Lipase-catalyzed synthesis of phenolic lipids from fish liver oil and dihydrocaffeic acid

Abstract

The enzymatic synthesis of phenolic lipids by lipase-catalyzed transesterification of dihydrocaffeic acid (DHCA) with fish liver oil was investigated in a selected organic solvent medium. These synthesized phenolic lipids have potential use as nutraceutical products. Using a molar ratio of 1:8 DHCA to fish liver oil in hexane:2-butanone mixtures of 75:25 and 85:15 (v/v), the lipase-catalyzed reaction resulted in maximum conversion of 55.8 and 65.4%, respectively. The maximum conversion of phenolic monoacylglycerols in hexane:2-butanone mixture of 75:25 and 85:15 (v/v) was 40.3 and 37.7%, respectively; using the same solvent mixtures, the conversions of the phenolic diacylglycerol were 15.8 and 36.8%, respectively. Hexane:2-butanone mixture of 75:25 (v/v) was, therefore, the best organic solvent mixture for the production of phenolic monoacylglycerols, while that of 85:15 (v/v) was best for the production of phenolic diacylglycerols. The phenolic lipids produced from the fish liver oil and DHCA demonstrated antioxidant property as indicated by its free radical scavenging capacity.

Synthesis and Characterization of Phenolic Lipids

“…However, the use of phenolic acids as natural antioxidants in foods and nutraceutical supplements has the limitation of low solubility in oil-based media. Nevertheless, lipase-catalyzed reactions of lipids with phenolic acids could produce structured lipids with phenolic moieties, which would have health beneits and improved solubility characteristics [32][33][34][35].…”

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

“…The enzymatic processes can be used in the production of fats and oils containing beneficial fatty acids and or/phenolic compounds Karboune et al, 2005;Sabally et al, 2006a,b and2007).…”

“…Using lipase as a biocatalyst and substrate models, recent research work in our laboratory Sabally et al, 2005a,b and2006a,b;Safari et al, 2006) confirmed the validity of such an approach. In addition, the synthesis of phenolic lipids, using endogenous oils, such as flax seed oil (Sabally et al, 2006b) and fish liver oil (Sabally et al, 2007), was also reported. The advantages of using enzyme-catalyzed reactions, in comparison to chemical processes, offer an increase in the selectivity of side chains, milder reaction conditions and a more natural approach towards the synthesis of end products (Laane et al, 1987).…”

“…Previous preliminary work in our laboratory has shown the validity of the biotechnological approach for the synthesis of phenolic lipids using fish liver and flaxseed oils and dihydrocaffeic acid (Sabally et al, 2006b and2007). In order to optimize the bioconversion yield and enzymatic activity, a wide range of parameters including the choice of biocatalyst, lipase concentration, organic solvent ratio, molar substrate ratio as well as the presence of molecular sieve and Silica gel were investigated.…”

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).…”