Synthesis of polyunsaturated fatty acid‐enriched triglycerides by lipase‐catalyzed esterification

Abstract

This paper reports on the synthesis of triglycerides by enzymatic esterification of polyunsaturated fatty acids (PUFA) with glycerol. A PUFA concentrate obtained from cod liver oil was used to optimize the reaction to favor triglyceride synthesis with lipases. The type and amount of lipase and organic solvent, glycerol content, temperature, water content, and amount and time of addition of molecular sieves were studied. The optimal reaction mixture and conditions were: 9 mL hexane, 60ºC, 0.5% (vol/vol) water, 1 g molecular sieves added after 24 h of reaction, glycerol/fatty acid molar ratio 1:3 and 100 mg of Novozym 435 (Novo Nordisk A/S) lipase. Under these conditions, an enriched triglyceride yield of 84.7% containing 27.4% eicosapentaenoic acid and 45.1% docosahexaenoic acid was obtained from a cod liver oil PUFA concentrate. JAOCS 75, 1329JAOCS 75, -1337JAOCS 75, (1998.KEY WORDS: Docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), lipase-catalyzed esterification, polyunsaturated fatty acids (PUFA), triglyceride synthesis.

Modeling the effect of free water on enzyme activity in immobilized lipase-catalyzed reactions in organic solvents

“…In general, the optimal content is found at water/dry lipase mass ratio (R W ) range 0-0.1 (g of water/g of dry lipase) and in many cases these values concur with the water content that remains in the enzyme in the immobilization process (R W between 0.01 and 0.05; 1-5% dry weight). A previous work on the synthesis of triglycerides with the lipase Novozym ® 435 also verified that the enzyme water contents of 2-3% dry weight were sufficient for an effective lipase-catalyzed reaction [21]. However, there must be some reason for the significant decrease in the reaction rate when the water concentration exceeds the values pointed out.…”

Synthesis and Characterization of Phenolic Lipids

“…Reactions are ideal for removal of faty acids from unstable oils, including conjugated or highly unsaturated faty acids, which efectively reduce unwanted oxidation reactions [67]. Lipase catalyzed hydrolysis reactions produce glycerol esters enriched in ω-3 faty acids from ish oil [68,69]. Because natural ish oils do not contain more than about one-third of their faty acids from the ω-3 family, hydrolysis reactions are particularly helpful for the purpose of concentration.…”

Lipase-catalyzed acidolysis of fish liver oil with dihydroxyphenylacetic acid in organic solvent media

“…Selective interesterification, biocatalyzed by a 1-3 specific lipase, offers a potential for producing triacylgycerols in which the distribution of fatty acids on the glycerol positions 1, 2, and 3 is better controlled thus resulting at the transformation of an more nutritive triacylglycerol. Cerdan et al (1998) were able to modify and concentrate the fatty acid composition of cod liver oil through the use of a 1-3, specific lipase from Pseudomonas resulting in an enriched triacylgycerol yield of 84.7% containing 27.4% eicosapentaeonic acid (EPA) and 45.1% docosahexaenoic acid (DHA), respectively. The rearrangement of the position of fatty acids on the glycerol backbone as well as the reductions of the trans fatty acid content has been accomplished by the use of biocatalysts (Gunstone, 1999).…”

“…Applications of lipase-catalyzed esterification are widely seen in the food industry. Cerdan et al (1998) studied the esterification of glycerol and n-3 PUFA from cod liver oil using three commercially available lipases; Lipozyme IM from Mucor miehei, Novozym 435 from…”

“…plates (Cerdan et al, 1998). The elution solvent used was chloroform/acetone/methanol mixture (95:4.5:0.5, v/v/v) and the plates were visualized by developing the plate with iodine vapor in a nitrogen stream.…”