Skip to main content
SpringerLink
Log in

Distributions of conjugated linoleic acid (CLA) isomers in tissue lipid classes of pigs fed a commercial CLA mixture determined by gas chromatography and silver ion-high-performance liquid chromatography

  • Article
  • Published:
Lipids

Abstract

Pigs were fed a commercial conjugated linoleic acid (CLA) mixture, prepared by alkali isomerization of sunflower oil, at 2% of the basal diet, from 61.5 to 106 kg live weight, and were compared to pigs fed the same basal diet with 2% added sunflower oil. The total lipids from liver, heart, inner back fat, and omental fat of pigs fed the CLA diet were analyzed for the incorporation of CLA isomers into all the tissue lipid classes. A total of 10 lipid classes were isolated by three-directional thin-layer chromatography and analyzed by gas chromatography (GC) on long capillary columns and by silver-ion high-performance liquid chromatography (Ag+-HPLC); cholesterol was determined spectrophotometrically. Only trace amounts (<0.1%; by GC) of the 9,11–18∶2 cis/trans and trans, trans isomers were observed in pigs fed the control diet. Ten and twelve CLA isomers in the diet and in pig tissue lipids were sepatated by GC and Ag+-HPLC, respectively. The relative concentration of all the CLA isomers in the different lipid classes ranged from 1 to 6% of the total fatty acids. The four major cis/trans isomers (18.9% 11 cis, 13 trans-18∶2; 26.3% 10 trans, 12 cis-18∶2; 20.4% 9 cis, 11 trans-18∶2; and 16.1% 8 trans, 10 cis-18∶2) constituted 82% of the total CLA isomers in the dietary CLA mixture, and smaller amounts of the corresponding cis,cis (7.4%) and trans,trans (10.1%) isomers were present. The distribution of CLA isomers in inner back fat and in omental fat of the pigs was similar to that found in the diet. The liver triacylglycerols (TAG), free fatty acids (FFA), and cholesteryl esters showed a similar patterns to that found in the diet. The major liver phospholipids showed a marked increase of 9 cis,11 trans-18∶2, ranging from 36 to 54%, compared to that present in the diet. However, liver diphosphatidylglycerol (DPG) showed a high incorporation of the 11 cis,13 trans-18∶2 isomer (43%). All heart lipid classes, except TAG, showed a high content of 11 cis,13 trans-18∶2, which was in marked contrast to results in the liver. The relative proportion of 11 cis,13 trans-18∶2 ranged from 30% in the FFA to 77% in DPG. The second major isomer in all heart lipids was 9 cis,11 trans-18∶2. In both liver and heart lipids the relative proportions of both 10 trans,12 cis-18∶2 and 8 trans,10 cis-18∶2 were significantly lower compared to that found in the diet. The FFA in liver and heart showed the highest content of trans,trans isomers (31 to 36%) among all the lipid classes. The preferential accumulation of the 11 cis,13 trans-18∶2 into cardiac lipids, and in particular the major phospholipid in the inner mitochondrial membrane, DPG, in both heart and liver, appears unique and may be of concern. The levels of 11 cis,13 trans-18∶2 naturally found in foods have not been established.

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

Abbreviations

CE:

cholesteryl ester

cis/trans :

refers to the group of CLA isomers, or a specific positional isomer, having either a cis/trans or a trans,cis configuration

CLA:

conjugated linoleic acid

DMOX:

4,4-dimethyloxazoline

DPG:

diphosphatidylglycerol (cardiolipin)

FAME:

fatty acid methyl esters

FFA:

free fatty acids

GC:

gas chromatography

GC-DD-FTIR:

direct deposition-Fourier transform infrared

GC-EIMS:

electron ionization mass spectrometry

HPLC:

high-performance liquid chromatography

PC:

phosphatidylcholine

PE:

phosphatidylethanolamine

SM:

sphingomyelin

TAG:

triacylglycerol

TLC:

thin-layer chromatography

References

  1. Ha, Y.L., Storkson, J., and Pariza, M.W. (1990) Inhibition of Benzo(a)pyrene-induced Mouse Forestomach Neoplasia by Conjugated Dienoic Derivatives of Linoleic Acid, Can. Res. 50 1097–1101.

