Activation and inhibition of benzo(a)pyrene and aflatoxin b1 metabolism in human liver microsomes by naturally occurring flavonoids

Cancer Research

Volumn 41, Issue 1, 1981, Pages 67-72

  Buening, Mildred K ^a   Fortner, Joseph G ^b   Chang, Richard L ^c   Huang, Mou Tuan ^c   Wood, Alexander W ^c   Conney, Allan H ^c  

^a ELI LILLY AND COMPANY   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4' BROMOFLAVONE; AFLATOXIN B1; ALPHA NAPHTHOFLAVONE; APIGENIN; BENZO[A]PYRENE; BENZOFLAVONE; CHRYSIN; FISETIN; FLAVANONE; FLAVONE; FLAVONOID; GALANGIN; HESPERETIN; KAEMPFEROL; MORIN; MYRICETIN; NARINGENIN; NOBILETIN; QUERCETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE; TANGERETIN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; DRUG COMPARISON; DRUG INTERACTION; HUMAN CELL; IN VITRO STUDY; LIVER; LIVER MICROSOME; LIVER MICROSOME METABOLISM; NORMAL HUMAN; PHARMACOKINETICS; PRELIMINARY COMMUNICATION;

AFLATOXINS; BENZOPYRENE HYDROXYLASE; BENZOPYRENES; FLAVONOIDS; HUMANS; MICROSOMES, LIVER; NADH DEHYDROGENASE;

