Skip to main content
SpringerLink
Log in

Biochemistry of unsaturated fatty acid isomers

  • Published:
Journal of the American Oil Chemists’ Society

Abstract

Recognition that catalytic hydrogenation changes the configuration and position of double bonds and alters the physical properties of unsaturated fats prompted numerous early investigations on the bio-chemical effects of ldtrans isomers.” Recent research has provided data on positional isomer metabolism. Some aspects of fatty acid isomer metabolism are now reasonably well understood, but other issues are not resolved. Human and animal data have provided good evidence that isomers in partially hydrogenated oils are well adsorbed and incorporated into all organs and tissues. Analyses of human tissues also indicate that hydrogenated oils are the major source of fatty acid isomers in the US diet. Tissue composition data combined with isolated enzyme studies and isotope tracer experiments with whole organisms show unquestionably that structural differences between various fatty acid isomers influence specific biochemical transformations. Examples are differences in the reaction rates and/ or specificities of acyl transferase, lipase, desaturase and cholesteryl esterase/hydrolase for various positional fatty acid isomers. Isolated microsomes and mitochondria also have been used to identify dif-ferences in acyl CoA activation, oxidation, and elongation of posi-tional isomers. In addition, isotope tracer experiments show that preferential metabolism of individual positional isomers occurs in vivo. In vivo studies with hydrogenated vegetable oil diets containing adequate levels of linoleic acid produced no obvious physiological changes. Experiments with specific polyunsaturated isomers have produced changes in blood cell properties, pulmonary weight, lino-leic acid requirements and tissue lipid composition. These changes may be related to a number of factors such as membrane fluidity and permeability, cell function, synthesis of arachidonic acid, homo-gamma-linoleic acid or prostaglandins. Whether differences in the biochemistry of fatty acid isomers are desirable or undesirable and whether these differences contribute to long-term or subtle effects important to the etiology of atherosclerosis and cancer are not resolved.

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. Barbour, A.D., J, Biol. Chem. 101:63 (1933) and Sinclair, R.G., Ibid. 111.-515 (1935).

    CAS  Google Scholar 

  2. Scholfield, C.R., V.L. Davison and H.J. Dutton, JAOCS 44: 648 (1967).

    CAS  Google Scholar 

  3. Parodi, P.W., JAOCS 53:530(1976).

    Article  CAS  Google Scholar 

  4. Carpenter, D.L., and H.T. Slover, JAOCS 50:372 (1973).

    Article  CAS  Google Scholar 

  5. Johnston, A.E., H.J. Dutton, C.R. Scholfield and R.O. But- terfield, JAOCS 55:486 (1978).

    Article  CAS  Google Scholar 

  6. Houtsmuller, U.M.T., Fette Seifen Anstrichm. 80:162 (1978).

    Article  CAS  Google Scholar 

  7. Juillet, M.T., Ibid. 80:445 (1978).

    Article  CAS  Google Scholar 

  8. Scientific Literature Reviews on Generally Recognized as Safe (GRAS) Food Ingredients — Hydrogenated Soybean Oil, prepared for the US Food and Drug Administration by Tracer-Jitco Inc., 1973, NTIS-PB-228557.

  9. Vergroesen, A.J. (ed.), The Role of Fats in Human Nutrition, Academic Press, New York, 1975.

    Google Scholar 

  10. Emken, E.A., and Dutton, H.J. (eds.), Geometrical and Posi- tional Fatty Acid Isomers, American Oil Chemists’ Society, Champaign, IL, 1979.

    Google Scholar 

  11. Applewhite, T.H., JAOCS 58:260(1981).

    Article  CAS  Google Scholar 

  12. Perkins, E.G., and W.J. Visek (eds.), Dietary Fats and Health, American Oil Chemists’ Society, Champaign, IL, in press (1983).

