Chemoprotective effects of capsaicin and diallyl sulfide against mutagenesis or tumorigenesis by vinyl carbamate and N-nitrosodiinethylamine

Carcinogenesis

Volumn 16, Issue 10, 1995, Pages 2467-2471

  Surh, Young Joon ^a   Lee, Richard Chieh Jei ^a   Park, Kwang Kyun ^a,b   Mayne, Susan Taylor ^a   Liem, Amy ^a,c   Miller, James A ^a,c  

^a YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Yonsei University College of Medicine   (South Korea)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL SULFIDE; CAPSAICIN; CARBAMIC ACID DERIVATIVE; CYTOCHROME P450; DIMETHYLNITROSAMINE; MICROSOME ENZYME; N METHYL DEXTRO ASPARTIC ACID; UNSPECIFIC MONOOXYGENASE; VINYL DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BACTERIAL MUTATION; CARCINOGENESIS; CHEMOPROPHYLAXIS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME INACTIVATION; FEMALE; MOUSE; MUTAGENESIS; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM; SKIN TUMOR; TOPICAL DRUG ADMINISTRATION;

ANIMAL; ANTICARCINOGENIC AGENTS; ANTIMUTAGENIC AGENTS; CAPSAICIN; CARCINOGENS; COMPARATIVE STUDY; CYTOCHROME P-450 ENZYME SYSTEM; DIMETHYLNITROSAMINE; DISULFIRAM; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; MICE; MICE, INBRED ICR; MUTAGENICITY TESTS; MUTAGENS; SALMONELLA TYPHIMURIUM; SKIN NEOPLASMS; SULFIDES; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.; URETHANE;

EID: 0028862921     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/16.10.2467     Document Type: Article

References (46)

