Inhibition of epidermal xenobiotic metabolism in SENCAR mice by naturally occurring plant phenols

Cancer Research

Volumn 47, Issue 3, 1987, Pages 760-766

  Mukhtar, Hasan ^b   Bik, Daniel P ^a   Bickers, David R ^a  

^a UNIVERSITY HOSPITALS OF CLEVELAND   (United States)

^b LOUIS STOKES CLEVELAND VA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; TANNIN;

ANIMAL EXPERIMENT; CANCER INHIBITION; EPIDERMIS; METABOLIC INHIBITOR; METABOLISM; MOUSE; NONHUMAN; PRIORITY JOURNAL;

7-ALKOXYCOUMARIN O-DEALKYLASE; ANIMAL; ANTHRAQUINONES; ARYL HYDROCARBON HYDROXYLASES; COMPARATIVE STUDY; CYTOCHROME P-450 CYP1A1; FEMALE; FLAVONES; KINETICS; MICE; MICE, INBRED STRAINS; MICROSOMES; OXIDOREDUCTASES; OXYGENASES; PHENOLS; PLANTS; QUERCETIN; SKIN; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TANNIC ACID;

EID: 0023113476     PISSN: 00085472     EISSN: 15387445     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

1. Conney, A. H. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G. H. A. Clowes Memorial Lecture. Cancer Res., 42: 4875-4917, 1982.
2. Gram, T. E. Extrahepatic Metabolism of Drugs and Other Foreign Compounds. Jamaica, NY: Spectrum Publications, 1978.
3. Wilkins, 3. Mannering, G. J. Microsomal enzyme systems which catalyze drug metabolism. In: B. N. LaDu, N. G. Mandel, and E. L. Way (eds.), Fundamentals of Drug Metabolism and Disposition, pp. 206–252. Baltimore: Williams &Wilkins, 1971.
4. Gelboin, H. V. Benzo(a)pyrene metabolism, activation and carcinogenesis: role of regulation of mixed function oxidases and related enzymes. Physiol. Rev., 60: 1107-1166, 1980.
5. Weibel, F. J., Gelboin, H. V., Buu-Hoi, N. P., Stout, M. G., and Burnham, W. S. Flavones and polycyclic aromatic hydrocarbons as modulators of aryl hydrocarbon [benzo(a)pyrene] hydroxylase. In: P. O. P. Ts'o and J. T. Dipaolo (eds.), Chemical Carcinogenesis, pp. 249–270. New York: Marcel Dekker, Inc., 1974.
6. Slaga, T. J., Thompsom, S., and Berry, D. L. The effect of benzoflavones on polycyclic aromatic hydrocarbon metabolism and skin tumor initiation. Chem.-Biol. Interact., 17: 297-312, 1977.
7. Mukhtar, H., DelTito, B. J., Das, M., Cherniack, E. P., Cherniack, A. D., and Bickers, D. R. Clotrimazole, an inhibitor of epidermal benzo(a)pyrene metabolism, DNA-binding and carcinogenicity of the hydrocarbon. Cancer Res., 44: 4233-4240, 1984.
8. Das, M., Bickers, D. R., and Mukhtar, H. Effect of ellagic acid on hepatic and pulmonary xenobiotic metabolism in mice: studies on the mechanism of its anticarcinogenic action. Carcinogenesis (Lond.), 6: 1409-1413, 1985.
9. Mukhtar, H., Das, M., DelTito, B. J., and Bickers, D. R. Protection against 3-methylcholanthrene induced skin tumorigenesis in BALB/c mice by ellagic acid. Biochem. Biophys. Res. Commun., 119: 751-757, 1984.
10. Lesca, P. Protective effects of ellagic acid and other plant phenols on benzo(a)pyrene induced neoplasia in mice. Carcinogenesis (Lond.), 4: 1651-1653, 1983.
11. Chang, R. L., Huang, M. T., Wood, A. W., Wong, C. Q., Newmark, H. L., Yagi, H., Sayer, J. M., Jerina, D. M., and Conney, A. H. Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo(a)pyrene and (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene on mouse skin in the newborn mice. Carcinogenesis (Lond.), 6: 1127-1134, 1985.