    Google Scholar 

  13. Beare-Rogers, J.L., Prog. Chem. Fats Other Lipids 15:29 (1977).

    Article  CAS  Google Scholar 

  14. Rocquelin, G., Med. Nutr. 13:269 (1977).

    CAS  Google Scholar 

  15. Heimermann, W.H., R.T. Holman, D.T. Gordon, D.E. Kowaly- shyn and R.G. Jensen, Lipids 8:45 (1973).

    Article  CAS  Google Scholar 

  16. Lippel, K., F.D. Gunstone and J.A. Barve, Lipids 8:119 (1973).

    Article  CAS  Google Scholar 

  17. Lippel, K., D. Carpenter, F.D. Gunstone and I.A. Ismail, Lipids 8:124 (1973).

    Article  CAS  Google Scholar 

  18. Lawson, L.D., and R.T. Holman, Biochim. Biophys. Acta 665:60(1981).

    CAS  Google Scholar 

  19. Willebrands, A.F., and K.J. Van Der Veen, Ibid. 116:583 (1966).

    CAS  Google Scholar 

  20. Reitz, R.C., M. El-Sheikh, W.E.M. Lands, I.A. Ismail and F.D. Gunstone, Ibid. 176:480 (1969).

    CAS  Google Scholar 

  21. Okuyama, H., W.E.M. Lands, F.D. Gunstone and J.A. Barve, Biochemistry 11:4392 (1972).

    Article  CAS  Google Scholar 

  22. Karney, R.I., and G.A. Dhopeshwarkar, Lipids 14:257 (1979).

    Article  CAS  Google Scholar 

  23. Marchand, C.M., and J.L. Beare-Rogers, Lipids 13:329 (1978).

    Article  CAS  Google Scholar 

  24. Sgoutas, D.S., Biochemistry 9:1826 (1970).

    Article  CAS  Google Scholar 

  25. Kritchevsky, D., and A.R. Baldino, Artery 4:480 (1978).

    CAS  Google Scholar 

  26. Sgoutas, D.S., Biochim. Biophys. Acta 164:317 (1968).

    CAS  Google Scholar 

  27. Goller, H.J., D.S. Sgoutas, I.A. Ismail and F.D. Gunstone, Biochemistry 9:3072 (1970).

    Article  CAS  Google Scholar 

  28. Gurr, M.I., M.P. Robinson, A.T. James, L.J. Morris and D. Howling, Biochim. Biophys. Acta 280:415 (1972).

    CAS  Google Scholar 

  29. Mahfouz, M.M., A.J. Valicenti and R.T. Holman, Ibid. 618:1 (1980).

    CAS  Google Scholar 

  30. Pollard, M.R., F.D. Gunstone, A.T. James and L.J. Morris, Lipids 15:306 (1980).

    Article  CAS  Google Scholar 

  31. Mahfouz, M., and R.T. Holman, Lipids 15:63 (1980).

    Article  CAS  Google Scholar 

  32. Kameda, K., A.J. Valicenti and R.T. Holman, Biochim. Bio- phys. Acta 618:13–17 (1980).

    CAS  Google Scholar 

  33. Jezyk, P., and W.E.M. Lands, J. Lipid Res. 9:525 (1968).

    CAS  Google Scholar 

  34. Waku, Keizo, and W.E.M. Lands, Ibid. 9:12 (1968).

    Google Scholar 

  35. Reitz, R.C., W.E.M. Lands, W.W. Christie and R.T. Holman, J. Biol. Chem. 243:2241 (1968).

    CAS  Google Scholar 

  36. Lippel, K., Lipids 8:111 (1973).

    Article  CAS  Google Scholar 

  37. DuPlessis, L.M., and N. Grobbelaar, Lipids 14:943 (1979).

    Article  CAS  Google Scholar 

  38. Privett, O.S., E.M. Stearns and E.C. Nickell, J. Nutr. 92:303 (1967).

    CAS  Google Scholar 

  39. Nugteren, D.H., Biochim. Biophys. Acta 210:171 (1970).

    CAS  Google Scholar 

  40. Berthuis, R.K., D.H. Nugteren, H.J.J. Pabon and D.A. Van Dorp, Reel. Trav. Chim. Pays-Bas 87:461 (1968).

