Search

Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2023, Tutors: Maria Sarret Pons, Oriol Pérez Pinart, Emulsions are mixtures of two immiscible phases, a dispersed or internal phase and a dispersing or external phase, stabilized by different mechanisms depending on the emulsifier type. Emulsions are thermodynamically unstable, but their kinetical stability depends essentially on the type of emulsifier used. In this work simple emulsions are prepared, and it is analysed the stabilization effect of three different polyglycerides, non-ionic and natural origin surfactants resulting from the esterification reaction of fatty acids with some molecules of glycerine (in this case four molecules of glycerine). Moreover, three different glycerides are used as support agents (co-emulsifiers) made with the same fatty acid of polyglycerides; this way emulsions have the emulsifier and co-emulsifiers from the same fatty acid. The used compounds are derivatives from oleic, stearic and lauric acids. For each pair of compounds, the emulsion was characterized, and its stability was analysed. The results show that only oleic acid derivatives can be used to obtain emulsions with acceptable stability. The final goal of this work is to obtain a complete cosmetic formulation using the polyglyceride and glyceride that give the best results in the previous stability study. Since the prepared formulation is a moisturizing cream, the possibility of changing the usual oil (paraffin oil) by natural origin oils was also checked. This way the emulsions would have less allergenic reactions on skin and could be used in atopic skin cases

INTRODUCTION Marine microalgae protein has better solubility and digestibility than other protein-based feeds. Apart from protein, high-value biomolecules have an immense potential to enhance the quality of feed, but knowledge about them is scarce. OBJECTIVE Marine microalga Picochlorum sp. biomass molecular characterisation along with commonly used protein feed such as fishmeal and soymeal for potential feed ingredients. METHODOLOGY Liquid chromatography coupled with mass spectrometry (LC-MS) was used for biomolecular characterisation. The correlation of biomolecules sets was evaluated using principal component analysis (PCA) and heatmap clustering. RESULTS LC-MS identified 116 biomolecules cumulatively among microalga, fishmeal, and soymeal that includes fatty acids, acylglycerols, vitamins, sterols, pigments, nucleotides, unique amino acids, amines, sugars and miscellaneous. These 116 biomolecules were screened based on their functional importance as feed ingredients. Among the different sets of biomolecules, microalga contained a more diverse set of fatty acids, pigments, sterols, and vitamins than acylglycerols, unique amino acids, nucleotides, and sugars. Fishmeal contained a more diverse set of acylglycerols, unique amino acids, nucleotides, and amines, while soymeal contained the highest number of sugars and miscellaneous biomolecules. The PCA confirmed the significance level (P > 95%) and heatmap clustering showed the diversity and relatedness of biomolecules among the microalga, fishmeal, and soymeal. CONCLUSION This study showed that the marine microalga Picochlorum sp. biomass has a rich source of biomolecules and could complement fishmeal or soymeal in feed and is also sustainable and economical as compared to fishmeal and soymeal.

Pioglitazone HCl is an oral anti-diabetic agent used for the treatment of diabetes mellitus type II. The aim of the present work is to evaluate the pharmacodynamic activity of solid lipid nanoparticles of pioglitazone HCL prepared by using solvent injection technique and to compare with the control and test group. Among all the formulations, F5 was found to possess highest in-vitro drug release within 24 hrs i.e., 95.02±1.26%. The in vivo studies were performed using male albino rats of wistar strain (150-200g). Rats were divided in to five groups (n=6), group-I normal, group-II diabetes control, group-III placebo control, group-IV reference, group-V test group. Diabetes was induced by streptazocin (60 mg/kg) by intraperitonial route. The reference group was treated with marketed tablet of pioglitazone HCL, test groups were treated with SLNs suspended in 0.1% Tween 80 and given to animals through oral gavages. Blood samples were collected by retro-orbital puncture before treatment, and after treatment at time intervals 0, 2, 4, 6, 8, 10, 12 and 24h in anti-coagulated vials. Parameters like glucose, tri glycerides (TG), total cholesterol (TC) and HDL-C were estimated by calorimetric method. Diabetes induced rats showed elevated levels of glucose, TG, TC and reduced HDL. The oral administration of drug loaded SLNs in 0.1% Tween 80 solution showed reduced levels of glucose, TG and elevated levels of HDL-C and slightly reduced levels of TG in 24 h where as the marketed tablet showed reduced levels of glucose, TG and TC up-to 12 h and in 24thh the glucose levels get elevated. Thus the optimized SLNs showed prolonged activity.

