Lipids

, Volume 35, Issue 6, pp 681–687 | Cite as

Quantitative analysis of long-chain trans-monoenes originating from hydrogenated marine oil

  • Robert Wilson
  • Karin Lyall
  • J. Anne Payne
  • Rudolph A. Riemersma
Method

Abstract

Gas chromatography (GC) is used for the analysis of trans-fatty acids in partially hydrogenated vegetable oils. Although trans-isomers of C18 carbon length predominate in partially hydrogenated vegetable oils, trans-isomers of C20 and C22 carbon length occur in partially hydrogenated fish oil. We report a simple silver ion chromatographic combined with capillary GC technique for quantitative analysis of trans-monoenes derived from partially hydrogenated fish oil. Silver nitrate thinlayer chromatographic (TLC) plates are developed in toluene/hexane (50∶50, vol/vol). Fatty acid methyl esters are separated into saturates (Rf 0.79), trans-monoenes (Rf 0.49), cis-monoenes (Rf, 0.27), dienes (Rf, 0.10), and polyunsaturated fatty acids with three or more double bonds remaining at the origin. The isolated trans-monoenes are quantitatively analyzed by capillary GC. The technique of argentation TLC with GC analysis of isolated methyl esters is highly reproducible with 4.8% variation (i.e., coefficient of variation, CV%) in Rf values and 4.3 and 6.9% CV% in quantification within batch and between batch, respectively. Furthermore, the combined technique revealed that direct GC analysis underestimated the trans-content of margarines by at least 30%. In this study, C20 and C22trans-monoenes were found in relatively large quantities; 13.9% (range 10.3–19.6%) and 7.5% (range 5.3–11.5%), respectively, in margarine purchased in 1995, but these C20 and C22trans-monoenes were much reduced (0.1%) in a fresh selection of margarine purchased in 1998. Compositional data from labels underestimated the trans-content of margarines, especially those dervied from hydrogenated marine oil. Low levels of C20trans-monoenes (range 0.1–0.3%) and C22trans-monoenes (range 0.0–0.1%) were identified in adipose tissue obtained from healthy volunteers in 1995, presumably indicating consumption of partially hydrogenated fish oil.

