DOI QR코드

DOI QR Code

Protective Effects of Diallyl Sulfide against Thioacetamide-Induced Toxicity: A Possible Role of Cytochrome P450 2E1

  • Received : 2014.02.07
  • Accepted : 2014.03.06
  • Published : 2014.03.31

Abstract

Effects of diallyl sulfide (DAS) on thioacetamide-induced hepatotoxicity and immunotoxicity were investigated. When male Sprague-Dawley rats were treated orally with 100, 200 and 400 mg/kg of DAS in corn oil for three consecutive days, the activity of cytochrome P450 (CYP) 2E1-selective p-nitrophenol hydroxylase was dose-dependently suppressed. In addition, the activities of CYP 2B-selective benzyloxyresorufin O-debenzylase and pentoxyresorufin O-depentylase were significantly induced by the treatment with DAS. Western immunoblotting analyses also indicated the suppression of CYP 2E1 protein and/or the induction of CYP 2B protein by DAS. To investigate a possible role of metabolic activation by CYP enzymes in thioacetamide-induced hepatotoxicity, rats were pre-treated with 400 mg/kg of DAS for 3 days, followed by a single intraperitoneal treatment with 100 and 200 mg/kg of thioacetamide in saline for 24 hr. The activities of serum alanine aminotransferase and aspartate aminotransferase significantly elevated by thioacetamide were protected in DAS-pretreated animals. Likewise, the suppressed antibody response to sheep erythrocytes by thioacetamide was protected by DAS pretreatment in female BALB/c mice. Taken together, our present results indicated that thioacetamide might be activated to its toxic metabolite(s) by CYP 2E1, not by CYP 2B, in rats and mice.