EID: 0019364430     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Anders, M. W. Acetone enhancement of microsomal aniline parahydroxylase activity. Arch. Biochem. Biophys., 126: 269–275, 1968.
2. Buening, M. K., Fortner, J. G., Kappas, A., and Conney, A. H. 7,8-Benzofla-vone stimulates the metabolic activation of aflatoxin B, to mutagens by human liver. Biochem. Biophys. Res. Commun., 82: 348–355, 1978.
3. Conney, A. H., Pantuck, E. J., Pantuck, C. B., Buening, M., Jerina, D. M., Fortner, J. G., Alvares, A. P., Anderson, K. E., and Kappas, A. Role of environment and diet in the regulation of human drug metabolism. In: R. W. Estabrook and E. Lindenlaub (eds.), The Induction of Drug Metabolism. Symposia Medica Hoechst, F. K. Schattauer Verlag: Stuttgart-New York Vol. 14, pp. 583–605. 1979.
4. Essigmann, J. M., Croy, R. G., Nadzan, A. M., Busby, W. F., Jr., Reinhold, V. N., Büchi, G., and Wogan, G. N. Structural identification of the major DNA adduct formed by aflatoxin B, in vitro. Proc. Natl. Acad. Sci. U. S. A., 74: 1870–1874, 1977.
5. Harborne, J. B. Flavonoids. In: L. P. Miller (ed.), Phytochemistry, Vol. 2, pp. 344–380. New York: Van Nostrand Reinhold Company, 1973.
6. Harborne, J. B., Mabry, T. J., and Mabry, H. (eds.). The Flavonoids, pp. 377, 1011–1014, 1033–1036. New York: Academic Press, Inc., 1975.
7. Huang, M.-T., Chang, R. L., and Conney, A. H. Studies on the mechanism of activation of microsomal benzo(a)pyrene hydroxylase activity by 7,8-benzoflavone (BF). Fed. Proc., 39: 2053, 1980.
8. Imai, Y., and Sato, R. Activation and inhibition of microsomal hydroxylation by ethyl isocyanide. Biochem. Biophys. Res. Common., 25: 80–86, 1966.
9. Kapitulnik, J., Poppers, P. J., Buening, M. K., Fortner, J. G., and Conney, A. H. Activation of monooxygenases in human liver by 7,8-benzoflavone. Clin. Pharmacol. Ther., 22: 475–484, 1977.
10. Leibman, K. C. Effects of metyrapone on liver microsomal drug oxidations. Mol. Pharmacol., 5: 1–9, 1969.
11. Lin, J.-K., Kennan, K. A., Miller, E. C., and Miller, J. A. Reduced nicotinamide adenine dinucleotide phosphate-dependent formation of 2,3-dihydro-2,3-dihydroxyaflatoxin B, from afiatoxin B, by hepatic microsomes. Cancer Res., 38: 2424–2428, 1978.
12. Lin, J.-K., Miller, J. A., and Miller, E. C. 2,3-Dihydro-2-(guan7-yl)-3-hydroxy-aflatoxin B1, a major acid hydrolysis product of aflatoxin B1-DNA or ribo-somal-RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in vivo. Cancer Res., 37: 4430–4438, 1977.
13. Lu, A. Y. H., Levin, W., and Kuntzman, R. Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds and endogenous substrates. VII. Stimulation of benzphetamine N-demethyiation by lipid and detergent. Biochem. Biophys. Res. Commun., 60: 266–272, 1974.
14. McPherson, F. J., Bridges, J. W., and Parke, D. V. Studies on the nature of the in vitro enhancement of biphenyl 2-hydroxylation provoked by some chemical carcinogens. Biochem. Pharmacol., 25: 1345–1350, 1976.
15. Nebert, D. W., and Gelboin, H. V. Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme. J. Biol. Chem., 243: 6242–6249, 1968.
16. Pelkonen, O. Differential inhibition of aryl hydrocarbon hydroxylase in human foetal liver, adrenal gland and placenta. Acta Pharmacol. Toxicol., 41: 306–316, 1977.
17. Phillips. A. H., and Langdon, R. G. Hepatic triphosphopyridine nucleotide-cytochrome c reductase: Isolation, characterization, and kinetic studies. J. Biol. Chem., 237: 2652–2660, 1962.
18. Sloane, N. H. α-Naphthoflavone activation of 6-hydroxymethylbenzo- (α)pyrene synthetase. Cancer Res., 35: 3731–3734, 1975.
19. Stohs, S. J., Grafstrom, R. C., Burke, M. D., Moldeus, P. W., and Orrenius, S. G. The isolation of rat intestinal microsomes with stable cytochrome P-450 and their metabolism of benzo(a)pyrene. Arch. Biochem. Biophys., 177: 105–116, 1976.
20. Swenson, D. H., Lin, J.-K., Miller, E. C., and Miller, J. A. Aflatoxin B1-2,3-oxide as a probable intermediate in the covalent binding of aflatoxins B, and B2 to rat liver DNA and ribosomal RNA in vivo. Cancer Res., 37: 172–181, 1977.
21. Swenson, D. H., Miller, E. C., and Miller, J. A. Aflatoxin B1-2,3-oxide: Evidence for its formation in rat liver in vivo and by human liver microsomes in vitro. Biochem. Biophys. Res. Commun., 60: 1036–1043, 1974.
22. Swenson, D. H., Miller, J. A., and Miller, E. C. 2,3-Dihydro-2,3-dihydroxy-aflatoxin B1: an acid hydrolysis product of an RNA-aflatoxin B1 adduct formed by hamster and rat liver microsomes in vitro. Biochem. Biophys. Res. Commun., 53: 1260–1267, 1973.
23. Thorgeirsson, S. S., Atlas, S. A., Boobis, A. R., and Felton, J. S. Species differences in the substrate specificity of hepatic cytochrome P-448 from polycyclic hydrocarbon-treated animals. Biochem. Pharmacol., 28: 217–226, 1979.
24. Tredger, J. M., McPherson, F. J., Chakraborty, J., Bridges, J. W., and Parke, D. V. The effect of some glucocorticoids on hepatic microsomal hydroxylation in the rat and hamster. Naunyn-Schmiedebergs Arch. Pharmacol., 292: 267–270, 1976.
25. Van Cantfort, J., De Graeve, J., and Gielen, J. E. Radioactive assay for aryl hydrocarbon hydroxylase. Improved method and biological importance. Biochem. Biophys. Res. Commun., 79: 505–512, 1977.
26. Weibel, F. J., Gelboin, H. V., Bou-Hoi, N. P., Stout, M. G., and Burnham, W. S. Flavones and polycyclic hydrocarbons as modulators of aryl hydrocarbon (benzo(a)pyrene] hydroxylase. In: P. O. P. Ts’o and J. A. Di Paolo (eds.), Chemical Carcinogenesis, pp. 249–270. New York: Marcel Dekker Inc., 1974.
27. Wiebel, F. J., Leutz, J. C., Diamond, L., and Gelboin, H. V. Aryl hydrocarbon (benzo(a)pyrene) hydroxylase in microsomes from rat tissues: differential inhibition and stimulation by benzoflavones and organic solvents. Arch. Biochem. Biophys., 144: 78–86, 1971.