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An Efficient Methodology for the Preparation of Alkoxyglycerols Rich in Conjugated Linoleic Acid and Eicosapentaenoic Acid

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Journal of the American Oil Chemists' Society

Abstract

Saponification of a raffinate obtained by supercritical fluid fractionation of shark liver oil was utilized for the production of an unsaponifiable fraction enriched in nonesterified alkoxyglycerols. Re-esterification of the alkoxyglycerols produced with conjugated linoleic acid (CLA) and eicosapentaenoic acid in the presence of Candida antarctica lipase B was then studied. High yields (>90%) of diesterified alkoxyglycerols were obtained via esterification and transesterification with CLA, their respective ethyl ester, and eicosapentaenoic ethyl ester. The effect of a continuous purge stream of nitrogen on the kinetics of the reactions was also evaluated.

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References

  1. Willis WM, Lencki RW, Marangoni AG (1998) Lipid modification strategies in the production of nutritionally functional fats and oils. Crit Rev Food Sci Nutri 38: 1–36

    Article  Google Scholar 

  2. Mangold HK (1972) Chemistry and biology, In: Snyder FL (ed) Ether lipids. Academic, New York, pp 157–176

  3. Brohult A, Brohult J, Brohult S, Joelsson I (1977) Effects of alkoxyglycerols on the frequency of injuries following radiation therapy for carcinoma of the uterine cervix. Acta Obstet Gynecol Scand 56:441–448

    Article  CAS  Google Scholar 

  4. Andreesen R (1988) Ether lipids in the therapy of cancer. Prog Biochem Pharmacol 22:118–131

    CAS  Google Scholar 

  5. Palmblad J, Samuelsson J, Brohult J (1990) Interactions between alkylglycerols and human neutrophil granulocytes. Scand J Clin Lab Invest 50:363–370

    CAS  Google Scholar 

  6. Mukhopadhyay M (2000) Natural extracts using supercritical carbon dioxide. CRC Press, Boca Raton

    Google Scholar 

  7. Whigham LD, Cook ME, Atkinson RL (2000) Conjugated linoleic acid: implications for human health. Pharmacol Res 42:503–510

    Article  CAS  Google Scholar 

  8. Pariza MW, Park Y, Cook ME (2001) The biologically active isomers of conjugated linoleic acid. Prog Lipid Res 40:283–298

    Article  CAS  Google Scholar 

  9. Parodi PW (1997) cows’ milk fat components as potential anticarcinogenic agents. J Nutr 127:1055–1060

    CAS  Google Scholar 

  10. Ip C, Banni S, Angioni E, Carta G, McGinley J, Thompson HJ, Barbano D, Bauman DE (1999) Conjugated linoleic acid enriched butter fat alters mammary gland morphogenesis and reduces cancer risk in rats. J Nutr 129:2135–2142

    CAS  Google Scholar 

  11. Griinari JM, Bauman DE (1999) Advances in conjugated linoleic acid research, vol 1. AOCS Press, Champaign

  12. Kelly ML, Berry JR, Dwyer DA, Griinari JM, Chouinard PY, Van Amburgh ME, Bauman DE (1998) Dietary fatty acid sources affect conjugated linoleic acid concentrations in milk from lactating dairy cows. J Nutr 128:881–885

    CAS  Google Scholar 

  13. Kelly ML, Kolver ES, Bauman DE, Van Amburgh ME, Muller LD (1998) Effect of intake of pasture on concentrations of conjugated linoleic acid in milk of lactating cows. J Dairy Sci 81:1630–1636

    Article  CAS  Google Scholar 

  14. Sardesai VM (1992) Nutritional role of polyunsaturated fatty acids. J Nutr Biochem 3:154–166

    Article  CAS  Google Scholar 

  15. McGuire MK, Park Y, Behre RA, Harrison LY, Shultz TD, McGuire MA (1997) Conjugated linoleic acid concentrations of human milk and infant formula. Nutr Res 17:1277–1283

    Article  CAS  Google Scholar 

  16. Shimada Y, Sugihara A, Nakano H, Kuramoto T, Nagao T, Gemba M, Tominaga Y (1997) Purification of docosahexaenoic acid by selective esterification of fatty acids from tuna oil with Rhizopus delemar lipase. J Am Oil Chem Soc 74:97–101

    CAS  Google Scholar 

  17. McNeil GP, Ackman RG, Moore SR (1996) Lipase-catalyzed enrichment of long-chain polyunsaturated fatty acids. J Am Oil Chem Soc 73:1403–1407

    Article  Google Scholar 

  18. Breivik H, Haraldsson GG, Kristinsson B (1997) Preparation of highly purified concentrates of eicosapentaenoic acid and docosahexaenoic acid. J Am Oil Chem Soc 74:1425–1429

    CAS  Google Scholar 

  19. Torres CF, Munir F, Lessard LP, Charles G. Hill Jr. (2002) Lipase-mediated acidolysis of tristearin with CLA in a packed-bed reactor: a kinetic study. J Am Oil Chem Soc 79:655–661

    Article  CAS  Google Scholar 

  20. Haraldsson GG, Thorarensen A (1994) The generation of glyceryl ether lipids with eicosapentaenoic acid and docosahexaenoic acid by lipase. Tetrahedron Lett 35:7681–7684

    Article  CAS  Google Scholar 

  21. Hurtado-Benavides AM, Señoráns FJ, Ibáñez E, Reglero G (2004) Countercurrent packed column supercritical CO2 extraction of olive oil. Mass transfer evaluation. J Supercritical Fluids 28:29–35

    Article  CAS  Google Scholar 

  22. Torres CF, Vazquez L, Señorans FJ, Reglero G (2005) A detailed study of the analysis of alkoxyglycerols and other non-polar lipids by HPLC coupled with evaporative light scattering detector. J Chromatogr A 1078:28–34

    Article  CAS  Google Scholar 

  23. Hernandez-Perez M, Rabanal RM, Pascual PJ, Brito A (1998) Squalene content in livers from deep-sea sharks caught in Canary Island waters. Mar Freshw Res 48:573–576

    Article  Google Scholar 

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Acknowledgments

This work corresponds to preliminary studies of the project AGL2006-02031/ALI by Ministerio de Educación y Ciencia (Spain). This work was also supported by the Comunidad Autonoma de Madrid (ALIBIRD, project number S-505/AGR-0153). A postdoctoral contract (Programa Ramon y Cajal) for Carlos Torres was provided by the Ministerio de Ciencia y Tecnologia (Spain). A predoctoral fellowship for Luis Vazquez, provided by the Comunidad Autonoma de Madrid, is also acknowledged. We also want to thank the SOLUTEX company (Spain) for their support.

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Authors and Affiliations

  1. Sección Departamental Ciencias de la Alimentación, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049, Cantoblanco, Madrid, Spain

    Carlos F. Torres, Luis Vazquez, Francisco J. Señoráns & Guillermo Reglero

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  1. Carlos F. Torres
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  2. Luis Vazquez
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  3. Francisco J. Señoráns
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  4. Guillermo Reglero
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Correspondence to Guillermo Reglero.

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Torres, C.F., Vazquez, L., Señoráns, F.J. et al. An Efficient Methodology for the Preparation of Alkoxyglycerols Rich in Conjugated Linoleic Acid and Eicosapentaenoic Acid. J Amer Oil Chem Soc 84, 443–448 (2007). https://doi.org/10.1007/s11746-007-1062-4

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  • DOI: https://doi.org/10.1007/s11746-007-1062-4

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