Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Phytochemical Studies on Magnoliae Flos (I) Isolation of Lignans from the Flower Buds of Magnolia biondii

  • Lee, Dong Hwa (Department of Food Science and Nutrition, Andong National University) ;
  • Kwon, Soon Youl (Gyeongbuk Institute for Bio Industry) ;
  • Woo, Mi Hee (Department of Pharmacology, College of Pharmacy, Daegu Catholic University) ;
  • Lee, Je Hyun (Department of Korean Medicine, Dongguk University) ;
  • Son, Kun Ho (Department of Food Science and Nutrition, Andong National University)
  • Received : 2013.05.20
  • Accepted : 2013.06.24
  • Published : 2013.06.30
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Abstract

The 12 compounds were isolated from MeOH extract of Magnolia biondii and their structures were identified as seven lignans, two phenolics, one coumarin, and two flavonoid compounds, respectively. Among these constituents, tiliroside (3), kaempferol-7-methyl ether (4), 4-hydroxybenzoic acid (5), vanilic acid (6), and scopoletin (9) were isolated from Magnolia biondii for the first time.

Keywords

References

  1. Chen, G. and Feng, Y., Analysis of the extract substrates of Magnolia biondii Pamp. by GC/MS. Guangdong Yaoxueyuan Xuebao. 19, 99-100 (2003).
  2. Chen, W., Liu, Q., Feng, S., and Jiang, F., The research on anti-allergic rhinitis dose form of Ganxin spray. Zhongguo Xiandai Yingyong Yaoxue. 23, 94-96 (2006).
  3. Chen, Y., He, Y., Li, X., and Qin, X., Study of the chemical constitution of essential oils from Magnolia biondii Pamp. Linchan Huaxue Yu Gongye. 14, 46-50 (1994).
  4. Do, J.C., Yu, Y.J., Jung, K.Y., and Son, K.H., Flavonoids from the leaves of Polygala japonica. Kor. J. Phamacogn. 23, 9-13 (1992).
  5. Du, J., Wang, M., Chen, R., and Yu, D., Chemical constituents from the leaves of Magnolia denudata. JANPR. 3, 313-319 (2001).
  6. Fang, H., Guo, Q., Su, W., Deng, F., and Wang, K., RP-HPLC determination of magnolin in chinese medicine Xinyi. Yaowu Fenxi Zazhi. 2, 342-345 (2002).
  7. Iida, T., Nakano, M., and Ito, K., Hydroperoxy sesquterpene and lignan constituents of Magnolia kobus. Phytochemistry 21, 673-675 (1982). https://doi.org/10.1016/0031-9422(82)83163-4
  8. Kim, G.C., Lee, S.G., Park, B.S., Kim, J.Y., Song, Y.S., Kim, J.M., Yoo, K.S., Huh, G.Y., Jeong, M.H., Lim, Y.J., Kim, H.M., and Yoo, Y.H., Magnoliae flos induces apoptosis of RBL-2H3 cells via mitochondria and caspase. Int. Arch. Allergy Immunol. 131, 101-110 (2003). https://doi.org/10.1159/000070925
  9. Kimura, I., Chui, L., Fujitani, K., Kikuchi, T., and Kimura, M.,Inotropic effects of (${\pm}$)-higenamine and its chemically related compounds, (${\pm}$)-R-coclaurine and (${\pm}$)-S-reticuline, contained in the traditional Sino-Japanese medicines "Bushi" and "Shin-i" in isolated guinea pig papillary muscle. Japan. J. Pharmcol. 50, 75-78 (1989). https://doi.org/10.1254/jjp.50.75
  10. Kimura, I., Kimura, M., Yoshizaki, M., Yanada, K., Kadota, S., and Kikuchi, T., Neuromuscular blocking action of alkaloids from a Japanese crude drug "SHIN-I" (Flos Magnoliae) in frog skeletal muscle. Planta Med. 48, 43-47 (1983). https://doi.org/10.1055/s-2007-969876
  11. Kimura, M., Suzuki, J., Yamada, T., Yoshizaki, M., Kikuchi, T., Kadata, S., and Matsuda, S., Anti-inflammatory effect of neolignans newly isolated from the crude drug "SHIN-I" (Flos Magnoliae). Planta Med. 51, 291-293 (1985). https://doi.org/10.1055/s-2007-969493
  12. Kobayashi, S., Kimura, I., and Kimura, M., Inhibitory effect of magnosalin derived from Flos magnoliae on tube formation of rat vascular endothelial cells during the angiogenic process. Biol. Pharm. Bull. 19, 1304-1306 (1996). https://doi.org/10.1248/bpb.19.1304
  13. Kuroyanagi, M., Fukuoka, M., Yoshihira, K., and Natori, S., Confirmation of the structure of tiliroside, An acylated kaempferol glycoside, by 13C-nuclear magnetic resonance. Chem. Pharm. Bull. 26, 3594-3596 (1978). https://doi.org/10.1248/cpb.26.3594