Identification of sources of increased content of oleic acid glycerides (oleates) and determination of the nature of its variability are prerequisites for improving oil quality. The purpose of this study was to establish the variability of the content of oleic acid glycerides (oleates) in maize oil depending on the genotype and ripening temperature. The experiments were carried out on a series of common maize inbreds and inbred-carriers of the su1, ae, and su2 mutations, which were grown for three years. The fatty acid composition of the oil was analysed by the Peisker gas chromatographic method. Genotype–environment interactions were assessed using the Eberhard– Russell algorithm. It was found that the carriers of the su1 and su2 mutations had the highest oleate content. The oleate content of maize oil generally increased with increasing ripening temperature. Unrelated inbreds based on one mutation significantly differed in the genetically determined level of oleate and showed non-identical responses to the ripening temperature. In inbreds of the first type, the content of oleates changed significantly with temperature fluctuation, while inbreds of the second type provided a fairly stable level of the trait under these conditions.

Background As one of the most important modified products of rosin, rosin glyceride was widely used in many aspects. However, the preparation of rosin glyceride is always unfriendly due to the use of liquid catalyst, such as H2SO4 and H3PO4. Methods The rosin glyceride with low acid value was synthesized in vacuum conditions using a novel Lewis acidic ionic liquid 1–butyl–3–methylimidazolium chloroscandinate[BuMeim][Sc2Cl7] as catalyst. The [BuMeim][Sc2Cl7] is of excellent catalytic activity and stability. The efficient catalytic activity was studied via the combined Density Functional Theory (DFT) and experimental conditions. Significant findings The DFT proved the free energy of the esterification could reach to 31.6 Kcal/mol, which illuminates that the excellent coordination of the anions and cations in the [BuMeim][Sc2Cl7] greatly reduces the reaction energy barrier and promotes the efficient progress of the reaction. As a result, [BuMeim][Sc2Cl7] is a good catalyst for the esterification of rosin and glycerol to prepare rosin glyceride. Furthermore, [BuMeim][Sc2Cl7] could be a potential catalysts for the other esterification.

Pyrolysis behavior of resins is essential for their high-temperature application. Herein, the high-temperature stability and pyrolysis kinetics and mechanism of rosin glyceride (RGE), hydrogenated ...

The lipolytic behaviors and postprandial effects of butterfat and its fractions (30L and 30S) procured by dry fractionation at 30 °C were investigated using in vivo digestion. A total of 142 triacylglycerols (TAGs), 64 diacylglycerols (DAGs), 14 monoacylglycerols (MAGs), and 7 free fatty acids (FFAs) in the butterfat fractions and their hydrolysates were identified by combining high-performance liquid chromatography coupled with electrospray ionization-tandem quadrupole time-of-flight mass spectrometry with solid-phase extraction. The first-step hydrolysis from TAGs to sn-1,2 DAGs occurred slower in the high-melting-temperature solid fat (30S) fraction, which is rich in long-chain FAs compared to that of the low-melting-temperature liquid oil (30L) fraction, which is rich in short-chain unsaturated FAs (the hydrolysis rates were 39.22% vs 60.11%, respectively, in the 30 min gastric phase), and these differences were also reflected in the delayed and relatively flat postprandial lipemia levels in rats force-fed with 30S fraction. This study revealed the importance of TAG composition and lipid physical state in regulating digestion and absorption, which is related to nutrition science and the dairy or pharmaceutical industry.

Aim. Evaluation of donors’ properties of corn inbreds - carriers of endospermic mutations su1 and su2 on the oleates content. Methods. A series of hybrids obtained in top- crosses of 10 inbreds of the common type with four testers – low-oleic and high-oleic inbreds of the common type and inbreds – carriers of the su1 and su2 mutations were analyzed. Oleates’s content was determined by the gas chromatographic method. Results. The highest effects of the general combining ability were shown by the inbreds obtained from high-oil synthetics and the inbreds - carriers the su1 and su2 mutations. Hybrids of low-oleic inbreds with the sources of su1 and su2 mutations had an increased content of oleates in comparison with maternal forms, and hybrids of high-oleic inbreds with the sources of these mutations inherited the oleates content in an intermediate type. In F2 hybrids from crosses of inbreds of the common type with the inbreds - carriers of the su1 and su2 mutations, transgressions were observed. Conclusions. The increased content of oleates in corn inbreds inbreds and hybrids is most likely controlled by oleate - coding loci of chromosome 4 and 6 linked to mutant genes su1 and su2. The carriers of these genes can be used as sources of increased oleate content in the corn breeding for oil quality. Key words: Zea mays L., endospermic mutants, oleates content, top-crosses

