In Vitro Free Radical and ONOO- Scavengers from Sophora flavescens

  • Jung, Hee-Jin (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Kang, Sam-Sik (Natural Products Research Institute, Seoul National University) ;
  • Hyun, Sook-Kyung (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Choi, Jae-Sue (Faculty of Food Science and Biotechnology, Pukyong National University)
  • 발행 : 2005.01.01

초록

Activity-guided fractionation of the CH$_2Cl_2$-soluble fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scaveng ers: trans-hexadecyl ferulic acid (1) cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8, 9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compounds: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3${\beta}$,7,4'-trihydroxy-5-methoxy-8-(${\gamma},{\gamma}$- imethylallyl )-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8- (${\gamma},{\gamma}$-dimethylallyl ) -flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compounds 1-4 and 8 exhibited DPPH free radical scavenging effects at IC$_{50}$ values of 33.01 ${\pm}$ 0.20, 57.06 ${\pm}$ 0.16, 39.84 ${\pm}$ 0.36, 35.83 ${\pm}$ 0.47, and 18.11 ${\pm}$ 0.04${\mu}$M, respectively. L-Ascorbic acid, when used as a positive control, exhibited an IC$_{50}$ value of 7.39 ${\pm}$ 0.01 ${\mu}$M. Compounds 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC$_{50}$ values of 5.76 ${\pm}$ 1.19, 15.06 ${\pm}$ 1.64, 8.17 ${\pm}$ 4.97, 1.95 ${\pm}$ 0.29 and 4.06 ${\pm}$ 2.41 ${\mu}$M, respectively. Penicillamine (IC$_{50}$= 2.36 ${\pm}$ 0.79${\mu}$M) was used as a positive control. In addition, compounds 2,4,6,8, and 10 were isolated from this plant for the first time.

