Skip to main content
SpringerLink
Log in

Techniques for the isolation and identification of steroids in insects and algae

  • Symposium: Sterol Analysis Held at the AOCS Annual Meeting in New York, NY, April 29, 1980
  • Published:
Lipids

Abstract

Analytical techniques, methods and instrumentation employed for the extraction, isolation separation, purification and identification of steroids from algae and insects are presented. The techniques include adsorption and argentation column chromatography and counter-current distribution for separating the individual steroids, and thin layer chromatography and gas liquid chromatography for monitoring the purification process. Double bond, steric and alkyl substituent separation factors and relative retention times are reported for a large number of sterols on 4 different column systems. Their use permits the tentative structural assignment of sterols. Ultraviolet, infrared, nuclear magnetic resonance (NMR) and mass spectral analyses are discussed in light of their significance in the isolation and identification of steroids from insects and algae. Numerous examples are presented, including the use of 220 MHz NMR spectrometry, which permits the differentiation and characterization of C-24 epimetric sterols and allows for a semiquantitative estimate of the 24α- and 24β-epimers present in a mixture.

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. Horning, E.C., W.J.A. VandenHeuvel and B.G. Creech, Methods Biochem. Anal. 9:69 (1963).

    Google Scholar 

  2. Vroman, H.E. and C.F. Cohen, J. Lipid Res. 8:150 (1967).

    PubMed  CAS  Google Scholar 

  3. Sliwoski, J.K. and E. Caspi, J. Steroid Biochem. 8:42 (1977).

    Google Scholar 

  4. Patterson, G.W. and R.W. Krauss, Plant Cell Physiol. 6:211 (1965).

    CAS  Google Scholar 

  5. Thompson, M.J., C.F. Cohen and S.M. Lancaster, Steroids 5:745 (1965).

    Article  CAS  Google Scholar 

  6. Issidorides, C.H., I. Kitagawawa and E. Mosetig, J. Org. Chem. 27:4693 (1963).

    Google Scholar 

  7. Doyle, P.J., G.W. Patterson, S.R. Dutky and C.F. Cohen, Phytochemistry 10:2093 (1970).

    Article  Google Scholar 

  8. Thompson, M.J., S.R. Dutky, Y. Lehner, L.N. Standifer and E.W. Herbert, Jr., Phytochemistry 17:1053 (1978).

    Article  CAS  Google Scholar 

  9. Goodman, D.S. and T. Shiratori, J. Lipid Res. 5:578 (1964).

    PubMed  CAS  Google Scholar 

  10. Kaplanis, J.N., M.J. Thompson, S.R. Dutky and W.E. Robbins, Steroids 34:333 (1979).

    Article  PubMed  CAS  Google Scholar 

  11. Horn, D.H.S., in “Naturally Occuring Insecticides,” edited by M. Jacobson and D.G. Crosby, Dekker, Inc., New York, (1971) p. 333.

    Google Scholar 

  12. Vandenheuvel, W.J.A., C.C. Sweeley and E.C. Horning, J. Am. Chem. Soc. 82:3841 (1960).

    Article  Google Scholar 

  13. Patterson, G.W., Anal. Chem. 43:1165 (1971).

    Article  CAS  Google Scholar 

  14. Doyle, P.J., G.W. Patterson, S.R. Dutky and M.J. Thompson, Phytochemistry 11:951 (1972).

    Article  Google Scholar 

  15. Fieser, L. and M. Fieser, “Steroids,” Reinhold Publishing Corp., New York, NY, 1959.

    Google Scholar 

  16. Dorfman, L., Chem. Rev. 53:47 (1953).

    Article  CAS  Google Scholar 

  17. Thompson, M.J., J.N. Kaplanis, W.E. Robbins and J.A. Svoboda, Adv. Lipid Res. 11:219 (1973).

    PubMed  CAS  Google Scholar 

  18. Chan, J.T. and G.W. Patterson, Plant Physiol. 52:246 (1973).

    Article  PubMed  CAS  Google Scholar 

  19. Svoboda, J.A., R.F.N. Hutchins, M.J. Thompson and W.E. Robbins, Steroids 14:469 (1969).

    Article  PubMed  CAS  Google Scholar 

  20. Dusza, J., J. Org. Chem. 25:93 (1960).

    Article  CAS  Google Scholar 

  21. Dobriner, K., E.R. Katzennellenbogen and R.N. Jones, “Infrared Absorption Spectra of Steroids,” Interscience Publishers, Inc., New York, NY, 1953.

    Google Scholar 

  22. Roberts, G., B.S. Gallagher and R.N. Jones, “Infrared Absorption Spectra of Steroids,” Vol. II, Interscience Publishers, Inc., New York, NY, 1958.

    Google Scholar 

  23. Svoboda, J.A., M.J. Thompson and W.E. Robbins, Lipids 7:156 (1972).

    Article  CAS  Google Scholar 

  24. Svodoba, J.A., M.J. Thompson and J.A. Svoboda, Steroids 15:113 (1970).

    Article  Google Scholar 

  25. Doyle, P.J., G.W. Patterson, S.R. Dutky and C.F. Cohen, Phytochemistry 10:2093 (1971).

    Article  CAS  Google Scholar 

  26. Wyllie, S.G. and C. Djerassi, J. Org. Chem. 33:305 (1968).

    Article  CAS  Google Scholar 

  27. Massey, I.J. and C. Djerassi, J. Org. Chem. 44:2448 (1979).

    Article  CAS  Google Scholar 

  28. Shoolery, J.N. and M.T. Rogers, J. Am. Chem. Soc. 80:5121 (1958).

    Article  CAS  Google Scholar 

  29. Slomp, G. and F.A. MacKellar, J. Am. Chem. Soc. 84:204 (1962).

    Article  CAS  Google Scholar 

  30. Bhacca, N.S. and D.H. Williams, “Application of NMR Spectroscopy in Organic Chemistry,” Holden-Day, Inc., San Francisco, CA, 1964.

    Google Scholar 

  31. Scallen, T.J. and W. Krueger, J. Lipid Res. 9:120 (1968).

    PubMed  CAS  Google Scholar 

  32. Thompson, M.J., S.R. Dutky, G.W. Patterson and E.L. Gooden, Phytochemistry 11:1781 (1972).

    Article  CAS  Google Scholar 

  33. Nes, W.R., K. Krevitz and S. Behzadan, Lipids 11:118 (1976).

    Article  CAS  Google Scholar 

  34. Khalil, M.W., D.R. Idler and G.W. Patterson, Lipids 15:69 (1980).

    CAS  Google Scholar 

  35. Huber, R. and W. Hoppe, Chem. Ber. 98:2403 (1965).

    PubMed  CAS  Google Scholar 

  36. Kaplanis, J.N., M.J. Thompson, S.R. Dutky and W.E. Robbins, Steroids, in press.

Download references

Author information

Authors and Affiliations

  1. Insect Physiology Laboratory, Agricultural Research, Science and Education Administration, 20705, Beltsville, MD

    Malcolm J. Thompson, Samson R. Dutky, James A. Svoboda & John N. Kaplanis

  2. Department of Botany, University of Maryland, 20742, College Park, MD

    Glen W. Patterson

Authors
  1. Malcolm J. Thompson
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Glen W. Patterson
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Samson R. Dutky
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. James A. Svoboda
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. John N. Kaplanis
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Thompson, M.J., Patterson, G.W., Dutky, S.R. et al. Techniques for the isolation and identification of steroids in insects and algae. Lipids 15, 719–733 (1980). https://doi.org/10.1007/BF02534026

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02534026

Keywords

Search

Navigation