Lignans from the Stem Barks of Kalopanax septemlobus

  • Published : 2006.12.30

Abstract

Four lignans were isolated from the $CH_2Cl_2-soluble$ fraction of the stem barks of Kalopanax septemlobus and their structures were established as (-)-7R,8S-dehydrodiconiferyl alcohol (1), (-)-simulanol (2), (-)-secoisolariciresinol (3), and $({\pm})-liriodendrin$ (4) based on the spectroscopic methods including MS, $^1H-$ and $^{13}C-NMR$ spectral data.

Keywords

References

  1. Agrawal, P.K. and Rastogi, R.P., Two lignans from Cedrus deodara. Phytochemistry, 21, 1459-1461 (1982) https://doi.org/10.1016/0031-9422(82)80172-6
  2. Choi, J., Han, Y.N., Lee, K.T., Park, K.Y., Kwak, T.S., Kwon. S.H., and Park, H.J., Anti-lipid peroxidative principles from the stem bark cf Kalopanax pictus Nakai. Arch. Pharm. Res., 24, 536-540 (2001) https://doi.org/10.1007/BF02975161
  3. Hong, S.S., Han, D.I., Hwang, B.Y., Choi, W.H., Kang, H.S., Lee, M.K., Lee, D.K. Lee, K.S., and Ro, J.S. Chemical components from the stem barks of Kalopanax septemlobus. Kor. J. Pharmacogn., 32, 302-306 (2001)
  4. Jung, B.S. and Shin, M.K., Encyclopedia of illustrated Korean natural drugs. Young Lim Sa, Seoul, pp. 437-438 (1990)
  5. Jung, K.Y., Son, K.H., and Do, J.C., Flavonol glycosides from the leaves of Kalopanax pictum. Kor. J. Pharmacogn., 23, 280-282 (1992)
  6. Kim, D.H., Bae. E.A., Han, M.J., Park, H.J., and Choi, J.W., Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites. Biol. Pharm. Bull., 25, 68-71 (2002) https://doi.org/10.1248/bpb.25.68
  7. Kim, D.H., Yu, K.W., and Bae, E.A., Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites. Biol. Pharm. Bull., 21, 360-365 (1998a) https://doi.org/10.1248/bpb.21.360
  8. Kim, D.W., Bang, K.H., Rhee, Y.H., Lee, K.T., and Park, H.J., Growth inhibitory activities of kalopanaxsaponins A and I against human pathogenic fungi. Arch. Pharm. Res., 21, 688-691 (1998b) https://doi.org/10.1007/BF02976758
  9. Kim, Y.K., Kim, R.G., Park, S.J., Ha, J.H., Choi, J.W., Park, H.J., and Lee, K.T., In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells. Biol. Pharm. Bull., 25, 472-476 (2002) https://doi.org/10.1248/bpb.25.472
  10. Lee, K.T., Sohn, I.C., Park, H.J., Kim, D.W., Jung, G.O., and Park, K.Y., Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bisdesmosides isolated from the stem bark of Kalopanax pictus. Planta Med., 66, 329-332 (2000) https://doi.org/10.1055/s-2000-8539
  11. Lee, M.W., Kim, S.U., and Hahn, D.R., Antifungal activity of modified hederagenin glycosides from the leaves of Kalopanax pictum var. chinense. Biol. Pharm. Bull., 24, 718-719 (2001) https://doi.org/10.1248/bpb.24.718
  12. Li, D.W., Hyun, J.E., Jeong, C.S., Kim, Y.S., and Lee, E.B., Antiinflammatory activity of ${\alpha}$-hederin methyl ester from the alkaline hydrolysate of the butanol fraction of Kalopanax pictus bark extract. Biol. Pharm. Bull., 26, 429-433 (2003) https://doi.org/10.1248/bpb.26.429
  13. Li, D.W., Lee, E.B., Kang, S.S., Hyun, J.E., and Whang, W.K., Activity-guided isolation of saponins from Kalopanax pictus with anti-inflammatory activity. Chem. Pharm. Bull., 50, 900-903 (2002) https://doi.org/10.1248/cpb.50.900