Abbreviations

BHT

butylated hydroxytoluene

CV

coefficient of variation

FAME

fatty acid methyl ester

GC

gas chromatography

HDL

high density lipoprotein

LDL

low density lipoprotein

MS

mass spectrometry

MUFA

monounsaturated fatty acids

PUFA

polyunsaturated fatty acids

Rf

distance migrated by compound divided by the distance of solvent mobility

SPE

solid phase extraction

TLC

thin-layer chromatography

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Aro, A., Antoine, J.M., Pizzoferrato, L., Reykdal, O., and van Poppel, G. (1998) trans-Fatty Acids in Dairy And Meat Products From 14 European Countries: The Transfair Study, J. Food Comp. Anal. 11, 150–160.CrossRefGoogle Scholar
  2. 2.
    Aro, A., Van Amelsvoort, J., Becker, W., Van Erp-Baart, M.A., Kafatos, A., Leth, T., and van Poppel, G. (1998) Trans-Fatty Acids in Dietary Fats and Oils from 14 European Countries: The Transfair Study, J. Food Comp. Anal. 11, 137–149.CrossRefGoogle Scholar
  3. 3.
    van Erp-Baart, M.-A., Cout, C., Caudrado, C., Kafatos, A., Stanley, J., and van Poppel, G. (1998) Trans-Fatty Acids in Bakery Products from 14 European Countries: The Transfair Study, J. Food Comp. Anal. 11, 161–169.CrossRefGoogle Scholar
  4. 4.
    Ovesen, L., Leth, T., and Hansen, K. (1998) Fatty Acid Composition and Contents of trans Monounsaturated Fatty Acids in Frying Fats and in Margarine and Shortenings Marketed in Denmark, J. Am. Oil Chem. Soc. 75, 1079–1083.Google Scholar
  5. 5.
    Fritche, J., and Steinhart, H. (1997) Trans-Fatty Acid Content in German Margarines, Fett-Lipids 99, 214–217.CrossRefGoogle Scholar
  6. 6.
    Wolff, R.L. (1994) Contribution of Trans-18∶1 Acids from Dairy Fat to European Diets, J. Am. Oil Chem. Soc. 71, 277–283.Google Scholar
  7. 7.
    Ratnayake, W.M.N., Pelletier, G., Hollywood, R., Bacler, S., and Leyte, D. (1998) Trans-Fatty Acids in Canadian Margarine: Recent Trends, J. Am. Oil Chem. Soc. 75, 1587–1594.Google Scholar
  8. 8.
    Ratnayake, W.M.N. (1998) Analysis of Trans-Fatty Acids, in Trans-Fatty Acids in Human Nutrition, (Sébédio, J.L., and Christie, W.W., eds.), pp. 115–162, Oily Press, Dundee.Google Scholar
  9. 9.
    Wolff, R.L., and Bayard, C.C. (1995) Improvement in the Resolution of Individual Trans-18∶1 Isomers by Capillary Gas-Liquid Chromatography Use of a 100-M CP-Sil-88 Column, J. Am. Oil Chem. Soc. 72, 1197–1201.Google Scholar
  10. 10.
    van Bruggen, P.C., Duchateau, G.E., Mooren, M.W., and van Oosten, H.J. (1998) Precision of Low Trans-Fatty Acid Level Determination in Refined Oils. Results of a Collaborative Capillary Gas-Liquid Chromatography Study, J. Am. Oil Chem. Soc. 75, 483–488.Google Scholar
  11. 11.
    Chen, Z.Y., Ratnayake, W.M.N., Fortier, L., Ross, R., and Cunnane, S.C. (1995) Similar Distribution of Trans-Fatty Acid Isomers in Partially Hydrogenated Vegetable Oils and Adipose Tissue of Canadians, Can. J. Physiol. Pharmacol. 73, 718–723.PubMedGoogle Scholar
  12. 12.
    Duchateau, G.E., van Oosten, H.J., and Vasconcellos, M.A. (1996) Analysis of Cis-and Trans-Fatty Acid Isomers in Hydrogenated and Refined Vegetable Oils by Capillary Gas-Liquid Chromatography, J. Am. Oil Chem. Soc. 73, 275–282.CrossRefGoogle Scholar
  13. 13.
    Sebedio, J.-L., and Ackman, R.G. (1983) Hydrogenation of a Menhaden Oil: I. Fatty Acid and C20 Monoethylenic Compositions as a Function of the Degree of Hydrogenation, J. Am. Oil Chem. Soc. 60, 1986–1991.Google Scholar
  14. 14.
