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Antioxidative Effects of Sulfur Containing Compounds in Garlic on Oxidation of Human Low Density Lipoprotein Induced by Macrophages and Copper Ion

마크로파아지 및 구리 이온으로 유도한 사람 low density lipoprotein의 산화에 대한 마늘 유황 화합물의 항산화 효과

  • Yang, Seung-Taek (Department of Food Science and Biotechnology, Kyungsung University)
  • 양승택 (경성대학교 식품생명공학과)
  • Published : 2008.01.31

Abstract

Sulfur containing compounds in garlic have all be used as one of the traditional folk medicine as well as food source. The present study was performed to investigate the antioxidative compounds of 1-methyl-1-cysteine, dimethyl trisulfide and 2-vinyl-4H-1,3-dithiin. The antioxidative activity of sulfur containing compounds on human LDL was investigated by monitoring a thiobarbituric acid substances (TBARS). Sulfur containing compounds inhibited on oxidation of LDL mediated by $CuSO_4$ and macrophages in dose dependent manner with almost completely inhibition at $80{\mu}g/ml$. Antioxidant activities of sulfur containing compounds on LDL oxidation were 2-vinyl-4H-1,3-dithiin, 1-methyl-1-cysteine, and dimethyl trisulfide in order. Inhibitory effects of sulfur containing compounds on oxidation of LDL mediated by $CuSO_4$ and macrophages were degraded at much greater rate than native LDL, the LDL oxidation process was arrested as shown by the lower conjugated dienes formation at the concentration of $60{\mu}g/ml$. Sulfur containing compounds in garlic revealed at high antioxidative activity at low physiological concentration for human LDL oxidation in vitro specially, it was indicated that the antioxidative activity of 3-viny l-4H-1,2-dithiin was higher than that of the other sulfur containing compounds.

마늘의 주성분인 유황 함유 화합물을 이용하여 사람 low density lipoprotein (LDL)의 산화에 대하여 항산화 활성을 실험하였다. 유황함유화합물인 1-methyl-1-cysteine, dimethyl trisulfide 및 1-vinyl-4H-1,3-dithiin의 농도를 각각 40, 60, $80{\mu}g/ml$ 씩 첨가하여 $Cu^{2+}$ 및 macrophages 유도로 LDL을 산화할 때 항산화 효능을 TBARS로 측정한 결과 용량 의존형으로 나타났으며 유황 함유 화합물이 모두 효능이 있었으며 항산화력은 2-vinyl-4H-1,3-dithiin > 1-methyl-1-cysteine > methyl trisulfide 순이었다. 이 때 유황 함유 화합물의 LDL에 대한 공액 2중결합에 대한 항산화 실험에서도 항산화 효과가 있었으며 $60{\mu}g/ml$의 농도에서 거의 억제되었다. 유황 함유 화합물 중에서는 2-vinyl-4H-1,3-dithiin이 다른 유황 함유 화합물에 비하여 약간 높은 항산화 효능을 나타내었다. Endothelial cell을 이용한 LDL의 산화에 대한 억제율은 2-vinyl-4H-1,3-dithiin이 가장 높게 나타났다.

