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Lipids

, Volume 6, Issue 2, pp 93–99 | Cite as

Glycerides ofLimnanthes douglasii seed oil

  • Bruce E. Phillips
  • C. R. SmithJr.
  • W. H. Tallent
Article

Abstract

Brockerhoff-type procedures were used to determine the amounts of each acyl group at each glyceride position ofLimnanthes douglasii seed oil. During the course of the analyses, small quantities of three acids isomeric with those previously found in the oil were identified by their ozonolysis products and their gas-liquid chromatographic (GLC) behavior. The newly discovered constituents of the oil were 3-octadecenoic acid (0.1%), 5-octadecenoic acid (0.9%) and 11-eicosenoic acid (3%). The saturated acids and those with ω-9-unsaturation are esterified most often to β-glyceride positions inLimnanthes seed, while the acids with Δ5-unsaturation occur generally at the outer glyceride positions. Although the Δ5-unsaturated acids as a group exhibited no obvious preference for one outer position over the other, individual acids were unequally distributed between the 1- and 3-sn-glycerol positions. The probabilities of occurrence of the various triglycerides were calculated from the stereospecific analysis data by assuming a 1-random, 2-random, 3-random distribution of the acyl groups. The calculations are in agreement with the composition of the whole oil, as determined by GLC.

Keywords

Glyceride Ozonolysis Pancreatic Lipase Tristearin Preparative Thin Layer Chromatographic 
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.