Lipid digestion characteristics in human, bovine, and caprine milk were investigated using an infant in vitro digestion model. Our results suggested that particle size in bovine and caprine milk increased initially and then decreased over time, whereas the particle size in human milk continuously decreased. The lipolysis degree of human milk (86.8%) was higher than that in bovine (80.2%) and caprine (82.7%) milk (P < 0.05). Compared to human milk, bovine and caprine milk released higher unsaturated fatty acids and lower SFAs. In addition, 12 and 84 glyceride species were significantly different between bovine and human milk, during gastrointestinal digestion (P < 0.05). Another 13 and 92 glyceride species were found to be significantly different between caprine and human milk. A total of 30 and 31 lipids were screened as biomarkers to further clarify the differences related to lipid digestion properties of human, bovine, and caprine milk.

In the present work, oil-in-water (O/W) emulsion systems were prepared by using the PEG-7 lauric acid glycerides as the emulsifiers and the liquid paraffin as the oil phase. The influence of processing parameters such as emulsification temperature, stirring speed, emulsifier concentration, oil-water volume ratio and polymer addition on the stability of the emulsion systems was investigated. In order to determine the optimal conditions for the preparation of the emulsion systems based on PEG-7 lauric acid glycerides, a laser drop size analyser and a rotational rheometer were used. As the stability of the O/W emulsion systems increased, the average droplet size of the O/W emulsions measured by the laser droplet size analyser became smaller and the viscosity, storage modulus and loss modulus of the O/W emulsions measured by the rotational rheometer became larger. The following optimal conditions were determined in this study: emulsification temperature 80°C, stirring speed 500 r/min, emulsifier concentration 5 wt%, oil-water volume ratio 1:1 and added amount of xanthan gum 0.2 wt%. The droplet morphology of the O/W emulsion prepared under the optimal conditions, which was characterised by a super high magnification microscope, is small. Furthermore, the long-term stability of the emulsion system prepared under the optimal conditions was investigated over a period of time (4 weeks). The O/W emulsion proves to be well stable even after 4 weeks, with a water separation rate of 0%.

The specific purpose of this scientific article is to obtain scientific information about the pattern composition of monoglycerides (MG), diglycerides (DG) and triglycerides (TG) in palm kernel oil (PKO) ethanolysis products at three stages and of the mole ratios of ethanol in ethoxy solution (ethanol 90% - NaOH 1%) to PKO (assumed as trilaurin). Ethanolysis reactions of PKO had been carried out in three stages, as follows: Level I ethanolysis was carried out at 60°C, at a stirring speed of 1000 rpm for 3 mins, in the treatment of the mole ratios of ethanol in ethoxy solution (ethanol 90% - NaOH 1%) to PKO of the 10, 12, 14, 16, 18 and 20, resulting in ethanolysis product I and the residual reaction I. Level II ethanolysis was ethanolysis of the residual reaction I, resulting in ethanolysis product II and residual reaction II. Level III ethanolysis was ethanolysis of the residual reaction II, resulting in ethanolysis product III. The mean yield of all treatments for PKO Ethanolysis Levels I, II, and III were 12.26±0.46%, 11.20±2.61%, and 11.78±2.99% (w/w), respectively. The highest total yield of PKO ethanolysis level I, II, and III was 41.04±9.74% (w/w) from the mole ratio treatment of 20, while the lowest yield was 27.54±3.39%; (w/w) from the mole ratio treatment of 10. The average amount of MG, DG, and TG from all treatments were 9.740%, 12.801%, and 2.675%, respectively. The highest MG content was obtained from the mole ratio treatment of 20 at Ethanolysis Level I (11.83%).

In this paper, a new method was developed for the determination of glyceryl dilinoleate, 1,3-dipalmitate glyceride, and glyceryl 1,3-distearate in milk by ultra-performance liquid chromatography—ev...