1. Block, G., Patterson, B. and Subar, A. (1992) Fruit, vegetables, and cancer prevention: a review of the epidemiological evidence. Nutr. Cancer, 18, 1-29.
2. Stavric, B. (1994) Role of chemopreventers in human diet. Clin. Biochem., 27, 319-332.
3. Ferguson, L.R. (1994) Antimutagens as cancer chemopreventive agents in the diet. Mutat. Res., 307, 395-410.
4. Huang, M.-T., Osawa, T., Ho, C.-T. and Rosen, R.T. (1994) Food Phytochemicals for Cancer Prevention II. Teas, Spices and Herbs ACS Symposium Series no. 547, American Chemical Society, Washington, DC.
5. Unmknshnan, M.C. and Kuttan, R. (1990) Tumor reducing and anticarcinogemc activity of selected spices. Cancer Lett., 51, 85-89.
6. Espinosa-Aguirre, J.J., Reyes, R.E., Rubio, J., Ostrosky-Wegman, P. and Martinez, G. (1993) Mutagenic activity of urban air samples and its modulation by chilli extracts. Mutat. Res., 303, 55-61.
7. Mukhtar, H., Agarwal, R. and Katiyar, S.K. (1995) Inhibition of mouse skin tumor promotion by ethanol extract of ginger root. Proc. Am. Ass. Cancer Res., 36, 594 (abstract no. 3535).
8. Modly, C.E., Das, M., Don, BS. C., Marcelo, C.L., Mukhtar, H. and Bickers D.R. (1986) Capsaicin as an in vitro inhibitor of benzo[a]pyrene metabolism and its DNA binding in human and murine keratinocytes. Drug Metab. Dispos., 14, 413-417.
9. Teel, R.W. (1991) Effects of capsaicin on rat liver S9-mediated metabolism and DNA binding of aflatoxin. Nutr. Cancer, 15, 27-32.
10. Teel, R.W. (1993) Effect of phytochemicals on the mutagenicity of the tobacco-specific nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) in Salmonella tvphimunum strain TA1535. Phytother. Res., 7, 248-251.
11. Zhang, Z., Hamilton, S.M., Stewart, C., Strother, A. and Teel JLW. (1993) Inhibition of liver microsomal cytochrome P450 activity and metabolism of the tobacco-specific nitrosamine NNK by capsaicin and ellagic acid. Anticancer Res., 13, 2341-2346.
12. Surh, Y.-J. and Lee, S.S. (1995) Capsaicin, a double-edged sword: toxicity, metabolism, and chemopreventive potential. Life Sci., 56, 1845-1855.
13. Miller, M.S., Brendel, K., Burks, T.F. and Sipes, I.G. (1983) Interaction of capsaicinoids with drag-metabolizing systems. Biochem. Pharmacol., 32, 547-551.
14. Hamid, M R., Bachmann, E. and Metwally, S.A (1985) Interaction of capsaicin with mixed function oxidases: ex-vivo and in-vivo studies. J. Drug Res. Egypt, 16, 29-36.
15. Surh, Y.-J., Ahn, S.H., Kim, K.-C., Park, J.-B., Sohn, Y.W. and Lee, S.S. (1995) Metabolism of capsaicinoids: evidence for aliphatic hydroxylation and its pharmacological implications. Life Sci., 56, PL305-PL311.
16. Iwama, M., Tojima, T., Iitoi, Y., Takahashi, N. and Kanke, Y. (1990) Effects of capsaicin and ethanol on hepatic drag-metabolizing enzymes in rat. Int. J. Vitam. Nutr. Res., 60, 100-103.
17. Gannett, P.M., Iverscn, P. and Lawson, T. (1990) The mechanism of inhibition of cytochrome P450IIE1 by dihydrocapsaicin. Bioorg. Chem., 18, 185-198.
18. Guengerich, F.P, Kim, D.H. and Iwasaki, M. (1991) Role of human P450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. ToxicoL, 4, 168-179.
19. Koop, D.R. (1992) Oxidative and reductive metabolism by cytochrome P450 2E1. FASEB J., 6, 724-730.
20. Yang, C.S., Yoo, J.-S. H., Ishizaki, H. and Hong, J. (1990) Cytochrome P450IIE1: roles in nitrosamine metabolism and mechanisms of regulation. Drug Metab. Rev., 22, 147-159.
21. Gucngerich, F.R, Shimada, T., Yun, C.-H., Yamazaki, H., Raney, K.D., Their JC, Coles, B. and Harris, T.M. (1994) Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2EI and 3A4 enzymes. Environ. Hlth Perspect., 102 (suppl. 9), 49-53.
22. Brady, J.F., Li, D., Ishizaki, H. and Yang, C.S. (1988) Effect of diallyl sulfide on rat liver microsomal nitrosamine metabolism and other monooxygenase activities. Cancer Res., 48, 5937-5940.
23. Brady, J.F., Ishizaki, H., Fukuto, J.M., Lin, M.C., Fadel, A., Gaped, M. and Yang, C.S. (1991) Modulation of rat hepatic microsomal monooxygenase enzymes and cytotoxicity by diallyl sulfide. Toxicol. Appl. Pharmacol., 108, 342-354.
24. Brady, J.F., Ishizaki, H., Fukuto, J.M., Lin, M.C., Fadel, A., Gape, J.M. and Yang, C.S. (1991) Inhibition of cytochrome P-450 2E1 by diallyl sulfide and its metabolites. Chem. Res. Toxicol., 4, 642-647.
