Alaternin and emodin with hydroxyl radical inhibitory and/or scavenging activities and hepatoprotective activity on tacrine-induced cytotoxicity in HepG2 cells

Archives of Pharmacal Research

Volumn 27, Issue 9, 2004, Pages 947-953

  Hyun, Ah Jung ^b   Hae, Young Chung ^c   Yokozawa, Takako ^d   Youn, Chul Kim ^e   Sook, Kyung Hyun ^a   Jae, Sue Choi ^a  

^a Pukyong National University   (South Korea)

^b Korea Maritime University   (South Korea)

^c Pusan National University   (South Korea)

^d UNIVERSITY OF TOYAMA   (Japan)

^e Wonkwang University   (South Korea)

Author keywords

Alaternin; Anthraquinone; Cassia tora L.; DCF; Emodin; ESR spectroscopy; Hepatoprotective activity; Hydroxyl radical; Tacrine

Indexed keywords

2 HYDROXYEMODIN; 2-HYDROXYEMODIN; DRUG DERIVATIVE; EMODIN; HYDROXYL RADICAL; SCAVENGER; TACRINE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; DRUG ANTAGONISM; DRUG EFFECT; HUMAN; LIVER; METABOLISM; TUMOR CELL LINE;

CELL LINE, TUMOR; EMODIN; FREE RADICAL SCAVENGERS; HUMANS; HYDROXYL RADICAL; LIVER; TACRINE;

EID: 16644403117     PISSN: 02536269     EISSN: 02536269     Source Type: Journal    
DOI: 10.1007/bf02975849     Document Type: Article

References (48)

