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. 1991 Jun 1;88(11):4830–4834. doi: 10.1073/pnas.88.11.4830

Unusual isomeric polyunsaturated fatty acids in liver phospholipids of rats fed hydrogenated oil.

R T Holman 1, F Pusch 1, B Svingen 1, H J Dutton 1
PMCID: PMC51760  PMID: 2052561

Abstract

Linoleic acid (18:2 omega 6) and linolenic acid (18:3 omega 3) are precursors of two series of essential fatty acids (EFA) formed by alternate desaturations and elongations. In EFA deficiency (EFAD), oleic acid (18:1 omega 9) and palmitoleic acid (16:1 omega 7) undergo the same reactions to form polyunsaturated fatty acids (PUFA) of other structures. Partially hydrogenated soybean oil (PHSO) contains isomeric 18:1 acids that can be converted to unusual isomers of 18:2 by liver microsomes. To test whether 18:2, 20:3, and 20:4 of unusual structure occur in phospholipids as a consequence of EFAD or ingestion of PHSO, rats were fed corn oil, an EFA-deficient diet, or PHSO to provide isomeric 18:1 acids. At 2.5 months the phospholipids were isolated from livers and converted to methyl esters, and the 18:2, 20:2, 20:3, and 20:4 fractions were isolated. The 18:2 and 20:2 fractions were ozonized, and, by using a computer solution of simultaneous equations, the structures and proportions of each isomer were calculated. The 20:3 and 20:4 fractions were analyzed by ozonolysis and capillary gas chromatography. When corn oil was fed, the major isomer in each group was 9,12-18:2, 11,14-20:2, 8,11,14-20:3, and 5,8,11,14-20:4. Patterns in EFAD- and PHSO-fed groups were more diverse, with large proportions of unusual isomers. Feeding EFA-deficient diet and PHSO induced measurable amounts of unusual PUFA at each step of the cascade, and these PUFA may compete in metabolism of normal PUFA and are substrates for oxidative formation of autacoids of unknown structures and function.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Dutton H. J., Johnson S. B., Pusch F. J., Lie Ken Jie M. S., Gunstone F. D., Holman R. T. Composition of mixed octadecadienoates via ozonolysis, chromatography and computer solution of linear equations. Lipids. 1988 May;23(5):481–489. doi: 10.1007/BF02535524. [DOI] [PubMed] [Google Scholar]
  2. FOLCH J., LEES M., SLOANE STANLEY G. H. A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem. 1957 May;226(1):497–509. [PubMed] [Google Scholar]
  3. Hill E. G., Johnson S. B., Lawson L. D., Mahfouz M. M., Holman R. T. Perturbation of the metabolism of essential fatty acids by dietary partially hydrogenated vegetable oil. Proc Natl Acad Sci U S A. 1982 Feb;79(4):953–957. doi: 10.1073/pnas.79.4.953. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Holman R. T., Johnson S. B., Ogburn P. L. Deficiency of essential fatty acids and membrane fluidity during pregnancy and lactation. Proc Natl Acad Sci U S A. 1991 Jun 1;88(11):4835–4839. doi: 10.1073/pnas.88.11.4835. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Holman R. T., Mahfouz M. M. Cis and trans-octadecenoic acids as precursors of polyunsaturated acids. Prog Lipid Res. 1981;20:151–156. doi: 10.1016/0163-7827(81)90028-x. [DOI] [PubMed] [Google Scholar]
  6. Lawson L. D., Hill E. G., Holman R. T. Dietary fats containing concentrates of cis or trans octadecenoates and the patterns of polyunsaturated fatty acids of liver phosphatidylcholine and phosphatidylethanolamine. Lipids. 1985 May;20(5):262–267. doi: 10.1007/BF02534257. [DOI] [PubMed] [Google Scholar]
  7. Lawson L. D., Hill E. G., Holman R. T. Suppression of arachidonic acid in lipids of rat tissues by dietary mixed isomeric cis and trans octadecenoates. J Nutr. 1983 Sep;113(9):1827–1835. doi: 10.1093/jn/113.9.1827. [DOI] [PubMed] [Google Scholar]
  8. Mahfouz M. M., Valicenti A. J., Holman R. T. Desaturation of isomeric trans-octadecenoic acids by rat liver microsomes. Biochim Biophys Acta. 1980 Apr 18;618(1):1–12. doi: 10.1016/0005-2760(80)90047-8. [DOI] [PubMed] [Google Scholar]
  9. Marcel Y. L., Christiansen K., Holman R. T. The preferred metabolic pathway from linoleic acid to arachidonic acid in vitro. Biochim Biophys Acta. 1968 Sep 2;164(1):25–34. doi: 10.1016/0005-2760(68)90067-2. [DOI] [PubMed] [Google Scholar]
  10. Mensink R. P., Katan M. B. Effect of dietary trans fatty acids on high-density and low-density lipoprotein cholesterol levels in healthy subjects. N Engl J Med. 1990 Aug 16;323(7):439–445. doi: 10.1056/NEJM199008163230703. [DOI] [PubMed] [Google Scholar]
  11. Mohrhauer H., Christiansen K., Gan M. V., Deubig M., Holman R. T. Chain elongation of linoleic acid and its inhibition by other fatty acids in vitro. J Biol Chem. 1967 Oct 10;242(19):4507–4514. [PubMed] [Google Scholar]
  12. Morris L. J. Separations of lipids by silver ion chromatography. J Lipid Res. 1966 Nov;7(6):717–732. [PubMed] [Google Scholar]
  13. Reitz R. C., Lands W. E., Christie W. W., Holman R. T. Effects of ethylenic bond position upon acyltransferase activity with isomeric cis,cis-octadecadienoyl coenzyme A thiol esters. J Biol Chem. 1968 May 10;243(9):2241–2246. [PubMed] [Google Scholar]
  14. SAND D., SEN N., SCHLENK H. POSITIONAL ISOMERISM OF UNSATURATED FATTY ACIDS IN THE RAT. QUANTIFICATION OF ISOMERIC MIXTURES. J Am Oil Chem Soc. 1965 Jun;42:511–516. doi: 10.1007/BF02540093. [DOI] [PubMed] [Google Scholar]
  15. Sperecher H. W., Dutton H. J., Gunstone F. D., Holman R. T. Metabolic conversions and the positional distributions in liver lecithin of some unnatural dienoic acids in the rat. Lipids. 1967 Mar;2(2):122–126. doi: 10.1007/BF02530910. [DOI] [PubMed] [Google Scholar]

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