  14. Li, S., Iliefski, T., Lundquist, K., and Wallis, A.F.A., Reassignment of relative stereochemistry at C-7 and C-8 in arylcoumaran neolignans. Phytochemistry, 46, 929-934 (1997) https://doi.org/10.1016/S0031-9422(97)00360-9
  15. Park, H.J., Kim, D.H., and Choi, J.W., A potent anti-diabetic agent from Kalopanax pictus. Arch. Pharm. Res., 21, 24-29 (1998) https://doi.org/10.1007/BF03216748
  16. Park, H.J., Kwon, S.H., Lee, J.H., Lee, K.H., Miyamoto, K., and Lee, K.T., Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides. Planta Med., 67, 118-121 (2001) https://doi.org/10.1055/s-2001-11516
  17. Porzel, A., Sung, T.V., Schmidt, J., Lischewski, M., and Adam, G., Studies on the chemical contituents of Kalopanax septemlobus. Planta Med., 58, 481-482 (1992) https://doi.org/10.1055/s-2006-961526
  18. Sano, K., Sanada, S., Ida, Y., and Shoji, J., Studies on the constituents of the bark of Kalopanax pictus Nakai. Chem. Pharm. Bull., 39, 865-870 (1991) https://doi.org/10.1248/cpb.39.865
  19. Shao, C.J., Kasai, R., Ohtani, K., Tanaka, O., and Kohda, H., Saponins from leaves of Kalopanax pictus (Thunb.) Nakai, Harigiri: Structures of kalopanax saponins JLa and JLb. Chem. Pharm. Bull., 38, 1087-1089 (1990) https://doi.org/10.1248/cpb.38.1087
  20. Shao, C.J., Kasai, R., Ohtani, K., Xu, J.D., and Tanaka, O., Saponins from leaves of Kalopanax septemlobus (Thunb.) Koidz.: Structures of kalopanaxsaponins La, Lb and Lc. Chem. Pharm. Bull., 37, 3251-3254 (1989a) https://doi.org/10.1248/cpb.37.3251
  21. Shao, C.J., Kasai, R., Xu, J.D., and Tanaka, O., Saponins from roots of Kalopanax septemlobus (Thunb.) Koidz., Ciqiu: Structures of kalopanaxsaponin C, D, E, and F. Chem. Pharm. Bull., 37, 311-314 (1989b) https://doi.org/10.1248/cpb.37.311
  22. Shin, J.S., Kim, Y.M., Hong, S.S., Kang, H.S., Yang, Y.J., Lee, D.K., Hwang, B.Y., Ro, J.S., and Lee, M.K., Induction of neurite outgrowth by (-)-(7R,8S)-dihydrodehydrodiconiferyl alcohol from PC12 cells. Arch. Pharm. Res., 28, 1337-1340 (2005) https://doi.org/10.1007/BF02977898
  23. Tan, R.X., Jakupovic, J., and Jia, Z.J., Aromatic constituents from Vladimiria souliei. Planta Med., 56, 475-477 (1990) https://doi.org/10.1055/s-2006-961015
  24. Xie, L.H., Akao, T., Hamasaki, K., Deyama, T., and Hattori, M., Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chem. Pharm. Bull., 51, 508-515 (2003) https://doi.org/10.1248/cpb.51.508
  25. Yang, Y.P., Cheng, M.J., Teng, C.M., Chang, Y.L., Tsai, I.L., and Chen, I.S. Chemical and anti-platelet constituents from Formosan Zanthoxylum simulans. Phytochemistry, 61, 567-572 (2002) https://doi.org/10.1016/S0031-9422(02)00268-6
  26. Yeo, H., Chin, Y.W., Park, S.Y., and Kim, J., Lignans of Rosa multiflora roots. Arch. Pharm. Res., 27, 287-290 (2004) https://doi.org/10.1007/BF02980061
  27. Yuen, M.S. M., Xue, F., Mak, T.C. W., and Wong, H.N.C., On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton. Tetrahedron, 54, 12429-12444 (1998) https://doi.org/10.1016/S0040-4020(98)00725-X