Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Anti-oxidative Phenolic Compounds from Sophorae Fructus

  • Published : 2004.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

Four isoflavonoids and three flavonoids, and a gallotannin were isolated from the fruits of Sophora japonica (Leguminosae). Their structures were identified as genistein (1), sophoricoside (2), genistein-4'-O--L-rhamnopyranoside (3), $genistein-4'-O-{\alpha}-L-rhamnopyranosly-(1{\rightarrow}2)-{\beta}-D-glucopyranoside$ (4), $kaempferol-3-O-{\alpha}-D-sophoroside$ (5), $kaempferol-3-O-{\beta}-D-glucopyranosyl-(1{\rightarrow}2)-{\alpha}-L-rhamnopyranosly-(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (6), rutin (7) and gallic acid $4-O-{\beta}-D-(6'-O-galloyl)-glucopyranoside$ (8) by chemical and spectroscopic analysis and comparisons with previously reported spectral data. Compounds 3 and 8 were isolated for the first time from this plant. Anti-oxidative activity was evaluated for the isolated compounds. 8 exhibited potent anti-oxidative activity against the radical scavenging ability of DPPH with the $IC_{50}$ value of $17.1\;{\mu}g/ml$.

Keywords

References

  1. Djerrassi, C., Dictionary of Natural Products. Vol 5. Chapman and Hall, pp. 5471 and 5796 (1994)
  2. Harbome, J.B., and Mabry, T.J., The Flavonoids. Chapman and Hall, pp. 105 (1982)
  3. Harbome, J.B., and Mabry, T.J., The Flavonoids. Chapman and Hall, pp. 105 (1982)
  4. Kim, T.W., The Woody Plants of Korea in Color., Kyo-Hak Publishing Co., Seoul, Korea. pp. 399 (1995)
  5. Kim, Y.R., Isolation of rutin from Amaranthus mangotanus. Kor. J. Pharmacogn. 31: 249-251 (2000)
  6. Lee, YA., Cho, S.M., and Lee, M.W., Flavonoids from the Roots of Rhodiola sachalinensis. Kor. J. Phannacogn. 33: 116-119 (2002)
  7. Lewis P.T., and Wahala K., Regiospecific 4-O--glucosidation of isoflavones. Tetrahedron Letters., 39, 9559-9562 (1998) https://doi.org/10.1016/S0040-4039(98)02124-8
  8. Michael, E.E., Manual of cultivated broad-leaved trees & shrubs. Volume, Timber Press, Protland, Oregon. pp. 325-327 (1986)
  9. Nature, and Medicin study association of Korea, Life-Chinese Medicine' FolkMedicine. DongBu-MunHwaSa. pp. 21 (1985)
  10. Nonaka, G., and Nishioka I., Tannins and Related Compounds. X. Rhubarb (2) : Isolation and structures of a glycerol gallate, gallic acid glucoside gallates, galloylgiucoses and isolindleyin. Chem. Pham. Bull. 31:1652-1658 (1983) https://doi.org/10.1248/cpb.31.1652
  11. Park, Y.K., Lee, H.J., Choi, D.H., Kwon, Y.H., and Oh, J.S., Extractives from the Bark of Sophora japonica L. Mokchae Konghak. 30: 42-47 (2002)
  12. Agrawal, P.K., Carbon-13 NMR of flavonoids. Elsevier. pp. 347 (1989)
  13. Saxena, Y.K., and Madhuri Singai, Genistein 4'-O-$\alpha$-L-rhamno pyranoside from Pithecellobium dulce. Fitoterapia. 69: 305-306 (1998)
  14. Shirataki, Y., Takaya, Y., Yokoe, I., and Komatsu, M., Soporaside A, A new aromatic glycoside from the roots of Sophora japonica. Chern, Pharm. Bull. 35: 1637-1640 (1987) https://doi.org/10.1248/cpb.35.1637
  15. Takeda, T., Ishiguro, I., Masegi, M., and Ogihara, Y., New isoflavone glycosides from the woods of Sophora japonica. Phytochemistry. 16: 619-620 (1997) https://doi.org/10.1016/0031-9422(77)80038-1
  16. Jeffrey, B., Harbome, F.R.S., and Herbert, B., The Handbooks of Natural Flavonoids. Vol 2. pp. 671 (1999)
  17. Wenzel, D., Kuntz, S., Brendel, M.D., and Daniel, H., Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells. Cancer Res., 60, 3823-3831 (2000)