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Biotechnology and Applied Biochemistry (2006) 43, (25–32) (Printed in Great Britain)

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Synthesis of acylglycerols from w-3 fatty acids and conjugated linoleic acid isomers

Charles P. Zuta*, Benjamin K. Simpson*¹ and Faustinus K. Yeboah†

*Department of Food Science and Agricultural Chemistry, McGill University (Macdonald Campus), 21,111 Lakeshore Rd., Ste. Anne de Bellevue, QC, Canada, H9X 3V9, and †Ecopia Biosciences Inc, 7290 Frederic Banting, Saint-Laurent, QC, Canada HAS 2A1

Key words: acylglycerols (glycerides), conjugated linoleic acid, mackerel oil, polyunsaturated fatty acids, structured lipids, transesterification.

Abbreviations used: AOCS, American Oil Chemists' Society; AV, acid value; c9,t11 etc., cis-9, trans-11 etc; CLA, conjugated linoleic acid; DHA, docosahexaenoic acid; EPA, eicosapentaenoic acid; ESI, electrospray ionization; GC, gas chromatography; LSD, least significant difference; MS/MS, tandem MS; PUFA, polyunsaturated fatty acid; SPE, solid-phase extraction; TAG, triacylglycerol.

¹To whom correspondence should be addressed (email benjamin.simpson@mcgill.ca).

n-3 PUFA (w-3 polyunsaturated fatty acid) concentrate from mackerel oil enriched in EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) was used to esterify isomers of CLA (conjuated linoleic acid) to produce acylglycerols (glycerides). Catalysis was potentiated by immobilized lipases from the yeast Candida antarctica and the mould Mucor miehei. C. antarctica lipase showed higher reactivity and much faster initial rate of incorporation of CLA into acylglycerols than its M. miehei counterpart. Synthesis with molecular sieves also achieved a better rate of incorporation of fatty acids into acylglycerols than using vacuum or systems without water removal. Esterification achieved at 40 °C with C. antarctica lipase was significantly different from that achieved at 60 or 50 °C. However, there was no significant (P<0.05) difference between esterification at 50 °C and 60 °C. The molar ratio of glycerol to fatty acid was found to influence the initial rate of incorporation, with the lower ratios showing higher initial rates compared with the higher ratios. The present study shows that direct esterification is an effective mechanism for producing acylglycerols from fatty acids in a controlled system.

Received 19 April 2005/4 July 2005; accepted 12 July 2005

Published as Immediate Publication 12 July 2005, doi:10.1042/BA20050082

© 2006 Portland Press Ltd