Cytotoxic Compounds from the Stem Bark of Magnolia obovata

  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu) ;
  • Youn, Ui-Joung (College of Pharmacy, Chungnam National University) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Published : 2008.06.30

Abstract

Two sesquiterpenes (1 - 2), a tetralone (3), and two phenylpropanoids (4 - 5) were isolated from the stem bark of Magnolia obovata Thunberg (Magnoliaceae) through repeated column chromatography. Their structures were identified as ${\beta}-eudesmol$ (1), cryptomeridiol (2), 4R-4,8-dihydroxy-${\beta}-tetralone$ (3), trans-pcoumaryl aldehyde (4), and p-coumaric acid (5) on the basis of spectroscopic analysis including two dimensional NMR and mass. Compounds 1 - 3 were tested in vitro for their cytotoxic activity against the K562, HeLa, A549, and HCT116 cancer cell lines. However, compounds 1 - 3 were inactive in this assay system.

Keywords

References

  1. Bae, E.A., Han, M.J., Kim, N.J., and Kim, D.H., Anti-Helicobacter pylori activity of herbal medicines. Biol. Pharm. Bull. 21, 990-992 (1998) https://doi.org/10.1248/bpb.21.990
  2. Chang, B.S., Lee, Y.M., Ku, Y., Bae, K.H., and Chung, C.P., Antimicrobial activity of magnolol and honokiol against periodontopathic microorganisms. Planta Med. 64, 367-369 (1998) https://doi.org/10.1055/s-2006-957453
  3. Fujita, M., Itokawa, H., and Sashida, Y., Honokiol, a new phenolic compound isolated from the bark of Magnolia obovata. Chem. Pharm. Bull. 20, 212-213 (1972) https://doi.org/10.1248/cpb.20.212
  4. Fukuyama, Y., Otoshi, Y., Miyoshi, K., Nakamura, K., Kodama, M., Nagasawa, M., Hasegawa, T., Okazaki, H., and Sugawara, M., Neurotrophic sesquiterpene-neolignans from Magnolia obovata: structure and neurotrophic activity. Tetrahedron 48, 377-392 (1992) https://doi.org/10.1016/S0040-4020(01)89002-5
  5. Hamasaki, Y., Kobayashi, I., Zaitu, M., Tsuji, K., Kita, M., Hayasaki, R., Muro, E., Yamamoto, S., Matsuo, M., Ichimaru, T., and Miyazaki, S., Magnolol inhibits leukotriene synthesis in rat basophilic leukemia-2H3 cells. Planta Med. 65, 222-226 (1999) https://doi.org/10.1055/s-1999-13984
  6. Iiyama, K., Lam, T.B.T., and Stone, B.A., Phenolic acid bridges between polysaccharides and lignin in wheat internodes. Phytochemistry 29, 733-737 (1990) https://doi.org/10.1016/0031-9422(90)80009-6
  7. Ikeda, K., Sakai, Y., and Nagase, H., Inhibitory effect of magnolol on tumor metastasis in mice. Phytotherapy Res. 17, 933-937 (2003) https://doi.org/10.1002/ptr.1264
  8. Kim, Y.K., and Ryu, S.Y., Cytotoxic components from stem bark of Magnolia obovata. Planta Med. 65, 291-292 (1999) https://doi.org/10.1055/s-2006-960784
  9. Kokubun, T., Veitch, N.C., Bridge, P.D., and Simmonds, M.S.J., Dihydroisocoumarins and a tetralone from Cytospora eucalypticola. Phytochemistry 62, 779-782 (2003) https://doi.org/10.1016/S0031-9422(02)00606-4
  10. Min, B.S., Nakamura, N., Miyashiro, H., Kim Y.H., and Hattori, M., Inhibition of human immunodeficiency virus type I reverse transcriptase and ribonuclease H activities by constituents of Juglans mandshurica. Chem. Pharm. Bull. 48, 194-200 (2000) https://doi.org/10.1248/cpb.48.194
  11. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  12. Namba, T., Tsunezuka, M., and Hattori, M., Dental caries prevention by traditional Chinese medicines. Part II. Potent antibacterial action of Magnoliae Cortex extracts against Streptococcus mutans. Planta Med. 44, 100-106 (1982) https://doi.org/10.1055/s-2007-971412
  13. Shoji, Y., Takashi, N., Akihide, K., Toshihiro, N., and Itsuo, N., Isolation and characterization of phenolic compounds from Magnoliae Cortex produced in China. Chem. Pharm. Bull. 39, 2024-2036 (1991) https://doi.org/10.1248/cpb.39.2024
  14. Stange, R.R., Sims, J.J., Midland, S.L., and McDonald, R.E., Isolation of a phytoalexin, trans-p-coumaryl aldehyde, from Cucubita maxima, Cucurbitaceae. Phytochemistry 52, 41-43 (1999) https://doi.org/10.1016/S0031-9422(99)00111-9
  15. Youn, U., Chen, Q.C., Lee, IS., Kim, H.J., Hung, T.M., Na, M.K., Lee, J., Min, B.S., and Bae, K., Sesquiterpene-neolignans from the stem bark of Magnolia obovata and their cytotoxic activity. Nat. Prod. Sci. 14, 51-55 (2008)
  16. Viqar, U.A., Tanveer, A.F., Kaniz, F., Azar, S., and Rasheeda, K., J. Nat. Prod. 55, 730-735 (1992) https://doi.org/10.1021/np50084a004
  17. Wang, J.P., Ho, T.F., Chang, L.C., and Chen, C.C., Anti-inflammatory effect of magnolol, isolated from Magnolia officinalis, on A23187-induced pleurisy in mice. J. Pharm. Pharmacol. 47, 857-860 (1995) https://doi.org/10.1111/j.2042-7158.1995.tb05754.x
  18. Watanabe, K., Pharmacology of magnolia bark with special reference to gastrointestinal functions. Gendai Toyo Igaku. 7, 54-59 (1986)
  19. Watanabe, K., Watanabe, H., Goto, Y., Yamamoto, N., and Yoshizaki, M., Studies on the active principles of magnolia bark. Centrally acting muscle relaxant activity of magnolol and honokiol. Jpn. J. Pharmacol. 25, 605-607 (1975) https://doi.org/10.1254/jjp.25.605
  20. Watanabe, K., Watanabe, H., Goto, Y., Yamaguchi, M., Yamamoto, N., and Hagino, K., Pharmacological properties of magnolol and honokiol extracted from Magnolia officinalis: central depressant effects. Planta Med. 49, 103-108 (1983) https://doi.org/10.1055/s-2007-969825
  21. Yamahara, J., Miki, S., Matsuda, H., and Fujimura, H., Screening test for calcium antagonists in natural products. The active principles of Magnolia obovata. Yakugaku Zasshi 47, 1153-1161 (1990)
  22. Zhao, Y., Yue, J., Lin, Z., Dang, J., and Sun, H., Eudesmane sesquiterpenes from Laggera pterodonta. Phytochemistry 44, 459-464 (1997) https://doi.org/10.1016/S0031-9422(96)00521-3