Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Protective Effects of Methanol Extract and Alisol B 23-acetate of Alisma orientale on Acetaminophen-Induced Hepatotoxicity in Rats

  • Yang, Ki-Ho (Research Institute of Korean Oriental Medicine, Sunchon National University) ;
  • Choi, Seong-Hee (Department of Food Science, Sunmoon University) ;
  • Park, Jong-Cheol (Research Institute of Korean Oriental Medicine, Sunchon National University)
  • Received : 2012.05.09
  • Accepted : 2012.05.22
  • Published : 2012.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Hepatoprotective effects of methanol extract and alisol B 23-acetate of Alisma orientale were studied in acetaminophen (APAP)-treated rats. APAP increased hepatic content of lipid peroxide, which was suppressed by methanol extract and alisol B 23-acetate. The liver of rats treated with APAP had higher P-450, aminopyrine N-demethylase and aniline hydroxylase activities than those of normal control rats. The increases in hepatic drug metabolizing enzymes by the i.p. injection of APAP were significantly alleviated by the administration of methanol extract or alisol B 23-acetate. The injection of APAP also resulted in a substantial reduction of hepatic glutathione content and glutathione S-transferase activity, and the decreases were partially, but significantly, restrained by the oral administration of methanol extract prior to the i.p. injection of APAP. Hepatic activities of glutathione reductase (GR) and ${\gamma}$-glutamylcystein synthetase ${\gamma}$-GCS) were also decreased significantly in APAP-treated rats. The decreases in hepatic GR and ${\gamma}$-GCS activities by APAP injection were improved partially, but significantly, with administration of methanol extract of A. orientale. Treatment with alisol B 23-acetate also improved the hepatic ${\gamma}$-GCS activity significantly, but not GR.

Keywords

References

  1. Banerjee, A., Linscheer, W.G., Chiji, H., Murthy, U.K., Cho, C., Nandi, J., and Chan, S.H., Induction of an ATPase inhibitor protein by propylthiouracil and protection against paracetamol (acetaminophen) hepatotoxicity in the rat. Br. J. Pharmacol., 124, 1041-1047 (1998). https://doi.org/10.1038/sj.bjp.0701917
  2. Bidlack, W.R. and Lowery, G.L., Multiple drug metabolism: p-nitroanisole reversal of acetone enhanced aniline hydroxylation. Biochem. Pharmacol, 31, 311-317 (1982). https://doi.org/10.1016/0006-2952(82)90176-9
  3. Boyne, A.F. and Ellman, G.L., A methodology for analysis of tissue sulfhydryl components. Anal. Biochem., 46, 639-653 (1972). https://doi.org/10.1016/0003-2697(72)90335-1
  4. Chang, I.M., Kim, Y.S., Yun, H.S., and Kim, S.O., Liver-protective activities of alisol compounds against $CCl_4$ intoxication. Kor. J. Pharmacog, 13, 112-115 (1982).
  5. Chasseaud, L.F., Role of glutathione and glutathione S-transferase in the metabolism of chemical carcinogenesis and other electrophilic agents. Adv. Cancer Res., 29, 175-274 (1979).
  6. Choi, J.W. and Park, J.C., Protective effect of marine natural products on the hepatic lipid peroxidation in acetaminophen-treated rats. Yakhak Hoeji, 40, 574-581 (1996).
  7. Cohen, S.D., Pumford, N.R., Khairallah, E.A., Boekelheide, K., Pohl, L.R., Amouzadeh, H.R., and Hinson, J.A., Selective protein covalent binding and target organ toxicity. Toxicol. Appl. Pharmacol., 143, 1-12 (1997). https://doi.org/10.1006/taap.1996.8074
  8. Cover, C., Liu, J., Farhood, A., Malle, E., Waalkes ,M.P., Bajt, M.L., and Jaeschke, H., Pathophysiological role of the acute inflammatory response during acetaminophen hepatotoxicity. Toxicol. Appl. Pharmacol., 216, 98-107 (2006). https://doi.org/10.1016/j.taap.2006.04.010
  9. Dimova, S., Hoet, P.H.M., and Nemery, B., Paracetamol (acetaminophen) citotoxicity in rat type II pneumocytes and alveolar macrophages in vitro. Biochem. Pharmacol., 59, 1467-1475 (2000). https://doi.org/10.1016/S0006-2952(00)00257-4
  10. Habig, W.H., Pabist, M.J., and Jakoby, W.B., The first step in mercapturic acid formation. J. Biol. Chem., 249, 7130-7139 (1974).
