Cytotoxic Compounds from the Roots of Pulsatilla koreana

  • Published : 2009.12.31

Abstract

Seven compounds including hederagenin 3-[(O-${\alpha}$-L-rhamnopyranosyl-($1{\rightarrow}2$)-${\alpha}$-L-arabinopyranosyl) (1), $3{\beta}$-[(O-${\alpha}$-L-rhamnopyranosyl-($1{\rightarrow}2$)-${\alpha}$-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid (2), caffeic acid methyl ester (3), ferulic acid (4), orebiusin A (5), latifonicinin C (6) and 5-(hydroxymethyl)-2-furfuraldehyde (7) were isolated from the ethyl acetate fraction of the roots of Pulsatilla koreana. Their chemical structures were established based on physicochemical and spectroscopic data analyses. All isolates were investigated for their cytotoxic activity against cancer cell lines. Among them, compound 1 showed inhibitory activity against A549, COLO 205, and L1210 cancer cell lines with $IC_{50}$ values of 15.8, 36.5, and 22.8 ${\mu}g$/mL, respectively.

Keywords

References

  1. Abd-Alla, H.I., Shaaban, M., Shaaban, K.A., Abu-Gabal, N.S., Shalaby, N.M.M., and Laatsch, H., New bioactive compounds from Aloe hijazensis. Nat. Prod. Res. 23, 1035-1049 (2009) https://doi.org/10.1080/14786410802242851
  2. Bae, K.H., The Medicinal Plants of Korea. Kyo-Hak Press, Seoul 1999; pp. 139
  3. Bang, S.C., Kim, Y., Lee, J.H., and Ahn, B.Z., Triterpenoid saponins from the roots of Pulsatilla koreana. J. Nat. Prod. 68, 268-272 (2005a) https://doi.org/10.1021/np049813h
  4. Bang, S.C., Lee, J.H., Song, G.Y., Kim, D.H., Yoon, M.Y., and Ahn, B.Y., Antitumor activity of Pulsatilla koreana saponins and their structureactivity relationship. Chem. Pharm. Bull. 53 1451-1454 (2005b) https://doi.org/10.1248/cpb.53.1451
  5. Ikuta, A. and Itokawa, H., 30-Noroleanane saponins from callus tissues of Akebia quinata. Phytochemistry. 28, 2663-2665 (1989) https://doi.org/10.1016/S0031-9422(00)98063-4
  6. Kiru, H., Kitayama, S., Nakatani, F., Tomimori, T., and Namba, T., Studies on Nepalese crude drugs. III. On the saponins of Hedera nepalensis K. Koch. Chem. Pharm. Bull. 33, 3324-3329 (1985) https://doi.org/10.1248/cpb.33.3324
  7. Lee, H.S., Beon, M.S., and Kim, M.K., Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J. Agric. Food Chem. 49, 4656-4661 (2001) https://doi.org/10.1021/jf010609z
  8. Mimaki, Y., Kuroda, M., Asano, T., and Sashida, Y., Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J. Nat. Prod., 62, 1279-1283 (1999) https://doi.org/10.1021/np9901837
  9. Mineo, S., Yutaka, Z., Ryoichi, T., Tomoko, M., and Naokata, M., Studies on aldose reductase inhibitors from natural products. V.1) Active components of Hachimi-Jio-gan (Kampo medicine). Chem. Pharm. Bull. 41, 1469-1471 (1993)
  10. Pyo, M.K., Lee, Y., and Yun-Choi, H.S., Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovata. Arch. Pharm. Res. 25, 325 (2002) https://doi.org/10.1007/BF02976634
  11. Siddiqui, B.S., Perwaiz, S., and Begum, S., Studies on the chemical constituents of the fruits of Cordia latifolia. Nat. Prod. Res. 20, 131-137 (2006) https://doi.org/10.1080/14786410500045614
  12. Sun, H.H., Wang, H.D., Zhao, M.S., and Xun, S., Phenolic compounds of Isodon oresbius J. Nat. Prod. 59, 1079-1080 (1996) https://doi.org/10.1021/np960430w
  13. Van le, T.K., Hung, T.M., Thuong, P.T., Ngoc, T.M., Kim, J.C., Jang, H. S., Cai, X.F., Oh, S.R., Min, B.S., Woo, M.H., Choi, J.S., Lee, H.K., and Bae, K., Oleanane-type triterpenoids from Aceriphyllum rossii and their cytotoxic activity. J. Nat. Prod. 72, 1419-1423 (2009) https://doi.org/10.1021/np900273z
  14. Ye, W.C., Nine, N.J., Shou, X.Z., Jing, H.L., Tao, Y., McKervey, M.A., and Stevenson, P., Triterpenoids from Pulsatilla chinensis. Phytochemistry. 42, 799-802 (1996) https://doi.org/10.1016/0031-9422(96)00043-X
  15. Ye, W.C., Ou, B.X., Ji, N.N., Zhao, S.X., Ye, T., McKervey, M.A., and Stevenson, P., Patensin, a saponin from Pulsatilla patens var. multifida. Phytochemistry. 39, 937-939 (1995) https://doi.org/10.1016/0031-9422(95)00021-X
  16. Zhang, X.Q., Liu, A.R., and Xu, L.X., Determination of ranunculin in Pulsatilla chinensis and synthetic ranunculin by reversed phase HPLC. Yao Hsueh Hsueh Pao. 25, 932-935 (1990)