Search

Here, we developed an efficient strategy for the production of lauric acid-enriched monoacylglycerol (MAG) via enzymatic glycerolysis using black soldier fly (Hermetia illucens) larvae (BSFL) oil. The effects of the substrate molar ratio, reaction temperature, type of immobilized lipase, and organic solvent on the MAG content and conversion degree of BSFL oil were optimized. The maximum substrate conversion rate (97.88%) and MAG content (70.84%) were obtained in a tert-butanol system at 50 °C with a glycerol/BSFL oil molar ratio of 4:1 by using immobilized MAS1 lipase as a catalyst. The MAG content in the purified product reached 97.7%, with lauric acid accounting for 50.2%. Improved oxidation stability was observed after glycerolysis. Overall, this study provides a new strategy for the preparation of lauric acid-enriched MAG from BSFL oil., (© 2021. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)

Phospholipids play important roles in biological process even at a very low level. For example, bis(monoacylglycerol)phosphate (BMP) is involved in the pathogenesis of lysosomal storage diseases, and polyphosphoinositides (PPI) play critical roles in cellular signaling and functions. Phosphatidylglycerol (PG), a structural isomer of BMP, mediates lipid-protein and lipid-lipid interactions, and inhibits platelet activating factor and phosphatidylcholine transferring. However, due to their low abundance, the analysis of these phospholipids from biological samples is technically challenging. Therefore, the cellular function and metabolism of these phospholipids are still elusive. This chapter overviews a novel method of shotgun lipidomics after methylation with trimethylsilyl-diazomethane (TMS-D) for accurate and comprehensive analysis of these phospholipid species in biological samples. Firstly, a modified Bligh and Dyer procedure is performed to extract tissue lipids for PPI analysis, whereas modified methyl-tert-butylether (MTBE) extraction and modified Folch extraction methods are described to extract tissue lipids for PPI analysis. Secondly, TMS-D methylation is performed to derivatize PG/BMP and PPI, respectively. Then, we described the shotgun lipidomics strategies that can be used as cost-effective and relatively high-throughput methods to determine BMP, PG, and PPI species and isomers with different phosphate position(s) and fatty acyl chains. The described method of shotgun lipidomics after methylation achieves feasible and reliable quantitative analysis of low-abundance lipid classes. The application of this novel method should enable us to reveal the metabolism and functions of these phospholipids in healthy and disease states.

The time course study of high monoester mixtures from soybean oil (HMMS) synthesis, as healthier alternatives to trans food products, in a supercritical CO 2 (SCCO 2 ) medium with and without enzyme, was investigated. Phosphorous nuclear magnetic resonance ( 31 P-NMR) was used to quantify the absolute amount of partially esterified acylglycerols (PEGs). Carbon NMR was utilized to determine the type and position of the fatty acids (FAs) of HMMS. Enzyme and time significantly influenced the synthesis of 1-monoglycerides (1-MGs), 2-MGs, and 1,2-diglycerides (1,2-DGs) in this alcoholysis of soybean oil with 1,2-propanediol, based on high catalytic activity and operational stability of Novozym 435 in SCCO 2 during short reaction time. Results suggest that 4 h is a suitable reaction time for this lipase-catalyzed interesterification (LIE) system for the synthesis of 2-MGs with a yield of 20%. The highest polyunsaturated fatty acid (PUFA) (65%) in the triglyceride (TG) of HMMS was produced after 4 h of reaction. After 6 h of reaction, a high level (20%) of saturated fatty acids (SFAs) was found in the TGs of HMMS, which were distributed between the sn-2 (5%) and sn-1, 3 (15%) positions.

2-monoglyceride (2-MAG) was essential to produce high purity of 1, 3-Oleoyl-2-palmitoylglycerol (OPO), an important infant formula additive. Traditional synthesis of 2-MAG requires chemical solvent to solve the high melting point substrate, yielding the risk of solvent residue in OPO. This paper developed a solvent-free synthesis route of 2-MAG by alcoholysis of high melting point tripalmitin (PPP). Ethyl palmitate (EP), one of the reaction byproducts, was added in the beginning of alcoholysis process to promote the solubleness of high melting point PPP, avoiding the addition of toxic chemical solvent. The product of alcoholysis was separated by two-step molecular distillations. Separated DAG was used to produce 2-MAG and the final conversion of 2-MAG reached about 85.90%, with the purity of 92.36%. 2-MAG was trans-esterified to OPO with ethyl oleate, and the yield of OPO was up to 85.06% with 80.17% palmitic acid located on sn-2 position. The solvent-free synthesis route avoids the usage of hazardous chemical solvents, providing safer infant formula additive.