The formation of precipitates in biodiesel (comprising fatty acid methyl esters [FAMEs] obtained from plant oils) can lead to the clogging of fuel filters. Such precipitates are often caused by the solidification of acylglycerols (monoacylglycerols [MAGs], diacylglycerols [DAGs], and triacylglycerols [TAGs]) that have higher melting points than FAMEs. Based on our prior study on the solidification behavior of MAG/FAME binary mixtures, the present work investigated the behavior of various DAGs and TAGs combined with FAMEs. Differential scanning calorimetry was used to clarify the effects of acylglycerols on the cold-flow properties of biodiesel. When DAGs and TAGs were added to FAMEs, the liquidus temperatures (above which the mixtures were completely liquid) increased steeply even at low concentrations. This same behavior was observed previously in trials with MAGs, indicating that all acylglycerols readily precipitate in combination with FAMEs. However, thermodynamic analyses established that the reasons for such precipitation were different for different compounds. MAGs precipitates because they contain two hydroxyl groups and therefore have a low affinity for FAMEs. In contrast, TAGs precipitates as a result of their high enthalpies of fusion (which in turn are caused by high molecular weights), while both factors affect the precipitation of DAGs. A non-solid-solution thermodynamic model that assumes a eutectic system was found to accurately predict the liquidus temperatures of binary and multicomponent mixtures containing various acylglycerols with FAMEs.

A three-liquid-phase system (TLPS) was developed and used as a novel enzymatic one-pot multistep reaction (EOMR) system. In this system, lipase and phospholipase were enriched in a single liquid phase with a high recovery (ca. 98%) and then used for the simultaneous catalysis of mutually inhibiting and interfering reactions (hydrolysis of phospholipids and glyceride in crude oil). A novel emulsion containing the two dispersed droplets (W2/O/W2 and W1/W2 emulsion structures) could be the key reason for this phenomenon because the emulsion system not only provided a new catalytic interface but also relieved the product inhibition. As a result, the content of free fatty acid (main hydrolysate of the glyceride) and the removal of phospholipid from the crude oil could be increased to 96 and 95%, respectively, within 1 h. The product obtained from the EOMR was directly used in the production of biodiesel via enzymatic esterification, and the content of fatty acid methanol ester could be increased to 93% within 2 h. Furthermore, the enzymes in the middle phase could also be reused, at least for eight rounds without significant loss in catalytic efficiency. Therefore, the TLPS could be considered as an ideal catalytic platform for the EOMR.

The main objective of this study is to assess the efficiency of Ni/γ-Al2O3 calcined at different temperatures and Ni-Sn/γ-Al2O3 with different Ni:Sn atomic ratios catalysts for hydrolysis-reforming-hydrogenation reactions in a one-pot of the soybean oil. Ni/γ-Al2O3 catalysts were prepared by incipient wetness impregnation, further dried at 110 °C and calcined. Ni-Sn/γ-Al2O3 catalysts were prepared by using the same steps of the monometallic ones and calcined at 300 °C. The catalysts were characterized by N2-isotherms, XRF, XRD, TPR, DRS-UV–vis, and H2-TPD. Before the reaction, the catalysts were reduced under H2 at 550 °C. γ-Al2O3 was the best catalyst for the hydrolysis reaction that enabled the complete conversion of triglycerides to glycerol and the respective formation of soybean oil fatty acids. Ni/γ-Al2O3 calcined at 300 °C, which had the highest metallic surface area after reduction, was the best monometallic catalyst for stearic acid production. The addition of tin has improved the hydrolysis reaction and the glycerol aqueous-phase reforming, enhancing in-situ H2 production and, consequently, the selectivity towards saturated fatty acids. The beneficial effect afforded by Sn may be due to the presence of Sn at defective Ni sites or by the formation of a Ni-Sn (Ni3Sn) alloy. The results indicate that a triglyceride-based biorefinery approach, in which glycerides, glycerol, hydrogen, saturated and unsaturated fatty acids c be tuned in by catalysts and reaction conditions.

Refined Bleached Deodorized Palm Oil (RBDPO) is a derived product of crude palm oil that has two fraction (olein and stearin) in ambient temperature. This research aim to analyze the variation of treatment on RBDPO. The design of research was non-factorial with three variable of treatment such RBDPO with glycerol (A), RBDPO (B) and RBDPO with lipase enzyme. The concentration of glycerol, ester, mono- and diglyceride was tested by Gas Chromatography method. The data will be analyzed by using descriptive method with boxplot and histogram. The result showed that the highest concentration of glycerol; ester; mono- and diglyceride respectively were showed in treatment B (1,5922%); C (9,5699%); C (0,1783%); C (3,3329). The boxplot graphic described the differences among the treatment.