Keywords

References

  1. Babiy, A. V., J. M. Gebicki and D. R. Sullivan. 1990. Vitamin E content and low density lipoprotein oxidizabillity induced by free radicals. Atherosclerosis 81, 175-182. https://doi.org/10.1016/0021-9150(90)90064-P
  2. Baumann, J., F. Bruchhausen and G. Wurm. 1980. Flavonoids and related compounds as inhibitors of arachidonic acid peroxidation. Prostaglandins 20, 627-639. https://doi.org/10.1016/0090-6980(80)90103-3
  3. Bjorkhem, I., F. Henricheson-Freychuss, O. Breuer, V. Diczfaiusy, L. Berflund and P. Henrikson. 1991. The antioxidant butylated hydroxy toluene protects against atheroscler. Thromb. 11, 15-22.
  4. Bridges, A. B., N. A. Scott and J. F. Belch. 1991. Probucol, a superoxide free radical scavenger in vitro. Atherosclerosis 89, 263-265. https://doi.org/10.1016/0021-9150(91)90068-E
  5. Brown, M. S. and J. L. Goldstein. 1983. Lipoprotein metabolism in the macrophage: Implications for cholesterol deposition in atherosclerosis. Ann. Rev. Biochem. 52, 223-261. https://doi.org/10.1146/annurev.bi.52.070183.001255
  6. Cavallito, C. J., J. S. Buck and C. M. Suter. 1944. Allicin, the antibacterial principles of Allium sativim. II Determination of the chemical structure. J. Am. Chem. Soc. 66, 1952-1954. https://doi.org/10.1021/ja01239a049
  7. Cristol, L. S., I. Jialal and M. Grundy. 1992. Effect of low dose probucol therapyon LDL oxidation and the plasma lipoprotein profile in male volunteers. Atherosclerosis 97, 11-20. https://doi.org/10.1016/0021-9150(92)90046-J
  8. Esterbauer, H., G. Striegl, H. Puhl and M. Rotheneder. 1989. Continuous monitoring of in vitro oxidation of human low density lipoprotein. Free Rad. Res. Commun. 6, 67-75. https://doi.org/10.3109/10715768909073429
  9. Esterbauer, H., M. Dieber-Rotheneder, G. Striegl and G. Wage. 1991. Role of vitamin E in preventing the oxidation of low density lipoprotein. Am. J. Clin. Nutr. 53, 314-321. https://doi.org/10.1093/ajcn/53.1.314S
  10. Esterbauer, H., J. Gebicki, H. Puhl and G. Jurgens. 1992. The role of lipid peroxidation and antioxidative modification of LDL. Free Rad. Biol. Med. 13, 341-390. https://doi.org/10.1016/0891-5849(92)90181-F
  11. Goldstein, J. 1. and M. S. Brown. 1983. Lipid metabolism in the macrophage. Annu. Rev. Biochem. 52, 223-262. https://doi.org/10.1146/annurev.bi.52.070183.001255
  12. Goldstein, J. L. Y. K. Ho, S. K. Basu and M. S. Brown. 1979. Binding site on macrophages that mediates uptake and degradation of acetylated low density lipoprotein, producing massive cholesterol deposition. Proc. Nat. Acad. Sci. U.S.A. 76, 333-337. https://doi.org/10.1073/pnas.76.1.333
  13. Harats, D., M. Ben-Naim, Y. Dabach, G. Hollander, O. Stein and Y. Stein. 1989. Cigarette smoking renders LDL susceptible to peroxidative modification and enhanced metabolism by macrophages. Atherosclerosis 79, 245-252. https://doi.org/10.1016/0021-9150(89)90130-5
  14. Havel, R. J., H. A. Eder and J. H. Bragdon. 1955. The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. J. Clin Invest. 34, 1345-1352. https://doi.org/10.1172/JCI103182
  15. Heinecke, J. W. 1987. Free radical modification of low-density lipoprotein: Mechanisms and biological consequences. Free Rad. Biol. Med. 3, 65-73. https://doi.org/10.1016/0891-5849(87)90040-2
  16. Morel, D. W., P. E. DiCorleto, G. M. Chisholm. 1984. Endothelial and smooth muscle cells after low density lipoproteins in vitro by free radical oxidation. Arteriosclerosis 4, 357-364. https://doi.org/10.1161/01.ATV.4.4.357
  17. Janero, D. R. 1991. Therapeutic potential of vitamin E in the pathogenesis of spontaneous atherosclerosis. Free Rad. Biol. Med. 11, 129-144. https://doi.org/10.1016/0891-5849(91)90193-7
  18. Jessup, W., S. M. Rankin, C. V. De Whalley, R. S. Hoult, J. Scott and D. S. Leake. 1990. $\alpha$-tocopherol consumption during low-density-lipoprotein oxidation. Biochem. J. 265, 399-405. https://doi.org/10.1042/bj2650399
  19. Jialal, I., G. L. Vega and S. M. Grundy. 1990. Physiologic levels of ascorbate inhibit the oxidative modification of low density lipoproteins. Atherosclerosis 82, 185-191. https://doi.org/10.1016/0021-9150(90)90039-L
  20. Jialal, I., E. P. Norkus, L. Cristol and S. M. Grundy. 1991. $\beta$-Carotene inhibits the oxidative modification of low-density lipoprotein. Biochim. Biophys. Acta. 1086, 134-138. https://doi.org/10.1016/0005-2760(91)90164-D
  21. Kendler, B. S. 1987. Garlic (Allium sativum) and onion (Allium cepa): A review of their ralationship to cardiovascular disease. Prev. Med. 16, 670-685. https://doi.org/10.1016/0091-7435(87)90050-8
  22. Leake, D. S. and S. M. Rankin. 1990. The oxidative modification of low density lipoproteins by macrophages. Biochem. J. 270, 741-748. https://doi.org/10.1042/bj2700741
  23. Lowry, O. H., N. J. Rosebrough, A. L. Farr and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. biol. Chem. 193, 265-275.
  24. Moore, G. S. and R. D. Atkins. 1977. The fungicidal and fungistatic effects of aqueous garlic extract on medically important yeast fungi. Mycologia. 69. 341-348. https://doi.org/10.2307/3758659
  25. Ross, R. 1993. The pathogensis of atherosclerosis: perspective for the 1990s. Nature 362, 801-809. https://doi.org/10.1038/362801a0
  26. Robak, J., F. Shridi, M. Wolbis, M. Krolikowska and J. Sol. 1988. Screening of the influence of flavonoids of lipoxygenase and cycloxygenase activity as well as on non-enzymatic lipid oxidation. Pharmacol. Pharm. 40, 451-458. https://doi.org/10.1111/j.2042-7158.1988.tb06317.x
  27. Srivastava, K, C., A. Bordia and S. K. Verma. 1995. Garlic (Allium sativum) for disease prevention. South African J. Sci. 91, 68-77.
  28. Steinbrecher, U. P., H. Zhang and M. Lougheed. 1990. Role of oxidatively modified LDL in atherosclerosis. Free Rad. Biol. Med. 9, 155-178.
  29. Witztum, J. L. and D. Steinberg. 1991. Role of oxidized low density lipoprotein in atherogenesis. J. Clin. Invest. 88, 1785-1792. https://doi.org/10.1172/JCI115499
  30. Yaki, K. 1976. A simple fluoimetric assay for lipoprotein in blood plasma. Biochem. Med. 15, 212-217. https://doi.org/10.1016/0006-2944(76)90049-1
  31. Tallarida, R. J. and R. B. Murray. 1987. Manual of pharmacological calculations with computer programs. pp. 145-148. 2th eds., Springer Verlag, New York.

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