1. Asha, V. V., Akhila, S., Wills, P. J. and Subramoniam, A., Futher studies on the antihepatotoxic activity of Phyllanthus maderaspatensis Linn. J. Ethnopahrmacol., 92, 67-70 (2004).
2. Benoit, G. G., Naud, C. F., Simard, M. A., and Astier, A. L., Noninterference of cytochrome P4501A2 in the cytotoxicity of tacrine using genetically engineered V79 Chinese hamster cells for stable expression of the human or rat isofrom an two human hepatocyte cell lines. Chem. Pharmacol., 53, 423-427 (1997).
3. Bruck, R. B., Aeed, H., Shirin, H., Matas, Z., Zaidel, L., Avni, Y. and Halpern, Z., The hydroxyl radical scavengers dimethyl-sulfoxide and dimethylthiourea protect rats against thioacetamide-induced fulminant hepatic failure. J. Hepatol., 31, 27-38 (1999).
4. Chen, C. W., He, B., and Chen, Q., Biochemical study of Chinese rhubarb anthraquinone derivatives on the inhibition of NADH oxidase and succinate oxidase of the mitochondrion. Shenwu Hauxue Zazhi, 4, 36-41 (1988).
5. Cho, H., Jun, J. Y., Song, E. K., Kang, K. H., Baek, H. Y., Ko, Y. S., and Kim, Y. C., Bakuchiol: a hepatoprotective compounds of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells. Planta Med., 67, 750-751, (2001).
6. Choi, J. S., Chung, H. Y., Jung, H. A., Park, H. J., and Yokozawa, T., Comparative evaluation of antioxidant potential of alaternin (=2-hydroxyemodin) and emodin. J. Agric. Food Chem., 48, 6347-6351 (2000).
7. Choi, J. S., Lee, H. J., and Kang, S. S., Alaternin, cassiaside and rubrofusarin gentiobioside, radical scavenging principles from the seeds of Cassia tora on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Arch. Pharm. Res., 17, 462-466 (1994).
8. Choi, J. S., Lee, H. J., Park, H. J., Kim, H. G., Young, H. S., and Mun, S. I., Screening for antioxidant activity of plant and marine algae and its active principles from Prunus davidiana. Kor. J. Pharmacogn., 24, 299-303 (1993).
9. Demierezer, L. Ö., Kuruüzüm-Uz, A., Bergere, I., Schiewe, H. J., and Zeeck, A., The structures of antioxidant and cytotoxic agents from natural sources: anthraquinones and tannins from roots of Rumex patientia. Phytochemistry, 58, 1213-1217 (2001).
10. Doucet-Personeni, C., Bentley, P. D., Fletcher, R. J., Kinkaid, A., Kryger, G., Pirard, B., Taylor, A., Taylor, R., Viner, R., Silman, I., Sussman, J. L., Greenblatt, H. M., and Lewis, T., A structure-based design approach to the development of novel, reversible AchE inhibitors. J. Med. Chem., 44, 3203-3215 (2001).
11. Galm, O., Fabry, U., Efferth, T., and Osieka, R., Synergism between rViscumin and cisplatin is not dependent on ERCC-1 expression. Cancer Lett., 187, 143-151 (2002).
12. Halliwell, B. and Gutteridge, J. M. C., Biologically relevant metal ion-dependent hydroxyl radical generation. An update. FEBS Lett., 307, 108-112 (1992).
13. Halliwell, B. and Gutteridge, J. M. C., Oxygen free radical and iron in relation to biology and medicine; some problems and concepts. Arch. Biochem. Biophys., 246, 501-514 (1986).
14. Hipeli, S. and Elstner, E. F., OH-radical type reactive oxygen species: a short review on the mechanisms of OH-radical and peroxynitrite toxicity. Z. Naturforsch., 52C, 555-563 (1997).
15. Hsiao, G. H., Shen, M. Y., Lin, K. H., Lan, M. H., Wu, L. Y., Chu, D. S., Lin, C. H., Su, C. H., and Sheu, J. R., Antioxidative and hepatoprotective effects of Antrodia camphorata extract. J. Agric. Food Chem., 51, 3302-3308 (2003).
16. Huang, S. S., Yeh, S. F. and Hong, C. Y., Effect of anthraquinone derivative on lipid peroxidation in rat heart mitochondria: structure-activity relationship. J. Nat. Prod., 58, 1365-1371 (1995).
17. Komarov, A. M., Hall, J. M., and Weglicki, W. B., Azidothymidine promotes free radical generation by activated macrophage and hydrogen peroxide-iron-mediated oxidation in a cell-free system. Biochim. Biophysic. Acta., 1688, 257-264 (2004).
18. Lebel, C. P. and Bondy, S. C., Sensitive and rapid quantitation of oxygen reactive species formation in rat synaptosomes. Neurochem. Int., 17, 435-441 (1990).
19. Li, L., Abe, Y., Kanagawa, K., Ushi, N., Imai, K., Mashino, T., Moshizuki, M., and Miyata, N., Distinguishing the 5,5-dimethyl-1-pyrroline N-oxide (DMPO)-OH radical quenching effect from the hydroxyl radical scavenging effect in the ESR spin-trapping method. Anal. Chim. Acta, 512, 121-124 (2004).
20. Lin, C. C, Chang, C. H., Yang, J. J., Namba, T., and Hattori, M., Hepatoprotective effects of emodin from Ventilago leiocarpa. J. Ethnopharmacol., 52, 107-111 (1996).
21. Lloyd, R. V., Hanna, P. M., and Mason, R. P., The origin of the hydroxyl radical oxygen in the fenton reaction. Free Radic. Biol. Med., 22, 885-888 (1997).
22. Moraes, J. E., Quina, F. H., Nascimento, C. A. O., Silva, D. N. and Chiavone-Filho, O., Treatment of saline wastewater contaminated with hydrocarbons by the photo-fenton process. Environ. Sci. Technol., 38, 1183-1187 (2004).
23. Morita, T., Jinno, K., Kawagishi, H., Arimoto, Y., Suganuma, H., Inakuma, T., and Sugiyama, K., Hepatoprotective effect of myristin from nutmeg (Myristica fragrans) on lipopolysaccharide/D-galactosamine-induced liver injury. J. Agric. Food Chem., 51, 1560-1565 (2003).
