Skip to main content
Log in

Chlorinated fatty acids in lipid class fractions from cardiac and skeletal muscle of Chinook salmon

  • Articles
  • Published:
Lipids

Abstract

Analysis of chlorinated fatty acids (CFA) in tissues can be difficult because of their low concentrations. This task becomes even more difficult when samples are from organisms living in remote locations with very little exposure to environmental contamination. Therefore, enrichment of CFA is necessary prior to analysis. In this study, CFA were enriched from fractionated lipid classes of cardiac and skeletal muscle of Chinook salmon (Oncorhynchus tshawytscha) to determine CFA distribution among lipid classes and tissue types and to demonstrate the sensitivity of this method to detect CFA at trace concentrations. The lipids extracted from cardiac and skeletal muscle of O. tshawytscha were separated into fractions containing TAG, FFA, and phospholipids. After transesterification, the FAME derivatives from each lipid class were analyzed by GC with a halogen-selective detector (XSD) to determine the concentrations of dichlorostearic acid and dichloropalmitic acid. Other chlorinated compounds detected byGC-XSD were analyzed by GC-MS. CFA were observed in all lipid classes in both cardiac and skeletal muscle tissues. However, the highest concentrations of CFA were found in the phospholipids of both tissue types, about 1–2 mg/g lipid. It was also shown that dichloropalmitic acid concentrated in cardiac phospholipids whereas dichlorostearic acid was found primarily in the phospholipids of skeletal tissue. CFA concentrations in TAG and FFA fractions were below 150 mg/g lipid. This study demonstrates a small-scale approach to the study of CFA at trace concentrations and their distribution among lipid classes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

ASE:

accelerated solvent extraction

CFA:

chlorinated FA

PICI:

positive ion chemical ionization

PL:

polar lipid

SPE:

solid-phase extraction

XSD:

halogen-selective detector

References

  1. Walker, C.H., Hopkin, S.P., Sibly, R.M., and Peakall, D.B. (1996) Principles of Ecotoxicology, pp. 60–87, Taylor & Francis, London.

    Google Scholar 

  2. Rappe, C. (1987) Global Distribution of Polychlorinated Dioxins and Dibenzofurans, in Solving Hazardous Waste Problems. Learning from Dioxins (Exner, J.H., ed.), pp. 20–33, ACS Symposium Series No. 338, American Chemical Society, Washington, DC.

    Google Scholar 

  3. Beckmen, K.B., Blake, J.E., Ylitalo, G.M., Stott, J.L., and O'Hara, T.M. (2003) Organochlorine Contaminant Exposure and Associations with Hematological and Humoral Immune Functional Assays with Dam Age as a Factor in Free-Ranging Northern Fur Seal Pups (Callorhinus ursinus), Mar. Pollut. Bull. 46, 594–606.

    Article  PubMed  CAS  Google Scholar 

  4. Olsson, M., Andersson, Ö., Bergman, A., Blomkvist, G., Frank, A., and Rappe, C. (1992) Contaminants and Diseases in Seals from Swedish Waters, Ambio 8, 561–562.

    Google Scholar 

  5. Sladen, W.J.L., Menzie, C.M., and Reichel, W.L. (1966) DDT Residues in Adelie Penguins and a Crabeater Seal from Antarctica, Nature 210, 670–673.

    Article  PubMed  CAS  Google Scholar 

  6. Beyer, W.N., Heinz, G.H., and Redmon-Norwood, A.W. (1996) Environmental Contaminants in Wildlife: Interpreting Tissue Concentrations, pp. 117–152, Lewis Publishers, Boca Raton, Florida.

    Google Scholar 

  7. Hakansson, H., Sundin, P., Andersson, T., Brunstrom, B., Denker, L., Engwall, M., Ewald, G., Gilek, M., Holm, G., Honkasalo, S., et al. (1991) In vivo and in vitro Toxicity of Fractionated Fish Lipids, with Particular Regard to Their Content of Chlorinated Organic Compounds, Pharmacol. Toxicol. 69, 459–471.

    Article  PubMed  CAS  Google Scholar 

  8. Wesen, C. (1995) Chlorinated Fatty Acids in Fish Lipids, Ph.D. Thesis, Lund University, Lund, Sweden.

    Google Scholar 

  9. Cherr, G.N., Shenker, J.M., Lundmark, C., and Turner, K.O. (1987) Toxic Effects of Selected Bleach Kraft Mill Effluent Constituents on Sea Urchin Sperm Cells, Environ. Toxicol. Chem. 6, 561–569.

    CAS  Google Scholar 

  10. Mu, H., and Wesen, C. (1996) Gas Chromatographic and Mass Spectrometric Identification of Tetrachloroalkanoic and Dichloroalkenoic Acids in Eel Lipids, J. Mass Spectrom. 31, 517–526.

    Article  CAS  Google Scholar 

  11. Milley, J.E., Boyd, B.K., Curtis, J.M., Musial, C., and Uthe, J.F. (1997) Dichloromyristic Acid, a Major Component of Organochlorine Load in Lobster Digestive Gland, Environ. Sci. Technol. 31, 535–541.

