Two Acylglycerylgalactosides and a New Sesquiterpene Galactoside from the Flowers of Hemisteptia lyrata Bunge

  • Ha, Tae-Joung (Yeongnam Agricultural Research Institute, National Institute of Crop Science, RDA) ;
  • Lee, Jin-Hwan (Yeongnam Agricultural Research Institute, National Institute of Crop Science, RDA) ;
  • Hwang, Seon-Woo (Division of Applied Life Science (BK21 program), Institute of Agriculture & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Lee, Jun (Division of Applied Life Science (BK21 program), Institute of Agriculture & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Kang, Nam-Suk (Yeongnam Agricultural Research Institute, National Institute of Crop Science, RDA) ;
  • Park, Keum-Yong (Yeongnam Agricultural Research Institute, National Institute of Crop Science, RDA) ;
  • Suh, Duck-Yong (Yeongnam Agricultural Research Institute, National Institute of Crop Science, RDA) ;
  • Park, Ki-Hun (Division of Applied Life Science (BK21 program), Institute of Agriculture & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University) ;
  • Yang, Min-Suk (Division of Applied Life Science (BK21 program), Institute of Agriculture & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University)
  • Published : 2006.03.30

Abstract

The flowers of Hemisteptia lyrata B. afforded two known acylglycerylgalactosides, 2',3'-di-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (1) and 2'-O-(9Z,12Z,15Z-octadecatrienoyl)glyceryl ${\beta}$-D-galactopyranoside (2), and a new sesquiterpene galactopyranoside, 7-eudesmene-1${\beta}$,4${\beta}$-diol-1-O-${\beta}$-D-galactopyranoside (3). This is the first time that galactopyranosides (1-3) have been isolated from the genus Hemisteptia. Their structures and stereochemistry were elucidated by 1D and 2D NMR data, including COSY, NOESY and HMBC experiments.

Keywords

References

  1. Peoples Press (1977) In Encyclopedia of the Traditional Chinese Materia Medica. pp. 1458-1459, Shanghai, P. R. China
  2. Ha, T. J., Park, K. H., Jang, D. S., Lee, J. R., Park, K. M. and Yang, M. S. (2003) New sesquiterpene lactones from Hemisteptia lyrata Bunge. Heterocycles 60, 623-629 https://doi.org/10.3987/COM-02-9669
  3. Ha, T. J., Lee, K. D., Lee, J. R., Lee. J., Park, K. H. and Yang, M. S. (2001) Studies on the constituents from the flowers of Hemisteptia lyrata (Bunge) (I). Kor. J. Pharmacogn. 32, 238-241
  4. Ha, T. J., Hwang, S. W., Jung, H. J., Park, K. H. and Yang, M. S. (2002) Apigenin, tyrosinase inhibitor from the flowers of Hemisteptia lyrata Bunge. Agric. Chem. Biotechnol. 45, 170-172
  5. Ha, T. J., Jang, D. S., Lee, K. D., Lee, J. R., Park, K. H. and Yang, M. S. (2002) Studies on the constituents from the flowers of Hemisteptia lyrata Bunge II, Kor. J. Pharmacogn. 33, 92-95
  6. Ha, T. J., Jang, D. S., Lee, J. R., Lee, K. D., Lee, J., Hwang, S. W., Jung, H. J., Nam, S. H., Park, K. H. and Yang, M. S. (2003) Cytotoxic effects of sesquiterpene lac- tones from the flowers of Hemisteptia lyrata B. Arch. Pharm. Res. 26, 925-928 https://doi.org/10.1007/BF02980201
  7. Ha, T. J., Yang, M. S., Pak, Y. B., Lee, J. R., Lee, K. D., Kim, H. M. and Park, K. H. (2002) New guaiane-type sesquiterpene lactones from Hemisteptia lyrata Bunge. Heterocycles 57, 151-155 https://doi.org/10.3987/COM-01-9387
  8. Jang, D. S., Park, K. H., Lee, J. R., Ha, T. J., Park, Y. B., Nam, S. H. and Yang, M. S. (1999) Antibacterial activities of sesquiterpene lactones isolated from Hemisteptia lyrata, Chrysanthemum zawadskii and Chrysanthemum boreale. J. Korean Soc. Agric. Chem. Biotechnol. 42, 176-179
  9. Jimeno, M. L., Fernandez-Mayoralas, A., Martin-Lomas, M. and Alemany, A. (1987) $^{13}C$-N.m.r. studies of peracetylated derivatives of O-\alpha-and O-$\beta_{-D}$-galactopyranosyl-(1→3)-and- (1→4)-$\alpha_{-D}$-galactopyranose. Carbohydr. Res. 161, 144-149 https://doi.org/10.1016/0008-6215(87)84013-2
  10. Son, B. W. (1990) Glycolipids from Gracilaria verrucosa. Phytochemistry 29, 307-309 https://doi.org/10.1016/0031-9422(90)89057-G
  11. Kobayashi, M., Hayashi, K., Kawazoe, K. and Kitagawa, I. (1992) Marine natural products. XXIX_{1)}. Heterosigma-glycolipids I, II, III, and IV, four diacyl-glyceroglycolipids prossessing \omega-3-polyunsaturated fatty acid residues, from the raphidophycean dinoflagellate Heterosigma akashiwo. Chem. Pharm. Bull. 40, 1404-1410 https://doi.org/10.1248/cpb.40.1404
  12. Wang, R., Furumoto, T., Motoyama, K., Okazaki, K., Kondo, A. and Fukui, H. (2002) Possible antitumor promoters in Spinacia oleracea (spinach) and comparison of their contents among cultivars. Biosci. Biotechnol. Biochem. 66, 248-254 https://doi.org/10.1271/bbb.66.248
  13. Weil, M. J., Zhang, Y. and Nair, M. G. (2005) Tumor cell proliferation and cyclooxygenase inhibitory constituents in horseradish (Armoracia rusticana) and wasabi (Wasabia japonica). J. Agric. Food Chem. 53, 1440-1444 https://doi.org/10.1021/jf048264i
  14. Larsen, E., Kharazmi, A., Christensen, L. P. and Christensen, S. B. (2003) An anti-inflammatory galactolipid from rose hip (Rosa canina) that inhibits chemotaxis of human peripheral blood neutrophils in vitro. J. Nat. Prod. 66, 994- 995 https://doi.org/10.1021/np0300636
  15. Murakami, A., Nakamura, Y., Koshimizu, K. and Ohigashi, H. (1995) Glyceroglycolipids from Citrus hystrix, a traditional herb in Thailand,, potently inhibit the tumor-promoting activity of 12-O-tetradecanoylphorbol 13-acetate in mouse skin. J. Agric. Food Chem. 43, 2779-2783 https://doi.org/10.1021/jf00058a043
  16. Herz, W. and Watanabe, K. (1983) Sesquiterpene alcohols and triterpenoids from Liatris microcephala. Phytochemistry 22, 1457-1459 https://doi.org/10.1016/S0031-9422(00)84035-2
  17. Feliciano, A., Medarde, M., Gordaliza, M., Del Olmo, E. and Del Corral, M. (1989) Sesquiterpenoids and phenolics of Pulicaria paludosa. Phytochemistry 28, 2717-2721 https://doi.org/10.1016/S0031-9422(00)98074-9