  11. Huh, J., Dongeui Bogam. Yeogang Publishing Co, Seoul, pp 2727, 1994 (in Korean)
  12. Imai, Y., Matsumura, H., and Aramaki, Y., Hypocholesterolemic effect of alisol A-24 monoacetate and its related compounds in rats. Jap. J. Pharm., 20, 222-228 (1970). https://doi.org/10.1254/jjp.20.222
  13. Imai, Y., Ito, A., and Sato, K., Evidence for biochemically different types of vesicles in the hepatic microsomal fraction. J. Biochem., 60, 417-428 (1996)
  14. Jaeschke, H., Knight, T.R., and Bajt, M.L., The role of oxidant stress and reactive nitrogen species in acetaminophen hepatotoxicity. Toxicol. Lett., 144, 279.288 (2003). https://doi.org/10.1016/S0378-4274(03)00239-X
  15. Knight, T.R., Fariss, M.W., Farhood, A., and Jaeschke, H., Role of lipid peroxidation as a mechanism of liver injury after acetaminophen overdose in mice. Toxicol. Sci., 76, 229-236 (2003). https://doi.org/10.1093/toxsci/kfg220
  16. Kubo, M., Matsuda, H., Tomohiro, N., and Yoshikawa, M., Studies on Alismatis rhizome I anti-allergic effects of methanol extract and six terpene components from Alismatis Rhizoma (dried rhizome of Alisma orientale). Biol. Pharm. Bull., 20, 511-516 (1997). https://doi.org/10.1248/bpb.20.511
  17. Lee, S.M., Kim, J.H., Zhang, Y., An, R.B., Min, B.S., Joung, H., and Lee, H.K., Anti-complementary activity of protostane-type triterpenes from Alismatis Rhizoma. Arch. Pharm. Res., 26, 463-465 (2003). https://doi.org/10.1007/BF02976863
  18. Lowry, O.H., Rosebrough, N.J., Farr, A.L., and Randall, R.J., Protein measurement with the folin phenol reagent. J. Biol. Chem., 193, 267-275 (1951).
  19. Matsuda, H., Kageura, T., Toguchida, I., Murakami, T., Kishi , A., and Yoshikawa, M., Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages: absolute stereostructures of alismaketones B 23-acetate and -C 23-acetate. Bioorg. Med. Chem. Lett. 9, 3081-3086 (1999). https://doi.org/10.1016/S0960-894X(99)00536-3
  20. Mitchell, J.R., Jollow, D.J., Potter, W.Z., Davis, D.C., Gillette, J.R., and Brodie, B.B., Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J. Pharmacol. Exp. Ther., 187, 185-194 (1973a).
  21. Mitchell, J.R., Jollow, D.J., Potter, W.Z., Gillette, J.R., and Brodie, B.B., Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J. Pharmacol. Exp. Ther., 187, 211-217 (1973b).
  22. Mize, C.E. and Langdon, R.G., Hepatic glutathione reductase. In: Purification and general kinetic properties. J. Biol. Chem., 237, 1589-1593 (1962).
  23. Moore, M., Thor, H., Moore, G., Nelson, S., Moldeus, P., and Orreniu, S., The toxicity of acetaminophen and N-acetyl-p-benzoquinone imine in isolated hepatocytes is associated with thiol depletion and increased $Ca^{2+}$. J. Biol. Chem., 260, 13035-13040 (1985).
  24. Nakajima, Y., Satoh, Y., Katsumata, M., Tsujiyana, K., Ida, Y., and Shoji, J., Terpenoids of Alisma orientale rhizome and the crude drug Alismatis Rhizoma. Phytochemistry, 36, 119-127 (1994). https://doi.org/10.1016/S0031-9422(00)97024-9
  25. Nash, T., The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem. J., 55, 416-421 (1953). https://doi.org/10.1042/bj0550416
  26. Nelson, S.D. and Bruschi, S.A., Mechanism of acetaminophen-induced liver disease. in Kaplowitz N, Deleve LD (eds.), in Drug-Induced Liver Disease, Marcel-Dekker, Inc, New York, pp287-325, 2003.
