Skip to main content
SpringerLink
Log in

Identification and quantification of important steryl esters in aspen wood

  • Published:
Journal of the American Oil Chemists' Society

Abstract

Steryl esters make up a major portion of the total lipids in aspen wood, and contribute significantly to pitch deposit problems during pulping. Fungal treatment of aspen is an attractive method for removing these compounds because it is inexpensive and environmentally acceptable; however, the mechanism of steryl ester removal remains unclear. Identification of the steryl esters will lead to a better understanding of how they are removed by fungi. The steryl ester fraction from aspen wood was obtained by acetone extraction then further purified by silica gel column chromatography and argentation-silica gel column chromatography. This led to the isolation of three major fractions: fraction I, fraction II, and fraction III. The major steryl esters of fractions I and II were identified by gas chromatography, gas chromatography-mass spectroscopy, and proton nuclear magnetic resonance analysis of the intact fraction as well as sterol and fatty acid moieties obtained after base hydrolysis. Identification of the steryl esters was carried out by mass spectra comparisons with steryl ester standards synthesized in the laboratory and comparison with mass spectra libraries (Wiley and NIST) by mass fragmentography. Fraction I contained primarily the palmitate, stearate, and eicosanoate esters of α- and β-amyrin. Fraction II consisted mainly of the palmitate, stearate, and eicosanoate esters of tirucalla-7,24-dien-3β-ol and lupeol.

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

References

  1. Allen, L.H., B.B. Sitholé, J.M. Macleod, C.L. Lapointe, and F.J. McPhee, The Importance of Seasoning and Barking in the Kraft Pulping of Aspen, J. Pulp Paper Sci. 17:J85-J91 (1991).

    CAS  Google Scholar 

  2. Chen, T., Z. Wang, Y. Zhou, C. Breuil, O.K. Aschim, E. Yee, and L. Nadeau, Using Solid-Phase Extraction to Assess Why Aspen Causes More Pitch Problems Than Softwoods in Kraft Pulping, Tappi J. 78:143–149 (1995).

    CAS  Google Scholar 

  3. Sjöström, E., Wood Chemistry: Fundamentals and Applications, Academic Press Inc., San Diego, 1993, pp. 90–113.

    Google Scholar 

  4. Sitholé, B.B., J.L. Sullivan, and L.H. Allen, Identification, and Quantification of Acetone Extractives of Wood and Bark by Ion Exchange and Capillary GC with a Spreadsheet Program, Holzforsch. 46:409–416 (1992).

    Article  Google Scholar 

  5. Blanchette, R.A., R.L. Farrell, T.A. Burnes, P.A. Wendler, W. Zimmerman, T.S. Brush, and R.A. Snyder, Biological Control of Pitch in Pulp and Paper Production by Ophiostoma piliferum, Tappi J. 75:102–106 (1992).

    CAS  Google Scholar 

  6. Brush, T.S., R.L. Farrell, and C. Ho, Biodegradation of Wood Extractives from Southern Yellow Pine by Ophiostoma piliferum, Ibid.Tappi J. 77:155–159 (1994).

    CAS  Google Scholar 

  7. Fisher, K., M. Akhtar, R.A. Blanchette, T.A. Burnes, K. Messner, and T.K. Kirk, Reduction of Resin Content in Wood Chips During Experimental Biological Pulping Processes, Holzforsch. 48:285–290 (1994).

    Article  Google Scholar 

  8. Chen, T., Z. Wang, Y. Gao, C. Breuil, and J.V. Hatton, Wood Extractives and Pitch Problems: Analysis and Partial Removal by Biological Treatment, Appita 47:463–466 (1994).

    CAS  Google Scholar 

  9. Rocheleau, M.J., B.B. Sitholé, L.H. Allen, S. Iverson, R. Farrell, and Y. Noel, Fungal Treatment of Aspen Chips for Wood Resin Reduction: A Laboratory Evaluation, J. Pulp Paper Sci. 24:37–42 (1998).

    CAS  Google Scholar 

  10. Rocheleau, M.J., B.B. Sitholé, L.H. Allen, and Y. Noel, Fungal Treatment of Aspen Chips for Wood Resin Reduction: Effect on Aged Aspen Wood Chips at Room Temperature and at 5°C, Holzforsch 53:16–20 (1999).

    Article  CAS  Google Scholar 

  11. Leone, R., and C. Breuil, Filamentous Fungi Can Degrade Aspen Steryl Esters and Waxes, Intl. Biodet. Biodeg. 41:133–137 (1998).

    Article  CAS  Google Scholar 

  12. Peng, J., R. Leone, A.N. Serreqi, and C. Breuil, Are Aspen Sterols and Steryl Esters Changed Structurally by Kraft Pulping and Bleaching?, Tappi J. 82:204–211 (1999).

    CAS  Google Scholar 

  13. Hassner, A., and V. Alexanian, Direct Room Temperature Esterification of Carboxylic Acids, Tetrahedron Lett. 46: 4475–4478 (1978).

    Article  Google Scholar 

  14. Chen, T., C. Breuil, S. Carrière, and J.V. Hatton, Solid-Phase Extraction Can Rapidly Separate Lipid Classes from Acetone Extracts of Wood and Pulp, Tappi J. 77:235–240 (1994).

    CAS  Google Scholar 

  15. Itoh, T., T. Tamura, and T. Matsumoto, Proton Magnetic Resonance Spectra of Tetracyclic Triterpene Alcohols Under the Influence of a Lanthanide Shift Reagent, Steroilds 27:275–285 (1976).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Wood Science, Faculty of Forestry, University of British Columbia, 4041-2424 Main Mall, V6T 1Z4, Vancouver, British Columbia, Canada

    Alessio N. Serreqi, Robert Leone, Luis F. Del Rio, Shirley Mei, Marc Fernandez & Colette Breuil (Chair of Forest Products Biotechnology)

Authors
  1. Alessio N. Serreqi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Robert Leone
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Luis F. Del Rio
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shirley Mei
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Marc Fernandez
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Colette Breuil
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Colette Breuil.

About this article

Cite this article

Serreqi, A.N., Leone, R., Del Rio, L.F. et al. Identification and quantification of important steryl esters in aspen wood. J Amer Oil Chem Soc 77, 413–418 (2000). https://doi.org/10.1007/s11746-000-0066-9

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11746-000-0066-9

Key Words

Search

Navigation