In India’s folklore, extracts of moss Octoblepharum albidum used in the treatment of fever, bacterial infections, and diabetes. The present study aimed to establish the chemical and pharmacological profile of the ethanolic extract of O. albidum (OA-Et). By using column chromatography, OA-Et yielded three known metabolites, namely 6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one(1), 4,4,7a-trimethyl-2-(prop-1-en-2-yl)-2,4,5,6,7,7a-hexahydrobenzofuran-6-ol(2) and 1-(6-hydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-2,3-dihydrobenzofuran-7-yl)-ethan-1-one(3), which were reported for the first time from this species. The isolated metabolites(1–3) and OA-Et were screened against ferric ions, DPPH free-radicals, superoxide free-radicals, α-glucosidase, α-amylase and aldose-reductase assays, and particularly OA-Et subjected to glycemia activities in albino rats. Among all, 3 and OA-Et depicted significant inhibitory profiles against free-radicals. Particularly, 3 and OA-Et depicted better IC50 values on α-glucosidase and α-amylase, rather than aldose-reductase. Also, the OA-Et (200 mg/kg b.w) treated group revealed significant drop-in body weight (p > 0.001), plasma glucose (p > 0.001), total cholesterol (p > 0.005), total glycerides (p > 0.005), and LDL levels (p > 0.005) in STZ-induced diabetic rats. The HDL levels were markedly augmented in OA-Et (p > 0.005) treated diabetic rats when related to controlled rats. OA-Et abolished increased lipid peroxidation content (p > 0.001) in the pancreas, liver, and kidneys. Histopathological examination of the pancreas of the OA-Et treated group protected the Langerhans islets with the number of islet cells found statistically significant (p > 0.05) compared to diabetic control pancreas. Thus, O. albidum has an aptitude to acts against diabetes by particularly acting against digestive enzymes, i.e., α-glucosidase and α-amylase.

Amylosucrase (ASase, E.C. 2.4.1.4) is a powerful transglycosylation enzyme that can transfer glucose from sucrose to the hydroxyl (-OH) group of various compounds. In this study, recombinant ASases from Deinococcus geothermalis (DgAS) and Bifidobacterium thermophilum (BtAS) were used to synthesize biosurfactants based on the computational analysis of predicted docking simulations. Successful predictions of the binding affinities, conformations, and three-dimensional structures of three surfactants were computed from receptor-ligand binding modes. DgAS and BtAS were effective in the synthesis of biosurfactants from glyceryl caprylate, glyceryl caprate, and polyglyceryl-2 caprate. The results of the transglycosylation reaction were consistent for both ASases, with glyceryl caprylate acceptor showing the highest concentration, as confirmed by thin layer chromatography. Furthermore, the transglycosylation reactions of DgAS were more effective than those of BtAS. Among the three substrates, glyceryl caprylate glycoside and glyceryl caprate glycoside were successfully purified by liquid chromatography–mass spectrometry (LC–MS) with the corresponding molecular weights.

Excessive torque on tool surfaces resulting in friction and wear in the process of well drilling remains a big challenge for the oil and gas exploration industry. In this study, two kinds of glycer...

Biodiesel is a substitute fuel that is environmentally friendly, biodegradable, and sustainable. The need for biodiesel continues to increase. Biodiesel is made through the process of transesterification of triglycerides and alcohol. Glycerol is a side-effect of biodiesel products with a capacity of 10% of the total weight of its production. Glycerol is the simplest glyceride compound and has several functions as a primary ingredient in chemical production. Through acetylation, glycerol is converted to a material that has a higher sale value. Both homogeneous and heterogeneous catalysts are the acetylation approach to achieve the desired product, namely acetyl glycerol esters (mono-, di- and triacetin). However, in the process, the catalyst’s type and characteristics significantly affect the yield and conversion of the product and the deactivation or reusability of the catalyst, which can inhibit the catalyst’s utilization and effectiveness; therefore, it must be studied further. Besides, the parameters that affect the reaction will also be assessed.

Drug delivery to the lymphatic system is gaining increasing attention, particularly in fields such as immunotherapy where drug access to lymphocytes is central to activity. We have previously described a prodrug strategy that facilitates the lymphatic delivery of a model immunomodulator, mycophenolic acid (MPA) via incorporation into intestinal triglyceride transport pathways. The current study explored a series of structurally related glyceride and phospholipid mimetic prodrugs of MPA in an attempt to enhance lymph targeting and to better elucidate the design criteria for lipid mimetic prodrugs. MPA was conjugated to a glyceride or phospholipid backbone at various positions using different spacers employing ester, ether, carbonate and amide bonds. Patterns of prodrug hydrolysis were evaluated in rat digestive fluid, and lymphatic transport and plasma pharmacokinetics were assessed in lymph duct cannulated rats. Prodrugs with different spacers between MPA and the glyceride backbone resulted in up to 70-fold differences in gastrointestinal stability. MPA conjugation at the 2 position of the glyceride backbone and via an ester bond were most effective in promoting lymphatic transport. Phospholipid prodrug derivatives, or glyceride derivatives with MPA attached at the 1 position or when linked via ether, carbonate or amide bonds were poorly incorporated into lymphatic transport pathways.