    CAS  Google Scholar 

  2. Ip, C., Chin, S.F., Scimeca, J.A., and Pariza, M.W. (1991) Mammary Cancer Prevention by Conjugated Dienoic Derivative of Linoleic Acid, Can. Res. 51, 6118–6124.

    CAS  Google Scholar 

  3. Shultz, T.D., Chew, B.P., and Seaman, W.R. (1992) Differential Stimulatory and Inhibitory Responses of Human MCF-7 Breast Cancer Cells to Linoleic Acid and Conjugated Linoleic acid in Culture, Anticancer Res. 12, 2143–2146.

    PubMed  CAS  Google Scholar 

  4. Ip, C., Singh, M., Thompson, H.J., and Scimeca, J.A. (1994) Conjugated Linoleic Acid Suppresses Mammary Carcinogenesis and Proliferative Activity of the Mammary Gland in the Rat, Cancer Res. 54, 1212–1215.

    PubMed  CAS  Google Scholar 

  5. Liew, C., Schut, H.A.J., Chin, S.F., Pariza, M.W., and Dashwood, R.H. (1995) Protection of Conjugated Linoleic Acids Against 2-Amino-3-methylimidazo[4,5-f]quinoline-Induced Colon Carcinogenesis in the F344 Rat: A Study of Inhibitory Mechanisms, Carcinogenesis 16, 3037–3043.

    PubMed  CAS  Google Scholar 

  6. Chew, B.P., Wong, T.S., Shultz, T.D., and Magnuson, N.S. (1997) Effects of Conjugated Dienoic Derivatives of Linoleic Acid and β-Carotene in Modulating Lymphocyte and Macrophage Function, Anticancer Res. 17, 1099–1106.

    PubMed  CAS  Google Scholar 

  7. Ip, C., Jiang, C., Thompson, H.J., and Scimeca, J.A. (1997) Retention of Conjugated Linoleic Acid in the Mammary Gland Is Associated with Tumor Inhibition During the Post-Initiation Phase of Carcinogenesis, Carcinogenesis 18, 755–759.

    Article  PubMed  CAS  Google Scholar 

  8. Visonneau, S., Cesano, A., Tepper, S.A., Scimeca, J.A., Santoli, D., and Kritchevsky, D. (1997) Conjugated Linoleic Acid Suppresses the Growth of Human Breast Adenocarcinoma Cells in SCID Mice, Anticancer Res. 17, 969–974.

    PubMed  CAS  Google Scholar 

  9. Nicolosi, R.J., Rogers, E.J., Kritchevsky, D., Scimeca, J.A., and Huth, P.J. (1997) Dietary Conjugated Linoleic Acid Reduces Plasma Lipoproteins and Early Aortic Atherosclerosis in Hypercholesterolemic Hamsters, Artery 22, 266–277.

    PubMed  CAS  Google Scholar 

  10. Lee, K.N., Kritchevsky, D., and Pariza, M.W. (1994) Conjugated Linoleic Acid and Atherosclerosis in Rabbits, Atherosclerosis 108, 19–25.

    Article  PubMed  CAS  Google Scholar 

  11. Park, Y., Albright, K.J., Liu, W., Storkson, J.M., Cook, M.E., and Pariza, M.W. (1997) Effect of Conjugated Linoleic Acid on Body Composition in Mice, Lipids 32, 853–858.

    PubMed  CAS  Google Scholar 

  12. Dugan, M.E.R., Aalhus, J.L., Schaefer, A.L., and Kramer, J.K.G. (1997) The Effects of Conjugated Linoleic Acid on Fat to Lean Repartitioning and Feed Conversion in Pigs, Can. J. Anim. Sci. 77, 723–725.

    CAS  Google Scholar 

  13. Li, Y., and Watkins, B.A. (1998) Conjugated Linoleic Acids Alter Bone Fatty Acid Composition and Reduce ex vivo Bone Prostaglandin E2 Biosynthesis in Rats Fed n-6 or n-3 Fatty Acids, Lipids 33, 417–425.

