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Antioxidant Properties of Flavone-6(4')-Carboxaldehyde Oxime Ether Derivatives  

Gulgun, Ayhan-Kilcigil (Faculty of Pharmacy, Ankara University)
Coban, Tulay (Department of Pharmaceutical Chemistry, Department of Toxicology)
Tuncbilek, Meral (Faculty of Pharmacy, Ankara University)
Benay, Can-Eke (Department of Pharmaceutical Chemistry, Department of Toxicology)
Oya, Bozda-Dundar (Faculty of Pharmacy, Ankara University)
Ertan, Rahmiye (Faculty of Pharmacy, Ankara University)
Iscan, Mumtaz (Department of Pharmaceutical Chemistry, Department of Toxicology)
Publication Information
Archives of Pharmacal Research / v.27, no.6, 2004 , pp. 610-614 More about this Journal
Abstract
The in vitro antioxidant properties of some flavone-6(4)-carboxaldehyde oxime ether deriva-tives (Ia-f, lIa-f) were determined by their effects on the rat liver microsomal NADPH-dependent lipid peroxidation (LP) levels by measuring the formation of 2-thiobarbituric acid reactive substances. The free radical scavenging properties of the compounds were also examined in vitro by determining their capacity to scavenge superoxide anions and interact with the stable free radical 2, 2-diphenyl-1-picrylhydrazyl (DPPH). The most active compounds, lib (Flavone-4'-carboxaldehyde-O-ethyl oxime) and Id (Flavone-6-carboxaldehyde-O-[2-(1-pyrolidino) ethyl] oxime), caused 98 and 79% inhibition of superoxide anion production and DPPH stable free radical at $10^{-3}{\;}M$, respectively.
Keywords
Flavone; Oxime ether; Lipid peroxidation; Superoxide dismutase; DPPH; Antioxidant;
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1 Cos, P, Li, Y , Mario, C., Hu Jia, P., Cimanga, K., Van Poel, B., Peters, L., Vlietick, A. J., and Vanden, B. D., Structure activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J. Nat. Prod., 61, 71-76 (1998)   DOI   ScienceOn
2 Deschner, E. E., Ruperto, J., Wong, G., and Newmark, H. L., Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis, 12, 1193-1196 (1991)   DOI   ScienceOn
3 Elangovan, V., Sekar, N., and Govindasamy, S., Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene- induced tumorigenesis. Cancer Lett., 87, 107-113 (1994)   DOI   ScienceOn
4 Griffits, H. R., Lunec, J., In Aruoma, O. I., and Halliwell, B., (Eds.), Molecular Biology of Free Radicals in Human Diseases, Oica International, London, pp. 327-366 (1998)
5 Iscan, M., Arinc, E., Vural, N., and Iscan, M. Y., In vivo effects of 3-methylcholantrene, phenobarbital, pyretrum and 2.4.5-T isooctylester on liver, lung and kidney microsomal mixedfunction oxidase system of guinea-pig: a comparative study. Comp. Biochem. physiol., 77C, 177-190 (1984)
6 Krishnaveni, M., Suja, V., Vasanth, S., and Shyamaladevi , C. S., Antiinflammatory and analgesic actions of 4,5,6-trihydroxy3', 7-dimethoxy flavone-from vicoa indica DC. Indian J. Pharmacol 29, 178-181 (1997)
7 Lowry, O. H., Rosenbrough, N. J., Farr, A. L., and Randall, R. J., Protein measurement with the Folin Phenol regent. J. Biol Chem., 193, 265-275 (1951)   PUBMED
8 Tuncbilek, M., Bozdag, O., Ayhan-Kilcigil, G., Altanlar, N., Buyukbingol, E., and Ertan, R., Synthesis and antimicrobial activity of some new flavonyl oxime ether derivatives. Arzneim.-Forsch./Drug Res., 49(11), 853-857 (1999)
9 Wiseman , H., Smith, C., Arnstein, H. R., Halliwell, B., and Cannon, M., The antioxidant action of ketoconazole and related azoles: comparison with tamoxifen and cholesterol. Chem. Biol. lnteract., 79(2), 229-243 (1991)   DOI   ScienceOn
10 Bishayee, S. and Balasubramanian, A. S., Lipid peroxide formation in rat brain. Neurochem., 18, 909-920 (1971)   DOI   PUBMED
11 Chang, W. S., Lee, Y. J., Lu, F. J., and Chiang, H. C., Inhibitory effects of flavonoids on xanthine oxidase. Anticancer Res., 13, 2165-2170 (1993)   PUBMED
12 Blois, M. S., Antioxidant determination by the use of a stable free radical. Nature, 181, 1199-1200(1958)   DOI   ScienceOn
13 Wills, E. D., Lipid peroxide formation in microsomes Relationship of hydroxylation to lipid peroxide formation Biochem. J., 113, 333-341 (1969)   DOI
14 Kornbrust, D. J. and Mavis, R. D., Microsomal lipid peroxidation. II. Stimulation by carbon tetrachloride. Mol. Pharmacol., 17, 408-414 (1980)   PUBMED
