A New Lavandulylated Flavonoid with Free Radical and ONOO­Scavenging Activities from Sophora flavescens

  • Jung Hee Jin (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Kang Sam Sik (Natural Products Research Institute and College of Pharmacy, Seoul National University) ;
  • Woo Ju Jung (Faculty of Food Science and Biotechnology, Pukyong National University) ;
  • Choi Jae Sue (Faculty of Food Science and Biotechnology, Pukyong National University)
  • Published : 2005.12.01

Abstract

A new lavandulylated flavonoid, 8-lavandulylkaempferol (1), was isolated from the roots of Sophora f1avescens AITON (Leguminosae). The structure of this compound was determined via spectroscopic analysis. Compound 1 was determined to be a scavenger on both 1, 1-diphenyl­2-picrylhydrazyl radicals and $ONOO^{-}$.

Keywords

References

  1. Blois, M. S., Antioxidant determination by the use of a stable free radical. Nature, 181, 1199-1202 (1958) https://doi.org/10.1038/1811199a0
  2. 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
  3. 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
  4. Harborne, J. B., Mabry, T. J., and Mabry, H., The Flavonoids, part I, Academic press, London, pp 100 (1975)
  5. Huang, K. C., The Pharmacology of Chinese Herbs, CRC Press, Boca Raton, pp 63-66 (1993)
  6. Jung, H. J., Kang, S. S., Hyun, S. K., and Choi, J. S., In vitro free radical and $ONOO^{-}$ scavengers from Sophora flavescens. Arch. Pharm. Res., 28, 534-540 (2005) https://doi.org/10.1007/BF02977754
  7. 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
  8. Kooy, N. W., Royall, J. A., Ischiropoulos, H., and Beckman, J. S., Peroxynitrite mediated oxidation of dihydrorhodamine 123. Free Radic. Biol. Med., 16, 149-156 (1994) https://doi.org/10.1016/0891-5849(94)90138-4
  9. 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
  10. 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
  11. Li, F. and Liy, Y. L., Studies on the isolation and structures of baohuoside II, III, IV, and V. Acta Pharmaceutica Sinica, 23, 672-681 (1988)
  12. Mabry, T. J., Markham, K. R., and Thomas, M. B., The Systematic Indentification of Flavonoids. Springer-Verlag, Berlin, pp 41-61 (1970)
  13. 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
  14. 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
  15. Perry, L. M. and Metzger, J., Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses. The MIT Press, Cambridge, pp 226 (1980)
  16. Ruangrungsi, N., Iinuma, M., Tanaka, T., Ohyama, M., Yokoyama, J., and Mizuno, M., Three flavanones with a lavandulyl group in the roots of Sophora exigua. Phytochemistry, 31, 999-1001 (1992) https://doi.org/10.1016/0031-9422(92)80056-K
  17. 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)
  18. Shirataki, Y., Tsuzuku, T., Yokoe, I., Hirano, R. T., and Komatsu, M., Studies on the constituents of Sophora species. XXIII. Constituents of the root of Sophora chrysophylla SEEM. Chem. Pharm. Bull., 38, 1712-1716 (1990) https://doi.org/10.1248/cpb.38.1712
  19. 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 (1998)
  20. 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
  21. 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