  14. Kwon, B.M., Jung, H.J., Lim, J.H., Kim, Y.S., Kim, M.K., Kim, Y.K., Bok, S.H., Bae, K.H., and Lee, I.R., Acyl-CoA; Cholesterol acyltransferase inhibitory activity of lignans isolated from Schizandra, Machilus, and Magnolia species. Planta Med. 65, 74-76 (1999). https://doi.org/10.1055/s-2006-960443
  15. Li, J., Tanaka, M., Kurasawa, K., Ikeda, T., and Nohara, T.,Lignan and neolignan derivatives from Magnolia denudata. Chem. Pharm. Bull. 53, 235-237 (2005). https://doi.org/10.1248/cpb.53.235
  16. Lim, J.P. and Park, Y.S., Anti-inflammatory activity of the ethanol extract from Magnoliae flos on PAR2-mediated edema. Korean J. Medicinal Corp Sci. 13, 245-249 (2005).
  17. Ma, Y. and Han, G., Biologically active lignins from Magnolia biondii pump. Zhongguo Zhong Yao ZaZhi 20, 102-104 (1995).
  18. Ma, Y., Huang, Q., and Han, G., A neolignan and lignans from Magnolia biondii. Phytochemistry 41, 287-288 (1996). https://doi.org/10.1016/0031-9422(95)00578-1
  19. Miyazawa, M., Kasahara, H., and Kameoka, H., Phenolic lignans from flower buds of Magnolia fargesii. Phytochemistry 31, 3666-3668 (1992). https://doi.org/10.1016/0031-9422(92)83756-O
  20. Nakano, T., Studies on the alkaloids of magnoliaceous plants. XVI. Alkaloids of Magnolia denudate Desr. Planta Med. 4, 67-68 (1956).
  21. Okuno, I., Uchida, K., Nakamura, M., and Sakurawi, K., Studies on choleretic constituents in Artemisia capillaries Thunb. Chem. Pharm. Bull. 36, 769-775 (1988). https://doi.org/10.1248/cpb.36.769
  22. Pan, J.X., Hensens, O.D., Zink, D.L., Chang, M.N., and Hwang, S.B., Lignans with platelet activating factor antagonist activity from Magnolia biondii. Phytochemistry 26, 1377-1379 (1987). https://doi.org/10.1016/S0031-9422(00)81816-6
  23. Talapatra, B., Chaudhuri, P.K., and Talapatra, S.K., (−)-Maglifloenone, a novel spirocyclohexadienoneneo lignan and other constituents from Magnolia liliflora. Phytochemistry 21, 747-750 (1982). https://doi.org/10.1016/0031-9422(82)83180-4
  24. Tsuruga, T., Ebizuka, Y., Nakajima, J., Chun, Y.T., and Noguchi, H., Biologically active constituents of Magnolia salicifolia: Inhibitors of induced histamine release from rat mast cells. Chem. Pharm. Bull. 39, 3265-3271 (1991). https://doi.org/10.1248/cpb.39.3265
  25. Wang, W., Shen, Y., and Qi, Y., A pharmacodynamic study on volatile oil of flos Magnolia. Shanxi YiyaoZazhi 29, 206-207 (2000).
  26. Wang, W., Shen, Y., Qi, Y., Liu, J., and Song, J., Anti-inflammatory mechanism of the volatile oil of Magnolia biondii Pamp. Zhongguo Shouyi Xuebao 25, 301-303 (2005).
  27. Watanabe, H., Ikeda, M., Watanabe, K., and Kikuchi, T., Effects on central dopaminergic systems of d-Coclaurine and d-Reticuline, extracted from Magnolia salicifolia. Planta Med. 42, 213-222 (1981). https://doi.org/10.1055/s-2007-971630
  28. Xu, G.H., Kim, J.A., Park, S.H., Son, A.R., Chang, T.S., Chang, H.W., Chung, S.R., and Lee, S.H., Isolation of melanin biosynthesis inhibitory compounds from the flowers of Magnolia denudata. Kor. J. Pharmacogn. 35, 152-156 (2004).
  29. Xu, L., Cui, B., and Yu, Z., RP-HPLC determination of magnolin and fargesin in Flos Magnoliae. Yaowu Fenxi Zazhi 23, 426-427 (2003).
  30. Yaguchi, Y., Sakurai, N., Nagai, M., and Inoue, T., Constituents of Myrica rubra; Structures of two glycosides of myricanol. Chem. Pharm. Bull. 36, 1419-1424 (1988). https://doi.org/10.1248/cpb.36.1419
  31. Yazaki, K., Fukui, H., and Tabata, M., Accumulation of p-O-${\beta}$-Dglucosylbenzoic acid and its relation to shikonin biosynthesis in lithospermum cell cultures. Phytochemistry 25, 1629-1632 (1986). https://doi.org/10.1016/S0031-9422(00)81223-6
  32. Yin, M.H., Kang, D.G., Choi, D.H., Kwon, T.O., and Lee, H.S., Screening of vasorelaxant activity of some medicinal plants used in oriental medicines. Journal of Ethnopharmacology 99, 113-117 (2005). https://doi.org/10.1016/j.jep.2005.02.013
  33. Yu, Z., Sun, Z., Su, B., and Liu, Q., Determination of biondnoid in flower buds of Magnolia biondii Pamp. by HPLC. Zhongcaoyao 35, 574-575 (2004).
  34. Zang, K., Zhu, F., Qu, X., and Liu, R., Proximate analysis of volatile oil of Magnolia liliflora by supercritical CO2 extraction. Huaxue Fenxi Jiliang 14, 25-27 (2005).