Skip to main content
Log in

Positional distribution of FA in TAG of enzymatically modified borage and evening primrose oils

  • Articles
  • Published:
Lipids

Abstract

Stereospecific analysis was carried out to establish positional distribution of FA in the TAG of DHA, EPA, and (EPA+DHA)-enriched oils. In this study, TAG of enzymatically modified oils were purified using a silicic acid column. The TAG were then subjected to positional distribution analysis using a modified procedure involving reductive cleavage with Grignard reagent. The results showed that in DHA-enriched borage oil (BO), DHA was randomly distributed over the three positions of TAG, whereas γ-linolenic acid (GLA) was mainly esterified at the sn-2 and-3 positions. In DHA-enriched evening primrose oil (EPO), however, DHA and GLA were concentrated in the sn-2 position. In EPA-enriched BO, EPA was randomly distributed over the three positions of TAG, similar to that observed for DHA. In EPA-enriched EPO, however, this FA was mainly located at the primary positions (sn-1 and sn-3) of TAG. In both oils, GLA was preferentially esterified at the sn-2 position. In (EPA+DHA)-enriched BO, EPA and DHA were mainly esterified at the sn-1 and -3 positions of TAG, whereas GLA was mainly located at the sn-2 position. In (EPA+DHA)-enriched EPO, GLA was mainly located at the sn-2 and-3 positions; EPA was preferentially esterified at the sn-1 and-3 positions, and DHA was found mainly at the sn-3 position.

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

AA:

arachidonic acid, 20∶4n−6

BO:

borage oil

EPO:

evening primrose oil

GLA:

γ-linolenic acid, 18∶3n−6

LA:

linoleic acid

SL:

structured lipids

References

  1. Horrobin, D.F. (1990) Gamma Linolenic Acid: An Intermediate in Essential Fatty Acid Metabolism with Potential as an Ethical Pharmaceutical and as a Food, Rev. Contemp. Pharmacother. 1, 1–41.

    Google Scholar 

  2. Rahmatullah, M.S.K.S., Shukla, V.K.S., and Mukherjee, K.D. (1994) γ-Linolenic Acid Concentrates from Borage and Evening Primrose Oil Fatty Acids via Lipase-Catalyzed Esterification, J. Am. Oil Chem. Soc. 71, 563–569.

    CAS  Google Scholar 

  3. Rahmatullah, M.S.K.S., Shukla, V.K.S., and Mukherjee, K.D. (1994) Enrichment of γ-Linolenic Acid from Evening Primrose Oil and Borage Oil via Lipase-Catalyzed Hydrolysis, J. Am. Oil Chem. Soc. 71, 569–573.

    CAS  Google Scholar 

  4. Yokochi, T., Usita, M.T., Kamisaka, Y., Nakahara, T., and Suzuki, O. (1990) Increase in the γ-Linolenic Acid Content by Solvent Winterization of Fungal Oil Extracted from Mortierella Genus, J. Am. Oil Chem. Soc. 67, 846–851.

    CAS  Google Scholar 

  5. Mukheriee, K.D., and Kiewitt, I. (1991) Enrichment of γ-Linolenic Acid from Fungal Oil by Lipase-Catalyzed Reactions, Appl. Microbiol. Biotechnol. 35, 579–584.

    Google Scholar 

  6. Weaver, B.J., and Holub, B.J. (1988) Health Effects and Metabolism of Dietary Eicosapentaenoic Acid, Prog. Food Nutri. Sci. 12, 111–150.

    CAS  Google Scholar 

  7. Lauritzen, L., Hansen, H.S., orgensen, M.H., and Michaelsen, K.F. (2001) The Essentiality of Long Chain n−3 Fatty Acids in Relation to Development and Function of the Brain and Retina, Prog. Lipid Res. 40, 1–94.

    Article  PubMed  CAS  Google Scholar 

  8. Senanayake, S.P.J.N., and Shahidi, F. (1999) Enzyme-Assisted Acidolysis of Borage (Borago officinalis L.) and Evening Primrose (Oenothera biennis L.) Oils: Incorporation of Omega-3 Polyunsaturated Fatty Acids, J. Agric. Food Chem. 47, 3105–3112.

    Article  PubMed  CAS  Google Scholar 

  9. Senanayake, S.P.J.N., and Shahidi, F. (1999) Enzymatic Incorporation of Docosahexaenoic Acid into Borage Oil, J. Am. Oil Chem. Soc. 76, 1009–1015.

    CAS  Google Scholar 

  10. Senanayake, S.P.J.N., and Shahidi, F. (2000) Structured Lipids Containing Long-Chain Omega-3 Polyunsaturated Fatty Acids, in Seafood in Health and Nutrition. Transformation in Fisheries and Aquaculture: Global Perspectives. Shahidi, F. (ed.), pp. 29–44, ScienceTech Publishing, St. John's, Newfoundland, Canada.

    Google Scholar 

  11. Jensen, G.L., McGarvey, N., Taraszewski, R., Wixon, S.K., Seidner, D.L., Pai, T., Yeh, Y.Y., Lee, T.W., and DeMichele, S.J. (1994) Lymphatic Absorption of Enterally Fed Structured Triacylglycerol Versus Physical Mix in a Canine Model, Am. J. Clin. Nutr. 60, 518–524.

    PubMed  CAS  Google Scholar 

  12. Mattson, F.H., and Volpenhein, R.A., (1962) Rearrangement of Glyceride Fatty Acids During Digestion and Absorption, J. Biol. Chem. 237, 53–55.

