Cytotoxic Isoquinoline Alkaloids from Chelidonium majus var. asiaticum

  • Lee, Jun (Department of Enviro-Biotechnology, Gyeongsang National University) ;
  • Shon, Mi-Yae (Department of Food Science, Jinju National University) ;
  • Jang, Dae-Sik (Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine) ;
  • Ha, Tae-Joung (Yeongnam Agricultural Research Institute, NICS, RDA) ;
  • Hwang, Seon-Woo (Department of Enviro-Biotechnology, Gyeongsang National University) ;
  • Nam, Sang-Hae (Department of Food Science, Jinju National University) ;
  • Seo, Eun-Kyoung (College of Pharmacy, Ewha Womans University) ;
  • Park, Ki-Hun (Department of Enviro-Biotechnology, Gyeongsang National University) ;
  • Yang, Min-Suk (Department of Enviro-Biotechnology, Gyeongsang National University)
  • Published : 2005.12.31

Abstract

Two known isoquinoline alkaloids, (+)-chelidonine (1) and (-)-stylopine (2), were isolated from $CHCl_3$-soluble fraction of whole plants of Chelidonium majus L. var. asiaticum, and their structures were identified by spectroscopic methods and X-ray crystallographic analysis. Two isolates (1 and 2) were examined for their in vitro cytotoxic activities against five human cancer cell lines including DU-145 (prostate), MCF (breast), A549 (lung), HePG2 (liver), and HT-29 (colon) by sulphorhodamine B (SRB) assay.

Keywords

References

  1. Joogyakdaesajun (in Korean) Kim, C.M.;Sin, M.K.;Ahn, D.K.;Lee, K.S.
  2. Ferns, fern-allies and seed-bearing plants of Korea Koh, K.S.;Jeon. E.S.
  3. Illustrated book of Korean medicinal herbs Ahn, D.K.
  4. J. Chromatogr. A v.542 Determination of isoquinoline alkaloids in Chelidonium majus L. by ion-pair high-performance liquid chromatography Chang, Q.N.;Li, Y.H. https://doi.org/10.1016/S0021-9673(01)88760-4
  5. J. Chromatogr. A v.543 Reversedphase high-performance liquid chromatographic separation of tertiary and quaternary alkaloids from Chelidonium majus L Liang, F.H.;Wassyl, N.;Viktor, G. https://doi.org/10.1016/S0021-9673(01)95760-7
  6. Planta Med. v.60 Separation of alkaloids in Chelidonium majus by reversed phase HPLC Eva, T.;Hana, B.;Hana, P.;Jiri, D. https://doi.org/10.1055/s-2006-959508
  7. Phytochemistry v.31 Isochelidonine, a benzophenanthridine alkaloid from Chelidonium majus Salvatore, D.R.;Giuseppe, D.V. https://doi.org/10.1016/0031-9422(92)80235-7
  8. Pharmacol. Res. v.33 Pharmacological activities of Chelidonium majus L(Papaveraceae) Maria, L.C.;Enrica, B. https://doi.org/10.1006/phrs.1996.0019
  9. Planta Med. v.64 Antispasmodic and relaxant activity of chelidonine, protopine, coptisine, and Chelidonium majus extracts on isolated guinea-pigs lleum Karl, O.H.;Majid, G.;Heinz, S. https://doi.org/10.1055/s-2006-957576
  10. Planta Med. v.43 Antiinflammatory activity of quaternary benzophenanthridine alkaloids from Chelidonium majus Lenfeld, J.;Kroutil, M.;Marsalek, E.;Slavik, J.;Preininger, V.;Simanek, V. https://doi.org/10.1055/s-2007-971493
  11. Phytother. Res. v.15 Inhibitory effects of sanguinarine on monoamine oxidase activity in mouse brain Lee, S.S.;Kai, M.;Lee, M.K. https://doi.org/10.1002/ptr.703
  12. Euro. J. Cell. Biol. v.80 The effects of chelidonine on tubulin polymerization, cell cycle progression and selected signal transmission pathways Annie, P.;Anna, M.J.;Pepita, C.B.;Ernest, H.;Johanna, C.S. https://doi.org/10.1078/0171-9335-00135
  13. Annales Pharmaceutici v.13 Cytotoxic acitivity of some Chelidonium majus alkaloids on human and animal tumor cell cultures in vitro Hladon, B.;Kowalewski, Z.;Bobkiewicz, T.;Gronostaj, K.
  14. Planta Med. v.62 Benzophenanthridine alkaloids of Chelidonium majus E. Inhibition of 5- and 12-lipoxygenase by a non-redox mechanism Vavreckova, C.;Gawlik, I.;Muller, K. https://doi.org/10.1055/s-2006-957924
  15. Planta Med. v.62 Benzophenanthridine alkaloids of Chelidonium majus II. Potent inhibitory action against the growth of human keratinocytes Vavreckova, C.;Gawlik, I.;Muller, K. https://doi.org/10.1055/s-2006-957955
  16. J. Nat. Prod. v.46 The alkaloids of Corydalis meifolia Bhakuni, D.S.;Chaturnedi, R. https://doi.org/10.1021/np50027a004
  17. Biomed. Res. v.25 Influence of chelidonine, an inhibitor of tubulin polymerization on tyrosine kinase activity in normal, transformed and malignant cell lines Joubert, A.;Lottering, M.L.;Panzer, A. https://doi.org/10.2220/biomedres.25.27
  18. Free Radic. Biol. Med. v.12 Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids Martinez, L.A.;Rios, J.L.;Paya, M.;Alcaraz, M.J. https://doi.org/10.1016/0891-5849(92)90116-X
  19. Arch. Pharm. Res. v.27 Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells Jang, S.I.;Kim, B.H.;Lee, W.Y.;An, S.J.;Choi, H.G.;Jeon, B.H.;Chung, H.T.;Rho, J.R.;Kim, Y.J.;Chai, K.Y. https://doi.org/10.1007/BF02975845
  20. J. Nat. Cancer Insti. v.82 New colorimetric cytotoxicity assay for anticancer drug screening Skehan, P.;Storeng, R.;Scudiero, D.;Monks, A.;McMahon, J.;Vistica, D.;Warren, J.T.;Bokesch, H.;Kenney, S.;Boyd, M.R. https://doi.org/10.1093/jnci/82.13.1107
  21. J. Org. Chem. v.45 Total synthesis of $({\pm})-chelidonine$ Cushman, M.;Choong, T. C.;Valko, J.T.;Koleck, M.P. https://doi.org/10.1021/jo01313a011
  22. J. Org. Chem. v.53 Exploratory, mechanistic, and synthetic aspects of silylarene-iminium salt SET photochemistry. Studies of diradical cyclization processes and applications to protoberberine alkaloid synthesis Dai-Ho, G.;Mariano, P.S. https://doi.org/10.1021/jo00256a038