Chemoenzymatic synthesis of structured triacylglycerols with conjugated linoleic acids (CLA) in central position

Villeneuve Pierre, Barouh Nathalie, Baréa Bruno, Piombo Georges, Figueroa-Espinoza Maria-Cruz, Turon Fabrice, Pina Michel, Lago Regina C.A.. 2007. Chemoenzymatic synthesis of structured triacylglycerols with conjugated linoleic acids (CLA) in central position. Food Chemistry, 100 : 1443-1452.

https://doi.org/10.1016/j.foodchem.2005.12.018

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Résumé : A chemoenzymatic process for the production of structured triacylglycerols (TAG) containing CLA at sn2 position and lauric acid at external ones is proposed. First, castor bean oil was chemically dehydrated and isomerised to obtain a new modified oil with very high proportion of CLA (>95%). Then, this new oil was used for enzymatic transesterification allowing the grafting of lauric acid at external positions of the TAG backbone by using 1,3 regioselective enzymes. Among these, Aspergillus niger lipase was not satisfactory giving very low lauroyl incorporation (<5%) On the contrary, lipases from Thermomyces lanuginosa (Lipozyme TL IM) and from Carica papaya latex allowed good reaction yields. The effect of the type of acyl donor was studied. With alkyl esters T. lanuginosa lipase provided a final incorporation of 58.9% after 72 h corresponding to 88.4% transesterification yield. Concerning C. papaya lipase, incorporation of lauroyl residues was lower than Lipozyme TL IM. This lipase exhibited higher performance with lauric acid accounting for 44.7% lauroyl incorporation at the end of reaction for a 67.1% transesterification yield. The effect of the substrates mole ratio was also evaluated. It was observed that a 1:3 TAG/acyl donor mole ratio was the most efficient for both lipases. Finally, fatty acids regiodistribution of the newly formed structured TAG was determined. With Lipozyme TL IM, the proportion of lauric acid incorporated at the sn2 position did not exceed 5.4% after 72 h while with C. papaya lipase a more pronounced incorporation of lauroyl residues at the central position (8.8%) was observed. © 2006 Elsevier Ltd. All rights reserved.

Mots-clés Agrovoc : triglycéride, biosynthèse, triacylglycérol lipase, estérase, acide linoléique, acide laurique, greffage, estérification, huile de ricin, Aspergillus niger, Carica papaya, lipase