    PubMed  CAS  Google Scholar 

  13. Kubow, S. (1996) The Influence of Positional Distribution of Fatty Acids in Native, Interesterified and Structure-Specific Lipids on Lipoprotein Metabolism and Atherogenesis, J. Nutr. Biochem. 7, 530–541.

    Article  CAS  Google Scholar 

  14. Brockerhoff, H. (1971) Stereospecific Analysis of Triglycerides, Lipids. 6, 943–956.

    Google Scholar 

  15. Carey, M.C., Small, D.M., and Bliss, C.M. (1983) Lipid Digestion and Absorption, Annu. Rev. Physiol. 45, 651–677.

    Article  PubMed  CAS  Google Scholar 

  16. Lawson, L.D., and Hughes, B.G. (1988) Triacylglycerol Structure of Plant and Fungal Oils Containing γ-Linolenic Acid, Lipids 23, 313–317.

    CAS  Google Scholar 

  17. Redden, R.P., Lin, X., Fahey, J., and Horrobin, D.F. (1995) Stereo-specific Analysis of the Major Triacylglycerol Species Containing γ-Linolenic Acid in Evening Primrose Oil and Borage Oil, J. Chromatography 704, 99–111.

    Article  CAS  Google Scholar 

  18. Senanayake, S.P.J.N., and Shahidi, F. (2000) Concentration of Docosahexaenoic Acid (DHA) from Algal Oil via Urea Complexation, J. Food Lipids 7, 51–61.

    CAS  Google Scholar 

  19. Brockerhoff, H., Ackman, R.G., and Hoyle, R.J. (1963) Specific Distribution of Fatty Acids in Marine Lipids, Arch. Biochem. Biophys. 100, 9–12.

    Article  PubMed  CAS  Google Scholar 

  20. Christie, W.W. (1982) Structural Analysis of Lipids by Means of Enzymatic Hydrolysis, in Lipid Analysis. (Christie, W.W., ed.), pp. 155–166, Pergamon Press, New York.

    Google Scholar 

  21. Laakso, P., and Christie, W.W. (1990) Chromatographic Resolution of Chiral Diacylglycerol Derivatives: Potential in the Stereospecific Analysis of Triacyl-sn-glycerols, Lipids 25, 349–353.

    PubMed  CAS  Google Scholar 

  22. Nwosu, C.V., and Boyd, L.C. (1997) Positional Distribution of Fatty Acids on Triacylglycerols of Menhaden (Brevoortia tyrannis) and Salmon (Salmo salar) Oils, J. Food Lipids 4, 65–74.

    CAS  Google Scholar 

  23. Verheij, H.M., and Dijkstra, B.W. (1994) Phospholipase A2: Mechanism and Structure, in Lipases (Woolley, P., and Petersen, B., eds.), pp. 119–138, Cambridge University Press, Cambridge.

    Google Scholar 

  24. Novo Nordisk Biochem North America, Inc., Product Sheet B 606c-GB, Franklinton, NC, 1999.

  25. Lee, K., and Akoh, C.C. (1996) Immobilized Lipase-Catalyzed Production of Structured Lipids with Eicosapentaenoic Acid at Specific Positions, J. Am. Oil Chem. Soc. 73, 611–615.

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  27. Wanasundra, U.N., and Shahidi, F. (1997) Positional Distribution of Fatty Acids in Triacylglycerols of Seal Blubber Oil, J. Food Lipids 4, 51–64.

    Google Scholar 

  28. Aursand, M., Jorgensen, L., and Grasdalen, H. (1995) Positional Distribution of ω3 Fatty Acids in Marine Lipid Triacylglycerols by High-Resolution 13C Nuclear Magnetic Resonance Spectroscopy, J. Am. Oil Chem. Soc. 72, 293–297.

    CAS  Google Scholar 

  29. Ikeda, I., Yoshida, H., Tomooka, M., Yosef, A., Imaizumi, K., Tsuji, H., and Seto, A. (1998) Effects of Long-Term Feeding of Marine Oils with Different Positional Distribution of Eicosapentaenoic and Docosahexaenoic Acids on Lipid Metabolism, Eicosanoid Production, and Platelet Aggregation in Hypercholesterolemic Rats, Lipids 33, 897–904.

    Article  PubMed  CAS  Google Scholar 

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

    CAS  Google Scholar 

  31. Shimada, Y., Nagao, T., Hamasaki, Y., Akimoto, K., Sugihara, A., Fujikawa, S., Komemushi, S., and Tominaga, Y. (2000) Enzymatic Synthesis of Structured Lipid Containing Arachidonic and Palmitic Acids, J. Am. Oil Chem. Soc. 77, 89–93.

    CAS  Google Scholar 

  32. Phan, C.T., and Tso, P. (2001) Intestinal Lipid Absorption and Transport, Front. Bioscience 6, D299-D319.

    CAS  Google Scholar 

  33. Nelson, C.M., and Innis, S.M. (1999) Plasma Lipoprotein Fatty Acids Are Altered by the Positional Distribution of Fatty Acids in Infant Formula Triacylglycerols and Human Milk, Am. J. Clin. Nutr. 70, 62–69.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Freidoon Shahidi.

About this article

Cite this article

Namal Senanayake, S.P.J., Shahidi, F. Positional distribution of FA in TAG of enzymatically modified borage and evening primrose oils. Lipids 37, 803–810 (2002). https://doi.org/10.1007/s11745-002-0964-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-002-0964-5

Keywords

Navigation