    PubMed  CAS  Google Scholar 

  14. Parodi, P.W. (1977) Conjugated Octadecadienoic Acids of Milk Fat, J. Dairy Sci. 60, 1550–1553.

    Article  CAS  Google Scholar 

  15. Fogerty, A.C., Ford, G.L., and Svoronos, D. (1988) Octadeca-9,11-dienoic Acid in Foodstuffs and in the Lipids of Human Blood and Breast Milk, Nutr. Rep. Internat. 38, 937–944.

    CAS  Google Scholar 

  16. Chin, S.F., Liu, W., Storkson, J.M., Ha, Y.L., and Pariza, M.W. (1992) Dietary Sources of Conjugated Dienoic Isomers of Linoleic Acid, a Newly Recognized Class of Anticarcinogens, J. Food Comp. Anal. 5, 185–197.

    Article  CAS  Google Scholar 

  17. Shantha, N.C., Crum, A.D., and Decker, E.A. (1994) Evaluation of Conjugated Linoleic Acid Concentrations in Cooked Beef, J. Agric. Food Chem. 42, 1757–1760.

    Article  CAS  Google Scholar 

  18. Lin, H., Boylston, T.D., Chang, M.J., Luedecke, L.O., and Shultz, T.D. (1995) Survey of the Conjugated Linoleic Acid Contents of Dairy Products, J. Dairy Sci. 78, 2358–2365.

    Article  PubMed  CAS  Google Scholar 

  19. Knekt, P., Järvinen, R., Seppänen, R., Pukkala, E., and ARomaa, A. (1996) Intake of Dairy Products and the Risk of Breast Cancer, Br. J. Cancer 73, 687–691.

    PubMed  CAS  Google Scholar 

  20. Ackman, R.G., Eaton, C.A., Sipos, J.C., and Crewe, N.F. (1981) Origin of cis-9,trans-11-and trans-9,trans-11-Octadecadienoic Acids in the Depot Fat of Primates Fed a Diet Rich in Lard and Corn Oil and Implications for the Human Diet, Can. Inst. Food Sci. Technol. J. 14, 103–107.

    CAS  Google Scholar 

  21. Fritsche, J., Mossoba, M.M., Yurawecz, M.P., Roach, J.A.G., Sehat, N., Ku, Y., and Steinhart, H. (1997) Conjugated Linoleic Acid (CLA) Isomers in Human Adipose Tissue, Z. Lebensm. Unters. Forsch. A 205, 415–418.

    Article  CAS  Google Scholar 

  22. Smith, G.N., Taj, M., and Braganza, J.M. (1991) On the Identification of a Conjugated Diene Component of Duodenal Bile as 9Z,11E-Octadecadienoic Acid, Free Radical Biol. Med. 10, 13–21.

    Article  CAS  Google Scholar 

  23. Iversen, S.A., Cawood, P., and Dormandy, T.L. (1985) A Method for the Measurement of a Diene-Conjugated Derivative of Linoleic Acid, 18∶2(9,11), in Serum Phospholipid, and Possible Origins, Ann. Clin. Biochem. 22, 137–140.

    PubMed  CAS  Google Scholar 

  24. Britton, M., Fong, C., Wickens, D., and Yudkin, J. (1992) Diet as a Source of Phospholipid Esterified 9,11-Octadecadienoic Acid in Humans, Clin. Sci. 83, 97–101.

    PubMed  CAS  Google Scholar 

  25. Huang, Y.-C., Luedecke, L.O., and Shultz, T.D. (1994) Effect of Cheddar Cheese Consumption on Plasma Conjugated Linoleic Acid Concentrations in Men, Nutr. Res. 14, 373–386.

    Article  CAS  Google Scholar 

  26. Ip, C., Briggs, S.P., Haegele, A.D., Thompson, H.J., Storkson, J., and Scimeca, J.A. (1996) The Efficacy of Conjugated Linoleic Acid in Mammary Cancer Prevention Is Independent of the Level or Type of Fat in the Diet, Carcinogenesis 17, 1045–1050.