    Google Scholar 

  41. Flower, R.J., H.S. Cheung and D.W. Cushman, Prostaglandins 4:325 (1973).

    Article  CAS  Google Scholar 

  42. Hwang, D.H., and J.E. Kinsella, Ibid. 17:543 (1979).

    Article  CAS  Google Scholar 

  43. Kurata, N., and D.S. Privett, Lipids 15:1029 (1980).

    Article  CAS  Google Scholar 

  44. Struijk, C.B., R.K. Beerthuis, H.J.J. Pabon and D.A. Van Dorp, Recl. Trav. Chim. Pays-Bas 85:1233 (1966).

    CAS  Google Scholar 

  45. Sprecher, H., and H.T. James, in Geometrical and Positional Fatty Acid Isomers, edited by E.A. Emken and H.J. Dutton, American Oil Chemists’ Society, Champaign, IL, 1979, chap. 11, pp. 303–338.

    Google Scholar 

  46. Gunstone, F.D., and I.A. Ismail, Chem. Phys. Lipids 1:209 (1967).

    Article  CAS  Google Scholar 

  47. Barve, J.A., and F.D. Gunstone, Ibid. 7:311 (1971).

    Article  CAS  Google Scholar 

  48. Gunstone, F.D., and M. Lie Ken Jie,Ibid. 4:1 (1970).

    Article  CAS  Google Scholar 

  49. Gensler, W.J., and J.J. Bruno, J. Org. Chem. 28:1254 (1963).

    Article  CAS  Google Scholar 

  50. Christie, W.W., and R.T. Holman, Chem. Phys. Lipids 1:407 (1967).

    Article  CAS  Google Scholar 

  51. Rakoff, H., and E.A. Emken, J. Labelled Compd. Radio- pharm. 19:19 (1982).

    Article  CAS  Google Scholar 

  52. Rakoff, H., and E.A. Emken, Chem. Phys. Lipids 31:215 (1982).

    Article  CAS  Google Scholar 

  53. Anderson, R.L., C.S. Fullmer and E.J. Hollenbach, J. Nutr. 105:393 (1975).

    CAS  Google Scholar 

  54. Reichwald-Hacker, I., K. Ilsemann and K.D. Mukherjee, Ibid. 109:1051 (1979).

    CAS  Google Scholar 

  55. Reichwald, I., S. Grosse-Oetringhaus, I. Kiewitt and K.D. Mukherjee, Biochim. Biophys. Acta 575:327 (1979).

    Google Scholar 

  56. Reichwald, I., S. Grosse-Oetringhaus, I. Kieweitt and K.D. Mukherjee, J. Nutr. 110:1122 (1980).

    Google Scholar 

  57. Wood, R., and R. Wiegand, Lipids 10:746 (1975).

    Article  CAS  Google Scholar 

  58. Wood, R., F. Chumbler and R. Wiegand, J. Biol. Chem. 252: 1965 (1977).

    CAS  Google Scholar 

  59. Wood, R., F. Chumbler, M. Matocha and A. Zoeller, Lipids 14:789(1979).

    Article  CAS  Google Scholar 

  60. Høy, C.E., and G. Hølmer, Lipids 16:102 (1981).

    Article  Google Scholar 

  61. Jacob, J. and G. Grimmer, J. Lipid Res. 8:308 (1967).

    CAS  Google Scholar 

  62. Ohlrogge, J.B., E.A. Emken and R.M. Gulley, Ibid. 22:955 (1981).

    CAS  Google Scholar 

  63. Ohlrogge, J.B., R.M. Gulley and E.A. Emken, Lipids 17:551 (1982).

    Article  CAS  Google Scholar 

  64. Heckers, V.H., F.W. Melcher and K. Dillmar, Fette Seifen Anstrichm. 81:217 (1979).

    Article  CAS  Google Scholar 

  65. Thomas, L.H., P.R. Jones, J.A. Winter and H. Smith, Am. J. Clin. Nutr. 34:877 (1981).

    CAS  Google Scholar 

  66. Elson, C.E., N.J. Benemenga, D.J. Canty, R.H. Grummer, J.J. Lalich, J.W. Porter and A.E. Johnston, Atherosclerosis 40: 115 (1981).

