Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
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Antioxidative and Cytotoxicity Activities of Compounds Isolated from Korean Rhus verniciflua S.

한국산 옻나무로부터 추출.분리한 생리활성 물질들의 항산화 효과 및 세포독성

  • Choi, Won-Sik (Dept. of Life Science, Soonchunhyang University) ;
  • Kim, Dong-Kil (Dept. of Life Science, Soonchunhyang University) ;
  • Lee, Young-Haeng (Dept. of Chemistry, Won-Kwang University) ;
  • Kim, Jang-Eok (Dept. of Agricultural Chemistry, Kyungpook National University) ;
  • Lee, Sung-Eun (Dept. of Agricultural Chemistry, Kyungpook National University)
  • Published : 2002.08.31
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Abstract

Antioxidative activities of solvent fractions obtained from Korean Rhus vernicifera, being used in food industry and as a traditional medicine, were examined by the methods of DPPH scavenging activity, inhibitory effect on autooxidation of linoleic acid, nitrite scavenging activity and the inhibitory effect on xanthine oxidase activity. Ethyl acetate fraction showed potent antioxidative activities. Three compounds were isolated from the ethyl acetate fraction by rotatory locular counter current chromatography (RLCCC), Sephadex LH-20 column chromatography and HPLC. The isolated compounds were 1,2,3-trihydroxybezene, methyl 3,4,5-trihydroxybenzoate and 3,4,5-trihydroxybenzoic acid determined by GC/MS and, $^1H$ and $^{13}C$ NMR. Among the isolated compounds, methyl 3,4,5-trihydroxybenzoate showed the strongest antioxidative activity than artificial antioxidants, BHA and BHT in various methods. However, these isolated compounds did not show cytotoxicity effects on the human cancer cell lines. Therefore, we may suggest that methyl 3,4,5-trihydroxybenzoate can be used as a food additive possessing the potent antioxidative activity.

한국산 옻나무의 메탄올추출물과 유기용매 분획의 항산화 효과를 조사하였다. 항산화 효과는 수소공여 억제능, 과산화지질 형성 억제능, xanthine oxidase저해 활성과 아질산염 소거능으로 측정한 결과, ethyl acetate 분획이 가장 뛰어난 효과를 나타내었다. 이 분획의 생리활성 물질을 분리하기 위하여, rotatory locular counter current chromatography(RLCCC), Sephadex LH-20 column chromatograpy와 HPLC등의 방법을 사용하여, 1,2,3-trihydroxybenzene, methyl 3,4,5-trihydroxybenzoat와 3,4,5-trihydroxybenzoic acid를 분리하였다. 이중 methyl 3,4,5-trihydroxybenzoate는 butylated hydroxyanisole(BHA)이나 butylated hydroxytoluene(BHT)보다도 강한 항산화 효과를 나타내었다. 그러나 세포독성 실험에서는 이들 물질들이 암세포주에 대하여 활성이 높지 않았다. 이상의 결과로 methyl 3,4,5-trihydroxybenzoate은 뛰어난 항산화 효과를 지닌 식품첨가물로서의 이용 가능성을 제시할 수 있다.

