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Influence of dietary arachidonic acid on metabolism in vivo of 8 cis, 11 cis, 14-eicosatrienoic acid in humans

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Lipids

Abstract

This study investigated the influence of dietary arachidonic acid (20∶4n-6) on Δ5 desaturation and incorporation of deuterium-labeled 8cis, 11cis, 14-eicosatrienoic acid (20∶3n-6) into human plasma lipids. Adult male subjects (n=4) were fed diets containing either 1.7 g/d (H120∶4 diet) or 0.21 g/d (LO20∶4 diet) of arachidonic acid for 50 d and then dosed with a mixture containing ethyl esters of 20∶3n-6[d4] and 18∶1n-9[d2]. A series of blood samples was sequentially drawn over a 72-h period, and methyl esters of plasma total lipid, triacylglycerol, phospholipids, and cholesteryl ester were analyzed by gas chromatography-mass spectrometry. Based on the concentration of 20∶3n-6[d4] in total plasma lipid, the estimated conversion of 20∶3n-6[d4] to 20∶4n-6[d4] was 17.7.±0.79% (HI20∶4 diet) and 2.13±1.44% (LO20∶4 diet). The concentrations of 20∶4n-6[d4] in total plasma lipids from subjects fed the HI20∶4 and LO20∶4 diets were 2.10±0.6 and 0.29±0.2 μmole/mL plasma/mmole of 20∶3n-6[d4] fed/kg of body weight. These data indicate that conversion of 20∶3n-6[d4] to 20∶4n-6[d4] was stimulated 7-8-fold by the HI20∶4 diet. Phospholipid acyltransferase was 2.5-fold more selective for 20∶3n-6[d4] than 18∶1n-9[d2], and lecithin:cholesterol acyltransferase was 2-fold more selective for 18∶1n-9[d2] than 20∶3n-6[d4]. These differences in selectivity were not significantly influenced by diet. Absorption of ethyl 20∶3n-6[d4] was about 33% less than ethyl 18∶1n-9[d2]. The sum of the n-6 retroconversion products from 20∶3n-6[d4] in total plasma lipids was about 2% of the total deuterated fatty acids. Neither absorption nor retroconversion appears to be influenced by diet.

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Abbreviations

CE:

cholesteryl ester

GC-MS:

gas chromatography-mass spectrometry

PL:

phospholipid

TG:

triglyceride

TLC:

thin-layer chromatography

TL:

total lipid

References

  1. Horrobin, D.F. (1992) Nutritional and Medical Importance of Gamma-Linolenic Acid, Prog. Lipid Res. 31, 163–194.

    Article  PubMed  CAS  Google Scholar 

  2. Horrobin, D.F. (ed.) (1990) Omega-6 Essential Fatty Acids. Pathology and Roles in Clinical Medicine, Alan R. Liss, Inc. New York.

    Google Scholar 

  3. Sardesai, V.M. (1992) Nutritional Role of Polyunsaturated Fatty Acids, J. Nutr. Biochem. 3, 154–166.

    Article  CAS  Google Scholar 

  4. Huang, Y.-S., and Mills, D.E. (eds.) (1996) in γ-Linolenic Acid: Metabolism and Its Roles in Nutrition and Medicine, AOCS Press, Champaign.

    Google Scholar 

  5. Huang, Y.-S., Mills, D.E., Cantrill, R.C., and Poisson, J.-P. (1996) In vivo and in vitro Metabolism of Linoleic and γ-Linolenic acids, in γ-Linolenic Acid: Metabolism and Its Roles in Nutrition and Medicine (Huang, Y.-S., and Mills, D.E., eds.) pp. 84–105, AOCS Press, Champaign.

    Google Scholar 

  6. Stone, K.J., Willis, A.L., Hart, M., Kirtland, S.J., Kernoff, P.B.A., and McNicol, G.P. (1979) The Metabolism of Dihomo-γ-Linolenic Acid in Man, Lipids 14, 174–180.

    PubMed  CAS  Google Scholar 

  7. Boustani, S.E., Causse, J.E., Descomps, B., Monnier, L., Mendy, F., and de Paulet, A.C. (1989) Direct in vivo Characterization of Delta 5 Desaturase Activity in Humans by Deuterium Labeling: Effect of Insulin, Metabolism 38, 315–321.

    Article  PubMed  Google Scholar 

  8. Emken, E.A., Rohwedder, W.K., Dutton, H.J., Dougherty, R., Iacono, J.M., and mackin, J. (1975) Dual-Labeled Technique for Human Lipid Metabolism Studies Using Deuterated Fatty Acid Isomers, Lipids 11, 135–142.

    Google Scholar 

  9. Rakoff, H. (1988) Preparation of Methyl cis-9,cis-12,cis-15-octadecatrienoate-15, 16-d2 and Methyl cis-9,cis-12,cis-15-octadecatrienoate-6, 6,7,7-d4, Lipids 23, 280–285.