키워드

참고문헌

  1. Balde, A. M., Claeys, M., Pieters, L. A., Wray, V., and Vlietinck, A. J., Ferulic acid esters from stem bark of Pavetta owariensis. Phytochemistry, 30, 1024-1026 (1991) https://doi.org/10.1016/0031-9422(91)85302-G
  2. Beckman, J. S., Beckman, T. W., Chen, J., Marshell, P. A., and Freeman, B. A., Apparent hydroxy radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. U.S.A., 87, 1620-1624 (1990) https://doi.org/10.1073/pnas.87.4.1620
  3. Blois, M. S., Antioxidant determination by the use of a stable free radical. Nature, 181, 1199-1202 (1958) https://doi.org/10.1038/1811199a0
  4. Ding, P. L., Hou, A. J., and Chen, D. F., Three new isoprenylated flavonoids from the roots of Sophora flavescens. J. Asian Nat. Prod. Res., 7, 237-243 (2005) https://doi.org/10.1080/10286020410001687554
  5. Ding, Y., Tian, R. H., Kinjo, J., Nohara, T., and Kitagawa, I., Three new oleanene glycosides from Sophora flavescens. Chem. Pharm. Bull., 40, 2990-2994 (1992) https://doi.org/10.1248/cpb.40.2990
  6. Hatano, T., Edamatsu, R., Hiramatsu, M., Mori, A., Fujita, Y., Yasuhara, T., Yoshida, T., and Okuda, T., Effects of the interaction of tannins with co-existing substances VI. Effects of tannins and related polyphenols on superoxide anion radical, and on 1,1-diphenyl-2-picrylhydrazyl radical. Chem. Pharm. Bull., 37, 2016-2021 (1989) https://doi.org/10.1248/cpb.37.2016
  7. Huang, K. C., The Pharmacology of Chinese Herbs, CRC Press, Boca Raton, pp 63-66 (1993)
  8. Jakupovic, J. J., Paredes, L., Bohlmann, F., and Watson, L., Prenyl flavans from Marshallia species. Phytochemistry, 27, 3273-3275 (1988) https://doi.org/10.1016/0031-9422(88)80041-4
  9. Jung, N. I., Yook, C. S., and Lee, H. K., Coumarins from the roots of Angelica decursiva – albiflora. Kor. J. Pharmacogn., 25, 311-318 (1994)
  10. Kang, T. H., Jeong, S. J., Ko, W. G., Kim, N. Y., Lee, B. H., Inagaki, M., Miyamato, T., Higuchi, R., and Kim, Y. C., Cytotoxic lavandulyl flavanones from Sophora flavescens. J. Nat. Prod., 63, 680-681 (2000) https://doi.org/10.1021/np990567x
  11. Kim, J. S., Byun, J. H., Kang, S. S., Son, K. H., Kim, H. P., and Chang, H. W., Isolation of flavonoids and a saponin from Echinosophora koreensis. Kor. J. Pharmacogn., 33, 110-115 (2002)
  12. Kim, J. S., Han, S. J., Byun, J. H., Xu, Y. N., Yoo, S. W., Kang, S. S., Son, K. H., Chang, H. W., and Kim, H. P., Minor constituents from the roots of Sophora flavescens. Nat. Prod. Sci., 7, 5-8 (2001)
  13. Komatsu, M., Tomimori, T., Hatayama, K., and Mikuriya, N., Studies on the constituents of Sophora species. IV. Constituents of the root of Sophora angustifolia Sieb. Et Zucc. (1). Yakugaku Zasshi, 90, 463-468 (1970) https://doi.org/10.1248/yakushi1947.90.4_463
  14. Kooy, N. W., Royall, J. A., Ischiropoulos, H., and Beckman, J. S., Peroxynitrite mediated oxidation of dihydrorhodamine 123. Free Radical Biol. Med., 16, 149-156 (1994) https://doi.org/10.1016/0891-5849(94)90138-4
  15. Kuroyanagi, M., Arakawa, T., Hirayama, Y., and Hayashi, T., Antibacterial and antiandrogen flavonoids from Sophora flavescens. J. Nat. Prod., 62, 1595-1599 (1999) https://doi.org/10.1021/np990051d
  16. Kyogoku, K., Hatayama, K., and Komatsu, M., Constituents of Chinese crude drug 'Kushen' (the root of Sophora flavescens Ait.). Isolation of five new flavonoids and formononetin. Chem. Pharm. Bull., 21, 2733-2738 (1973) https://doi.org/10.1248/cpb.21.2733
  17. Mizuno, M., Iinuma, M., Tanaka, T., Sakakibara, N., Fujikawa, T., Hanioku, S., Ishida, Y., Liu, X. S., and Murata, H., Flavonol glycosides in the roots of Epimedium diphyllum. Phytochemistry, 27, 3645-3647 (1988) https://doi.org/10.1016/0031-9422(88)80784-2
  18. Murakoshi, I., Kidoguchi, E., Haginiwa, J., Ohmiya, S., Higashiyama, K., and Otomasu, H., Isokuraramine and (-)- 7,11-dehydromatrine, lupin alkaloids from flowers of Sophora flavescens. Phytochemistry, 21, 2379-2384 (1982) https://doi.org/10.1016/0031-9422(82)85210-2
  19. Okuda, S., Murakoshi, I., Kamata, H., Kashida, Y., Haginiwa, J., and Tsuda, K., Studies on lupin alkaloids. I. The minor alkoloids of Japanese Sophora flavescens. Chem. Pharm. Bull., 13, 482-487 (1965) https://doi.org/10.1248/cpb.13.482
  20. Park, J. A., Kim, H. J., Jin, C. B., Lee, K. T., and Lee, Y. S., A new pterocarpan, (-)-maackiain sulfate, from the root of Sophora subprostrata. Arch. Pharm. Res., 26, 1009-1013 (2003) https://doi.org/10.1007/BF02994750
  21. Perry, L. M. and Metzger, J., Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses. The MIT Press, Cambridge, pp 226 (1980)
  22. Pincemail, J. J., Free radicals and antioxidants in human diseases, In Favier, A. E., Cadet, J., Kalyanaraman, B., Fontecave, M. and Pierre, J. L. (Eds.). Analysis of Free Radicals in Biological System. Birkhauser Verlag, Berlin, pp. 83-98 (1995)
  23. Rice-Evans, C. A., Miller, N., and Paganga, G., Structureantioxidant activity relationships of flavonoids and phenolic acids. Free Ridical Biol. Med., 20, 933-956 (1996) https://doi.org/10.1016/0891-5849(95)02227-9
  24. Ryu, S. Y., Lee, H. S., Kim, Y. K., and Kim, S. H., Determination of isoprenyl and lavandulyl positions of flavonoids from Sophora flavescens by NMR experiment. Arch. Pharm. Res., 20, 491-495 (1997) https://doi.org/10.1007/BF02973946
  25. Saito, K., Arai, N., Sekine, T., Ohmiya, S., Kubo, H., Otomasu, H., and Murakoshi, I., (-)-5$\alpha$-Hydroxysophocarpine, a new lupin alkaloid from the seeds of Sophora flavescens var. angustifolia. Planta Med., 56, 486-488 (1990) https://doi.org/10.1055/s-2006-961018
  26. Squadrito, G. L. and Pryor, W. A., Oxidative chemistry of nitric oxide: the roles of superoxide, peroxynitrite, and carbon dioxide. Free Radical Biol. Med., 25, 392-403 (1998) https://doi.org/10.1016/S0891-5849(98)00095-1
  27. Tabata, N., Ito, M., Tomoda, H., and Omura, S., Xanthohumols, diacyglycerol acyltransferase inhibitors, from Humulus lupulus. Phytochemistry, 46, 683-687 (1997) https://doi.org/10.1016/S0031-9422(97)00157-X
  28. Woo, E. R., Kwak, J. K., Kim, H. J., and Park, H., A new prenylated flavonol from the roots of Sophora flavescens. J. Nat. Prod., 61, 1595-1599 (1995) https://doi.org/10.1021/np980103j
  29. Wu, L. J., Miyasa, T., Ueno, A., Kuroyanagi, M., Noro, T., Fukushima, S., and Sasaki, S., Studies on the constituents of Sophora flavescens Aiton. II. Chem. Pharm. Bull., 33, 3231- 3236 (1985) https://doi.org/10.1248/cpb.33.3231
  30. Yoshikawa, M., Wang, H. K., Kayakiri, T. Taniyama, T., and Kitagawa, I., Saponin and sapogenol. XL. Structure of sophoraflavoside I, a bisdesmoside of soyasapogenol B, from Sophorae Radix, the root of Sophora flavescens Aiton. Chem. Pharm. Bull., 33, 4267-4274 (1985) https://doi.org/10.1248/cpb.33.4267
  31. Zhang, J. H., Zhao, Y. Y., Liu, Q. X., and Ye, X. J., Studies on the chemical constituents from Sophora flavescens Ait. China J. Chin. Mat. Med., 25, 37-38 (2000)