Metabolic Fate of 3H-Cholesteryl Linoleyl Ether, a Nondegradable Analog of Lipoprotein Cholesteryl Ester

  • Yechezkiel Stein
  • Olga Stein
  • Gideon Halperin
Conference paper
Part of the NATO Advanced Study Institutes Series book series (NSSA, volume 51)


Studies in the past have pointed out that in the human during the intravascular metabolism of very low density lipoproteins (VLDL) which culminates in the formation of low density lipoproteins (LDL) there is a considerable loss of cholesteryl ester (1). To follow the fate of cholesteryl ester during the metabolism of VLDL, various approaches were used to label the lipid portion of the lipoprotein. These can be divided into two main categories, i.e., endogenous labeling and exogenous labeling. The first was based on the injection of crystalline suspensions of labeled cholesterol of high specific activity which following uptake by the liver reappears in the VLDL secreted into plasma in the form of free and esterified cholesterol. One can remove the free cholesterol by exchange following incubation with erythrocytes, but this procedure changes the biological behavior of the lipoprotein (2) and also leaves a considerable portion of unesterified labeled cholesterol. Another approach utilizes the LCAT reaction in vitro to convert exogenously added labeled free cholesterol to cholesteryl ester, but this reaction as well does not go to completion. Therefore, several methods were developed to label lipoproteins with pure labeled cholesteryl ester by the introduction of the lipid into the lipoprotein in vitro (3).


High Density Lipoprotein Cholesteryl Ester Cholesteryl Ester Transfer Protein Cholesteryl Linoleate Oleyl Ether 
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  1. 1.
    R.J. Havel, J.C. Goldstein, and M.S. Brown, Lipoprotein and lipid transport, in: “Metabolic Control and Disease,” P.K. Bondy and L.E. Rosenberg, eds., 8th ed., W.B.Saunders, Philadelphia, 393–494 (1980).Google Scholar
  2. 2.
    O. Faergeman and R.J. Havel, Metabolism of cholesteryl esters of rat very low density lipoproteins, J.Clin.Invest. 55: 1210 (1975).Google Scholar
  3. 3.
    M. Krieger, M.S. Brown, J.R. Faust, and J.L. Goldstein, Replacement of endogenous cholesteryl esters of low density lipoprotein with exogenous cholesteryl linoleate. Reconstitution of a biologically active lipoprotein particle, J.Biol.Chem. 253: 4093 (1978).Google Scholar
  4. 4.
    O. Stein, G. Halperin, and Y. Stein, Biological labeling of very low density lipoproteins with cholesteryl linoleyl ether and its fate in the intact rat, Biochim.Biophys.Acta 620: 247 (1980).Google Scholar
  5. 6.
    G. Halperin and S. Gatt, The synthesis of cholesteryl alkyl ethers, Steroids 35: 39 (1980).PubMedCrossRefGoogle Scholar
  6. 7.
    W. Stoll, Eine neue Darstellungsweise von Cholesterinäthern, Z.Phys.Chem. 207: 147 (1932).Google Scholar
  7. 8.
    G. Halperin, O. Stein, and Y. Stein, Biological stability of 3h-cholesteryl oleyl ether in cultured fibroblasts and intact rat, FEBS Letts. 111: 104 (1980).CrossRefGoogle Scholar
  8. 9.
    Y. Stein, V. Ebin, H. Bar-On, and O. Stein, Chloroquine induced interference with degradation of serum lipoproteins in rat liver, studied in vivo and in vitro, Biochim.Biophys.Acta 486: 286 (1977).PubMedGoogle Scholar
  9. 10.
    N.M. Pattnaik and D.B. Zilversmit, Interaction of cholesteryl ester exchange protein with human plasma lipoproteins and phospholipid vesicles, J.Biol.Chem. 254: 2782 (1979).PubMedGoogle Scholar
  10. 11.
    P.J. Barter and J.I. Lally, In vitro exchanges of esterified cholesterol between serum lipoprotein fractions: Studies of humans and rabbits, Metabolism 28: 230 (1979).Google Scholar
  11. 13.
    O. Stein, D. Rachmilewitz, L. Sanger, S. Eisenberg, and Y. Stein, Metabolism of iodinated very low density lipoprotein in the rat; Autoradiographic localization in the liver; Biochim.Biophys.Acta 360: 205 (1974).PubMedGoogle Scholar
  12. 14.
    Y. Stein, G. Halperin, and O. Stein, The fate of cholesteryl linoleyl ether and cholesteryl linoleate in the intact rat after injection of biologically labeled human low density lipoprotein, Biochim.Biophys.Acta. In press (1981).Google Scholar
  13. 16.
    R.A. Davis and P.S. Roheim, Pharmacologically induced hypolipidemia. The ethinyl estradiol-treated rat, Atherosclerosis 30: 293 (1978).PubMedCrossRefGoogle Scholar
  14. 18.
    Y-s Chao, A.L. Jones, G.R. Hradek, E.E. Windier, J.S. Mooney and R.J. Havel, Electron microscopic morphometric and quantitative human low density lipoprotein by rat hepatocytes. Proc.31st Ann. Meeting Amer. Assoc. Study of Liver Dis., November 1980, Abstr. 10-B, p.10.Google Scholar

Copyright information

© Plenum Press, New York 1982

Authors and Affiliations

  • Yechezkiel Stein
    • 1
    • 2
  • Olga Stein
    • 1
    • 2
  • Gideon Halperin
    • 1
    • 2
  1. 1.Lipid Research Laboratory, Department of Medicine BHadassah University HospitalJerusalemIsrael
  2. 2.Department of Experimental Medicine and Cancer ResearchHebrew University-Hadassah Medical SchoolJerusalemIsrael

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