This work shows new and promising experimental data of soybean oil and canola oil glycerolysis using Novozym 435 enzyme as catalyst in a solvent-free system using ultrasound bath for the emulsifier, monoglyceride (MAG), and diacylglycerol (DAG) production. The experiments were conducted in batch mode to study the influence of process variables as temperature (40 to 70 °C), immobilized enzyme content (2.5 to 10 wt%, relative to substrates), molar ratio glycerol/oil (0.8:1 to 3:1), agitation (0 to 1200 rpm) and ultrasound intensity (0 to 132 W cm(-2)). Highest yields of DAG+MAG (75 wt%) were obtained with molar ratio glycerol/canola oil 0.8:1, 70 °C, 900 rpm, 120 min of reaction time, 10 wt% of enzyme concentration, and 52.8 W cm(-2) of ultrasound intensity. When soybean oil was used, the best results in terms of DAG+MAGs (65 wt%) were using molar ratio of glycerol/soybean oil 0.8:1, 70 °C, 900 rpm, 90 min of reaction time, 10 wt% of enzyme content, and 40 % of ultrasound intensity (52.8 W cm(-2)). The results showed that the lipase-catalyzed glycerolysis in a solvent-free system with ultrasound bath can be a potential route for high content production of DAGs and MAGs.

Distilled glycerides are obtained through distillation of the system mono-diglycerides which is produced from the esterification reaction between a triglyceride with glycerol. In this work, monoglycerides (MG) and diglycerides (DG) are produced through lipase-catalyzed glycerolysis of soybean oil using Candida antarctica B in a solvent-free system. To separate the products of the reaction in order to obtain essentially MG and an oil of DG, it is necessary to use a suitable process in order to preserve the stability of the components and to keep the products free of inappropriate solvents. So, after 24 h of enzymatic reaction, the mixture of acylglycerols and fatty acids was distilled into a centrifugal molecular distiller, since it provides a free solvent and lower temperature environment to increase the desired product concentration. Starting from a material with 25.06% of triglycerides (TG), 46.63% of DG, 21.72% of MG, 5.38% of free fatty acids (FFA), and 1.21% of glycerol, the MG purity in the distillate stream was 80% at evaporator temperature (T (E)) equal to 250 degrees C and feed flow rate (Q) equal to 10.0 mL/min. At these conditions, the MG recovery was 35%. The material collected in the residue stream presented DG-enriched oil with TG unhydrolyzed, residual MG, and low acidity (29.83% of TG, 53.20% of DG, 15.64% of MG, and 1.33% of FFA), which is suitable to replace TG oil in the human diet.

This work describes the influence of two polar lipids, Sn-1/3 and Sn-2 monopalmitin, on the activity of lipase in biphasic systems and in microemulsions. In previous communications, we have shown that Sn-2 monoglycerides can replace Sn-1,3 regiospecific lipases at the oil-water interface, causing a drastically reduced rate of lipolysis. We here demonstrate that even if the lipase is expelled from the interface, it can catalyze esterification of the Sn-2 monoglyceride with fatty acids in both macroscopic oil-water systems and in microemulsions, leading to formation of di- and triglycerides.

Five lipases were screened (Thermomyces lanuginosus free and immobilized forms, Candida antarctica B, Candida rugosa, Aspergillus niger, and Rhizomucor miehei) to study their ability to produce monoglycerides (MG) and diglycerides (DG) through enzymatic glycerolysis of soybean oil. Lipase from C. antarctica was further studied to verify the enzyme load (wt% of oil mass), the molar ratio glycerol/oil, and the water content (wt% of glycerol) on the glycerolysis reaction. The best DG and MG productions were in the range 45-48% and 28-30% (w/w, based on the total oil), respectively. Using immobilized lipases, the amount of free fatty acids (FFA) produced was about 5%. However, the amount of FFA produced when using free lipases, with 3.5% extra water in the system, is equivalent to the MG yield, about 23%. The extra water content provides a competition between hydrolysis and glycerolysis reactions, increasing the FFA production.

Monoglycerides (MG) are emulsifiers widely used in food and pharmaceutical industries. Current industrial processes for MG production consist of the interesterification of triglycerides with glycerol (GL), in the presence of inorganic catalysts at high temperatures (> 200 degrees C). This reaction is known as glycerolysis and produces a mixture of approx 50% of MG. This level of concentration is suitable for many applications, although, for some specific uses like margarine, shortening, icing, and cream filling, require distilled MGs, which are purified MG (min. 90%) obtained by the molecular distillation process. Therefore, in this work, a 23 factorial design was employed to evaluate the effects of reaction parameters in the MG content after the interesterification reaction of refined soybean oil with GL in the presence of sodium hydroxide as catalyst. After that, the MG content in the reaction product was enhanced through the molecular distillation process in order to obtain distilled MG.