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References

  1. 1.
    Smith, C.R., Jr., M.O. Bagby, T.K. Miwa, R.L. Lohmar and I.A. Wolff, J. Org. Chem. 25:1770–1774 (1960).CrossRefGoogle Scholar
  2. 2.
    Bagby, M.O., C.R. Smith, Jr., T.K. Miwa, R.L. Lohmar and I.A. Wolff, Ibid. 26:1261–1265 (1961).CrossRefGoogle Scholar
  3. 3.
    Fore, S.P., F.G. Dollear and G. Sumrell, Lipids 1:73–75 (1966).Google Scholar
  4. 4.
    Christie, W.W., and J.H. Moore, Biochim. Biophys. Acta 176:445–452 (1969).PubMedGoogle Scholar
  5. 5.
    Brockerhoff, H., and M. Yurkowski, J. Lipid Res. 7:62–64 (1966).PubMedGoogle Scholar
  6. 6.
    Lands, W.E.M., R.A. Pieringer, P.M. Slakey and A. Zschocke, Lipids 1:444–448 (1966).Google Scholar
  7. 7.
    Sampugna, J., and R.G. Jensen, Ibid. 4:444–449 (1969).Google Scholar
  8. 8.
    Marai, L., W.C. Breckenridge and A. Kuksis, Ibid. 4:562–570 (1969).PubMedGoogle Scholar
  9. 9.
    Wood, R., and F. Snyder, Arch. Biochem. Biophys. 131:478–494 (1969).PubMedCrossRefGoogle Scholar
  10. 10.
    Christie, W.W., Biochim. Biophys. Acta 187:1–5 (1969).PubMedGoogle Scholar
  11. 11.
    Kleiman, R., R.W. Miller, F.R. Earle and I.A. Wolff, Lipids 1:286–287 (1966).Google Scholar
  12. 12.
    Bagby, M.O., and C.R. Smith, Jr., Biochim. Biophys. Acta 137:476–477 (1967).Google Scholar
  13. 13.
    Litchfield, C., E. Miller, R.D. Harlow and R. Reiser, Lipids 2:345–350 (1967).Google Scholar
  14. 14.
    Hirschmann, H. (Chairman, IUPAC-IUB Sub-Committee on Lipid Nomenclature), Eur. J. Biochem. 2:127–131 (1967).CrossRefGoogle Scholar
  15. 15.
    Mikoljczak, K.L., and C.R. Smith, Jr., Biochim. Biophys. Acta 152:244–254 (1968).Google Scholar
  16. 16.
    Smith, C.R., Jr., in “Progress in the Chemistry of Fats and Other Lipids,” Vol. 11, Edited by R.T. Holman, Pergamon Press, in press.Google Scholar
  17. 17.
    Miwa, T.K., and I.A. Wolff, JAOCS 39:320–322 (1962).Google Scholar
  18. 18.
    Miller, R.W., M.E. Daxenbichler, F.R. Earle, and H.S. Gentry, Ibid. 41:167–169 (1964).Google Scholar
  19. 19.
    Tallent, W.H., R. Kleiman and D.G. Cope, J. Lipid Res. 7:531–535 (1966).PubMedGoogle Scholar
  20. 20.
    Powell, R.G., R. Kleiman and C.R. Smith, Jr., Lipids 4:450–453 (1969).PubMedGoogle Scholar
  21. 21.
    Phillips, B.E., C.R. Smith, Jr. and J.W. Hagemann, Ibid. 4:473–477 (1969).PubMedGoogle Scholar
  22. 22.
    Phillips, B.E., and C.R. Smith, Jr., Biochim. Biophys. Acta, in press.Google Scholar
  23. 23.
    Brockerhoff, H., J. Lipid Res. 6:10–15 (1965).PubMedGoogle Scholar
  24. 24.
    Brockerhoff, H., Ibid. 8:167–169 (1967).PubMedGoogle Scholar
  25. 25.
    Robertson, A.F., and W.E.M. Lands, Biochemistry 1:804–810 (1962).PubMedCrossRefGoogle Scholar
  26. 26.
    De Haas, G.H., and L.L.M. Van Deenen, Biochim. Biophys. Acta 84:469–471 (1964).Google Scholar
  27. 27.
    Kuksis, A., in “Lipid Chromatographic Analysis,” Vol. 1, Edited by G.V. Marinetti, Marcel Dekker, Inc. New York, 1967, p. 290–299.Google Scholar
  28. 28.
    Bezard, J., and B. Bugaut, J. Chromatogr. Sci. 7:639–644 (1969).Google Scholar
  29. 29.
    Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman and R.W. Riemenschneider, JAOCS 41:693–696 (1964).Google Scholar
  30. 30.
    Goodman, L.P., and L.R. Dugan, Jr., Lipids 5:362–364 (1970).PubMedGoogle Scholar
  31. 31.
    Kleiman, R., G.F. Spencer, F.R. Earle and I.A. Wolff, Ibid. 4:135–141 (1969).Google Scholar
  32. 32.
    Privett, O.S., and C. Nickell, JAOCS 43:393–400 (1966).Google Scholar
  33. 33.
    Miwa, T.K., Ibid. 40:309–313 (1963).Google Scholar
  34. 34.
    Kleiman, R., F.R. Earle and I.A. Wolff, Lipids 1:301–304 (1966).Google Scholar
  35. 35.
    Spencer, G.F., R. Kleiman, F.R. Earle, and I.A. Wolff, Ibid. 4:99–101 (1969).Google Scholar
  36. 36.
    Gunstone, F.D., I.A. Ismail and M. Lie Ken Jie, Chem. Phys. Lipids 1:376–385 (1967).CrossRefGoogle Scholar
  37. 37.
    Butterfield, R.O., E.B. Lancaster and H.J. Duntton, Separ. Sci. 1:329–337 (1966).Google Scholar
  38. 38.
    Entressangles, B., H. Sari and P. Desnuelle, Biochim. Biophys. Acta 125:597–600 (1966).PubMedGoogle Scholar
  39. 39.
    Anderson, R.E., N.R. Bottino and R. Reiser, Lipids 2:440–442 (1967).Google Scholar
  40. 40.
    Kleiman, R., F.R. Earle, W.H. Tallent and I.A. Wolff, Ibid. 5:513–518 (1970).Google Scholar
  41. 41.
    Desnuelle, P., and P. Savary, J. Lipid Res. 4:369–384 (1963).PubMedGoogle Scholar
  42. 42.
    Brockerhoff, H., Arch. Biochem. Biophys. 110:586–592 (1965).PubMedCrossRefGoogle Scholar
  43. 43.
    Bottino, N.R., G.A. Vandenberg and R. Reiser, Lipids 2:489–493 (1967).Google Scholar
  44. 44.
    Appelqvist, L.-A., and R.J. Dowdell, Ark. Kemi 28:539–549 (1968).Google Scholar
  45. 45.
    Mattson, F.H., and R.A. Volpenhein, J. Biol. Chem. 236:1891–1894 (1961).PubMedGoogle Scholar

Copyright information

© American Oil Chemists’ Society 1971

Authors and Affiliations

  • Bruce E. Phillips
    • 1
  • C. R. SmithJr.
    • 1
  • W. H. Tallent
    • 1
  1. 1.Northern Regional Research LaboratoryPeoria

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