12. Dixit, R., Teel, R. T., Daniel, F. B., and Stoner, G. D. Inhibition of benzo(a)pyrene and benzo(a)pyrene-trans-7,8-diol metabolism and DNA binding in mouse lung explants by ellagic acid. Cancer Res., 45: 2951-2956, 1985.
13. Das, M., Bickers, D. R., Santella, R. M., and Mukhtar, H. Altered patterns of cutaneous xenobiotic metabolism in ultraviolet-B induced squamous cell carcinoma in SKH-1 hairless mice. J. Invest. Dermatol., 84: 532-536, 1985.
14. Nebert, D. W., and Gelboin, H. V. Substrate-inducible microsomal aryl hydrocarbon hydroxylase in mammalian cell culture. I. Assay and properties of induced enzyme. J. Biol. Chem., 243: 6242-6249, 1968.
15. Greenlee, W. F., and Poland, A. 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-doxin. J. Pharmacol. Exp. Ther., 205: 596–605, 1978.
16. Pohl, R. J., and Fouts, J. R. A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal. Biochem., 107: 150-155, 1980.
17. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. Protein measurement with Folin phenol reagent. J. Biol. Chem., 193: 265-275, 1951.
18. Grisebach, H. Selected topics in flavonoid biosynthesis. In: T. Swain, J. B. Harborne, and C. F. Van Sumere (eds.), Recent Advances in Photochemistry, Vol. 12, pp. 221–248. New York: Plenum Publishing Corp., 1979.
19. Harborne, J. B. Flavonoids and the evolution of the angiosperms. Biochem. Syst. Ecol., 5: 7-12, 1977.
20. Wattenberg, L. W. Inhibition of neoplasia by minor dietary constituents. Cancer Res. (Suppl.), 43: 2448s-2453s, 1983.
21. Lasker, J. M., Huang, M. T., and Conney, A. H. In vitro and in vivo activation of oxidative drug metabolism by flavonoids. J. Pharmacol. Exp. Ther., 229: 162-170, 1984.
22. Sousa, R. L., and Marietta, M. A. Inhibition of cytochrome P-450 activity in rat liver microsomes by the naturally occurring flavonoid, quercetin. Arch. Biochem. Biophys., 240: 345-357, 1985.
23. Buening, M. K., Chang, R. L., Huang, M. T., Fortner, J. G., Wood, A. W., and Conney, A. H. Activation and inhibition of benzo(a)pyrene and aflatoxin B1metabolism in human liver microsomes by naturally occurring flavonoids. Cancer Res., 41: 67-72, 1981.
24. Huang, M. T., Chang, R. L., Fortner, J. G., and Conney, A. H. Studies on the mechanism of activation of microsomal benzo(a)pyrene hydroxylation by flavonoids. J. Biol. Chem., 256: 6829-6836, 1981.
25. Huang, M. T., Johnson, E. F., Mueller-Eberhardt, U., Koop, D. R., Coon, M. J., and Conney, A. H. Specificity in the activation and inhibition by flavonoids of benzo(a)pyrene hydroxylation by cytochrome P-450 isozymes from rabbit liver microsomes. J. Biol. Chem., 256: 10897-10901, 1981.
26. Bickers, D. R., Das, M., Steele, J. D., and Mukhtar, H. Multiplicity of epidermal cytochrome P-450: HPLC separation of solubilized microsomes in neonatal Sprague-Dawley rats. J. Invest. Dermatol., 87: 130, 1986.
27. Huang, M. T., Wood, A. W., Newmark, H. L., Sayer, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. Inhibition of the mutagenicity of bay-region diolepoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids. Carcinogenesis (Lond.) 4: 1631-1637, 1983.
