants in human health and disease. 1994;107-128 Academic Press, London.
29. Mangiapane H., Thomson J., Salter A., Brown S., Bell G. P., White D. A. The inhibition of the oxidation of low density lipoproteins by (+)-catechin, a naturally occurring flavonoid. Biochem. Pharmacol. 43:1992;445-450.
30. de Whalley C., Rankin S. M., Hoult J. R., Jessup W., Leake D. Flavonoids inhibit the oxidative modification of low density lipoproteins by macrophages. Biochem. Pharmacol. 39:1990;1743-1750.
31. Salah N., Miller N. J., Paganga G., Tijburg L., Bolwell G. P., Rice-Evans C. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 322:1995;339-346.
32. 2+-mediated oxidative modification of low density lipoproteins. Biol. Pharm. Bull. 18:1995;1-4.
33. Vaya J., Belinky P. A., Aviram M. Antioxidants constituents from licorice roots isolation, structure elucidation and antioxidative capacity towards LDL oxidation . Free Radic. Biol. Med. 23:1997;302-313.
34. Belinky P. A., Aviram M., Fuhrman B., Rosenblat M., Vaya J. The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation. Atherosclerosis. 137:1998;49-61.
35. Fuhrman B., Buch S., Vaya J., Belinky P. A., Coleman R., Hayek T., Aviram M. Licorice ethanolic extract and its major polyphenol glabridin protect LDL against lipid peroxidation in vitro and ex-vivo studies in humans and in the atherosclerotic apolipoprotein E deficient mice . Am. J. Clin. Nutr. 66:1997;267-275.
36. Steinberg D., Parthasarathy S., Carew T. E., Khoo J. C., Witztum J. L. Beyond cholesterol modifications of low-density lipoprotein that increase its atherogenicity . N. Engl. J. Med. 320:1989;915-923.
37. Jurgens G., Hoff H. F., Chisolm G. M., Esterbauer H. Modification of human serum low density lipoprotein by oxidation-characterization and pathophysiological implications. Chem. Phys. Lipids. 45:1987;315-360.
38. Esterbauer H., Rotheneder M., Striegl G., Waeg G., Ashy A., Sattler W., Jurgens G. Vitamin E and other lipophilic antioxidants protect LDL against oxidation. Fat. Sci. Technol. 91:1989;316-324.
39. Witztum J. L., Steinberg D. Role of oxidized low density lipoprotein in atherogenesis. J. Clin. Invest. 88:1991;1785-1792.
40. Schwartz C. J., Valente A. J., Sprague E. A., Kelley J. L., Nerem R. M. The pathogenesis of atherosclerosis an overview . Clin. Cardiol. 14:1991;1-16.
41. Aviram M. Beyond cholesterol modifications of lipoproteins and increased atherogenicity . Neri Serneri G. G., Gensini G. F., Abbate R., Prisco D. Atherosclerosis, inflammation and thrombosis. 1993;15-36 Scientific Press, Florence, Italy.
42. Daugherty A., Roselaar S. E. Lipoprotein oxidation as a mediator of atherogenesis insights from pharmacological studies . Cardiovas. Res. 29:1995;297-311.
43. Kinoshita T., Saitoh T., Shibata S. The occurrence of an isoflavene and the corresponding isoflavone in licorice root. Chem. Pharm. Bull. 24:1976;991-994.
44. Okada K., Tamura Y., Yamamoto M., Inoue Y., Takagaki R., Takahashi K., Demizu S., Kajiyama K., Hiraga Y., Kinoshita T. Identification of antimicrobial and antioxidant constituents from licorice of russian and xinjiang origin. Chem. Pharm. Bull. 37:1989;2528-2530.
45. Aviram M. Plasma lipoprotein separation by discontinuous density gradient ultracentrifugation in hyperlipoproteinemic patients. Biochem. Med. 30:1983;111-118.
46. Buege J. A., Aust S. D. Microsomal lipid peroxidation. Methods Enzymol. 52:1978;302-310.
47. El-Saadani M., Esterbauer N., El-Sayed M., Goher M., Nassar A. Y., Jurgens G. A spectrophotometric assay for lipid peroxides in serum lipoproteins using a commercially available reagent. J. Lipid Res. 30:1989;627-630.
48. Lowry O. H., Rosebrough N. J., Farr A. L., Randall R. J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
49. Aviram M., Rosenblat M. Macrophage-mediated oxidation of extracellular low density lipoprotein requires an initial binding of the lipoprotein to its receptor. J. Lipid Res. 35:1994;385-398.
50. Patterson M. K. J. Measurement of growth and viability of cells in culture. Methods Enzymol. 58:1979;141.
51. Blois M. S. Antioxidant determination by the use of a stable free radical. Nature. 181:1958;1199-1200.
52. Chevion S, Berry E. M., Kitrossky N., Kohen R. Evaluation of plasma low molecular weight antioxidant capacity by cyclic voltammetry. Free Radic. Biol. Med. 22:1997;411-421.
53. 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.
54. Gotoh N., Shimizu K., Komuro E., Tsuchiya J., Noguchi N., Niki E. Antioxidant activities of probucol against lipid peroxidations. Biochim. Biophys. Acta. 1128:1992;147-154.