A Cytotoxic Monoterpene-Neolignan from the Stem Bark of Magnolia officinalis

  • Youn, Ui-Joung (College of Pharmacy, Chungnam National University) ;
  • Lee, Ik-Soo (College of Pharmacy, Chungnam National University) ;
  • Chen, Quan Cheng (College of Pharmacy, Chungnam National University) ;
  • Na, Min-Kyun (College of Pharmacy, Yeungnam University) ;
  • Jung, Hyun-Ju (Department of Oriental Pharmacy, Wonkwang University) ;
  • Lee, Sang-Myung (KT&G Central Research Institute) ;
  • Choi, Jae-Sue (Faculty of Food Sciences and Biotechnology. Pukyoung National University) ;
  • Woo, Mi-Hee (College of Pharmacy, Catholic University of Daegu) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu)
  • 투고 : 2011.02.28
  • 심사 : 2011.04.19
  • 발행 : 2011.06.30

초록

A monoterpene-neolignan, piperitylmagnolol (1), was isolated from the stem bark of Magnolia officinalis, together with syringaresinol (2), caffeic acid (3), and sinapaldehyde (4). The isolated compounds were established on the basis of spectroscopic and physicochemical analyses including 1D- and 2D-NMR techniques, as well as on comparing the spectral data with those in the literature and of authentic samples. Compounds 1 - 4 were tested for their cytotoxic activity against the HeLa, K562, A549, and HCT116 cancer cell lines in vitro. Of the isolates, piperitylmagnolol (1) exhibited cytotoxic activity against the tested cancer cell lines with $IC_{50}$ values of 7.7 - 9.5 ${\mu}g/ml$.

키워드

참고문헌

  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. Fujita, M., Itokawa, H., and Sashida, Y., Components of Magnolia obovata. III. Occurrence of magnolol (5,5'-diallyl-2,2'-dihydroxybiphenyl) and honokiol in M. obovata and other allied plants. Yakugaku Zasshi 20, 212-213 (1972).
  3. 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
  4. Kashiwagi, T., Nakashima, T., Tebayashi, S.I., and Kim, C.S., Determination of the absolute configuration of quercivorol, (1S,4R)-pmenth- 2-en-1-ol, an aggregation pheromone of the ambrosia beetle Platypus quercivorus (Coleoptera: Platypodidae). Biosci. Biotechnol. Biochem. 70, 2544-2546 (2006). https://doi.org/10.1271/bbb.60211
  5. 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
  6. 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
  7. Park, J.A., Kim, H.J., Jin, C., Lee, K.T., and Lee, Y.S., A new pterocarpan, (−)-maackiain sulfate, from the roots of Sophora subprostrata. Arch. Pharm. Res. 26, 1009-1013 (2003). https://doi.org/10.1007/BF02994750
  8. Sakakibara, N., Nakatsubo, T., Suzuki, S., Shibata, D., Shimada, M., and Umezawa, T., Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method. Org. Biomol. Chem. 5, 802-815 (2007). https://doi.org/10.1039/b616705e
  9. Shin, T.Y., Kim, D.K., Chae, B.S., and Lee, E.J., Antiallergic action of Magnolia officinalis on immediate hypersensitivity reaction. Arch. Pharm. Res. 24, 249-255 (2001). https://doi.org/10.1007/BF02978266
  10. 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
  11. Syu, W., Shen, C.C., Lu, J.J., Lee, G.H., Sun, C.M., Antimicrobial and cytotoxic activities of neolignans from Magnolia officinalis. Chem. Biodiv. 1, 530-537 (2004). https://doi.org/10.1002/cbdv.200490046
  12. Teng, C.M., Yu, S.M., Chen, C.C., Huang, Y.L., and Huang, T.F., EDRFrelease and calcium-channel blockade by magnolol, an antiplatelet agent isolated from Chinese herb Magnolia officinalis, in rat thoracic aorta. Life Sci. 47, 1153-1161 (1990). https://doi.org/10.1016/0024-3205(90)90176-R
  13. Watanabe, K., Pharmacology of magnolia bark with special reference to gastrointestinal functions. Gendai Toyo Igaku 7, 54-59 (1986).
  14. 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
  15. 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