Inhibition of 7-ethoxycoumarin O-deethylase activity in rat liver microsomes by naturally occurring flavonoids: Structure-activity relationships

Xenobiotica

Volumn 28, Issue 2, 1998, Pages 117-125

  Moon, Ja Young ^a   Lee, Dong Wook ^a   Park, Ki Hyun ^a  

^a Korea Ginseng Corporation   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLCHOLANTHRENE; 7 ETHOXYCOUMARIN DEETHYLASE; APIGENIN; CATECHIN; CHRYSIN; FISETIN; FLAVANONE; FLAVONE; FLAVONOID; FLAVONOL; GALANGIN; HESPERETIN; HYDROXYL GROUP; KAEMPFEROL; MORIN; MYRICETIN; NARINGENIN; QUERCETIN;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; ENZYME ACTIVE SITE; ENZYME INHIBITION; LIVER MICROSOME; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 0031913738     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982598239623     Document Type: Article

References (39)

1. ALLDRICK, A. J., LAKE, B. G. and ROWLAND, I. R., 1989, Modification of in vivo heterocyclic amine genotoxicity by dietary flavonoids. Mutagenesis, 4, 365-370.
2. BEVELER, S., TESTA, B. and PERRISSOUD, D., 1988, Flavonoids as inhibitors of rat liver monooxygenase activities. Biochemical Pharmacology, 37, 1971-1979.
3. BIRT, D. F., WALKER, B., TIBBELS, M. G. and BRESNICK, E., 1986, Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol. Carcinogenesis, 7, 959-963.
4. BUENING, M. K., CHANG, R. L., HUANG, M. T., FORTNER, J. G., WOOD, A. W. and CONNY, A. H., 1981, Activation and inhibition of benzo(a)pyrene and aflatoxin B1 metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Research, 41, 67-72.
5. CHAE, Y. H., MARCUS, C. B., HO, D. K., CASSADY, J. M. and BAIRD, W. M., 1991, Effects of synthetic and naturally occurring flavonoids on benzo[a]pyrene metabolism by hepatic microsomes prepared from rats treated with cytochrome P-450 inducers. Cancer Letters, 60, 15-24.
6. COTELLE, N., BERNIER, J.-L., CATTEAU, J.-P., POMMERY, J., WALLET, J.-C. and GAYDOU, E. M., 1996, Antioxidant properties of hydroxy-flavones. Free Radical Biology and Medicine, 20, 35-43.
7. DAS, N. P. and RATTY, A. K., 1986, Effects of flavonoids on induced nonenzymatic lipid peroxidation. Plant Flavonoids in Biology and Medicine, edited by V. Cody, E. Middleton Jr and J. B. Harborne (New York: Alan R. Liss), pp. 243-247.
8. DIGIOVANNI, J., 1990, Chemical Carcinogenesis and Mutagenesis, edited by C. S. Cooper and P. L. Grover (Berlin: Springer), pp. 159-253.
9. ELLIOTT, A. J., SCHEIBER, S. A., THOMAS, C. and PARDINI, R. S., 1992, Inhibition of glutathione reductase by flavonoids. A structure-activity study. Biochemical Pharmacology, 44, 1603-1608.
10. FERRIOLA, P. C., CODY, V. and MIDDLETON, E. JR, 1989, Protein kinase C inhibition by plant flavonoids: kinetic mechanisms and structure-activity relationships. Biochemical Pharmacology, 38, 1617-1624.
11. GIGON, P. L., GRAM, T. E. and GILLETTE, J. R., 1969, Studies on the rate of reduction of hepatic microsomal cytochrome P-450 by reduced nicotinamide adenine dinucleotide phosphate: effect of drug substrates. Molecular Pharmacology, 5, 109-122.
12. GLUSKER, J. P. and ROSSI, M., 1986, Molecular aspects of chemical carcinogens and bioflavonoids. In Plant Flavonoids in Biology and Medicine: Biochemical, Pharmacological and Structure-Activity Relationships, edited by V. Cody, E. Middleton Jr and J. B. Harborne (New York: Alan R. Liss), pp. 395-410.
13. GREENLEE, W. F. and POLAND, A., 1978, An improved assay of 7-ethoxycoumarin O-deethylase activity: induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of Pharmacology and Experimental Therapeutics, 205, 596-605.
14. HAUGEN, D. A., COON, M. J. and NEBERT, D. W., 1976, Induction of multiple forms of mouse liver cytochrome P-450. Evidence for genetically controlled de novo protein synthesis in response to treatment with beta-naphthoflavone of phenobarbital. Journal of Biological Chemistry, 251, 1817-1827.
15. HAVSTEEN, B., 1983, Flavonoids, a class of natural products of high pharmacological potency. Biochemical Pharmacology, 32, 1141-1148.
16. +-ATPase: aspects of the structure-activity relationship and action mechanism. Life Sciences, 45, 1111-1117.
17. HUANG, M. T., CHANG, R. L., FORTNER, J. G. and CONNEY, A. H., 1981, Studies on the mechanism of activation of microsomal benzo[a]pyrene hydroxylation by flavonoids. Journal of Biological Chemistry, 256, 6829-6836.
18. JOVANOVIC, S. V., STEENKEN, S., TOSIC, M., MARJANOVIC, B. and SIMIC, M. G., 1994, Flavonoids as antioxidants. Journal of the American Chemical Society, 116, 4846-4851.
