Skip to main content
SpringerLink
Log in

Stereospecific analysis of triglycerides

  • Published:
Lipids

Abstract

Stereospecific analysis determines how the fatty acids of triglycerides are distributed over the three different positions of the glycerol. The special problem is the differentiation of position I-1 and L-3 of glycerol. In the presently known methods, triglycerides are first degraded to mixtures of diglycerides, either by the action of a lipase or by degradation with a Grignard reagent. The isomeric diglycerides are then resolved with the help of a stereospecific enzyme, either a diglyceride kinase or (after conversion of the diglycerides to phospholipids) a phospholipase. It is then possible to analyze or calculate the fatty acid composition for each position on the glycerol. The key to a successful stereospecific analysis is the preparation of a representative diglyceride mixture by a truly random degradation of the triglyceride. The Grignard degradation is the most reliable method, but it is not always applicable, and it is accompanied by some isomerization of glycerides. There is room for improvement in the method. Analyse of natural fats have shown most of them to be asymmetric, i.e., the composition of fatty acids in position 1 differs markedly from that of position 3. Several rules of fatty acid distribution have become apparent.

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. Brockerhoff, H., J. Lipid Res. 6:10 (1965).

    PubMed  CAS  Google Scholar 

  2. Wolfrom, M.L., J. Org. Chem. 28:281 (1963).

    Google Scholar 

  3. Baddiley, J., J.G. Buchanan and B. Carss, J. Chem. Soc. 1957:1869.

  4. IUPAC-IUB Commission on Biochemical Nomenclature (CBN), Eur. J. Biochem. 2:127 (1967).

    Article  Google Scholar 

  5. Baer, E., and H.O.L. Fischer, J. Biol. Chem. 128:475 (1939).

    CAS  Google Scholar 

  6. Pasteur, L., “Receuil de Travaux,” Compiled by Pasteur Vallery-Radot. Paris, le Cercle du Libre Precieux, 1966.

  7. Schlenk, W., Jr., JAOCS 42:945 (1965).

    PubMed  CAS  Google Scholar 

  8. Kleiman, R., R.W. Miller, F.R. Earle and I.A. Wolff, Lipids 1:286 (1966).

    CAS  PubMed  Google Scholar 

  9. Schlenk, W., Jr., “Optische Aktivitat bei Triglyceriden,” Festschrift Carl Wurster zum 60. Geburtstag. C.A., 1962:14930 f.

