Skip to main content
SpringerLink
Log in

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

  • Articles
  • Published:
Lipids

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

HPLC:

high-performance liquid chromatography

IPP:

isopentenyl pyrophosphate

MS:

mass spectrometry

NMR:

nuclear magnetic resonance

SFC:

supercritical fluid chromatography

UV:

ultraviolet

References

  1. Mooibroek, H., and Cornish, K. (2000) Alternative Sources of Natural Rubber, Appl. Microbiol. Biotechnol. 53, 355–365.

    Article  PubMed  CAS  Google Scholar 

  2. Lynen, F., and Henning, U. (1960) The Biological Pathway to Natural Rubber, Angew. Chem. 72, 820–829.

    CAS  Google Scholar 

  3. Aebi, P.B.A.M. (1999) The Dolichol Pathway of N-Linked Glycosylation, Biochim. Biophys. Acta 1426, 239–257.

    PubMed  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    PubMed  CAS  Google Scholar 

  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.

    PubMed  CAS  Google Scholar 

  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.

    PubMed  CAS  Google Scholar 

  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.

    PubMed  CAS  Google Scholar 

  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. 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.

    Article  PubMed  CAS  Google Scholar 

  11. Tangpakdee, J., and Tanaka, Y. (1998) Long-Chain Polyprenols and Rubber in Young Leaves of Hevea brasiliensis, Phytochemistry 48, 447–450.

    Article  CAS  Google Scholar 

  12. Tanaka, Y., and Kawahara, S. (1989) Sequence Analysis of Polyprenols by 500 MHz 1H NMR Spectroscopy, Chem. Phys. Lipids, 51, 183–189.

    Article  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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 

Download references

Author information

Author notes

  1. Akio Kobayashi

    Present address: Department of Biotechnology, Graduate School of Engineering, Osaka University, 565-0871, Osaka, Japan

Authors and Affiliations

  1. Department of Biotechnology, Graduate School of Engineering, Osaka University, 565-0871, Osaka, Japan

    Takeshi Bamba, Ei-ichiro Fukusaki & Shin-ichiro Kajivama

  2. Department of Chemistry, Graduate School of Engineering Science, Osaka University, 560-8531, Osaka, Japan

    Koichi Ute & Tatsuki Kitayama

Authors
  1. Takeshi Bamba
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ei-ichiro Fukusaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shin-ichiro Kajivama
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Koichi Ute
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tatsuki Kitayama
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Akio Kobayashi
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Bamba, T., Fukusaki, Ei., Kajivama, Si. et al. The occurrence of geometric polyprenol isomers in the rubber-producing plant, Eucommia ulmoides oliver. Lipids 36, 727–732 (2001). https://doi.org/10.1007/s11745-001-0778-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-001-0778-5

Keywords

Search

Navigation