    Article  CAS  Google Scholar 

  67. Jackson, R.L., J.D. Morrisett, H.J. Pownall, A.M. Gotto, Jr., A. Kamio, H. Imai, R. Tracy and F.A. Kummerow, J. Lipid Res. 18:182 (1977).

    CAS  Google Scholar 

  68. Mounts, T.L., Lipids 11:676 (1976).

    Article  CAS  Google Scholar 

  69. Lanser, A.C., T.L. Mounts and E.A. Emken, Lipids 13:103 (1978).

    Article  CAS  Google Scholar 

  70. Lanser, A.C., and E.A. Emken, Lipids 16:15 (1981).

    Article  CAS  Google Scholar 

  71. Lanser, A.C., JAOCS 59: 307A (1982), Abstract 288.

    Google Scholar 

  72. Emken, E.A., W.K. Rohwedder, H.J. Dutton, W.J. DeJarlais, R.O. Adlof, J. Mackin, R. Dougherty and J.M. Iacono, Metab- olism 28:575 (1979).

    Article  CAS  Google Scholar 

  73. Emken, E.A., W.K. Rohwedder, H.J. Dutton, W.J. Dejarlais, R.O. Adlof, J.F. Mackin, R.M. Dougherty and J.M. Iacono, Lipids 14:547 (1979).

    Article  CAS  Google Scholar 

  74. Emken, E.A., H.J. Dutton, W.K. Rohwedder, Henry Rakoff, R.O. Adlof, R.M. Gulley and J.J. Canary, Lipids 15:864 (1980).

