Phytochemical Constituents of the Aerial Parts from Aster hispidus

  • Lee, Sung-Ok (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University) ;
  • Choi, Sang-Zin (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University) ;
  • Choi, Sang-Un (Korea Research Institute of Chemical Technology) ;
  • Ryu, Shi-Yong (Korea Research Institute of Chemical Technology) ;
  • Lee, Kang-Ro (Natural Products Laboratory, College of Pharmacy, SungKyunKwan University)
  • Published : 2004.12.30

Abstract

The chromatographic separation of the MeOH extract of the aerial parts from Aster hispidus (Compositae) led to the isolation of eight compounds. Their structures were established by spectroscopic methods to be ${\beta}-amyrin$ (1), oleanolic acid (2), (2R)-1, 2-O-(9Z, 12Z, $15Z-dioctadecatrienoyl)-3-O-{\beta}-D-galactopyranosyl\;glycerol$ (3), trans-phytol (4), 9, 12, 15-octadecatrienoic acid (5), kaempferol (6), 3,5-dicaffeoyl quinic acid (7), 3,4-dicaffeoyl quinic acid (8) and kaempferol-3-O-rutinoside (9). Compounds 1, $3{\sim}6$ and 9 showed non-specific moderate cytotoxicity against five human tumor cell lines $(5.44{\sim}23.51\;{\mu}g/ml)$. The other compounds were of marginal activity against tested five human cancer cell lines $(9.05{\sim}>30.0\;{\mu}g/ml)$.

Keywords

References

  1. Ahmad, V.U., Rahman, A.U., Handbook of natural products data; volumn 2 Pentacyclic triterpenoids. Elsevier Science, pp.111 (1994).
  2. Basnet, P, Matsushige, K, Hase, K, Kadota, S., and Namba, T.,, Four di-O-caffeoyl quinic acid derivatives from Propolis. Potent hepatoprotective activity in experimental liver injury models. Biol. Pharm. Bull., 19, 1479-1484 (1996) https://doi.org/10.1248/bpb.19.1479
  3. Clifford, M.N., Coffee bean dicaffeoylquinic acids. Phytochemistry, 25, 1767-1769 (1986) https://doi.org/10.1016/S0031-9422(00)81260-1
  4. Dey, P.M., and Harborne, J.B., Methods in Plant Biochemistry (VoL 4). Academic Press, London, pp.72 (1990)
  5. Goodman, R.A, Oldfield, E., and Allerhand, A, Assignments in the natural-abundance carbon-13 nuclear magnetic resonance spectrum of chlorophyll a and a study of segmental motion in neat phytol J. Am. Chem. Soc., 95, 7553-7558 (1973) https://doi.org/10.1021/ja00804a003
  6. Han, J.T., Bang, O,K., Kim, D.O., Lee, C.Y, and Baek, N.l., Flavonol glycosides from the aerial parts of Aceriphyllum rossii and their antioxidant activities. Arch. Pharm. Res.. 27. 390-395 (2004) https://doi.org/10.1007/BF02980079
  7. lwahashi, H., Morishita, H., Osaka, N., and Kido, R., 3-0Feruloyl- 4-0-caffeoylquinic acid from Coffee beans. Phytochemistry, 24, 630-632 (1985) https://doi.org/10.1016/S0031-9422(00)80793-1
  8. Jung, J.H., and Kang, S.S., Diacylglycerylgalactosides from Arisaema amurense. Phytochemistry, 42, 447-452 (1996) https://doi.org/10.1016/0031-9422(95)00929-9
  9. Kobayashi, M., Hayashi, K, Kawazoe, K, and Kitagawa, I., Marine natural products. X X IX. Heterosigma-glycolipid I, II, III, and IV. four diacylglyceroglycolipids possessing $\omega$3polyunsaturated fatty acid residues, from the raphidophycean dinoflagellate Heterosigma akashiwo. Chem. Pharm. Bull., 40, 1404-1410 (1992) https://doi.org/10.1248/cpb.40.1404
  10. Lee, S.H., Kim, KS., Shim, S.H., Park, Y.M., and Kim, B.K., Constituents from the non-polar fraction of Artemisia apiacea. Arch. Pharm. Res., 26, 902-905 (2003) https://doi.org/10.1007/BF02980197
  11. Lee, W.B., Kwon, H.C., Cho, OR, Lee, KC., Choi, S.U., Baek, N.l., and Lee, KR., Phytochemical constituens of Cirsium setidens Nakai and their cytotoxicity against human cancer cell lines. Arch. Pharm. Res., 25, 628-635 (2002) https://doi.org/10.1007/BF02976934
  12. Mahato, S.B., Kundu, A.P., $^{13}C$ NMR spectra of pentacyclic triterpenoids a complilation and some salient features. Phytochemistry, 37, 1517-1575 (1994) https://doi.org/10.1016/S0031-9422(00)89569-2
  13. Markham, K.R., Temal, B., Stanly, R., Geiger, H., and Mabry, T. J., Carbon-13 NMR studies of tlavonoids-III. Naturally occurring flavonoid glycosides and their acetylated derivatives, Tetrahedron, 34, 1389-1397 (1978) https://doi.org/10.1016/0040-4020(78)88336-7
  14. Sims, J.J., and J.R., Pettus, J.A, Isolation of free cis and transPhytol from the red Alga Gracilaria andersoniana. Phytochemistry, 15, 1076-1077 (1976) https://doi.org/10.1016/S0031-9422(00)84413-1
  15. Skehan, P, Storeng, R., Scudiero, D., Monks, A, McMahon, J, Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., and Boyd, M.R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107