Inhibition of 15-lipoxygenases by flavonoids: Structure-activity relations and mode of action

Biochemical Pharmacology

Volumn 65, Issue 5, 2003, Pages 773-781

  Sadik, Christian David ^a   Sies, Helmut ^a   Schewe, Tankred ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

15 Lipoxygenase; Antioxidants; Flavones; Flavonols; Luteolin; Quercetin

Indexed keywords

APIGENIN; ARACHIDONATE 15 LIPOXYGENASE; BAICALEIN; CATECHOL; CHRYSIN; DAIDZEIN; EPICATECHIN; FISETIN; FLAVONE; FLAVONOID; GALANGIN; GENISTEIN; HESPERETIN; HYDROXYL GROUP; KAEMPHEROL; LINOLEIC ACID; LUTEOLIN; MORIN; MYRICETIN; NARINGENIN; QUERCETIN; RUTOSIDE; TAXIFOLIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG POTENCY; ENZYME INACTIVATION; ENZYME INHIBITION; IC 50; NONHUMAN; PRIORITY JOURNAL; REACTION TIME; RETICULOCYTE; SOYBEAN; STRUCTURE ACTIVITY RELATION;

EID: 0037333276     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(02)01621-0     Document Type: Article

References (40)

1. Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker; 1997.
2. Middleton E. Jr., Kandaswami C., Theoharides T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52:2000;673-751.
3. Virgili F, Scaccini C, Hoppe PP, Krämer K, Packer L. Plant phenols and cardiovascular disease: antioxidants and cell modulators. In: Krämer K, Hoppe PP, Packer L, editors. Nutraceuticals in health and disease prevention. New York: Marcel Dekker; 2001. p. 187-215.
4. Rice-Evans C.A., Miller N.J., Paganga G. Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radic. Biol. Med. 20:1996;933-956.
5. Schewe T., Sadik C., Klotz L.O., Yoshimoto T., Kühn H., Sies H. Polyphenols of cocoa: inhibition of mammalian 15-lipoxygenase. Biol. Chem. 382:2001;1687-1696.
6. Schewe T., Kühn H., Sies H. Flavonoids of cocoa inhibit recombinant human 5-lipoxygenase. J. Nutr. 132:2002;1825-1829.
7. Berliner J.A., Heinecke J.W. The role of oxidized lipoproteins in atherogenesis. Free Radic. Biol. Med. 20:1996;707-727.
8. Cornicelli J.A., Trivedi B.K. 15-Lipoxygenase and its inhibition: a novel therapeutic target for vascular disease. Curr. Pharm. Des. 5:1999;11-20.
9. Cathcart M.K., Folcik V.A. Lipoxygenases and atherosclerosis: protection versus pathogenesis. Free Radic. Biol. Med. 28:2000;1726-1734.
10. Cyrus T., Witztum J.L., Rader D.J., Tangirala R., Fazio S., Linton M.F., Funk C.D. Disruption of the 12/15-lipoxygenase gene diminishes atherosclerosis in apo E-deficient mice. J. Clin. Invest. 103:1999;1597-1604.
11. George J., Afek A., Shaish A., Levkovitz H., Bloom N., Cyrus T., Zhao L., Funk C.D., Sigal E., Harats D. 12/15-Lipoxygenase gene disruption attenuates atherogenesis in LDL receptor-deficient mice. Circulation. 104:2001;1646-1650.
12. da Silva E.L., Tsushida T., Terao J. Inhibition of mammalian 15-lipoxygenase-dependent lipid peroxidation in low-density lipoprotein by quercetin and quercetin monoglycosides. Arch Biochem. Biophys. 349:1998;313-320.
13. da Silva E.L., Abdallah D.S.P., Terao J. Inhibitory effect of flavonoids on low-density lipoprotein peroxidation catalyzed by mammalian 15-lipoxygenase. IUBMB Life. 49:2000;289-295.
14. Upston J.M., Neuzil J., Stocker R.J. Oxidation of LDL by recombinant human 15-lipoxygenase: evidence for alpha-tocopherol-dependent oxidation of esterified core and surface lipids. J. Lipid Res. 37:1996;2650-2661.
15. Belkner J., Stender H., Kühn H. The rabbit 15-lipoxygenase preferentially oxygenates LDL cholesterol esters, and this reaction does not require vitamin E. J. Biol. Chem. 273:1998;23225-23232.
16. Heydeck D., Upston J.M., Viita H., Ylä-Herttuala S., Stocker R. Oxidation of LDL by rabbit and human 15-lipoxygenase: prevalence of nonenzymatic reactions. J. Lipid Res. 42:2001;1082-1088.
17. Robak J., Shridi F., Wolbis M., Krolikowska M. Screening of the influence of flavonoids on lipoxygenase and cyclooxygenase activity, as well as on nonenzymic lipid oxidation. Pol. J. Pharmacol. Pharm. 40:1988;451-458.
