Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylated glycerols

Abstract

Novel functional groups can be introduced into vegetable oils using enzymes, resulting in value-added products. The transesterification kinetics of ethyl ferulate with MAG, DAG, and TAG were examined. Transesterification was catalyzed by immobilized Candida antarctica lipase B in solventless batch and packed-bed reactors. Initial reaction rates with TAG were slightly sensitive to water activity, whereas rates with MAG and DAG were water activity independent. Transesterification was also three-to sixfold faster with MAG and DAG. These observations indicate that the reaction is rate limited by the acyl acceptor, and that oils with free hydroxyl groups are preferred acyl acceptors in comparison with TAG, which must undergo partial hydrolysis before becoming reactive.

A novel, two consecutive enzyme synthesis of feruloylated monoacyl- and diacyl-glycerols in a solvent-free system

“…And these effects inhibit the catalytic action of lipase. These results are in good agreement with previous reports (Stamatis et al 1999;Guyot et al 1997;Buisman et al 1998;Laszlo and Compton 2006).…”

“…Feruloylated mono-and di-acylglycerols are lipophilic antioxidants and potential UV absorbers (Compton 2005;Warner and Laszlo 2005). Enzymatic syntheses of these lipids (Laszlo and Compton 2006;Compton et al 2000;Laszlo et al 2003;Sabally et al 2006), although having superiority over chemical synthesis in view of the heat-sensitivity and oxidation-susceptibility of ferulic acid, have low yields, low time efficiency, and specific solvent requirements, etc.…”

Enhanced Enzymatic Preparation of Lipophilic Feruloylated Lipids Using Distearin as Feruloyl Acceptors: Optimization by Response Surface Methodology

“…However, using distearin and diolein as feruloyl acceptors, EF conversions rapidly increased, which were faster than that of Enova oil. EF conversions of distearin and diolein were both higher than those 90 EF conversion at 144 h of previous reports using soybean oil and partially deacylated soybean oil as feruloyl acceptors 5,13 , which may be attributed to little steric hindrance of distearin and diolein and efficiency removal of by-product ethonal using vacuum from the transesterification system. In the transesterification products of 48 h using distearin and diolein as feruloyl acceptor, the lipophilic FMAG FDAG yields were 75.7 2.1 and 72.8 1.1 , respectively, which were higher than that 45.7 2.2 using monostearin as feruloyl acceptor 14 .…”

“…But the great stearic hindrance of TAG made the reaction efficiency very low. For enhancing reaction rate, partially deacylated soybean oil was used as feruloyl acceptors 13 . For further reducing the stearic hindrance effect of feruloyl acceptors on the reaction, a novel enzymatic transesterification of EF with monostearin was developed 14 .…”

Improved enzymatic production of phenolated acylglycerols through alkyl phenolate intermediates

“…However, their applications in oil-based food processing and cosmetic industries are limited due to their low solubility in hydrophobic media (Buisman et al, 1998;Figueroa-Espinoza and Villeneuve 2005). To improve the lipophilicity of phenolic acids, an alternative method is incorporation of phenolic acids into triacylglycerols through enzymatic reactions (Compton et al 2000;Sabally et al 2005Sabally et al , 2006Sabally et al , 2007Laszlo and Compton 2006). However, direct transesterification of phenolic acids with triacylglycerols is generally suffered from long reaction time and low efficiency (Figueroa-Espinoza and Villeneuve 2005;Compton et al 2000).…”