    Mensink, R.P., Katan, M.B. (1990) Effects of Dietary trans-Fatty Acids on High Density and Low Density Lipoprotein Cholesterol Levels in Healthy Subjects, N. Engl. J. Med. 323, 439–445.PubMedCrossRefGoogle Scholar
  15. 15.
    Aro, A. (1998) Epidemological of Trans-Fatty Acids and Coronary Heart Disease, in Trans-Fatty Acids in Human Nutrition (Sébédio, J.L., and Christie, W.W., eds.), pp. 235–260, Oily Press, Dundee.Google Scholar
  16. 16.
    Expert Panel on Trans-Fatty Acids and Coronary Heart Disease (1995) Trans-Fatty Acids and Coronary Heart Disease Risk, Am. J. Clin. Nutr. 62, 655S-708S.Google Scholar
  17. 17.
    Thomas, L.H., Jones, P.R., Winter, J.A., and Smith, H. (1981) Hydrogenated Oils and Fats: The Presence of Chemically Modified Fatty Acids in Human Adipose Tissue, Am. J. Clin. Nutr. 34, 877–886.PubMedGoogle Scholar
  18. 18.
    Christie, W.W. (1989) Preparation of Methyl Esters and Other Derivatives, in Gas Chromatography and Lipids (Christie, W.W., ed.), pp. 64–84, The Oily Press, Ayr.Google Scholar
  19. 19.
    Wilson, R., Henderson, R.J., Burrow, I.C., and Sargent, J.R. (1993) The Enrichment of n-3 Polyunsaturated Fatty Acids Using Aminopropyl Solid-Phase Extraction Columns, Lipids 28, 51–54.Google Scholar
  20. 20.
    Wilson, R., and Sargent, J.R. (1992) High-Resolution Separation of Polyunsaturated Fatty Acids by Argentation Thin-Layer Chromatography, J. Chromatogr. 623, 403–407.CrossRefGoogle Scholar
  21. 21.
    Spitzer, V., Marx, F., and Pfeilsticker, K. (1994) Electron-Impact Mass-Spectra of the Oxazoline Derivatives of Some Conjugated Diene and Triene C-18 Fatty Acids, J. Am Oil Chem. Soc. 71, 873–876.Google Scholar
  22. 22.
    Nestel, P., Noakes, M., Belling, B., McArthur, R., Clifton, P., Janus, E., and Abbey, M. (1992) Plasma Lipoprotein and Lp(A) Changes with Substitution of Elaidic Acid for Oleic Acid in the Diet, J. Lipid Res. 32, 1029–1036.Google Scholar
  23. 23.
    Almendingen, K., Jordal, O., Kierulf, P., Sandstad, B., and Pedersen, J.I. (1995) Effects of Partially Hydrogenated Fish Oil, Partially Hydrogenated Soybean Oil, and Butter on Serum-Lipoproteins and Lp[A] in Men, J. Lipid Res. 36, 1370–1384.PubMedGoogle Scholar
  24. 24.
    Garland, M., Sacks, F.M., Colditz, G.A., Rimm, E.B., Sampson, L.A., Willett, W.C., and Hunter, D.J. (1998) The Relation Between Dietary Intake and Adipose Tissue Composition of Selected Fatty Acids in U.S. Women, Am. J. Clin. Nutr. 67, 25–30.PubMedGoogle Scholar
  25. 25.
    Pettersen, J., and Optvedt, J. (1992) Trans-Fatty Acids. 5. Fatty Acid Composition of Lipids of the Brain and Other Organs in Suckling Pigs, Lipids 27, 761–769.PubMedGoogle Scholar
  26. 26.
    Høy, C.-E., and Hølmer, G. (1988) Dietary Linoleic Acid and the Fatty Acid Profiles in Rats Fed Partially Hydrogenated Marine Oils, Lipids 23, 973–980.PubMedGoogle Scholar
  27. 27.
    Hølmer, G. (1998). Biochemistry of Trans-Monoenoic Fatty Acids, in Trans-Fatty Acids in Human Nutrition (Sébédio, J.L., and Christie, W.W., eds.), pp. 163–189, The Oil Press, Dundee.Google Scholar
  28. 28.
    Roberts, T.L., Wood, D.A., Riemersma, R.A., Gallagher, P.J. and Lampe, F.C. (1995) Trans Isomers of Oleic Acid and Linoleic Acids in Adipose Tissue and Sudden Cardiac Death, Lancet 345, 278–282PubMedCrossRefGoogle Scholar

Copyright information

© AOCS Press 2000

Authors and Affiliations

  • Robert Wilson
    • 2
  • Karin Lyall
    • 2
  • J. Anne Payne
    • 2
  • Rudolph A. Riemersma
    • 2
    • 1
  1. 1.Department of Medical PhysiologyUniversity of TromsøTromsøNorway
  2. 2.Cardiovascular Research UnitUniversity of EdinburghEdinburghScotland

Personalised recommendations