Antilipoperoxidant Activity of Antraquinone and Stilbene from Polygonum cuspidatum

호장으로부터 분리한 안트라퀴논 및 스틸벤 화합물의 지질과산화 저해활성

  • Published : 2007.04.30

Abstract

Polygonum cuspidatum has been used as treatments of dermatitis, gonorrhea, inflammation, and hyperlipidaemia in traditional medicine. We examined liver protective effect on CCl$_4$ inducing hepatotoxicity and anti-oxidative activity by TBA method. Phytochemical examination of Polygonum cuspidatum led to the isolation and characterization of emodin 8-O-${\beta}$-D-glucopyranoside (compound 1), and trans-resveratrol 3-O-${\beta}$-D-glucopyranoside (compound 2). Compounds 1 and 2 enhanced the inhibition of anti-lipid peroxidative effects in liver homogenate. In chemical parameters obtained from serum analysis, compounds 1 and 2 also revealed significant decrease in hepatotoxicity. These results suggested that the antraquinone and stilbene which were isolated from Polygonum cuspidatum might be used as therapeutic agent of hepatitis.

Keywords

References

  1. 李昌福 : 大韓植物圖鑑, 鄕文社. 서울 p. 303 (1980)
  2. Yang, F., Zhang, T. and Ito, Y. : Large-scale separation of resveratrol, anthraglycoside A and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc by high-speed countercurrent chromatography. Journal of Chromatography A 919, 443 (2001)
  3. Zhao, R. Z., Liu, S. and Zhou, L. I. : Rapid quantitative HPTLC analysis, on one plate, of emodin, resveratrol, and polydatin in the chinese herb Polygonum cuspidatum. Chromatographia. 61, 311 (2005) https://doi.org/10.1365/s10337-005-0514-y
  4. Matsuda, H., Shimoda, H., Morikawa, T. and Yoshikawa, M. : Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): Structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorganic & Medicinal Chemistry Letters. 11, 1839 (2001)
  5. Xiao, K., Xuan, L., Xu, Y. and Bai, D. : Stilbene glycoside sulfates from Polygonum cuspidatum. J. Nat. Prod. 63, 1373 (2000)
  6. Liu, X., Wu, L., Song, G., Liu, K., Zhang, X. and Zhang, Y. : Study on chemical constituents of Polygonum cuspidatum Sieb. Shenyang Yaoke Daxue Xuebao. 16, 17 (1999)
  7. Park, C. S., Lee, Y. C., Kim, J. D. and Kim, C. H. : Inhibitory effects of Polygonum cuspidatum water extract (PCWE) and its component resveratrol on acyl-coenzyme A-cholesterol acyltransferase activity for cholesteryl ester synthesis in HepG2 cells. Vascular Pharmacology 40, 279 (2004) https://doi.org/10.1016/j.vph.2004.01.003
  8. Kim, Y. S., Kim, H. H., Yoo, M. J. and Shin, D. H. : Bactericidal Effect of the extracts of Polygonum cuspidatum on Bacillus cereus. Food Sci. Biotechnol. 13, 430 (2004)
  9. Agarwal, S. K., Singh, S. S., Verma, S. and Kumar, S. : Antifungal activity of anthraquinone derivatives from Rheum emodi. J. Ethnopharmacol. 72, 436 (2000)
  10. Jayatilake, G. S., Jayasuriya, H., Lee, E. S., Koonchanok, N. M., Geahien, R. L., Ashendel, C. L., McLaughlin, J. L. and Chang. C. J : Kinase Inhibitors from Polygonum cuspidatum. J. Natural Products 56, 1805 (1993)
  11. Jayasuria, H., Koonchanok, N. M., Geahlen, R., McLaughlin, J. L. and Chang, C. J. : Emodin, a protein tyrosine kinase inhibitor from Polygonum cuspidatum. Journal of Natural Products. 55, 696 (1992)
  12. Kong, L., Yang, C. and Qiu, X. : Effects of processing on antioxidation of Rheum palmatum and Polygonum cuspidatum. Zhongguo Zhongyao Zazhi. 26, 388 (2001)
  13. Meng, J. and Hang, H. : Study on antioxidative activity and stability of Polygonum cuspidatum extract. Huaxue Shijie. 41, 418 (2000)
  14. Wang, S., Zheng, Z., Weng, Y., Yu, Y., Zhang, D., Fan, W., Dai, R. and Hu, Z. : Angiogenesis and anti-angiogenesis activity of Chinese medicinal herbal extracts. Life Sciences 74, 2467 (2004) https://doi.org/10.1016/j.lfs.2003.03.005
  15. Kumar, A., Dhawan, S. and Aggarwal, B. B. : Emodin (3- methyl-1,6,8-trihydroxyanthraquinone) inhibits TNF-induced NF-$\kappa$-B activation, I$\kappa$-B degradation, and expression of cell surface adhesion proteins in human vascular endothelial cells. Oncogene. 17, 913 (1998)
  16. 김지연, 양기숙 : 호장근의 사염화탄소로 유도된 지질과산화 저해 활성. 약학회지 43, 572 (1999)
  17. Francis, G. W., Aksnes, D. W. and Holt, O. : Assignment of the $^1H$ and $^{13}C$ NMR spectra of anthraquinone glycoside from Rhamnus frangula. Magn. Reson. Chem. 36, 769 (1998)
  18. Ayse, K., Isabelle, B., and Schiewe, A. Z. : The structures of antioxidant and cytotoxic agents from natural source: anthraquinones and taurins from roots of Rumex patientia. Phytochem. 58, 1213 (2001) https://doi.org/10.1016/S0031-9422(01)00160-1
  19. Vastano, B. C., Chen, Y., Zhu, N., Ho, C. T., Zhou, Z. and Rosen, R. T. : Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum. J. Agric. Food Chem. 48, 253 (2000)
  20. Pierre, W., Alain, T., Joseph, D., Gerard, D. and Jean, M. : Trans-resveratrol-3-O-$\beta$--glucoside (PICEID) in cell suspension cultures of Vitis vinifera. Phytochem. 42, 1591 (1996)
  21. Toppel, A. L. : Lipid peroxidation damageto cell components. Fed. Proc. 32, 1870 (1973)
  22. Curtis, M. T., Gilfor, D. and Farber, J. L. : Lipid peroxidation increases the molecular order of microsomal membranes. Arch. Biochem. Biophys 235, 644 (1984)
  23. Chen, L. C., Borges, T., Glauert, H. P., Knight, S. A., Sunde, R. A. and Schramm, H. C. : Modulation of selenium dependent glutathione peroxidase by perfluorodecanoic acid in rat. J. Nutr. 120, 198 (1990)
  24. Kimura, Y., Okuda, H. and Arichi, S. : Effects of stilbene on arachidonate metabolism in leukocytes. Biochimica et Biophysica Acta 834, 275 (1985)
  25. Lee, H. J. and Choi, M. S. : Changes of plasma and hepatic lipids, hydroxy-methyl-glutaryl CoA reductase activity and acyl-CoA: Cholesterol acyltransferase activity by supplementation of hot water extraxts from Rosa rugosa, Crataegus pinnetifida and Polygonum cuspidatum in high cholesterol fed rats. J. Food. Sci. Nutr. 3, 344 (1998)