    CAS  Google Scholar 

  10. Christie, W.W. (1973) Lipid Analysis, pp. 85–102, Pergamon Press Ltd., New York.

    Google Scholar 

  11. Nelson, G.J., Kelley, D.S., Emken, E.A., Phinney, S.D., Kyle, D., and Ferretti, A. (1997) A Human Dietary Arachidonic Acid Supplementation Study Conducted in a Metabolic Research Unit: Rationale and Design, Lipids 32, 415–420.

    PubMed  CAS  Google Scholar 

  12. USDA Handbook 8, 1–23. Composition of Foods, Raw, Processed, Prepared. Releases and Supplements (1976-present). Nutrient Data Laboratory/Agricultural Research Service, Riverdale, MO.

  13. Lindgren, F.T., Jensen, L.C., and Hatch, F.T. (1972) The Isolation and quantitative Analysis of Serum Lipoproteins, in Blood Lipids and Lipoproteins (Nelson, G.J., ed.) pp. 186–188, Wiley-Interscience, New York.

    Google Scholar 

  14. Narayan, K.A. (1975) Electrophoresis Methods for the Separation of Serum Lipoproteins, in Analysis of Lipids and Lipoproteins (Perkins, E.G., ed.) pp. 225–249, American Oil Chemists’ Society, Champaign.

    Google Scholar 

  15. Folch, J., Lees, M., and Sloane-Stanley, G.E. (1957) A Simple Method for the Isolation and Purification of Total Lipids from Animal Tissues, J. Biol. Chem. 226, 497–509.

    PubMed  CAS  Google Scholar 

  16. French, J.A., and Anderson, D.W. (1973) Separation and Quantitative Recovery of Lipid Classes: A Convenient Thin-Layer Chromatographic Method, J. Chromatogr. 80, 133–136.

    Article  PubMed  CAS  Google Scholar 

  17. Peter, H.W., and Wolf, H.U. (1973) A New Method for the in situ Determination of Phospholipids After Thin-Layer Separation, J. Chromatogr. 82, 15–30.

    Article  PubMed  CAS  Google Scholar 

  18. Schenck, P.A., Rakoff, H., and Emken, E.A. (1996) Δ8 Desaturation in vivo of Deuterated Eicosatrienoic Acid by Mouse Liver, Lipids 31, 593–600.

    Article  PubMed  CAS  Google Scholar 

  19. Rohwedder, W.K., Emken, E.A., and Wolf, D.J. (1985) Analysis of Deuterium-Labeled Blood Lipids by Chemical Ionization Mass Spectrometry, Lipids 20, 303–311.

    PubMed  CAS  Google Scholar 

  20. Statistical Analysis System Institute (1987) SAS Guide for Personal Computers, 6th edn., SAS Institute Inc., Cary.

    Google Scholar 

  21. Emken, E.A., Adlof, R.O., Rohwedder, W.K., and Gulley, R.M. (1993) Influence of Linoleic Acid on Desaturation and Uptake of Deuterium-Labeled Palmitic and Stearic Acids in Humans, Biochim. Biophys. Acta 1170, 173–181.

    PubMed  CAS  Google Scholar 

  22. Nelson, G.J., Schmidt, P.C., Bartolini, G., Kelley, D.S., Phinney, S.D., Kyle, D., Silbermann, S., and Schaefer, E.J. (1997) The Effect of Dietary Arachidonic Acid on Plasma Lipoprotein Distributions, Apoproteins, Blood Lipid Levels, and Tissue Fatty Acid Composition in Humans, Lipids 32, 427–433.

    PubMed  CAS  Google Scholar 

  23. Nelson, G.J., and Ackman, R.G. (1988) Absorption and Transport of Fat in Mammals with Emphasis on n-3 Polyunsaturated Fatty Acids, Lipids 23, 1005–1014.

    PubMed  CAS  Google Scholar 

  24. Nordoy, A., Barstad, L., Connor, W.E., and Hatcher, L. (1991) Absorption of the n-3 Eicosapentaenoic and Docosahexaenoic Acids as Ethyl Esters and Triglycerides by Humans, Am. J. Clin. Nutr. 53, 1185–1190.

    PubMed  CAS  Google Scholar 

  25. Chernenko, G.A., Barrowman, J.A., Kean, K.T., Herzberg, G.R., and Keough, K.M.W. (1989) Intestinal Absorption and Lymphatic Transport of Fish Oil (MaxEPA) in the Rat, Biochim. Biophys. Acta 1004, 95–102.

    PubMed  CAS  Google Scholar 

  26. Hamazaki, T., Urakaze, M., Makuta, M., Ozawa, A., Soda, Y., Tatsum, H., Yano, S., and Kumagai, A. (1987) Intake of Different Eicosapentaenoic Acid-Containing Lipids and Fatty Acid Pattern of Plasma Lipids in the Rats, Lipids 22, 994–998.

