Synthesis and Cytotoxic Activity of (R)-(-)-PGME Amide of Diterpene Acid

  • Lim, Jin-A (Department of Herbal Resources, Professional Graduate School of Oriental Medicine, and Institute of Basic Natural Sciences, Wonkwang University) ;
  • Yook, Chan-Nam (Department of Food and Nutrition, Wonkwang Health Science College) ;
  • You, Il-Soo (Department of Applied Materials Engineering, Iksan National College) ;
  • Oh, Hyun-Ju (Department of Beauty Art. Honam University) ;
  • Kim, Myung-Ju (Department of Skin & Beauty, Kwangju Health Science College) ;
  • Baek, Seung-Hwa (Department of Herbal Resources, Professional Graduate School of Oriental Medicine, and Institute of Basic Natural Sciences, Wonkwang University)
  • Published : 2005.04.25

Abstract

(R)-(-)-PGME amide of diterpene acid (2) was assigned the absolute configuration from NMR correlation experiments. The compound (2) was tested for its growth inhibitory effects against tumor cell lines by the MTT method.

Keywords

References

  1. Lorimer, S. D., Barns, G., Evans, A. C. Foster, L. M, May BCH, Perry, N. B., Tangney, R. S. Cvtotoxicity and antimicrobial activity of plants from New Zealand's subantarctic islands. Phytomed 2, 327-333, 1996.
  2. Van, Klink, J. W., Perry, N. B. Diterpenes from Anisotome flexuosa. PERU Report 7 March 1997.
  3. Bandeen, P., Perry, N. B., Weavers, R. T. Unpublished results. PERU report 1998.
  4. Harada, N., NaKanishi, K. Circular Dichroic SpectroscopyExciton coupling in Organic Stereochemistry, University Science Books, Mill Valley, CA, 1983.
  5. Fiud, J. C, Horeau, A. Kagan, H. B. In Stereochemistry, Kagan HB. Ed, Geroge Thieme Publishers, Stuttagart, Vol. 3. 1997.
  6. Van, Klink, J. W., Barlow, A. J., Perry, N. B., Weabers, R. T. A new irregular diterpene skeleton from Anisotome flexuosa. Tetrahedron Lett 40, 1409-1412, 1999.
  7. Yabuuchi, T., Kusumi, T. Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acid. J. Org. Chem 65, 397-404, 2000.
  8. Ohtani, I., Kusumi, T., Kashman, Y., KaKisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc 113, 4092-4096, 1991.
  9. Trost, B. M., Belletire, J. L., Godleski, S., McDougal, P. G., Balkovec, J. M, Baldwin, J. J., Christy, M E., Ponticello, G. S., Varga, S. L., Springer, J. P. On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols. J. Org. Chem 51(12):2370-2374, 1986.
  10. Kusumi, T., Takagashi, H., Xu, P., Fukushima. T., Asakawa, Y, Hashimoto, T., Kan, Y., Inouye, Y., New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds. Tetrahedron Lett 35, 4397, 1994.
  11. Kusumi, T., Takagashi, H., Xu, P., Fukushima. T., Asakawa, Y, Hashimoto, T., Kan, Y., Inouye, Y., New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds. Tetrahedron Lett 35, 4397, 1994.
  12. Nagai, Y., Kusurni, T. New chiral anisotropic reagents for determining the absolute configuration of carboxylic acids, Tetrahedron Lett 36, 1853-1856, 1995.