Skip to main content
SpringerLink
Log in

Stereospecific analysis of triacyl-sn-glycerols in Docosahexaenoic acid-rich fish oils

  • Published:
Journal of the American Oil Chemists’ Society

Abstract

This paper presents the positional distribution of fatty acids in docosahexaenoic acid (22∶6n-3)-rich fish oil triacyl-sn-glycerols (TG). Stereospecific analysis of TG was carried out by a nonenzymatic method. The TG of bonito head oil, obtained after a winterization process, contained 22∶6n-3 at concentrations of 28,7, and 49 mole % in thesn-1,sn-2, andsn-3 positions, respectively. In the TG of oil before the winterization process, 22∶6n-3 was concentrated in thesn-3 position, followed evenly by thesn-1 andsn-2 positions. Tuna orbital oil, obtained after winterization, showed the preferential association of 22∶6n-3 to thesn-3 position, followed by thesn-1 position. This distribution pattern was similar to that observed for seal oil TG rather than sardine oil TG. The bonito head and tuna orbital oils are useful as fish oils with characteristics different from those of common fish oils, such as menhaden, sardine, and herring oils.

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

References

  1. Connor, W.E., M. Neuringer, and S. Reisbick, Essential Fatty Acids: The Importance of n-3 Fatty Acids in the Retina and Brain,Nutr. Rev. 50:21–29 (1992).

    Article  CAS  Google Scholar 

  2. Yazawa, K., K. Watanabe, C. Ichikawa, and K. Kondo, Docosa-hexaenoic Acid in the Orbital Fat of Marine Fishes,INFORM 2:336 (abstract) (1991).

    Google Scholar 

  3. Brockerhoff, H., R.J. Hoyle, P.C. Hwang, and C. Litchfield, Positional Distribution of Fatty Acids in Depot Triglycerides of Aquatic Animals,Lipids 3:24–29 (1968).

    Article  CAS  Google Scholar 

  4. Litchfield, C., Predicting the Positional Distribution of Docosa-hexaenoic and Docosapentaenoic Acids in Aquatic Animal Triglycerides, —Ibid.3:417–419 (1968).

    Article  CAS  Google Scholar 

  5. Litchfield, C., Taxonomic Patterns in the Triglyceride Structure of Natural Fats,Fette Seifen Anstrichm. 75:223–231 (1973).

    Article  CAS  Google Scholar 

  6. Ando, Y., K. Nishimura, N. Aoyanagi, and T. Takagi, Stereo-specific Analysis of Fish Oil Triacyl-sn-glycerols,J. Am. Oil Chem. Soc. 69:417–424 (1992).

    Article  CAS  Google Scholar 

  7. Yazawa, K., and H. Kageyama, Physiological Activity of Docosahexaenoic Acid,J. Jpn. Oil Chem. Soc. (Yukagaku) 40:974–978 (1991).

    CAS  Google Scholar 

  8. Ackman, R.G., V.R. Orozco, and W.M.N. Ratnayake, Aspects of Positional Distribution of Fatty Acids in Triacylglycerols of Skin, White and Dark Muscle of MackerelScomber scombrus in Relation to Hypertension.Fat. Sci. Technol. 93:447–450 (1991).

    CAS  Google Scholar 

  9. Takagi, T., and Y. Ando, Stereospecific Analysis of Triacyl-sn-glycerols by Chiral High-Performance Liquid Chromatography,Lipids 26:542–547 (1991).

    Article  CAS  Google Scholar 

  10. Ando, Y., and T. Takagi, Micro Method for Stereospecific Analysis of Triacyl-sn-glycerols by Chiral-Phase High-Performance Liquid Chromatography,J. Am. Oil Chem. Soc. 70:1047–1049 (1993).

    Article  CAS  Google Scholar 

  11. Luddy, F.E., R.A. Barford, S.F. Herb, P. Magidman, and R.W. Riemenschneider, Pancreatic Lipase Hydrolysis of Triglycerides by Semimicro Technique, —Ibid. 41: 693–696 (1964).