24. Mothilal, K. K., Inbaraj, J. J., Gandhidasan, R., and Murugesan, R., Photosensitization with anthraquinone: optical and EPR spin trapping studies of photogeneration of reactive oxygen species. J. Photochem. Photobiol. A: Chem., 162, 9-16 (2004).
25. Nagashima, H., Nakamura, K., and Goto, T., Hepatotoxin rubratoxin B induced the secretion of TNF-, IL-8 and MCP-1 in HL60 cells. Biochem. Biophy. Res. Comm., 287, 829-832 (2001)
26. Ng, T. B., Liu, F., Lu, Y., Cheng, C. H. K., and Wang, Z., Antioxidant activity of compounds from the medicinal herb Aster tataricus. Comparative Biochem. Physiol. Part C, 136, 109-115 (2003).
27. Noro, T., Noro, K., Milyase, T., Kuroyanagi, M., Umehara, K., Ueno, A., and Fukushima, S., Inhibition of xanthine oxidase by anthraquinone. Chem. Pharm. Bull., 35, 4314-4316 (1987).
28. Oh, H. C., Kim, J. S., Song, E. K., Cho, H., Kim, D. H., Park, S. E., Lee, H. S., and Kim, Y. C., Sesquiterpenes with hepatoprotective activity from Cnidium monnieri on tacrine-induced cytotoxicity in Hep G2 cells. Planta Med., 68, 748-749 (2002a).
29. Oh, H. C., Lee, H. S., Kim, T. W., Chai, K. Y., Chung, H. T., Kwon, T. O., Jun, J. Y., Jeong, O. S., Kim, Y. C., and Yun, Y. G., Fucocoumarines from Angelica dahurica with hepatoprotective activity on tacrine-induced cytotoxicity in Hep G2 cells. Planta Med., 68, 463-464 (2002b).
30. Osseni, R. A., Debbasch, C., Christen, M. O, Rat, P., and Warnet, J. M., Tacrine-induced reactive oxygen species in a human liver cell line: the role of anethole dithilethione as a scavenger. Toxicol. In Vitro, 13, 683-688 (1999).
31. Oturan, M. A., Peiroten, J., Chartrin, P., and Acher, A. J., Complete destruction of p-nitrophenol in aqueous medium by electro-fenton reaction. Environ. Sci. Technol., 34, 3474-3476 (2000).
32. Pan, S. Y., Han, Y. F., Carlier, P. R., Pang, Y. P., Mak, D. H. F., Lam, B. Y. H., and Ko, K. M., Schisandrin B protects against tacrine- and bis(7)-tacrine-induced hepatotoxicity and enhances cognitive function in mice. Planta Med., 68, 217-220 (2002).
33. Rimbach, G., Weinberg, P. D., de Pascual-Teresa, S., Alonso, M. G., Ewins, B. A., Turner, R., Minihane, A. M.,Botting, N., Firley, B., Matsugo, S., Uchida, Y., and Cassidy, A., Sulfation of genistein alters its antioxidant properties and its effect on platelet aggregation and monocyte and endothelial function. Biochim. Biophys. Acta, 1670, 229-237 (2004).
34. Rota, C., Chignell, C. F., and Mason, R. P., Evidence for free radical formation during the oxidation of 2′,7′-dichlorofluorescin to the fluorescent dye 2′,7′-dichlorofluorescein by horseradish peroxidase: possible implications for oxidative stress measurements. Free Radic. Biol. Med., 27, 873-881 (1999).
35. Shao, Z. H., Xie, J. T., Vanden Hoek, T. L., Mehendale, S., Aung, H., Li, C. Q., Qin, Y., Schumacker, P. T., Becker, L. B., and Yuan, C. S., Antioxidant effects of American ginseng berry extract in cardiomyocytes exposed to acute oxidant stress. Biochim. Biophysic. Acta, 1670, 165-171 (2004).
36. Song, E. K., Cho, H., Kim, J. S., Kim, N, Y., An N. H., Kim, J. A., Lee, S. H., and Kim, Y. C., Diarylhepatonoids with free radical scavenging and hepatoprotective activity in vitro from Curcuma longa. Planta Med., 67, 876-877 (2001).
37. Song, E. K., Kim, J. H., Kim, J. S., Cho, H., Nan, J. X., Sohn, D. H., Ko, G. I., Oh, H. C., and Kim, Y. C., Hepatoprotective phenolic constituents of Rhodiala sachalinensis on tacrine-induced cytotoxicity in HepG2 cells. Phytother. Res., 17, 563-565 (2003).
38. 4-induced hepatic toxicity in rats. J. Agric. Food Chem., 51, 1571-1577 (2003).
39. Stohs, S. J. and Bagchi, D., Oxidative mechanisms in the toxicity of metal ions. Free Radic. Biol. Med., 18, 321-336 (1995).
40. Ueda, J. I., Saito, N., Shimazu, Y., and Ozawa, T., A comparison of scavenging abilities of antioxidants against hydroxyl radicals. Arch. Biochem. Biophys., 333, 377-384 (1996).
41. 4-induced liver damage. Food. Chem. Toxicol., 42, 609-617 (2004).
42. Watkins, P. B., Zimmerman H. J., Knapp, M. J., Gracon, S. I., and Lewis, K. W., Hepatotoxic effects of tacrine administration in patients with Alzheimers disease. J. Am. Med. Assoc., 271, 992-998 (1994).
43. Wu, C. H., Hsieh, C. L., Song, T. Y., and Yen, G. C., Inhibitory effects of Cassia tora L. on benzo[a]pyrene-mediated DNA damage toward HepG2 cells. J. Agric. Food Chem., 49, 2579-2586 (2001).
44. 2 cells. Biochem. Pharmacol., 57, 273-279 (1999).
45. Yen, G. C., Chen, H. W., and Duh, P. D., Extraction and identification of an antioxidative compound from jue ming zi (Cassia tora L.). J. Agric. Food Chem., 46, 820-824 (1998).
46. Yen, G. C., Chen, H. Y., and Peng, H. H., Antioxidant and pro-oxidant effects of various tea extracts. J. Agric. Food Chem., 45, 30-34 (1997).
47. Yen, G. C., Duh, P. D., and Chuang, A. Y., Antioxidant activity of anthraquinones and anthrone. Food Chem., 70, 437-441 (2000).
48. 2/NaOH/DMSO system by electron spin resonance. J. Agric. Food Chem., 47, 4653-4656 (1999).