Lipase-catalyzed glycerolysis was recently shown to be a viable technique to structure cottonseed and peanut oils into structural fats by converting native triacylglycerols into partial glycerides without changing overall fatty acid composition. Here, this approach was extended to a variety oils of differing fatty acid compositions. Reactions were performed at 65 ​°C for 48 ​h at a triacylglycerol:glycerol molar ratio of 1:1, using the non-regiospecific Candida antarctica lipase B. In all oil systems, a 20 ​°C increase in crystallization onset temperature was observed following glycerolysis. Solid fat content increases resulting from glycerolysis were greatest for oils containing >10% saturated fat along with a high oleic acid content. The solid fat content of tigernut oil at 5 ​°C increased from 8% to 34% following glycerolysis. Tigernut glycerolysis product was used to make margarine with plasticity similar to commercial margarine and butter. This research demonstrates that glycerolysis is a general strategy to convert liquid oils into structural fats used in food applications, and thus replace palm oil and hydrogenated fats., Graphical abstract Image 1, Highlights • Edible oil fatty acid content affects the composition of crystalline material. • High oleic content enhances structuring in oils of intermediate saturated fat levels. • Highly saturated monoacylglycerol crystal material melts gradually. • Partial glycerol crystals of high oleic oils showed a two-segment melting profile. • Glycerolysis-structured oils produced margarine comparable to commercial products.

Olanzapine (OLA), a first atypical antipsychotic moleculethat experiences low brain permeability because of efflux by P-glycoproteins (Pgp) in the brain and extensive hepatic first-pass metabolism....

LaZSM-5 zeolite was synthesized by the in situ method and used as catalysts to catalyze the synthesis of rosin glyceride. As a comparison, ZSM-5 was also synthesized and used as catalysts to catalyze the synthesis of rosin glyceride. The synthesized ZSM-5 and LaZSM-5 zeolite catalysts were characterized and analyzed. The experimental results showed that the in situ synthesis of LaZSM-5 made La into the skeleton of ZSM-5 zeolite and increased the amount of Lewis acid on the LaZSM-5 zeolite. Also, Lewis acid was the key to liquid-phase esterification reaction. Compared with ZSM-5 zeolite, LaZSM-5 zeolite contributed to a higher yield and better stability as a catalyst for the synthesis of rosin glycerides.

Lipid generated from housefly (Musca domestica L.) larvae fed by municipal waste is a renewable lipid resource, however, the low unsaturated degree prevents it from producing trimethylolpropane fatty acid triester as lubricant, due to its poor low-temperature performance. A new fatty acid esters complex consisting of trimethylolpropane fatty acid triester and 2-ethylhexyl fatty acid ester was produced from housefly larval lipid. Separated from molecular distillation, the acylglycerols were first trans-esterified into fatty acid methyl ester and then further trans-esterified with trimethylolpropane into trimethylolpropane esters. The purified trimethylolpropane fatty acid triester is with purity of 98.4% and further blended with 30 wt% 2-ethylhexyl fatty acid ester derived from housefly larval free fatty acid. The pour point was substantially lowered from −3 °C to −12 °C while the lubricity performance is within standard of ISO VG 32, with minor improvement of water separability compared with pure trimethylolpropane fatty acid triester. By blending two type bio-lubricants with different advantages on viscosity and pour point, the ester complex with favorable properties was produced using saturated non-food lipid source rather than unsaturated virginal vegetable oil. This study also offers a cleaner and energy-efficient approach for high value-added product production for non-food lipid industry.

A glyceride mixture of monoglyceride, diglyceride and TAG increases solubilisation and enhances emulsification of n-3 fatty acid (FA)-containing lipids in the stomach. This allows for better access of digestive enzymes, pivotal for the release of bioactive n-3 FA. The objective was to compare the effect of a glyceride formulation and an ethyl ester formulation of EPA + DHA on concentrations of EPA and DHA in plasma following single dosing. We conducted a double-blind crossover trial in which twenty healthy adults aged 50–70 years consumed a single dose (2·8 g EPA + DHA) of each EPA + DHA formulation without a meal in random order separated by a 2-week washout period. EPA and DHA were measured in plasma total lipid over the following 12 h. EPA and DHA in plasma total lipid increased over 12 h with both formulations. A 10-fold greater Δ concentration of EPA, 3-fold greater Δ concentration of DHA and 5-fold greater Δ concentration of EPA + DHA were seen with the glyceride-EPA + DHA. The time at which the maximal concentrations of n-3 FA occurred was 4 h earlier for EPA, 1 h earlier for DHA and 2 h earlier for EPA + DHA when consuming glyceride-EPA + DHA. A mixture of monoglyceride, diglyceride and TAG results in greater and faster incorporation of EPA and DHA into blood plasma lipid in the absence of a fatty meal. This may provide benefit to individuals on a low-fat diet or with digestive impairments and could result in greater efficacy in clinical trials using n-3 FA.