    Article  CAS  Google Scholar 

  12. Ewald, G. (1999) Ecotoxicological Aspects of Chlorinated Fatty Acids, Aquat. Ecosyst. Health Manag. 2, 71–80.

    Article  CAS  Google Scholar 

  13. Vereskuns, G. (1999) Chlorinated Fatty Acids in Freshwater Fish and Some Biological Effects of Dichlorostearic Acid, Ph.D. Thesis, Swedish University of Agricultural Sciences, Uppsala, Sweden.

    Google Scholar 

  14. Vissers, M.C.M., Stern, A., Kuypers, F., van den Berg, J., and Winterbourne, C.C. (1994) Membrane Changes Associated with Lysis of Red Blood Cells by Hypochlorous Acids, Free Radical Biol. Med. 16, 703–712.

    Article  CAS  Google Scholar 

  15. Bjorn, H., Sundin, P., Wesen, C., Mu, H., Martinsen, K., Kvernheim, A.L., Skramstad, J., and Odham, G. (1998) Chlorinated Fatty Acids in Membrane Lipids of Fish, Naturwissenschaften 85, 229–232.

    Article  PubMed  CAS  Google Scholar 

  16. Nilsson, G.A., Nilsson, O., Odenbrand, I., and Wesen, C. (2001) New Halogen-Specific Detector Applied to the Analysis of Chlorinated Fatty Acids, J. Chromatogr. 912, 99–106.

    Article  CAS  Google Scholar 

  17. Borisova, P. (2004) Chlorination of Fatty Acid Methyl Esters Using Ionic Liquid as a Solvent, Bachelor's Research Thesis, University of Alaska, Anchorage, Alaska.

    Google Scholar 

  18. Dodds, E.D., McCoy, M.R., Geldenhuys, A., Rea, L.D., and Kennish, J.M. (2004) Microscale Recovery of Total Lipids fom Fish Tissue by Accelerated Solvent Extraction, J. Am. Oil Chem. Soc. 81, 835–840.

    Article  CAS  Google Scholar 

  19. Ruiz, J., Antequera, T., Andres, A.I., Petron, M.J., and Muriel, E. (2004) Improvement of a Solid Phase Extraction Method for Analysis of Lipid Fractions in Muscle Foods, Anal. Chim. Acta 520, 201–205.

    Article  CAS  Google Scholar 

  20. Christie, W.W. (1989) Gas Chromatography and Lipids, pp. 66–68, Oily Press, Ayr, Scotland.

    Google Scholar 

  21. Åkesson-Nilsson, G. (2003). Isolation of Chlorinated Fatty Acid Methyl Esters Derived from Cell-Culture Medium and from Fish Lipids Using an Aminopropyl Solid-Phase Extraction Column, J. Chromatogr. A 996, 173–180.

    Article  PubMed  CAS  Google Scholar 

  22. Mu, H., Wesén, C., Novák, T., Sundin, P., Skramstad, J., and Odham, G. (1996) Enrichment of Chlorinated Fatty Acids in Fish Lipids Prior to Analysis by Capillary Gas Chromatography with Electrolytic Conductivity Detection and Mass Spectrometry, J. Chromatogr. A 731, 225–236.

    Article  CAS  Google Scholar 

  23. Clark, K. (2003) Chlorinated Fatty Acids in Muscle Lipids and Blubber of Harbour Porpoise and Harbour Seals. Honours Thesis, Swedish University of Agricultural Sciences, Uppsala, Sweden.

    Google Scholar 

  24. Blank, M.L., Cress, E.A., Smith, Z.L., and Snyder, G. (1992) Meats and Fish Consumed in the American Diet Contain Substantial Amounts of Ether-Linked Phospholipids, J. Nutr. 122, 1656–1661.

    PubMed  CAS  Google Scholar 

  25. Kim, H.Y., and Salem, N., Jr. (1990) Separation of Lipid Classes by Solid Phase Extraction, J. Lipid Res. 31, 2285–2289.

    PubMed  CAS  Google Scholar 

  26. Marinetti, G.V., Erbland, J., and Sotz, E. (1958) The Phosphatide Composition of Rat Tissues, Biochim. Biophys. Acta 30, 642–643.

    Article  PubMed  CAS  Google Scholar 

  27. Bell, M.V., Dick, J.R., and Buda, C. (1997) Molecular Speciation of Fish Sperm Phospholipids: Large Amounts of Dipolyunsaturated Phosphatidylserine, Lipids 32, 1085–1091.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to John M. Kennish.

About this article

Cite this article

King, M.D., Rea, L.D. & Kennish, J.M. Chlorinated fatty acids in lipid class fractions from cardiac and skeletal muscle of Chinook salmon. Lipids 41, 1133–1140 (2006). https://doi.org/10.1007/s11745-006-5063-0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-006-5063-0

Keywords

Navigation