28. Huang, M. T., Chang, R. L., Wood, A. W., Newmark, H. L., Sayer, J. M., Yagi, H., Jerina, D. M., and Conney, A. H. Inhibition of mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by tannic acid, hydroxylated anthraquinones and hydroxylated cinnamic acid derivatives. Carcinogenesis (Lond.), 6: 237-242, 1985.
29. Wood, A. W., Huang, M. T., Chang, R. L., Newmark, H. L., Lehr, R. E., Yagi, H., Sayer, J. M., Jerina, D. W., and Conney, A. H. Inhibition of mutagenicity of bay region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid. Proc. Natl. Acad. Sci. USA, 79: 5513-5517, 1982.
30. Sayer, J. M., Yagi, H., Wood, A. W., Conney, A. H., and Jerina, D. W. Extremely facile reaction between ultimate carcinogen benzo(a)pyrene-7,8-diol-9,10-epoxide and ellagic acid. J. Am. Chem. Soc., 104: 5562–5564, 1982.
31. Lesca, P., Lecointe, P., Paoletti, C., and Mansuy, D. Ellipticines as potent inhibitors of microsome dependent chemical mutagenesis. Chem.-Biol. Interact., 25: 279-287, 1979.
32. Lesca, P., and Mansuy, D. 9-Hydroxyellipticine: inhibitory effect on skin carcinogenesis induced in Swiss mice by 7,12-dimethylbenz(a)anthracene. Chem.-Biol. Interact., 30: 181-187, 1980.
33. Lesca, P., Lecointe, P., Paoletti, C., and Mansuy, D. Ellipticines as potent iinhibitors of aryl hydrocarbon hydroxylase: their binding to microsomal cytochrome P-450 and protective effect against benzo(a)pyrene mutagenicity. Biochem. Pharmacol., 27: 1203-1209, 1978.
34. Lesca, P., Lecointe, P., Paoletti, C., and Mansuy, D. The hydroxylation of the antitumor agent, ellipticine, by liver microsomes from differently pretreated rats. Biochem. Pharmacol., 26: 2169-2173, 1977.
35. Brown, J. P. A review of the genetic effects of naturally occurring flavonoids, anthraquinolines and related compounds. Mutat Res., 75: 243–277, 1980.
36. Saito, D., Shirai, A., Matsushima, T., Sugimura, T., and Hirono, I. Test of carcinogenicity of quercetine, a widely distributed mutagen in food. Teratog. Carcinog. Mutagen. 1: 213-221, 1980.
37. Gogler, R., Leschik, M., and Dengler, J. J. Disposition of quercetin in man after single and intravenous doses. Eur. J. Clin. Pharmacol., 9: 229–234, 1975.
38. Carson, R. S., and Frisch, A. W. The inactivation of influenza virus by tannic acid and related compounds. J. Bacteriol., 66: 572-575, 1953.
39. Konishi, E., and Hotta, S. Effects of tannic acid and its related compounds upon chikungunya virus. Microbiol. Immunol., 23: 609-667, 1979.
40. Okonogi, T., Hattoriz, Z., Ogiso, A., and Mitsui, S. Detoxification by persimmon tannin of snake venoms and bacterial toxins. Toxicon, 17: 524–527, 1979.
41. Jacobs, M. H., Stewart, D. R., and Butler, M. K. Some effects of tannic acid on the cell surface. Am. J. Med. Sci., 205: 154-157, 1943.
42. Hunter, F. R. The effect of tannic acid on the permeability of erythrocytes to nonelectrolytes. J. Cell. Comp. Physiol., 55: 175-188, 1960.
43. Oler, A., Neal, M. W., and Mitchell, E. K. Tannic acid: acute hepatotoxicity following administration by feeding tube. Food Cosmet. Toxicol., 4: 565-569,1976.
44. Hall, C. B. Inhibition of tannats pectinesterase by tannic acid. Nature (Lond.), 212: 717-718, 1966.