15 Nordmann, R., Free radicals, oxidative stress and antioxidant vitamins. C. R. Seances Soc. BioI. Fit., 187(3), 277-285 (1993)   PUBMED
16 Bozdag-Dundar, O., Waheed, A., Verspohl, E. J., and Ertan, R., Synthesis and hypoglycemic activity of some new flavone derivatives. 4th communication: 6-flavonyl-2,4-thiazolidinediones. Arzneim.-Forsch./Drug Res., 51, 623-627 (2001)
17 Rump, A. F., Schussler, M., Acar, D., Cordes, A., Ratke, R., Theisohn , M., Rosen, R., Klaus, W., and Fricke, U., Effects of different inotopes with antioxidant properties on acute regional myocardial ischemia in isolated rabbit hearts, General Pharmacmogy 26, 603-611 (1995)   DOI   PUBMED   ScienceOn
18 Ayhan-Kllclgil, G., Bozdag, O., Tuncbilek, M., Altanlar, N., and Ertan, R., Synthesis and antimicrobial activity of flavone-6-carboxaldehyde oxime ether derivatives. Pharmazie, 54, 228-229 (1999)   PUBMED
19 Litwinienko, G. and lngold, K. U., Abnormal solvent effects on hydrogen atom abstractions. 1. The reactions of phenols with 2,2-diphenyl-1-picrylhydrazyl (dpph) in alcohols. J. Org Chem., 68, 3433-3438 (2003)
20 Parke, D. V., lonnides, C., and Lewis, D. F. V., The role of the cytochrome P450 in the detoxication and activation of drugs and other chemicals. J. Physiol. Pharmacol., 69, 537-549 (1991)   DOI   ScienceOn
21 Dundar, B., Dundar, B. O., Can-Eke, B., Coban, T., Iscan, M., and Bayukbingbil, E., Synthesis and antioxidative properties of novel thiazolidinedione/imidazolidinedione compounds as retinoids. Pharmazie, 57, 438-441 (2002)   PUBMED
22 Olgen, S. and Coban, T., Antioxidant Evaluations of Novel N-H and N-Substituted Indole Esters. Biol. Pharm. Bull., 26, 736-738 (2003)   DOI   ScienceOn
23 Rice-Evans, C. and Diplock, A. T., Techniques in Free Radical Research. p. 291, Elsevier, Amsterdam, 1991
24 Kappus, H. A.,A survey of chemicals inducing lipid peroxidation in biological systems. Chem.phys. Lipids, 45, 105-115 (1987)   DOI   ScienceOn
25 Richardson, S. J., Free radicals in the genesis of Alzheimers disease. Ann.NY Acad. Sci., 695, 73-76 (1993)   DOI   PUBMED   ScienceOn
26 McCord, J. and Fridowich, I., An enzymic function for erythrocuprein (hemocuprein). J. Biol. Chem., 243, 6049-6055 (1969)
27 Wills, E. D., Mechanism of lipid peroxide formation in animal tissues. Biochem. J., 99, 667-676 (1966)   DOI
28 Robak, J., Shridi, F., Wolbis, M., and Krolikowska, M., Screening of the influence of flavonoids on lipoxygenase and cyclooxygenase activity, as well as on nonenzymic lipid peroxidation. Pol. J. Pharmacol. Pharm., 40, 451-458 (1988)   DOI
29 Al-Assadi, H. M., Rodgers, E. H., and Grant, M. H., Antioxidant prevent nickel chloride inhibition of cytochrome P450 dependent mixed function oxidation in guinea pig lung microsomes. Biochem. Soc.Trans., 21(1), 68S (1992)
30 Chang, H. W., Baek, S. H., Chung, K. W., Son, K. H., Kim, H. P., and Kang, S. S., Inactivation of phospholipase A2 by naturally occurring bioflavonoid, ochnaflavone. Biochem. Biophys. Res. Commun., 205, 843-849 (1994)   DOI   ScienceOn
31 Sala, A., Recio, M. C., Schinelle, G. R., Manez, S., Giner, R. M., Cerda-Nicolas, M., and Rios, J. L., Assessment of the antiinflammatory scavenger activity of tiliroside. European J. Pharmacology 461, 53-61 (2003)   DOI   ScienceOn
32 Mori, A., Nishino, C., Enoki,N., and Tawata, S., Antibacterial activity and mode of action of plant flavonoids against proteus vulgaris and staphylococcus aureus. Phytochemistry, 26, 2231-2234 (1987)   DOI   ScienceOn
33 Dix, T. A. and Aikens, J., Mechanism and biological relevance of lipid peroxidation initiation. Chem. Res. Toxicol., 6, 2-18 (1993)   DOI   ScienceOn
34 Iscan, M., A comparative study of the effects of cadmium and nickel on liver microsomal drug metabolizing enzymes of guinea-pig in vitro. Compo Biochem. Physiol., 79C, 429-433 (1984)
35 Wleklik, M., Luczak, M., Panaslak, W., Kobus, M., and Lammer Zarawska, E., Structural basis for antiviral activity of flavonoids naturally occurring compounds. Acta Virol., 32, 522-525 (1988)   PUBMED
36 Amelia, M., Bronner, C., Briancon, F., Haag, M., Anton, R., and Landry, Y, Inhibition of mast cell histamine release by flavonoids and bioflavonoids. Planta Medica, 6-20 (1985)