, Volume 36, Issue 7, pp 727–732 | Cite as

The occurrence of geometric polyprenol isomers in the rubber-producing plant, Eucommia ulmoides oliver

  • Takeshi Bamba
  • Ei-ichiro Fukusaki
  • Shin-ichiro Kajivama
  • Koichi Ute
  • Tatsuki Kitayama
  • Akio Kobayashi


The chain length and geometric isomerism of polyprenols from Eucommia ulmoides Oliver were analyzed using supercritical fluid chromatography. After intensive effort to establish separation conditions for geometric isomers, a phenyl-bonded silica gel-packed column was found that cleanly separated poly-trans and-cis prenols. The presence of longchain poly-trans prenols (>9 mers) was confirmed for the first time in plants. Trans isomers were found in the leaf, seed coat, and root, but not in the bark and seed. Poly-trans prenols in this plant may act as intermediates for trans-polyisoprene biosynthesis.


Bark Seed Coat Natural Rubber Supercritical Fluid Chromatography Polymerization Degree 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.



high-performance liquid chromatography


isopentenyl pyrophosphate


mass spectrometry


nuclear magnetic resonance


supercritical fluid chromatography




Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Mooibroek, H., and Cornish, K. (2000) Alternative Sources of Natural Rubber, Appl. Microbiol. Biotechnol. 53, 355–365.PubMedCrossRefGoogle Scholar
  2. 2.
    Lynen, F., and Henning, U. (1960) The Biological Pathway to Natural Rubber, Angew. Chem. 72, 820–829.Google Scholar
  3. 3.
    Aebi, P.B.A.M. (1999) The Dolichol Pathway of N-Linked Glycosylation, Biochim. Biophys. Acta 1426, 239–257.PubMedGoogle Scholar
  4. 4.
    Rowland, R.L., Latimer, P.H., and Giles, J.A. (1956) Flue-Cured Tobacco. I. Isolation of Solanesol, an Unsaturated Alcohol, J. Am. Chem. Soc. 78, 4680–4683.CrossRefGoogle Scholar
  5. 5.
    Swiezewska, E., Sasak, W., Mankowski, T., Jankowski, W., Vogtman, T., Krajewska, I., Hertel, J., Skoczylas, E., and Chojnacki, T., (1994) The Search for Plant Polyprenols, Acta Biochim. Pol. 41, 221–260.PubMedGoogle Scholar
  6. 6.
    Burgos, J., Hemming, F.W., Pennock, J.F., and Morton, R.A. (1963) Dolichol: A Naturally-Occurring C100 Isoprenoid, Biochem. J. 88, 470–482.PubMedGoogle Scholar
  7. 7.
    Thorne, K.J.I., and Kodieck, E. (1966) The Structure of Bactoprenol, Lipid Formed by Lactobacilli from Mevalonic Acid, Biochem. J. 99, 123–127.PubMedGoogle Scholar
  8. 8.
    Wanke, M., Chojnacki, T., and Swiezewska, E. (1998) The Diversity of Polyprenol Pattern in Leaves of Fruit Trees Belonging to Rosaceae and Cornaceae, Acta Biochim. Pol. 45, 811–818.PubMedGoogle Scholar
  9. 9.
    Hendricks, S.B., Wildman, S.G., and Jones, E.J. (1946) Differentiation of Rubber and Gutta Hydrocarbon in Plant Materals, Rubber Chem. Tech. 19, 427–438.Google Scholar
  10. 10.
    Bamba, T., Fukusaki, E., Kajiyama, S., Ute, K., Kitayama, T., and Kobayashi, A. (2001) High-Resolution Analysis of Polyprenols by Supercritical Fluid Chromatography, J. Chromatogr. A 911, 113–119.PubMedCrossRefGoogle Scholar
  11. 11.
    Tangpakdee, J., and Tanaka, Y. (1998) Long-Chain Polyprenols and Rubber in Young Leaves of Hevea brasiliensis, Phytochemistry 48, 447–450.CrossRefGoogle Scholar
  12. 12.
    Tanaka, Y., and Kawahara, S. (1989) Sequence Analysis of Polyprenols by 500 MHz 1H NMR Spectroscopy, Chem. Phys. Lipids, 51, 183–189.CrossRefGoogle Scholar
  13. 13.
    Rip, J.W., Rupar, C.A., Ravi, K., and Carroll, K.K. (1985) Distribution, Metabolism and Function of Dolichol and Polyprenols, Prog. Lipid Res. 24, 269–309.PubMedCrossRefGoogle Scholar
  14. 14.
    Bamba, T., Fukusaki, E., Kajiyama, S., Okazawa, A., Ute, K., Kitayama, T., and Kobayashi, A. (2000) Elucidation of Polyisoprene Biosynthesis in Plants (the first report)—Analysis of Plant Polyisoprene, [Abstract] Abstracts Annual Meeting of the Japan Society for Bioscience, Biotechnology and Biochemistry, 74, p. 2.Google Scholar

Copyright information

© AOCS Press 2001

Authors and Affiliations

  • Takeshi Bamba
    • 1
  • Ei-ichiro Fukusaki
    • 1
  • Shin-ichiro Kajivama
    • 1
  • Koichi Ute
    • 2
  • Tatsuki Kitayama
    • 2
  • Akio Kobayashi
    • 1
  1. 1.Department of Biotechnology, Graduate School of EngineeringOsaka UniversityOsakaJapan
  2. 2.Department of Chemistry, Graduate School of Engineering ScienceOsaka UniversityOsakaJapan

Personalised recommendations