Omega 3 and 6 fatty acids are very good consumed to improve human health. For this reason, research is needed to determine the glyceride profile and identification of omega 3 and 6 fatty acids in fat molecules so that the potential of catfish oil as a source of omega 3 and 6 can be known. Catfish oil was extracted by the soxletation method. Fatty acid composition was analyzed by gas chromatography (GC-FID) which was previously esterified using BF3. The results showed that the composition of unsaturated fatty acids more than saturated fatty acids. Omega-3 fatty acids are found consisting of linolenic acid, eicosapentanoic acid (EPA) and docosahexanoic acid (DHA) and omega 6, namely linoleic acid. The comparison of omega 3 and omega 6 in catfish oil is still within the recommended comparison terms. Judging from the composition and position of catfish oil fatty acids which contain omega 3 and omega 6 fatty acids. Thus catfish oil has the potential as a source of omega 3 and 6 from one of the freshwater fish that are consumed by many people.

Lipase-catalyzed esterification is an efficient technique in the production of polyunsaturated fatty acid (PUFA) concentrates which are applied for nutrition and health purposes. In this project, a solvent-tolerant lipase from Streptomyces pratensis MV1 was immobilized and purified by a hydrophobic support. The purified lipase revealed enhanced activity and stability towards chemicals, organic solvents, and a broad range of pH values. The production of lipase was enhanced to 7.0 U/mL after optimization by a central composite design. Acylglycerols (AGs) rich in α-linolenic acid (45%, w/w) were produced and a favorable n-6/n-3 free fatty acid (FFA) ratio of 1.1 was achieved in fenugreek seed oil using the immobilized lipase. The ability of S. pratensis lipase in ester synthesis and the improvement of n6/n3 FFA ratio make it a suitable candidate in food production industries. Electronic supplementary material The online version of this article (10.1007/s13197-020-04784-w) contains supplementary material, which is available to authorized users.

Mono- and diacylglycerols (MAG and DAG, respectively) of polyunsaturated fatty acids (PUFA) are raising an increasing interest as novel non-ionic food emulsifiers owing to the recognized health-promoting effects of PUFA. We here reported on the lipase-catalyzed hydrolysis of hempseed oil in a homogeneous medium based on oil and t-BuOH/water carried out in a continuous flow packed-bed reactor (PBR). The biotransformation was carried out by feeding the reaction mixture upwards the PBR at varying flow rates through a peristaltic pump. The system was coupled in-line with a second glass column filled with an ion-exchange resin to retain hydrolyzed free fatty acids (FFA), thus allowing the straightforward purification of the glyceride component. A mixture of MAG and DAG (yield 40%, 620 mg) composed of linoleic and α-linolenic acid (82%) and oleic acid (16%) was obtained in less than 2 hours. The lipase-based PBR was used for 10 cycles without any loss of activity.

Lipid drug conjugates (LDCs) are the chemical entities, which are commonly referred to as lipoidal prodrug. They contain the bioactive molecules, covalently or non-covalently linked with lipids like fatty acids, glycerides or phospholipids. Lipid drug conjugates are fabricated with the aim of increasing drug payload. It also prevents leakage of a highly polar bioactive(s) from the lipophilic matrix. Conjugating lipidic moieties to bioactive molecules improves hydrophobicity. It also modifies other characteristics of bioactive(s). These conjugates possess numerous merits encompassing enhanced tumor targeting, lymphatic system targeting, systemic bioavailability and decreased toxicity. Different conjugation approaches, chemical linkers and spacers can be used to synthesize LDCs based on the chemical behaviour of lipidic moieties and bioactive(s). The factors such as coupling/ conjugation methods, the linkers etc. regulate and control the release of bioactive(s) from the LDCs. It is considered as a crucial parameter for the better execution of the LDCs. The purpose of this review is to explore widely the potential of LDCs as an approach for improving the therapeutic indices of bioactive(s). In this review, the conjugation methods, various lipids used for preparing LDCs, and advantages of using LDCs are summarized. Though LDCs might be administered without using a carrier; however, majority of them are incorporated in an appropriate nanocarrier system. In the conjugates, the lipidic component may considerably improve the loading of lipoidal bioactive(s) in the lipid compartments. This results in high % drug entrapment in nanocarriers with greater stability. Several nanometric carriers such as polymeric nanoparticles, micelles, liposomes, emulsions and lipid nanoparticles, which have been explored, are reviewed here.