    Article  CAS  Google Scholar 

  75. Emken, E.A., R.O. Adlof, W.K. Rohwedder and R.M. Gulley, J. Lipid Res. 24:34(1983).

    CAS  Google Scholar 

  76. Sgoutas, D., R. Jones, P. Benfanis and F. Szlam, Biochim. Biophys. Acta 441:14 (1976).

    CAS  Google Scholar 

  77. Cook, H.W., Lipids 16:920 (1981).

    Article  CAS  Google Scholar 

  78. Moore, C.E., and G.A. Dhopeshwarkar, Lipids 16:479 (1981).

    Article  CAS  Google Scholar 

  79. Ono, K., and D.S. Fredrickson, J. Biol. Chem. 239:2482 (1964).

    CAS  Google Scholar 

  80. Wenzel, D.G., and J.W. Kleoppel, Toxicology 18:27 (1980).

    Article  CAS  Google Scholar 

  81. Kinsella, J.E., D.H. Hwang, P. Yu, J. Mai and J. Shimp. Bio- chem. J. 184:701 (1979).

    CAS  Google Scholar 

  82. Kinsella, J.E., P.H. Yu and J.B. Mai, Lipids 14:1032 (1979).

    Article  CAS  Google Scholar 

  83. Yu, P., J. Mai and J.E. Kinsella, Lipids 15:975 (1980).

    Article  CAS  Google Scholar 

  84. Sano, M., and O.S. Privett, Lipids 15:337 (1980).

    Article  CAS  Google Scholar 

  85. Hwang, D.H., and J.E. Kinsella, Prostaglandins Med. 1:121 (1978).

    Article  CAS  Google Scholar 

  86. Cook, H.W., Can. J. Biochem. 58:121 (1980).

    CAS  Google Scholar 

  87. Raccuglia, G., and O.S. Privett, Lipids 5:85 (1970).

    Article  CAS  Google Scholar 

  88. Moore, C.F., R.B. Alfin-Slater and L. Aftergood, J. Nutr. 110:2284(1980).

    CAS  Google Scholar 

  89. Ohlrogge, J.B., E.D. Barber, W.E.M. Lands, F.D. Gunstone and I.A. Ismail, Can. J. Biochem. 54:736 (1976).

    Article  CAS  Google Scholar 

  90. Vandenhoff, G., F.D. Gunstone, J. Barve and W.E.M. Lands, J. Biol. Chem. 250:8720 (1975).

    CAS  Google Scholar 

  91. Tsao, Yuan-Kai, and W.E.M. Lands, Science 207:777 (1980).

    Article  Google Scholar 

  92. Graff, G., and W.E.M. Lands, Chem. Phys. Lipids 17:301 (1976).

    Article  CAS  Google Scholar 

  93. Hill, E.G., S.B. Johnson and R.T. Holman, J. Nutr. 109: 1759 (1979).

    CAS  Google Scholar 

  94. Privett, O.S., F. Phillips, H. Shimasaki, T. Nozawa and E.C. Nickell, Am. J. Clin. Nutr. 30:1009 (1977).

    CAS  Google Scholar 

  95. Vles, R.O., and J.J. Gottenbos, Voeding 33:428 (1972).

    CAS  Google Scholar 

  96. Vles, R.O., and J.J. Gottenbos, Ibid. 33:455 (1972).

    Google Scholar 

  97. Alfin-Slater, R.B., and L. Aftergood, in Geometrical and Posi- tional Fatty Acid Isomers, edited by E.A. Emken and H.J. Dutton, American Oil Chemists’ Society, Champaign, IL, 1979, pp. 5 3–74.

    Google Scholar 

  98. Yu, P., J. Mai and J.E. Kinsella, Am. J. Clin. Nutr. 33:598 (1980).

    CAS  Google Scholar 

  99. DeSchrijver, R., and O.S. Privett, Lipids 17:27 (1982).

    Article  CAS  Google Scholar 

  100. Kritchevsky, D., Fed. Proc. 41:2813 (1982).

    CAS  Google Scholar 

  101. Lohmar, T.G., World Soybean Conference, edited by L.D. Hill, Interstate Printers, Inc., Danville, IL, 1976, p. 883.

    Google Scholar 

  102. Mattson, F.A., F.J. Hollenbach and A.M. Klingman, Am. J. Clin. Nutr. 28:726 (1975).

    CAS  Google Scholar 

  103. Vergroesen, A.J., Proc. Nutr. Soc. 31:323 (1972).

    Article  CAS  Google Scholar 

  104. Gottenbos, J.J., and R.O. Vles, JAOCS 57:Abstract 66 (1980).

    Article  Google Scholar 

  105. Brown, R.R., NCI Workshop of Dietary Fat and Cancer, Bethesda, MD, 1979.

  106. Hwang, D.H., M.M. Mathias, J. Dupont and D.L. Meyer, J. Nutr. 105:995 (1975).

    CAS  Google Scholar 

  107. Schrock, C.G., and W.E. Connors, Am. J. Clin. Nutr. 28:1020 (1975).

    CAS  Google Scholar 

  108. Emken, E.A., Prog. Lipid Res. 20:135 (1981).

    Article  CAS  Google Scholar 

  109. Hsu, C.M.L., and F.A. Kummerow, Lipids 12:486 (1977).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Northern Regional Research Center, Agricultural Research Service, US Department of Agriculture, 61604, Peoria, IL

    E. A. Emken

Authors
  1. E. A. Emken
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Emken, E.A. Biochemistry of unsaturated fatty acid isomers. J Am Oil Chem Soc 60, 995–1004 (1983). https://doi.org/10.1007/BF02660215

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02660215

Keywords

Search

Navigation