19. KIM, S. Y., LEE, D. W. and PARK, K. H., 1990, Characterization of flavone-inducible cytochrome P-450 from rat liver. Korean Biochemical Journal, 23, 520-527.
20. LASKER, J. M., HUANG, M. T. and CONNEY, A. H., 1984, In vitro and in vivo activation of oxidative drug metabolism by flavonoids. Journal of Pharmacology and Experimental Therapeutics, 229, 162-170.
21. LEE, H., WANG, H.-W., SU, H.-Y. and HAO, N. J., 1994, The structure-activity relationships of flavonoids as inhibitors of cytochrome P-450 enzymes in rat liver microsomes and the mutagenicity of 2-amino-3-methyl-imidazol[4,5-f]quinoline. Mutagenesis, 9, 101-106.
22. LOWRY, O. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J., 1951, Protein measurement with the folin phenol reagent. Journal of Biological Chemistry, 193, 265-275.
23. MOON, J. Y., LEE, Y. H. and PARK, K. H., 1986, Differential inhibition of liver microsomal cytochrome P-450-dependent monooxygenases by hesperetin. Korean Biochemical Journal, 19, 315-323.
24. NEBERT, D. W. and GELBOIN, H. V., 1968, Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. Journal of Biological Chemistry, 243, 6242-6249.
25. OMURA, T. and SATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry, 239, 2370-2378.
26. PAOLINI, M., SAPIGNI, E., HRELIA, P., SCOTTI, M., MOROTTI, M. and CANTELLI-FORTI, G., 1991, Wide spectrum detection of precarcinogens in short-term bioassays by simultaneous superinduction of multiple forms of cytochrome P-450 isoenzymes. Carcinogenesis, 12, 759-766.
27. PARK, S. S., FUJINO, T., MILLER, H., GUENGERICH, K. P. and GELBOIN, H. V., 1984, Monoclonal antibodies to phenobarbital-induced rat liver cytochrome P-450. Biochemical Pharmacology, 33, 2071-2081.
28. PARK, K. H. and KIM, C. Y., 1984, Induction of the different forms of cytochrome P-450 isozymes and comparison of aryl hydrocarbon hydroxylase levels on rat tissues by chemical treatment. Korean Biochemical Journal, 17, 10-19.
29. RATTY, A. K. and DAS, N. P., 1988, Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship. Biochemical Medicine and Metabolic Biology, 29, 69-79.
30. RATTY, A. K., SUNAMOTO, J. and DAS, N. P., 1988, Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochemical Pharmacology, 37, 989-995.
31. SIESS, M. H., GUILLERMIC, M., LE BON, A. M. and SUSCHETET, M., 1989, Induction of monooxygenase and transferase activities in rat by dietary administration of flavonoids. Xenobiotica, 19, 1379-1386.
32. SIESS, M. H., LECLERC, J., CANTIVENO-LAVIER, M. C., RAT, P. and SUSCHETET, M., 1995, Heterogenous effects of natural flavonoids on monooxygenase activities in human and rat liver microsomes. Toxicology and Applied Pharmacology, 130, 73-78.
33. SOUSA, R. L. and MARLETTA, M. A., 1985, Inhibition of cytochrome P-450 activity in rat liver microsomes by the naturally occurring flavonoid, quercetin. Archives of Biochemistry and Biophysics, 240, 345-357.
34. THOMAS, P. E., LU, A. Y. H., RYAN, D., WEST, S. B., KAWAREK, J. and LEVIN, W., 1976, Multiple forms of rat liver cytochrome P-450. Immunochemical evidence with antibody against cytochrome P-448. Journal of Biological Chemistry, 251, 1385-1391.
35. TSYRLOV, I. B., MIKHAILENKO, V. M. and GELBOIN, H. V., 1994, Isozyme-and species-specific susceptibility of cDNA-expressed CYP1A P-450s to different flavonoids. Biochemica et Biophysica Acta, 1205, 325-335.
36. VERNET, A. and SIESS, M. H., 1986, Comparison of the effects of various flavonoids on ethoxycoumarin deethylase activity of rat intestinal and hepatic microsomes. Food and Chemical Toxicology, 24, 857-861.
37. WAXMAN, D. J., KO, A. and WALSH, C., 1983, Regioselectivity and stereoselectivity of androgen hydroxylations catalyzed by cytochrome P-450 isozymes purified from phenobarbital-induced rat liver. Journal of Biological Chemistry, 258, 11937-11947.
38. WERRINGLOER, J. and ESTABROOK, R. W., 1975, Heterogeneity of liver microsomal cytochrome P-450: the spectral characterization of reactants with reduced cytochrome P-450. Archives of Biochemistry and Biophysics, 167, 270-286.
39. WIEBEL, F. J., GELBOIN, H. V., BUU-HOI, N. P., STOUT, M. G. and BURNHAM, W. S., 1974, Flavones and polycyclic hydrocarbons as modulators of aryl hydrocarbon [benzo(a)pyrene] hydroxylase. In Chemical Carcinogenesis, edited by P.O.P. Ts'O and J. A. Di Paolo (New York: Marcel Dekker Inc.), pp. 249-270.