    PubMed  CAS  Google Scholar 

  27. Belury, M.A., and Kempa-Steczko, A. (1997) Conjugated Linoleic Acid Modulates Hepatic Lipid Composition in Mice, Lipids 32, 199–204.

    PubMed  CAS  Google Scholar 

  28. Sugano, M., Tsujita, A., Yamasaki, M., Yamada, K., Ikeda, I., and Kritchevsky, D. (1997) Lymphatic Recovery, Tissue Distribution, and Metabolic Effects of Conjugated Linoleic Acid in Rats, J. Nutr. Biochem. 8, 38–43.

    Article  CAS  Google Scholar 

  29. Kramer, J.K.G., Fellner, V., Dugan, M.E.R., Sauer, F.D., Mossoba, M.M., and Yurawecz, M.P. (1997) Evaluating Acid and Base Catalysts in the Methylation of Milk and Rumen Fatty Acids with Special Emphasis on Conjugated Dienes and Total trans Fatty Acids, Lipids 32, 1219–1228.

    PubMed  CAS  Google Scholar 

  30. Sehat, N., Yurawecz, M.P., Roach, J.A.G., Mossoba, M.M. Kramer, J.K.G., and Ku, Y. (1998) Silver Ion High-Performance Liquid Chromatographic Separation and Identification of Conjugated Linoleic Acid Isomers, Lipids 33, 217–221.

    PubMed  CAS  Google Scholar 

  31. Kramer, J.K.G., and Hulan, H.W. (1978) A Comparison of Procedures to Determine Free Fatty Acids in Rat Heart, J. Lipid Res. 19, 103–106.

    PubMed  CAS  Google Scholar 

  32. Kramer, J.K.G., Fouchard, R.C., and Farnworth, E.R. (1983) A Complete Separation of Lipids by Three-Directional Thin-Layer Chromatography, Lipids 18, 896–899.

    CAS  Google Scholar 

  33. Christie, W.W. (1982) Lipid Analysis, 2nd edn., Pergamon Press, Oxford.

    Google Scholar 

  34. Stoffel, W., Chu, F., and Ahrens, E.H. (1959) Analysis of Long-Chain Fatty Acids by Gas-Liquid Chromatography. Micromethod for Preparation of Methyl Esters, Anal. Chem. 31, 307–308.

    Article  CAS  Google Scholar 

  35. Kates, M. (1986) Techniques of Lipidology, in Laboratory Techniques in Biochemistry and Molecular Biology (Burdon, R.H., and van Knippenberg, P.H., eds.), Vol. 3, Part 2, pp. 122–123, Elsevier, Amsterdam.

    Google Scholar 

  36. Yurawecz, M.P., Hood, J.K., Roach, J.A.G., Mossoba, M.M., Daniels, D.H., Ku, Y., Pariza, M.W., and Chin, S.F. (1994) Conversion of Allylic Hydroxy Oleate to Conjugated Linoleic Acid and Methoxy Oleate by Acid-Catalyzed Methylation Procedures, J. Am. Oil Chem. Soc. 71, 1149–1155.

    CAS  Google Scholar 

  37. Mossoba, M.M. (1993) Application of Capillary GC-FTIR, INFORM 4, 854–858.

    Google Scholar 

  38. Yurawecz, M.P., Schat, N., Mossoba, M.M., Roach, J.A.G., and Ku, Y. (1997) Oxidation Products of Conjugated Linoleic Acid and Furan Fatty Acids, in New Techniques and Applications in Lipid Analysis (McDonald, R.E., and Mossoba, M.M., eds.), pp. 183–215, AOCS Press, Champaign.

    Google Scholar 

  39. Belury, M.A., Moya-Camarena, S.Y., Liu, K.-L., and Vanden Heuvel, J.P. (1997) Dietary Conjugated Linoleic Acid Induces Peroxisome-Specific Enzyme Accumulation and Ornithine Decarboxylase Activity in Mouse Liver, J. Nutr. Biochem. 8, 579–584.