Keywords

References

  1. Fridovich, I. (1978) The biology of oxygen radicals. Science 201(4359), 875-880 https://doi.org/10.1126/science.210504
  2. Bodaness, R. S. and Chan, P. C. (1977) Singlet oxygen as a mediator in the hematoporphyrin-catalyzed photooxidation of NADPH to NADP+ in deuterium oxide. J. Biol. Chem. 252(23), 8554-8560
  3. Trush, M. A., Mimnaugh, E. G. and Gram, T. E. (1982) Activation of pharmacologic agents to radical intermediates. Implications for the role of free radicals in drug action and toxicity. Biochem. Plwrmacol. 31(21), 3335-3346 https://doi.org/10.1016/0006-2952(82)90609-8
  4. Aust, S. D., Morehouse, L. A. and Thomas, C. E. (1985) Role of metals in oxygen radical reactions. J. Free radicals Biol.Med. 1(1), 3-25 https://doi.org/10.1016/0748-5514(85)90025-X
  5. Amoma, O. I. (1994) Nutrition and health aspects of free radicals and antioxidants. Food Chem. Toxicot. 32, 671-683 https://doi.org/10.1016/0278-6915(94)90011-6
  6. Davies, K. J. A. and Goldberg, A. L. (1987) Proteins damaged by oxygen radicals are rapidly degraded in extracts of red blood cells. J. Biol. Chem. 262(17), 8227-8234
  7. Morita, J., N. Kashimura and T. Komano. (1980) The mechanism of interaction of bacteriophage $\Psi$X174 byautooxidizable synthetic polysaccharides. Agric. BioI. Chem. 44, 2971-2978
  8. Morita, J., N. Kashimura and T. Komano. (1982) Interacdve of Escherichia coil phages by sugar phosphate. Agric. Biol. Chem. 46, 279-280
  9. Adelman, R., Saul, R. L. and Ames, B. N. (1988) Oxidative damage to DNA: relation to species metabolic rate and life span. Proc. Natl. Acad. Sci. USA 85, 2706-2708 https://doi.org/10.1073/pnas.85.8.2706
  10. Halliwell, B. and Gutteridge, J. M. C. (1990) In Methods Enzyrrwl. 186; Oxygen radicals in biological systems. Part B. Role of free radicals and catalytic metal ions in human disease: An overview. Academic Press, London. pp. 1-85
  11. Davies, K. J. A. (1995) In Erwironment, Drugs and Food Additives, Portland Press, Portland. pp. 1-31
  12. Ames, B.N. (1983) DiStary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science 221(4617), 1256-1264 https://doi.org/10.1126/science.6351251
  13. Miquel, J., Quintanilha, A. T. and Weber, H. (1989) In Handbook of free radicals and antioxidants in biomedicine CRC Press, I: 223
  14. Pryor, W. A. (1980) In Free radicals in biology Vol. VI.Academic Press, New York. pp. 49-90
  15. Halliwell, B. (1996) Antioxidants in human health and disease. Ann. Rev. Nutr. 16, 33-50
  16. Halliwell, B. and Aruoma, 0. I. (1991) DNA damage by oxygen-derived species, Its mechanism and measurement in mammalian systems. FEBS Lett. 281(1-2), 9-19 https://doi.org/10.1016/0014-5793(91)80347-6
  17. Harman, D. (1982) hi Free radicals in Biolosy V. Academic Press, New York. pp. 255-275
  18. Yosida, T., Mon, K., Hatano, T, Okumura, T., Uehara, I., Komagoe, K., Fujita, Y. and Okuda, T. (1989) Radical-scavenging effects of tannins and related polyphenols on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull. 37(7),1919-1921 https://doi.org/10.1248/cpb.37.1919
  19. Haraguch, H., Ishikawa, H., Sanchez, Y, Ogura, T, Kubo, Y. and Kubo, I. (1997) Antiox idant constituents in Hetemthecainutoides. Bioorg. Med. Chem. 5, 865-871 https://doi.org/10.1016/S0968-0896(97)00029-1
  20. Beyer, W. F and Eridovich, I. (1987) Assaying for superoxide dismutase activity: some large consequences of minor changes in conditions. Anat: Biochem. 161(2), 559-566 https://doi.org/10.1016/0003-2697(87)90489-1
  21. Kato, H., Lee, I. E., Chuyen, N. V, Kim, S. B. and Hayase, E. (1987) Inhibition of nitrosamine formation by nondialyzable melanoidins. Agric. Biol. Chem. 51, 1333-1338
  22. Alley, M. C., Scudiero, D. A., Monks, A., Hursey, M. L., Czerwinski, M. J:, Fine, D. L.,Abbott, B. J., Mayo, J. G., Shoemark, R. H. and Boyd, M. R. (1988) Feasibility of drug screening with panels of human tumor cell lines using a imcroculture tetrazolium assay. Cancer Res. 48, 589-601
  23. Iio, M., Moriyamn, A., Matsumoto, Y, Takaki, N. and Fukumoto, M. (1985) Inhibition of xanfhine oxidase by flavonoids. Agric. Biol. Chem. 49, 2173-2176
  24. Cho, Y. J., An, B. J. and Choi, C. (1993) Isolation and enzyme inhibition of tannins from Korean Green Tea. 26(3), 84-87
  25. Hatano, T, Yauhara, T, Fukuda, T., Noro, T. and Okuda, T. (1990) Inhibitory effects of tannins and related polyphenols on xanthine oxidase. Chem. Pharm. Butt. 38, 1224-1229 https://doi.org/10.1248/cpb.38.1224