Enzymatic Synthesis of Extremely Pure Triacylglycerols Enriched in Conjugated Linoleic Acids

Abstract

This work was objectively targeted to synthesize extremely pure triacylglycerols (TAG) enriched in conjugated linoleic acids (CLAs) for medical and dietetic purposes. Extremely pure CLA-enriched TAG was successfully synthesized by using the multi-step process: TAG was primarily synthesized by lipase-catalyzed esterification of CLA and glycerol and then the lower glycerides [monoacylglycerol (MAG) and diacylglycerol (DAG)] in the esterification mixtures was hydrolyzed to free fatty acids (FFAs) by a monoand di-acylglycerol lipase (lipase SMG1), finally, the FFAs were further separated from TAG by low temperature (150 °C) molecular distillation. The operation parameters for the lipase SMG1-catalyzed hydrolysis were optimized using response surface methodology based on the central composite rotatable design (CCRD). The operation parameters included water content, pH and reaction temperature and all of these three parameters showed significant effects on the hydrolysis of lower glycerides. The optimal conditions were obtained with a water content of 66.4% (w/w, with respect to oil mass), pH at 5.7 and 1 h of reaction time at 19.6 °C. Under these conditions, the content of lower glycerides in the reaction mixture decreased from 45.2% to 0.3% and the purity of CLA-enriched TAG reached 99.7%. Further purification of TAG was accomplished by molecular distillation and the final CLA-enriched TAG product yielded 99.8% of TAG. These extremely pure CLA-enriched TAG would be used for in vivo studies in animals and humans in order to get specific information concerning CLA metabolism.

Acetalization Catalysts for Synthesis of Valuable Oxygenated Fuel Additives from Glycerol

“…Both are used to produce various oxygen-containing fuel additives. One of these methods is transesterification of glycerol with acetic acid, which makes it possible to prepare monoacetylglycerol (MAG), diacetylglycerol (DAG) and triacetylglycerol (TAG) [59][60][61]. Glycerol esters are widely used in the food, cosmetic, pharmaceutical, and plastics industries.…”

Preparation of High-Purity Trilinolein and Triolein by Enzymatic Esterification Reaction Combined with Column Chromatography

“…At reaction temperature of 100 , both trilinolein content and esterification degree reached the highest level when the esterification reaction approached equilibrium. Under the condition of reaction temperature 100 and negative pressure, the water produced by the esterification reaction is rapidly boiling and volatilizing, promoting the esterification reaction equilibrium to the right 23 . Further raising the reaction temperature to 110 120 , there was no significant difference in trilinolein content and esterification degree p 0.05 .…”

Preparation of Highly Pure n‐3 PUFA‐Enriched Triacylglycerols by Two‐Step Enzymatic Reactions Combined with Molecular Distillation

“…MAG and DAG lipases have attracted much attention in oils and fats modification due to their capability of synthesizing health beneficial partial glycerides [13][14][15][16][17][18][19]. However, to our knowledge, only two literatures have utilized this kind of lipase to remove partial glycerides by hydrolysis.…”

“…strain HTCC2649 was reported to remove partial glycerides by hydrolysis from camellia oil and the content of partial glycerides decreased from 98.83 to 27.9% after 12 h hydrolysis [20]. Another non-specific MAG and DAG lipase SMG1 from Malassezia globosa was also employed to hydrolyze partial glycerides from conjugated linoleic acids-enriched glyceride mixtures and the content of partial glycerides decreased from 45.2 to 0.3% [19]. Although MAG and DAG lipases exhibited great application potential in removing partial glycerides, no one has reported the removal of n-3 PUFA-enriched partial glycerides through hydrolysis using MAG and DAG lipases.…”