    Article  CAS  Google Scholar 

  40. Banni, S., Day, B.W., Evans, R.W., Corongiu, F.P., and Lombardi, B. (1995) Detection of Conjugated Diene Isomers of Linoleic Acid in Liver Lipids of Rats Fed a Choline-Devoid Diet Indicates That the Diet Does Not Cause Lipoperoxidation, J. Nutr. Biochem. 6, 281–289.

    Article  CAS  Google Scholar 

  41. Banni, S., Carta, G., Contini, M.S., Angioni, E., Deiana, M., Dessì, M.A., Melis, M.P., and Corongiu, F.P. (1996) Characterization of Conjugated Diene Fatty Acids in Milk, Dairy Products, and Lamb Tissues, J. Nutr. Biochem. 7, 150–155.

    Article  CAS  Google Scholar 

  42. Sébédio, J.L., Juanéda, P., Dobson, G., Ramilison, I., Martin, J.C., Chardigny, J.M., and Christie, W.W. (1997) Metabolites of Conjugated Isomers of Linoleic Acid (CLA) in the Rat, Biochim. Biophys. Acta 1345, 5–10.

    PubMed  Google Scholar 

  43. Norseth, J. (1979) The Effect of Feeding Rats Partially Hydrogeneted Marine Oil or Rapeseed Oil on the Chain Shortening of Erucic Acid in Perfused Hearts, Biochim. Biophys. Acta 575, 1–9.

    PubMed  CAS  Google Scholar 

  44. Ha, Y.L., Grimm, N.K., and Pariza, M.W. (1987) Anticarcinogens from Fried Ground Beef: Heat-Altered Derivatives of Linoleic Acid, Carcinogenesis 8, 1881–1887.

    PubMed  CAS  Google Scholar 

  45. Hoch, F.L. (1992) Cardiolipins and Biomembrane Function, Biochim. Biophys. Acta 1113, 71–133.

    PubMed  CAS  Google Scholar 

  46. Shigenaga, M.K., Hagen, T.M., and Ames, B.N. (1994) Oxidative Damage and Mitochondrial Decay in Aging, Proc. Natl. Acad. Sci. USA 91, 10771–10778.

    Article  PubMed  CAS  Google Scholar 

  47. Pariza, M.W., Park, Y., Albright, K.-J., Liu, W., Storkson, J.M., and Cook, M.E. (1998) Synthesis and Biological Activity of Conjugated Eicosadienoic Acid, Abstracts, 89th American Oil Chemists' Society Annual Meeting, May 10–13, Chicago, p. 21.

Download references

Author information

Authors and Affiliations

  1. U. S. Food and Drug Administration, 20204, Washington, DC

    Najibullah Sehat, Magdi M. Mossoba, Martin P. Yurawecz, John A. G. Roach, Klaus Eulitz & Youh Ku

  2. Lacombe Research Center, Agriculture and Agri-food Canada, T4L 1W1, Lacombe, Alberta, Canada

    Michael E. R. Dugan, Jennifer L. Aalhus & Allan L. Schaefer

  3. Southern Crop Protection, Food Research Center, Agriculture and Agri-Food Canada, 43 McGilvray St., ON, Guelph, Canada, N1G 2W1

    John K. G. Kramer (Visiting scientist on sabbatical leave at the U.S. Food and Drug Administration)

Authors
  1. John K. G. Kramer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Najibullah Sehat
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Michael E. R. Dugan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Magdi M. Mossoba
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Martin P. Yurawecz
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. John A. G. Roach
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Klaus Eulitz
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jennifer L. Aalhus
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Allan L. Schaefer
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Youh Ku
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Kramer, J.K.G., Sehat, N., Dugan, M.E.R. et al. Distributions of conjugated linoleic acid (CLA) isomers in tissue lipid classes of pigs fed a commercial CLA mixture determined by gas chromatography and silver ion-high-performance liquid chromatography. Lipids 33, 549–558 (1998). https://doi.org/10.1007/s11745-998-0239-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-998-0239-1

Keywords

Search

Navigation