18. Brash A.R. Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate. J. Biol. Chem. 274:1999;23679-23682.
19. Belkner J., Wiesner R., Rathman J., Barnett J., Sigal E., Kühn H. Oxygenation of lipoproteins by mammalian lipoxygenases. Eur. J. Biochem. 213:1993;251-261.
20. Sies H., Sharov V.S., Klotz L.O., Briviba K. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. J. Biol. Chem. 272:1997;27812-27817.
21. Ludwig P., Holzhütter H.G., Colosimo A., Silvestrini M.C., Schewe T., Rapoport S.M. A kinetic model for lipoxygenases based on experimental data with the lipoxygenase of reticulocytes. Eur. J. Biochem. 168:1987;325-337.
22. Härtel B., Ludwig P., Schewe T., Rapoport S.M. Self-inactivation by 13-hydroperoxylinoleic acid and lipohydroperoxidase activity of the reticulocyte lipoxygenase. Eur. J. Biochem. 126:1982;353-357.
23. Rice-Evans CA, Miller NJ. Structure-antioxidant activity of flavonoids and isoflavonoids. In: Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker; 1997. p. 199-219.
24. Heijnen C.G.M., Haenen G.R.M.M., Oostveen R.M., Stalpers E.M., Bast A. Protection of flavonoids against lipid peroxidation: the structure activity relationship revisited. Free Radic. Res. 36:2002;575-581.
25. Bors W., Heller W., Michel C., Saran M. Flavonoids as antioxidants: determination of radical-scavenging efficiencies. Methods Enzymol. 186:1990;343-355.
26. van Acker SABE, Bast A, van der Vijgh WJF. Structural aspects of antioxidant activity of flavonoids. In: Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker; 1997. p. 221-51.
27. Weitzel F., Wendel A. Selenoenzymes regulate the activity of 5-lipoxygenase via the peroxide tone. J. Biol. Chem. 268:1993;6288-6292.
28. Schewe T. 15-Lipoxygenase-1: a prooxidant enzyme. Biol. Chem. 383:2002;365-374.
29. Morel I, Cillard P, Cillard J. Flavonoid-metal interactions in biological systems. In: Rice-Evans CA, Packer L, editors. Flavonoids in health and disease. New York: Marcel Dekker; 1997. p. 163-77.
30. Spaapen L.J., Verhagen J., Veldink G.A., Vliegenthart J.F.G. Properties of a complex of Fe(III)-soybean lipoxygenase-1 and 4-nitrocatechol. Biochim. Biophys. Acta. 617:1980;132-140.
31. Schewe C., Klöcking R., Helbig B., Schewe T. Lipoxygenase-inhibitory action of antiviral polymeric oxidation products of polyphenols. Biomed. Biochim. Acta. 50:1991;299-305.
32. Kemal C., Louis-Flamberg P., Krupinski-Olsen R., Shorter A.L. Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Biochemistry. 26:1987;7064-7072.
33. Bertoldi M., Gonsalvi M., Voltattorni C.D. Green tea polyphenols: novel irreversible inhibitors of dopa decarboxylase. Biochem. Biophys. Res. Commun. 284:2001;90-93.
34. Wang X., Tian W. Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase. Biochem. Biophys. Res. Commun. 288:2001;1200-1206.
35. Awad H.M., Boursma M.G., Boeren S., van Bladeren P.J., Vervoort J., Rietjens I.M.C.M. Structure-activity study on the quinone/quinone methide chemistry of flavonoids. Chem. Res. Toxicol. 14:2001;398-408.
36. Bolton J.L., Trush M.A., Penning T.M., Dryhurst G., Monks T.J. Role of quinones in toxicology. Chem. Res. Toxicol. 13:2000;135-160.
37. Galati G., Sabzewari O., Wilson J.X., O'Brien P.J. Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology. 177:2002;91-104.
38. Walther M., Holzhütter H.G., Kuban R.J., Wiesner R., Rathmann J., Kühn H. The inhibition of mammalian 15-lipoxygenases by the anti-inflammatory drug ebselen: dual-type mechanism involving covalent linkage and alteration of the iron ligand sphere. Mol. Pharmacol. 56:1999;196-203.
39. Schnurr K., Kühn H., Rapoport S.M., Schewe T. 3,5-Di-t-butyl-4-hydroxytoluene (BHT) and probucol stimulate selectively the reaction of mammalian 15-lipoxygenase with biomembranes. Biochim. Biophys. Acta. 1254:1995;66-72.
40. Noguchi N., Yamashita H., Hamahara J., Nakamura A., Kühn H., Niki E. The specificity of lipoxygenase-catalyzed lipid peroxidation and the effects of radical-scavenging antioxidants. Biol. Chem. 383:2002;619-626.