25. Hong, J.-Y, Lin, M.C., Wang, Z.Y., Wang, E.-J. and Yang, C.S. (1994) Inhibition of chemical toxicity and carcinogenesis by diallyl sulfide and diallyl sulfone. In Huang, M.-T., Osawa, T., Ho, C.-T. and Rosen, R.T. (eds), Food Phytochemicals for Cancer Prevention. I. Fruits and Vegetables. ACS Symposium Series no. 546, American Chemical Society, Washington, DC, pp. 97-101.
26. Dahl, G.A., Miller, J.A. and Miller, E.C. (1978) Vinyl carbamate as a promutagen and a more carcinogenic analog of ethyl carbamate. Cancer Res., 38, 3793-3804.
27. Park, K.-K., Surh, Y.-J., Stewart, B.C. and Miller, J.A. (1990) Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate. Biochem, Biophys. Res. Commute, 169, 1094-1098.
28. Kim, S.G., Williams, D.E., Schuetz, E.G., Guzelian J.S. and Novak, R.F. (1988) Pyridine induction of cytochrome P-450 in the rat: role of P450j (alcohol-inducible form) in pyridine N-oxidation. J. Pharmacol. Exp. Ther., 246, 1175-1182.
29. Yoo, J.-S. H., Ishizaki, H. and Yang, C.S. (1990) Roles of cytochrome P450IIE1 in the dealkylation and denitrosation of IV-nitrosodimethylamine and iV-nitrosodiethylamine in rat liver microsomes. Carcinogenesis, 12, 2239-2243.
30. Maron, D.M. and Ames B-N. (1983) Revised methods for the Salmonella mutagenicity test. Mutat. Res., 113, 173-215.
31. Brady, J.F., Xiao, F., Wang, M.-H., Li, Y., Ning, S.M., Gapac, J.M. and Yang, C.S. (1991) Effects of disulfiram on hepatic P450IIE1, other microsomal enzymes, and hepatotoxicity in rats. ToxicoL Appl. Pharmacol., 108, 366-373.
32. Hong, J.-Y., Smith, T., Lee, M.-J., Li, W., Ma B.-L., Ning, S.M., Brady, J.F., Thomas, PE. and Yang, C.-S. (1991) Metabolism of carcinogenic nitrosamines by rat nasal mucosa and the effect of diallyl sulfide. Cancer Res., 51, 1509-1514.
33. Lee, S.S. and Kumar, S. (1980) Metabolism in vitro of capsaicin, a pungent principle of red pepper, with rat liver homogenates. In Coon.MJ., Conney, A.H., Estabrook, R.W., Gelboin, H.V., Gillette J.R. and O’Brien, PJ. (eds), Microsomes, Drug Oxidations and Chemical Carcinogenesis. Academic Press, New York, NY, Vol. 2, pp. 1009-1012.
34. Daly, J.W., Jerina, D.M. and Witkop, B. (1972) Arene oxide and the NIH shift: the metabolism, toxicity and carcinogenicity of aromatic compounds. Experientia, 28, 1129-1264.
35. Lawson, T. and Gannett, P. (1989) The mutagenicity of capsaicin and dihydrocapsaicin in V79 cells. Cancer Lett., 48, 109-113.
36. Park, K.-K., Liern, A., Stewart, B.C. and Miller, J.A. (1993) Vinyl carbamate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Carcinogenesis, 14, 441-450.
37. Guengerich, F.P. and Kim, D.-H. (1991) Enzymatic oxidation of ethyl carbamate and its role as an intermediate in the formation of 1JV6-ethenoadenosine. Chem. Res. ToxicoL, 4, 413-421.
38. Wargovich, M J. (1987) Diallyl sulfide, a flavor component of garlic (Allium sativum), inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis, 8, 487-489.
39. Hayes, M.A., Rushmore, T.H. and Goldberg, M.T. (1987) Inhibition of hepatocarcinogenesis response to 1, 2-dimethylhydrazine by diallyl sulfide, a component of garlic oil. Carcinogenesis, 8, 1155-1157.
40. Wattenberg, L.W., Spamins, V.L. and Barany, G. (1989) Inhibition of N-nitrosodiethylamine carcinogenesis in mice by naturally occurring organosulfur compounds and monoterpenes. Cancer Res., 49, 2689-2692.
41. Wargovich, MJ., Imada, O. and Stephens, L.C (1992) Initiation and postinitiation chemopreventive effects of diallyl sulfide in esophageal carcinogenesis. Cancer Lett., 64, 39-42.
42. Dorant, E., den Brandt, P.A., Goldbohm JLA., Hermus, RJ J. and Sturmans, F. (1993) Garlic and its significance for the prevention of cancer in humans: a critical view. Br. J. Cancer, 67, 424-429.
43. Teel JLW, Zhang, Z. and Hamilton, S.M. (1995) Modulation of cytochrome P450 activity in hepatic and lung microsomes of the hamster following oral administration of capsaicin. Proc. Am. Ass. Cancer Res., 36, 124 (abstract no. 737).
44. Nagabhushan, M. and Bhide, S.V. (1992) Curcumin as an inhibitor of cancer. J. Am. Coll. Nutr., 11, 192-198.
45. Huang, M.-T., Lou, Y.-R., Ma, W., Ncwmark, H.L., Reuhl, K.R. and Conney, A.H, (1994) Inhibitory effects of dietary curcumin on forestomach, duodena], and colon carcinogenesis in mice. Cancer Res., 54, 5841-5847.
46. Rao, C.V., Rivenson, A., Simi, B. and Reddy, B.S. (1995) Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound. Cancer Res., 55, 259-266.