  27. Ohkawa, H., Ohishi, N., and Yaki, K., Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal. Biochem., 95, 351-358 (1979). https://doi.org/10.1016/0003-2697(79)90738-3
  28. Omura, T. and Sato, R., The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem., 239, 2370-2378 (1964).
  29. Oshima, Y., Iwakawa, T., and Hikino, H., Alismol and alismoxide, sesquiterpenods of Alisma Rhizomes. Phytochemistry, 22, 183-185 (1983). https://doi.org/10.1016/S0031-9422(00)80084-9
  30. Park, J.C., Hur, J.M., and Kim, S.E., Isolation and quantitative analysis of alisol B 23-acetate from the Rhizome of Alisma orientale. J. Korean Soc. Food Sci. Nutr., 34, 243-246 (2005). https://doi.org/10.3746/jkfn.2005.34.2.243
  31. Park, J.O., Kim, K.S., and Sunwoo, K.O., Purification and characterization of hemagglutinating protein from rhizome of Alisma orientale. J. Korean Soc. Food Nutr., 24, 587-593 (1995).
  32. Pumford, N.R. and Halmes, N.C., Protein targets of xenobiotic reactive intermediates. Ann. Rev. Pharmacol. Toxicol., 37, 91-117 (1997). https://doi.org/10.1146/annurev.pharmtox.37.1.91
  33. Reed, D.J., Fariss, M.W., and Pascoe, G.A., Mechanisms of chemical toxicity and cellular protection systems. Fund. Appl. Toxicol., 6, 591-597 (1986). https://doi.org/10.1016/0272-0590(86)90171-5
  34. Reiter, R.J., Tan, D.X., Sainz, R.M., Mayo, J.C., and Lopez-Burillo, S., Melatonin: reducing the toxicity and increasing the efficacy of drugs. J. Pharmacy Pharmacol., 54, 1299-1321 (2002). https://doi.org/10.1211/002235702760345374
  35. Reitman, S. and Frankel, S., A colorimetric method for the determination of serum glutamic oxaloacetic and glutamic pyruvic transaminase. Am. J. Clin. Pathol., 28, 56-63 (1957). https://doi.org/10.1093/ajcp/28.1.56
  36. Richman, P.G. and Meister, A., Regulation of ${\gamma}$-glutamylcysteine synthesis by nonallosteric feedback inhibition by glutathione. J. Biol. Chem., 250, 1422-1426 (1975).
  37. Ross, D., Glutathione, free radicals and chemotherapeutic agents. Pharmacol. Ther., 37, 231-249 (1988). https://doi.org/10.1016/0163-7258(88)90027-7
  38. Sener, G., Sehirli, A.O., and Ayanoglu-Dulger, G., Protective Effects of melatonin, vitamine E and N-acetylcysteine against acetaminophen toxicity in mice: a comparative study. J. Pineal. Res., 35, 61-68 (2003). https://doi.org/10.1034/j.1600-079X.2003.00050.x
  39. Shaw, S., Herbert, V., Colman, N., and Jayatilleke, E., Efffect of ethanol-generated free radicals on gastric intrinsic factor and glutathione. Alcohol, 7, 153-157 (1990). https://doi.org/10.1016/0741-8329(90)90077-P
  40. Szabo, S., Nagy, L., and Plebani, M., Glutathione, protein sulfhydryls and cysteine proteases in gastric mucosal injury and protection. Clin. Chim. Acta., 206, 95-105 (1992). https://doi.org/10.1016/0009-8981(92)90010-N
  41. Thomas, S.H., Paracetomol (acetaminophen) poisoning. Pharmacol. Ther., 60, 91-120 (1993). https://doi.org/10.1016/0163-7258(93)90023-7
  42. Wiesner, I.S., Rawnsley, H.M., Brooks, F.P., and Senior, J. R., Sorbitol dehydrogenase in the diagnosis of liver disease. Am. J. Dig. Dis., 10, 147-151 (1965). https://doi.org/10.1007/BF02236665
  43. Yoshikawa, M., Fukuda, Y., Hatakeyana, S., Tanaka, N., Matsuda, H., Yamahara, H., and Murakami, N., Sulfoorientalos a, b, c and d, four new biologically active sesquiterpenes from Alismatis Rhizoma. Chem. Pharm. Bull., 41, 1194-1196 (1993). https://doi.org/10.1248/cpb.41.1194
  44. Yoshikawa, M., Murakami, T., Ikebata, A., Ishikado, A., Murakami, N., Yamahara, J., and Matsuda, H., Absolute stereostructures of alismalactone 23 acetate and alismaketone A 23 acetate, new seco-protostane and protostane-type triterpenes with vasorelaxant effects from Chinese Alismatis Rhizoma. Chem. Pharm. Bull., 45, 756-758 (1997). https://doi.org/10.1248/cpb.45.756