Keywords

References

  1. Amagase, H., Petesch, B. L., Matsuura, H., Kasuga, S. and Itakura, Y. (2001) Intake of garlic and its bioactive components. J. Nutr. 131, 955S-962S. https://doi.org/10.1093/jn/131.3.955S
  2. Belman, S. (1983) Onion and garlic oils inhibit tumor promotion. Carcinogenesis 4, 1063-1065. https://doi.org/10.1093/carcin/4.8.1063
  3. Blank, J. A., Sweatlock, J., Gasiewicz, T. A. and Luster, M. I. (1987) ${\alpha}$-Naphtoflavone antagonism of 2,3,7,8-tetrachlorodibenzo-p-dioxin induced murine lymphocyte ethoxyresorufin O-deethylase activity and immunosuppression. Mol. Pharmacol. 32, 169-172.
  4. Brady, J. F., Ishizaki, H., Fukuto, J. M., Lin, M. C., Fadel, A., Gapac, J. M. and Yang, C. S. (1991a) Inhibition of cytochrome P450 2E1 by diallyl sulfide and its metabolites. Chem. Res. Toxicol., 4, 642-647. https://doi.org/10.1021/tx00024a008
  5. Brady, J. F., Wang, M. H., Gong, J. Y., Xiao, F., Li, Y., Yoo, J. S., Ning, S. M., Lee, M. J., Fukuto, J. M. and Gapac, J. M., et al. (1991b) Modulation of rat hepatic microsomal monooxygenase enzymes and cytotoxicity by diallyl sulfide. Toxicol. Appl. Pharmacol. 108, 342-354. https://doi.org/10.1016/0041-008X(91)90123-V
  6. Buiatti, E. D., Decarli, A., Amadori, D., Avellini, C., Bianchi, S., Biserni, R., Cipriani, F., Cocco, P. and Giacosa, A., et al. (1989) A casecontrol study of gastric cancer and diet in Italy. Int. J. Cancer 44, 611-616. https://doi.org/10.1002/ijc.2910440409
  7. Chen, G. W., Chung, J. G., Hisieh, C. L. and Lin, J. G. (1998) Effects of the garlic components diallyl sulfide and diallyl disulfide on arylamine N-acetyltransferase activity in human colon tumor cells. Food Chem. Toxicol. 36, 761-770. https://doi.org/10.1016/S0278-6915(98)00046-5
  8. Chieli, E. and Malvaldi, G.. (1984) Role of the microsomal FAD-containing monooxygenase in the liver toxicity of thioacetamide S-oxide. Toxicology 31, 41-52. https://doi.org/10.1016/0300-483X(84)90154-9
  9. Davenport, D. M. and Wargovich M. J. (2005) Modulation of cytochrome P450 enzymes by organosulfur compounds from garlic. Food Chem. Toxicol. 43, 1753-1762. https://doi.org/10.1016/j.fct.2005.05.018
  10. Dyroff, M. C. and Neal, R. A., (1981) Identification of the major protein adduct formed in rat liver after thioacetamide administration. Cancer Res. 41, 3430-3435.
  11. Guengerich, F. P. and Shimada, T. (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P450 enzymes. Chem. Res. Toxicol. 4, 391-407. https://doi.org/10.1021/tx00022a001
  12. Haber, D., Siess, M. -H., de Waziers, I., Beaune, P. and Suschetet, M. (1994) Modification of hepatic drug-metabolizing enzymes in rat fed naturally occurring allyl sulphides. Xenobiotica 24, 169-182. https://doi.org/10.3109/00498259409043230
  13. Hajovsky, H., Hu, G., Koen, Y., Sarma, D., Cui, W., Moore, D. S., Staudinger, J. L. and Hanzlik, R. P. (2012) Metabolism and toxicity of thioacetamide and thioacetamide S-oxide in rat hepatocytes. Chem. Res. Toxicol. 25, 1955-1963. https://doi.org/10.1021/tx3002719
  14. Holsapple, M. P., Eads, M., Stevens, W. D., Wood, S. C., Kaminski, N. E., Morris, D. L., Poklis, A., Kaminski, E. J. and Jordan, S. D. (1993) Immunosuppression in adult B6C3F1 mice by chronic exposure to ethanol in a liquid diet. Immunopharmacology 26, 31-51. https://doi.org/10.1016/0162-3109(93)90064-W
  15. Hong, J. Y., Wang, Z. Y., Smith, T. J., Zhou, S., Shi, S., Pan, J. and Yang, C. S. (1992) Inhibition effects of diallyl sulfide on the metabolism and tumorigenicity of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in A/J mouse lung. Carcinogenesis 13, 901-904. https://doi.org/10.1093/carcin/13.5.901
  16. Hunter, A. L., Holscher, M. A. and Neal, R. A. (1977) Thioacetamideinduced hepatic necrosis. I. Involvement of the mixed-function oxidase enzyme system. J. Pharmacol. Exp. Ther. 200, 439-448.
  17. Hussain, S. P., Jannu, L. N. and Rao, A. R. (1990) Chemopreventive action of garlic on methylcholanthrene-induced carcinogenesis in the uterine cervix of mice. Cancer Lett. 49, 175-180. https://doi.org/10.1016/0304-3835(90)90155-Q
  18. Jeong, T. C., Kim, H. J., Yun, C. H., Lee, S. S., Yang, K. H., Han, S. S. and Roh, J. K. (1995) Induction of liver cytochrome P450 2B1 by ${\beta}$-ionone in Sprague Dawley rats. Biochem. Biophys. Res. Commun. 216, 198-202. https://doi.org/10.1006/bbrc.1995.2610
  19. Kaminski, N. E., Barnes, D. W., Jordan, S. D. and Holsapple, M. P. (1990) The role of metabolism in carbon tetrachloride-mediated immunosuppression: In vivo studies. Toxicol. Appl. Pharmacol. 102, 9-20. https://doi.org/10.1016/0041-008X(90)90079-A
  20. Kim, N. H., Hyun, S. H., Jin, C. H., Lee, S. K., Lee, D. W., Jeon, T. W., Lee, J. S., Chun, Y. J., Lee, E. S. and Jeong, T. C. (2004) Pretreatment with 1,8-cineole potentiates thioacetamide-induced hepatotoxicity and immunosuppression. Arch. Pharm. Res. 27, 781-789. https://doi.org/10.1007/BF02980149
  21. Koop, D. R. (1986) Hydroxylation of p-nitrophenol by rabbit ethanolinducible cytochrome P-450 isozyme 3a. Mol. Pharmacol. 29, 399-404.