    PubMed  CAS  Google Scholar 

  27. Krokan, H.E., Bjerve, K.S., and Mork, E. (1993) The Enteral Bioavailability of Eicosapentaenoic Acid and Docosahexaenoic Acid Is as Good from Ethyl Esters as from Glyceryl Esters in Spite of Lower Hydrolytic Rates by Pancreatic Lipase in vitro, Biochim. Biophys. Acta 1168, 59–67.

    PubMed  CAS  Google Scholar 

  28. Nilsson, A., and Melin, T. (1988) Absorption and Metabolism of Orally Fed Arachidonic and Linoleic Acid in the Rat. Am. J. Physiology 255, G612-G618

    CAS  Google Scholar 

  29. Chen, I.S., Hotta, S., Ikeda, I., Cassidy, M.M., Sheppard, A.J., and Vahouny, G.V. (1987) Digestion, Absorption and effects on Cholesterol Absorption of Menhaden Oil, Fish Oil Concentrate and Corn Oil by Rats, J. Nutr. 117, 1676–1680.

    PubMed  CAS  Google Scholar 

  30. Lawson, L.D., and Hughes, B.G. (1988) Human Absorption of Fish Oil Fatty Acids as Triacylglycerols, Free Acids, or Ethyl Esters, Biochem. Biophys. Res. Comm. 152, 328–335.

    Article  PubMed  CAS  Google Scholar 

  31. Poisson, J.-P., Huang, Y.-S., Mills, D.E., De Antueno, R.J., Redden, P.R., Lin, X., Narce, M., and Horrobin, D.F. (1993) Effect of Salt-Loading and Spontaneous Hypertension on in vitro Metabolism of [14C]Linoleic and [14C]Dihomo-gamma-linolenic Acids, Biochem. Med. Metab. Biol. 49, 57–66.

    Article  PubMed  CAS  Google Scholar 

  32. Emken, E.A., Adlof, R.O., and Gulley, R.M. (1994) Dietary Linoleic Acid Influences Desaturation and Acylation of Deuterium-Labeled Linoleic and Linolenic Acids in Young Adult Males, Biochim. Biophys. Acta 1213, 277–288.

    PubMed  CAS  Google Scholar 

  33. Barre, D.E., and Holub, B.J. (1992) The Effect of Borage Oil Consumption on Human Plasma Lipid Levels and the Phosphatidylcholine and Cholesterol Ester Composition of High Density Lipoprotein, Nutr. Res. 12, 1181–1194.

    Article  CAS  Google Scholar 

  34. Berger, A., and German, J.B. (1990) Phospholipid Fatty Acid Comparison of Various Mouse Tissues After Feeding α-Linolenate (18∶3n-3) or Eicosatrienoate (20∶3n-3), Lipids 25, 473–480

    PubMed  CAS  Google Scholar 

  35. Cook, H.W., Clarke, J.T.R., and Spence, W. (1983) Concerted Stimulation and Inhibition of Desaturation, Chain Elongation, and Esterification of Essential Fatty Acids by Cultured Neuroblastoma Cells, J. Biol. Chem. 258, 7587–7591.

    Google Scholar 

  36. Cook, H.W., and Spence, M.W. (1987) Studies of the Modulation of Essential Fatty Acid Metabolism by Fatty Acids in Cultured Neuroblastoma and Glioma Cells, Biochim. Biophys. Acta 918, 217–229

    PubMed  CAS  Google Scholar 

  37. Chen, Q., and Nilsson, A. (1993) Desaturation and Chain Elongation of n-3 and n-6 Polyunsaturated Fatty Acids in the Human CaCo-2 Cell Lines, Biochim. Biophys. Acta 1166, 193–201.

    PubMed  CAS  Google Scholar 

  38. Pugh, E.L., and Kates, M. (1977) Direct Desaturation of Eicosatrienoyl Lecithin to Arachidonoyl Lecithin by Rat Liver Microsomes, J. Biol. Chem. 252, 68–73.

    PubMed  CAS  Google Scholar 

  39. Luthria, D., and Sprecher, H. (1994) A Comparison of the Specific Activities of Linoleate and Arachidonate in Liver, Heart, and Kidney Phospholipids After Feeding Rats Ethyl Linoleate-9, 10,12,13-d4, Biochim. Biophys. Acta 1213, 1–4.

    PubMed  CAS  Google Scholar 

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Emken, E.A., Adlof, R.O., Duval, S.M. et al. Influence of dietary arachidonic acid on metabolism in vivo of 8 cis, 11 cis, 14-eicosatrienoic acid in humans. Lipids 32, 441–448 (1997). https://doi.org/10.1007/s11745-997-0058-4

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  • DOI: https://doi.org/10.1007/s11745-997-0058-4

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