  10. Morris, L.J., Biochem. Biophys. Res. Comm. 18:495 (1965).

    Article  PubMed  CAS  Google Scholar 

  11. Coleman, M.H., JAOCS 42:1040 (1965).

    PubMed  CAS  Google Scholar 

  12. Morris, L.J., Biochem. Biophys. Res. Comm. 20:340 (1965).

    Article  PubMed  CAS  Google Scholar 

  13. Litchfield, C., and R. Reiser, JAOCS 40:747 (1963).

    Google Scholar 

  14. Brockerhoff, H., Biochim. Biophys. Acta 159:296 (1968).

    PubMed  CAS  Google Scholar 

  15. Brockerhoff, H., Arch. Biochem. Biophys. 134:366 (1969).

    Article  PubMed  CAS  Google Scholar 

  16. Brockerhoff, H., Biochim. Biophys. Acta 212:92 (1970).

    PubMed  CAS  Google Scholar 

  17. Lands, W.E.M., R.A. Pieringer, P.M. Slakey and A. Zschocke, Lipids 1:444 (1966).

    CAS  PubMed  Google Scholar 

  18. Slakey, P.M., and W.E.M. Land, Ibid. 3:30 (1968).

    CAS  PubMed  Google Scholar 

  19. Buteau, G.H., Jr., and D. Fairbairn, Exp. Parasitol. 25:265 (1969).

    Article  PubMed  Google Scholar 

  20. Sugano, M., K. Imaizumi, S. Cho and M. Wada, Lipids 6:141 (1971).

    PubMed  CAS  Google Scholar 

  21. Brockerhoff, H., J. Lipid Res. 8:167 (1967).

    PubMed  CAS  Google Scholar 

  22. Christie, W.W., and J.H. Moore, Biochim. Biophys. Acta 176:445 (1969).

    PubMed  CAS  Google Scholar 

  23. Brockerhoff, H., R.J. Hoyle, and P.C. Hwang, Canad. J. Biochem. 44:1519 (1966).

    CAS  Google Scholar 

  24. Anderson, R.E., R. Bottino and R. Reiser, Lipids 2:440 (1967).

    CAS  PubMed  Google Scholar 

  25. Kleiman, R., F.R. Earle, W.H. Tallent and I.A. Wolff, Ibid. 5:513 (1970).

    PubMed  CAS  Google Scholar 

  26. Bottino, N.R., G.A. Vandenburg and R. Reiser, Ibid. 2:489 (1967).

    CAS  PubMed  Google Scholar 

  27. Pitas, R.E., J. Sampugna and R.G. Jensen, J. Dairy Sci. 50:1332, (1968).

    Article  Google Scholar 

  28. Breckenridge, W.C., and A. Kuksis, J. Lipid Res. 9:388 (1968).

    PubMed  CAS  Google Scholar 

  29. Brockerhoff, H., Arch. Biochem. Biophys. 110:586 (1965).

    Article  PubMed  CAS  Google Scholar 

  30. Sampugna, J., and R.G. Jensen, Lipids 3:519 (1968).

    CAS  PubMed  Google Scholar 

  31. Yurkowski, M., and H. Brockerhoff, Biochim. Biophys. Acta 125:55 (1966).

    PubMed  CAS  Google Scholar 

  32. Brockerhoff, H., Lipids 1:162 (1966).

    CAS  PubMed  Google Scholar 

  33. Lands, W.E.M., and P.M. Slakey, Ibid. 1:295 (1966).

    CAS  PubMed  Google Scholar 

  34. Jensen, R.G., J. Sampugna and J.G. Quinn, Ibid. 1:294 (1966).

    CAS  PubMed  Google Scholar 

  35. Brockerhoff, H., R.J. Hoyle and N. Wolmark, Biochim. Biophys. Acta 116:67 (1966).

    PubMed  CAS  Google Scholar 

  36. Sampugna, J. and R.G. Jensen, Lipids 4:444 (1969).

    PubMed  CAS  Google Scholar 

  37. Akesson, B., Eur. J. Biochem. 9:463 (1969).

    Article  PubMed  CAS  Google Scholar 

  38. Breckenridge, W.C., L. Marai and A. Kuksis, Canad. J. Biochem. 47:761 (1969).

    CAS  Google Scholar 

  39. De la Roche, I., E.J. Weber and D.E. Alexander, Lipids 6:531 (1971).

    Google Scholar 

  40. Christie, W.W., and J.H. Moore, Biochim. Biophys. Acta 210:46 (1970).

    PubMed  CAS  Google Scholar 

  41. Christie, W.W., and J.H. Moore, Lipids 4:345 (1969).

    PubMed  CAS  Google Scholar 

  42. Christie, W.W., and J.H. Moore, Biochim. Biophys. Acta 218:83 (1970).

    PubMed  CAS  Google Scholar 

  43. Brockerhoff, H., Comp. Biochem. Physiol. 19:1 (1966).

    Article  PubMed  CAS  Google Scholar 

  44. Brockerhoff, H., R.J. Hoyle, P.C. Hwang and C. Litchfield, Lipids 3:24 (1968).

    CAS  PubMed  Google Scholar 

  45. Walker, R.W., H. Barakat and J.G.C. Hung, Ibid. 5:684 (1970).

    PubMed  CAS  Google Scholar 

  46. Brockerhoff, H., and M. Yurkowski, J. Lipid Res. 7:62 (1966).

    PubMed  CAS  Google Scholar 

  47. Bagby, M.O., and C.R. Smith, Jr., Biochim. Biophys. Acta 137:475 (1967).

    PubMed  CAS  Google Scholar 

  48. Christie, W.W., Ibid. 187:1 (1969).

    PubMed  CAS  Google Scholar 

  49. Phillips, B.E., C.R. Smith, Jr., and W.H. Tallent, Lipids 6:93 (1970).

    Google Scholar 

  50. Mattson, F.H., and R.A. Volpenhein J. Lipid Res. 4:392 (1963).

    PubMed  CAS  Google Scholar 

  51. Weber, E.J., I.D. de la Roche and D.E. Alexander, Lipids, 6:525 (1971).

    CAS  Google Scholar 

  52. De la Roche, I.A., E.J. Weber and D.E. Alexander, Ibid., 6:537 (1971).

    Google Scholar 

  53. Breckenridge, W.C. and A. Kuksis, Ibid. 4:197 (1969).

    PubMed  CAS  Google Scholar 

  54. Ackman, R.G., C.A. Eaton and S.N. Hooper, Canad. J. Biochem. 46:197 (1968).

    CAS  Google Scholar 

  55. Marai, L., W.C. Breckenridge and A. Kuksis, Lipids 4:562 (1969).

    PubMed  CAS  Google Scholar 

  56. Ray, T.K., J.E. Cronan, Jr., R.D. Mavis and P.R. Vagelos, J. Biol. Chem. 245:6442 (1970).

    PubMed  CAS  Google Scholar 

  57. Brockerhoff, H., R.J. Hoyle and P.C. Hwang, Biochim. Biophys. Acta 144:541 (1967).

    PubMed  CAS  Google Scholar 

  58. Litchfield, C., Lipids 3:417 (1968).

    CAS  PubMed  Google Scholar 

  59. Lands, W.E.M., Ann. Rev. Biochem. 34:313 (1965).

    Article  PubMed  CAS  Google Scholar 

  60. Synder, F., and R. Wood, Radiation Res. 33:142 (1968).

    Article  Google Scholar 

  61. Wood, R., and R.D. Harlow, Arch. Biochem. Biophys. 131:495 (1969).

    Article  PubMed  CAS  Google Scholar 

  62. Wood, R., and F. Snyder, Ibid. 131:478 (1969).

    Article  PubMed  CAS  Google Scholar 

  63. Akesson, B., Eur. J. Biochem. 9:406 (1969).

    Article  PubMed  CAS  Google Scholar 

  64. Akesson, B., J. Elovson and G. Arvidson, Biochim. Biophys. Acta 218:44, (1970).

    PubMed  CAS  Google Scholar 

  65. Elovson, J., B. Akesson and G. Arvidson, Ibid. 176:214 (1969).

    PubMed  CAS  Google Scholar 

  66. Vander Wal, R.J., JAOCS 37:18 (1960).

    Google Scholar 

  67. Gunstone, F.D., Chem. Ind. (London).— 1214 (1962).

  68. Coleman, M.H., and W.C. Fulton, in “The Enzymes of Lipid Metabolism,” Edited by P. Desnuelle, Pergamon Press, New York, 1961, p. 127–137.

    Google Scholar 

  69. Christie, W.W., and J.H. Moore, Lipids 5:921 (1970).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Halifax Laboratory, Fisheries Research Board of Canada, Halifax, Nova Scotia

    H. Brockerhoff

Authors
  1. H. Brockerhoff
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Brockerhoff, H. Stereospecific analysis of triglycerides. Lipids 6, 942–956 (1971). https://doi.org/10.1007/BF02531179

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02531179

Keywords

Search

Navigation