    CAS  Google Scholar 

  12. Christie, W.W.,Lipid Analysis, 2nd edn., Pergamon Press, Oxford, England, 1982, pp. 155–161.

    Google Scholar 

  13. Christie, W.W., and J.H. Moore, A Semimicro Method for the Stereospecific Analysis of Triglycerides,Biochim. Biophys. Acta 176:445–452 (1969).

    CAS  Google Scholar 

  14. Brockerhoff, H., R.J. Hoyle, and P.C. Hwang, Positional Distribution of Fatty Acids in the Fats of a Polar Bear and a Seal,Can. J. Biochem. 44:1519–1525 (1966).

    Article  CAS  Google Scholar 

  15. Sawada, T., K. Takahashi, and M. Hatano, Triglyceride Composition of Tuna and Bonito Orbital Fats,Nippon Suisan Gakkaishi 59:285–290 (1993).

    CAS  Google Scholar 

  16. Bottino, N.R., G.A. Vandenburg and R. Reiser, Resistance of Certain Long-Chain Polyunsaturated Fatty Acids of Marine Oils to Pancreatic Lipase Hydrolysis,Lipids 2:489–493 (1967).

    Article  CAS  Google Scholar 

  17. Leger, C., P. Bergot, P. Luquet, J. Flanzy, and J. Heurot, Specific Distribution of Fatty Acids in the Triglycerides of Rainbow Trout Adipose Tissue. Influence of Temperature —Ibid. 12:538–543 (1977).

    CAS  Google Scholar 

  18. Privett, O.S., M.L. Blank and B. Verdino, Influence of Dietary Fat on Triglyceride Structure in the Rat,J. Nutr. 85:187–195 (1965).

    CAS  Google Scholar 

  19. Leray, C., T. Raclot, and R. Groscolas, Positional Distribution of n-3 Fatty Acids in Triacylglycerols from Rat Adipose Tissue During Fish Oil Feeding,Lipid 28:279–284 (1993).

    Article  CAS  Google Scholar 

  20. Paclot, T., R. Groscolas, and C. Leray, Composition and Structure of Triacylglycerols in Brown Adipose Tissue of Rats Fed Fish Oil, —Ibid. 29:759–764 (1964).

    Google Scholar 

  21. Maehr, H., G. Zenchoff, and D.L. Coffen, Enzymic Enhancement of n-3 Fatty Acid Content in Fish Oils,J. Am. Oil Chem. Soc. 71:463–467 (1994).

    Article  CAS  Google Scholar 

  22. Yamane, T., Y. Suzuki, Y. Sasaki, L. Vikersveen, and T. Hoshino, Production of n-3 Polyunsaturated Fatty Acid-Enriched Fish Oil by Lipase-Catalyzed Acidolysis without Solvent, —Ibid. 69:1104–1107 (1992).

    Article  CAS  Google Scholar 

  23. Tanaka, Y., J. Hirano, and T. Funada, Concentration of Docosahexaenoic Acid in Glyceride by Hydrolysis of Fish Oil withCandida cylindracea Lipase, —Ibid. 69:1210–1214 (1992).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Marine Bioresources Chemistry, Faculty of Fisheries, Hokkaido University, Minatocho, 041, Hokodate, Japan

    Yasuhiro Ando, Toru Ota & Yukiko Matsuhira

  2. Sagami Research Center, Nishi-Ohnuma, 229, Sagamihara, Japan

    Kazunaga Yazawa

Authors
  1. Yasuhiro Ando
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Toru Ota
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yukiko Matsuhira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kazunaga Yazawa
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Ando, Y., Ota, T., Matsuhira, Y. et al. Stereospecific analysis of triacyl-sn-glycerols in Docosahexaenoic acid-rich fish oils. J Amer Oil Chem Soc 73, 483–487 (1996). https://doi.org/10.1007/BF02523923

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02523923

Key words

Search

Navigation