Acylglycerol synthesis including EPA and DHA from rainbow trout (Oncorhynchus mykiss) belly flap oil and caprylic acid catalyzed by Thermomyces lanuginosus lipase under supercritical carbon dioxide

Abstract

Supercritical carbon dioxide (SCCO2) was studied as a medium for esterification of eicosapentaenoic acid (n-3 C20:5, EPA) or docosahexaenoic acid (n-3 C22:6, DHA) and caprylic acid (C8:0, CA) in structured triacylglycerols (sTAG) using Thermomyces lanuginosus lipase as biocatalyst. Process variables (both n-3 long chain polyunsaturated fatty acid: caprylic acid, n-3 LCPUFA:CA contents ratio), glycerol content (wt, %), and supercritical time, temperature and pressure were optimized by the Response Surface Methodology through a central composite design of 2 5-1 +star. Synthesis of sTAG with EPA, DHA and CA under SCCO2 was significantly affected by the n-3 LCPUFA:CA contents ratio and supercritical time. MALDI-TOF mass spectrometry revealed that acylglycerols with the highest levels of EPA or DHA content in the sn-2 position were obtained when the following variables conditions were applied: 50% (n-3 LCPUFA:CA contents ratio), 40 °C (supercritical temperature), 20 MPa (supercritical pressure), 4 h (supercritical time) and 20.0 wt, % (glycerol concentration). For such experimental conditions, esterification catalyzed by Thermomyces lanuginosus lipase under supercritical carbon dioxide allowed obtaining sTAG synthesized with 54.95% of CA, 11.64% of EPA and 13.77% of DHA.

Effect of Structured Phenolic Lipids with EPA/DHA and Gallic Acid against Metabolic-Associated Fatty Liver Disease (MAFLD) in Mice

“…Thus, SC pressure was the most crucial factor in phenolic acidolysis, and a low SC pressure leads to an increase in it (p < 0.05) (Figure 1g,h). Pando et al [36] reported the acylglycerol synthesis including EPA and DHA (sTAG) from rainbow trout (Oncorhynchus mykiss) belly flap oil and caprylic acid (CA) catalyzed by Thermomyces lanuginosus lipase under CO 2 SC. In this case, the synthesis of sTAG with EPA, DHA, and CA under CO 2 SC was significantly affected by the n-3 LCPUFA:CA content ratio and SC time.…”

“…As a result, "tailor-made" lipids can be obtained with favorable physical characteristics, chemical properties, and nutritional benefits. This structuring can be done through chemical or enzymatic transesterification reactions by altering the composition and distribution of FA in the glycerol molecule [14,[35][36][37][38][39][40]. Lipases can be used in supercritical media (SC) to produce sAG since the increase in the solubility of lipid and hydrophobic substrates in non-polar media produces reverse reactions to hydrolysis, favoring enzymatic synthesis such as esterification, interesterification, alcoholysis and acidolysis [41,42].…”

Optimisation of Healthy-Lipid Content and Oxidative Stability during Oil Extraction from Squid (Illex argentinus) Viscera by Green Processing

“…With the same purpose, the RSM has been successfully applied during EPA and DHA urea-concentration from Asian catfish oil (Pangasius bocourti) [51], seal blubber (Phoca groenlandica) oil [52], and rainbow trout (Oncorhynchus mykiss) by-products [53]. Additionally, RSM has also been applied for the optimisation of enzymatic synthesis of acylglycerols including EPA and DHA from salmon (S. salar) oil [54] and rainbow trout (O. mykiss) by-products [55].…”

Synthesis of EPA- and DHA-Enriched Structured Acylglycerols at the sn-2 Position Starting from Commercial Salmon Oil by Enzymatic Lipase Catalysis under Supercritical Conditions

“…However, this may be due to the efficiency of the matrix used for the SL. Thus, they show a different behavior from that observed in the initial oil, according to the fact that visualization of the compounds requires the use of a matrix, which would be one of the factors that favor the fragmentation of the compounds [ 14 , 46 ]. Additionally, the ionization process, although corresponding to a soft type, can induce the fragmentation of TG to originate DG or FFA, artificially increasing the content of the samples [ 47 , 48 ]; this fact would explain the difference between values observed in TLC of EPA/DHA sAG and Extraction 3.…”

“…As a result, “tailor-made” lipids can be obtained with favorable physical characteristics and chemical properties, as well as nutritional benefits [ 10 ]. In order to maximize the FA bioavailability, sAG should present a particular FA distribution at the glycerol skeleton [ 13 , 14 ]. Among biocatalysts, lipases have shown to be the most versatile on the basis of their regiospecificity for modifying oils and fats to obtain high-added-value products, such as EPA + DHA supplements, among other sAG.…”