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

Abstract

increased from 11 to 70%, when the ratio of the hexane:2-butanone reaction medium was changed from 85:15 to 75:25 (v/v), respectively, whereas that of phenolic diacylglycerols (DAGs) remained relatively unchanged (13 to 16%). However, the addition of molecular sieve and Silica gel to the reaction medium resulted in a decrease in the bioconversion yield by 34% and 62%, respectively. Under the optimized conditions, the phenolic lipids showed a significant relative increase in C20:5 n-3 and C22:6 n-3 content in the phenolic

Lipase-catalyzed transesterification of krill oil and 3,4-dihydroxyphenyl acetic acid in solvent-free medium using response surface methodology

“…There was a gradual increase in the BY to a maximum of 56.79% (24 h) and 47.46% (18 h), respectively, before its decrease to 46.15 and 40.46% after 36 h; this decrease may be due to a shift in the thermodynamic equilibrium of the reaction toward hydrolysis and/or to the acyl migration, as a result of an increase in the concentration of free fatty acids [22,23]. Although the reaction rate was slower for lipase-catalyzed transesterification in OSM of fish liver oil with DHCA and DHPA [7,12] as well as in SFM with DHPA [15], a similar trend to that in Fig. 2 was observed.…”

“…The difference in the catalytic efficiency between the two biocatalysts could be due to the differences in their affinity and regioselectivity toward the phospholipids of the krill oil as well as the PAs, DHPA and DHCA [25]. Likewise, Karam et al [7] showed that Lipozyme IM-20 catalyzed acidolysis of DHPA with fish liver oil resulted in a maximum BY of 14.1% after 10 days of reaction, whereas with Novozym 435 as biocatalyst, the maximum BY of 64.8% was obtained after 8 days of reaction. The reaction time for the acidolysis in SFM of krill oil (24 h) was much shorter than that for fish liver and flaxseed oils, where the highest BY was obtained after 7 days of reaction [15]; the shorter reaction time could be explained by the fact that the enzyme has better affinity for phospholipids than that for triacylglycerols, which could be due to their viscosity and polarity [23].…”

“…However, their hydrophilic nature limits their solubility in the hydrophobic medium and consequently reduces their potential use in edible fats and oils [6]. The incorporation of phenolic antioxidants into unsaturated lipids could result in the biosynthesis of novel biomolecules, phenolic lipids, that possess both functional and nutritional benefits [7].…”

“…Research work, carried out in our laboratory, has succeeded in the enzymatic synthesis in organic solvent media (OSM) of structured phenolic lipids with enhanced antioxidative and solubility properties [7][8][9][10][11][12][13]. However, the low volumetric productivity is a major drawback limiting the enzymatic synthesis of phenolic lipids in OSM at a large scale.…”

“…Although the optimization of a bioprocess for the biosynthesis of phenolic lipids, obtained with using fish and flaxseed oils, was already developed in our laboratory [7][8][9][10][11][12][13]15], the reported study is the first in which the phenolic lipids were synthesized by using krill oil. Krill oil is not only rich in polyunsaturated fatty acids, but also in amphipathic compounds, the phospholipids [3].…”