Protein inactivation either during the production process or along the gastrointestinal tract is the major problem associated with the development of oral delivery systems for biological drugs. This work presents an evaluation of the structural integrity and the biological activity of a model protein, catalase, after its encapsulation in glyceryl trimyristate-based solid lipid microparticles (SLMs) obtained by the spray congealing technology. Circular dichroism and fluorescence spectroscopies were used to assess the integrity of catalase released from SLMs. The results confirmed that no conformational change occurred during the production process and both the secondary and tertiary structures were retained. Catalase is highly sensitive to temperature and undergoes denaturation above 60 °C; nevertheless, spray congealing allowed the retention of most biological activity due to the loading of the drug at the solid state, markedly reducing the risk of denaturation. Catalase activity after exposure to simulated gastric conditions (considering both acidic pH and the presence of gastric digestive hydrolases) ranged from 35 to 95% depending on the carrier: increasing of both the fatty acid chain length and the degree of substitution of the glyceride enhanced residual enzyme activity. SLMs allowed the protein release in a simulated intestinal environment and were not cytotoxic against HT29 cells. In conclusion, the encapsulation of proteins into SLMs by spray congealing might be a promising strategy for the formulation of nontoxic and inexpensive oral biotherapeutic products.

Solid lipid nanoparticles (SLN) are colloidal lipid carriers, which used for improving the bioavailability of lipophilic and hydrophilic drugs. SLN are composed of biodegradable lipids such as hard fats, highly purified triglycerides, monoglycerides, complex glyceride mixtures or waxes which are solid at room temperature. In the present study, different formulation variables, including the type and quantity of lipid and surfactant were optimized for the preparation of SLN. SLN were prepared by a modified micro emulsion-based method and their particle size was evaluated. Two types of surfactants Tween 80 and Poloxamer 188 were used. Also, the monoglyceride (Glyceryl monostearate) and wax (Cetyl palmitate) were used as lipid. The optimum SLN formulae were at lipid concentration 5%. The optimum surfactant concentration was 6%. SLN with a surfactant Tween 80 were smaller in size than Poloxamer 188 SLN. Glyceryl monostearate formed a smaller size SLN than Cetyl palmitate. Increasing Glyceryl monostearate concentration in the lipid ratio resulted in the formation of small size SLN.

This study verified the formation profile of esters of 3-monochloropropane-1,2-diol (3-MCPDE), 2-monochloropropane-1,2-diol (2-MCPDE), and glycidol (GE), and evaluated the physicochemical changes (free-fatty acid, acylglycerols, and colour) that occurred during the deodorization of palm oil in different conditions of time (30, 60, 90, and 120 min) and temperature (210, 230, 250, and 270 °C). Levels of 3-MCPD and 2-MCPD esters ranged from 1.91 to 2.70 mg/kg and 0.68 to 1.44 mg/kg, respectively, and were formed at the mildest tested condition (210 °C, 30 min). No correlation was observed between these contaminants and physicochemical changes. GE levels varied from 0.12 to 8.51 mg/kg and showed correlation with color and diacylglycerol content. While the temperature had little influence on the formation of esters of 3-MCPD and 2-MCPD, the content of GE considerably raised above 250 °C.

Crystalline glycerides play an important role in the formation of multiphase systems such as emulsions and foams. The stabilization of oil/water interfaces by glyceride crystals has been extensively studied compared to only few studies which have been dedicated to oil/air interfaces. This study investigates the crystallization and network formation of tripalmitin (TP) and monopalmitin (MP) at the middle-chain triglyceride (MCT) oil/air interface. TP crystals were found to crystallize in the bulk before aggregating as large rectangular crystal conglomerates at the MCT oil/air interface. This leads to the slow formation of a plastic deformable, macroscopic crystal layer with high interfacial rheological moduli. MP crystals form directly at the MCT oil/air interface resulting in a comparatively fast formation of an elastic deformable network. Crystals with tentacle-like morphology were found to be responsible for the network elasticity. In this work, we show how interfacial crystallization dynamics and mechanical strength can be linked to the molecular structure and crystallization behavior of glyceride crystals. © 2020 American Chemical Society. ISSN:0743-7463 ISSN:1520-5827