  22. Lee, S. K., Kim, N. H., Lee, J., Kim, D. H., Lee, E. S., Choi, H. G., Chang, H. W., Jahng, Y. and Jeong, T. C. (2004) Induction of cytochrome P450s by rutaecarpine and metabolism of rutaecarpine by cytochrome P450s. Planta Med. 70, 753-757. https://doi.org/10.1055/s-2004-827207
  23. Lowry, O. H., Rosenbrough, N. J., Farr, A. L. and Randall, R. J. (1951) Protein measurement with the folin phenol reagent. J. Biol. Chem. 193, 265-275.
  24. Lubet, R. A., Meyer, R. T., Cameron, J. W., Nims, R. W., Burke, M. D., Wolff, J. and Guengerich, F. P. (1985) Dealkylation of pentoxyresorufin: a rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238, 43-48. https://doi.org/10.1016/0003-9861(85)90138-9
  25. Mangipudy, R. S., Chanda, S. and Mehendale, H. M. (1995) Tissue repair response as a function of dose in thioacetamide hepatotoxicity. Environ. Health Perspect. 103, 260-267. https://doi.org/10.1289/ehp.95103260
  26. Nash, T. (1953) The colorimetrical estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J. 55, 416-421. https://doi.org/10.1042/bj0550416
  27. Sabbele, N. R., van Oudenaren, A., Hooijkaas, H. and Benner, R. (1987) The effect of corticosteroids upon murine B cells in vivo and in vitro as determined in the LPS-culture system. Immunology 62, 285-290.
  28. Sadhna, A. S., Rao, A. R., Kucheria, K. and Bijani, V. (1988) Inhibitory action of garlic oil on the initiation of benzo[a]pyrene-induced skin carcinogenesis in mice. Cancer Lett. 40, 193-197. https://doi.org/10.1016/0304-3835(88)90010-9
  29. Singh, A. and Shukla, Y. (1998a) Antitumor activity of diallyl sulfide on polycyclic aromatic hydrocarbon-induced mouse skin carcinogenesis. Cancer Lett. 131, 209-214. https://doi.org/10.1016/S0304-3835(98)00152-9
  30. Singh, A. and Shukla, Y. (1998b) Antitumor activity of diallyl sulfide in two-stage mouse skin model of carcinogenesis. Biomed. Environ. Sci. 11, 258-263.
  31. Sparnins, V. L., Barany, G. and Wattenberg, L. W. (1988) Effects of organosulfur compounds from garlic and onions on benzo[a]pyreneinduced neoplasia and glutathione S-transferase activity in the mouse. Carcinogenesis 9, 131-134. https://doi.org/10.1093/carcin/9.1.131
  32. Wang, E. J., Li, Y., Lin, M., Chen, L., Stein, A. P., Reuhl, K. R. and Yang, C. S. (1996) Protective effects of garlic and related organosulfur compounds on acetaminophen-induced hepatotoxicity in mice. Toxicol. Appl. Pharmacol. 136, 146-154. https://doi.org/10.1006/taap.1996.0018
  33. Wang, T., Shankar, K., Ronis, M. J. J. and Mehendale, H. M. (2000) Potentiation of thioacetamide liver injury in diabetic rats is due to induced CYP2E1. J. Pharmacol. Exp. Ther. 294, 473-479.
  34. Wargovich, M. J. (1987) Diallyl sulfide, a flavor component of garlic (Allium sativum), inhibits dimethylhydrazine-induced colon cancer. Carcinogenesis 8, 487-489. https://doi.org/10.1093/carcin/8.3.487
  35. Wargovich, M. J., Woods, C., Eng, V. W., Stephens, L. C. and Gray, K. (1988) Chemoprevention of N-nitrosomethylbenzylamine-induced esophageal cancer in rats by the naturally occurring thioether, diallyl sulfide. Cancer Res. 48, 6872-6875.
  36. White, K. L., Jr., Lysy, H. H. and Holsapple, M. P. (1985) Immunosuppression by polycyclic aromatic hydrocarbons: a structure-activity relationship in B6C3F1 and DBA/2 mice. Immunopharmacology 9, 155-164. https://doi.org/10.1016/0162-3109(85)90011-6
  37. Yang, C. S., Yoo, J. S. H., Ishizaki, H. and Hong, J. Y. (1990) Cytochrome P450 2E1: Roles in nitrosamine metabolism and mechanisms of regulation. Drug Metab. Rev. 22, 147-159. https://doi.org/10.3109/03602539009041082
  38. Yun, H. M., Ban, J. O., Park, K. R., Lee, C. K., Jeong, H. S., Han, S. B. and Hong, J. T. (2014) Potential therapeutic effects of functionally active compounds isolated from garlic. Pharmacol. Ther. 142, 183-195. https://doi.org/10.1016/j.pharmthera.2013.12.005
  39. Zhang, P., Noordine, M. L., Cherbuy, C., Vaugelade, P., Pascussi, J. M., Duee, P. H. and Thomas, M. (2006) Different activation patterns of rat xenobiotic metabolism genes by two constituents of garlic. Carcinogenesis 27, 2090-2095. https://doi.org/10.1093/carcin/bgl064

Cited by

  1. Effects of Baicalin on Oral Pharmacokinetics of Caffeine in Rats vol.23, pp.2, 2015, https://doi.org/10.4062/biomolther.2014.134
  2. Pharmacokinetic Interaction of Chrysin with Caffeine in Rats vol.24, pp.4, 2016, https://doi.org/10.4062/biomolther.2015.197
  3. The anti-inflammatory and anti-fibrotic effects of tadalafil in thioacetamide-induced liver fibrosis in rats vol.96, pp.12, 2018, https://doi.org/10.1139/cjpp-2018-0338
  4. Glibenclamide protects against thioacetamide-induced hepatic damage in Wistar rat: investigation on NLRP3, MMP-2, and stellate cell activation vol.391, pp.11, 2018, https://doi.org/10.1007/s00210-018-1540-2
  5. Hepatic damage exacerbates cisplatin-induced acute kidney injury in Sprague-Dawley rats vol.81, pp.11, 2018, https://doi.org/10.1080/15287394.2018.1451179