Glycerol Trioleate Research Articles

Nutritional composition of Zizyphus lotus L. seeds

Zizyphus lotus seeds are an unutilized source of vegetable oil and protein and nothing has been reported on their physicochemical characteristics which would indicate the potential uses of these seeds. The percentage composition of the Zizyphus lotus seeds is (on a dry-weight basis): ash 1.05%, oil 32.92%, protein 19.11%, total carbohydrate 40.87% and moisture 6.05%. Calcium, potassium and magnesium constitute the major minerals of Zizyphus lotus seeds. The seed proteins are rich in threonine, glutamic acid, leucine, arginine and aspartic acid (26.73%, 17.28%, 13.11%, 9.47% and 7.76%, respectively). The main fatty acids of the oil are oleic (61.93%), linoleic (18.31%) and palmitic (9.14%) acids. Glycerol trioleate (OOO; O: oleic acid) was the most abundant triacylglycerol, representing 26.48% of the total triacyglycerols. β-Tocopherol was the major tocopherol (130.47 mg 100 g(-1) ). This oil was rich in Δ7-campestrol and β-sitosterol (147.82 and 82.10 mg 100 g(-1) oil), respectively. Zizyphus lotus seeds are rich in fat and protein which are of potential industrial significance. In addition, Zizyphus lotus L. seed oil contained many bioactive compounds. This fact is of great economic interest owing to several applications of Zizyphus lotus L. seeds in the food, cosmetics and medicinal industries.

Structure and remodeling behavior of drug-loaded high density lipoproteins and their atherosclerotic plaque targeting mechanism in foam cell model

This study is one of the first to test the relationship of formulation and structure of reconstituted high density lipoproteins (rHDL), drug behavior involved in remolding process and their targeting mechanism in a foam cell model. Tanshinone IIA-loaded rHDL (TA-rHDL) with different formulations and techniques were prepared and characterized. The targeting mechanism and drug behavior involved in remolding process were undertaken using a foam cell model. TA-rHDL prepared with cholesteryl ester (CE) and glycerol trioleate (TG) were spheres, or else discs. Guanidine hydrochloride denaturation experiments showed increased stability with TA-rHDL, compared to free apos. Phagocytosis tests demonstrated that the spherical TA-rHDL had targeting effect for foam cells through the scavenger receptor-BI and CE-TG interchange with TG-rich lipoproteins pathway under cholesteryl ester transfer protein. Discoidal TA-rHDL could reconstruct to spheres and target via a similar route as TA-rHDL spheres, showing a higher targeting efficiency. Lipophilic Tanshinone IIA could be re-entrapped in rHDL after remolding from discs to spheres and uptaken more by foam cells. Discoidal rHDL may serve as potential nanocarriers for targeting lipophilic cardiovascular drugs to atherosclerosis plaque.

The in-vitro percutaneous absorption of glycerol trioleate through hairless mouse skin.

The chemical composition of the aqueous receptor fluid in one-chambered diffusion cells used for in-vitro percutaneous absorption studies has been shown to significantly affect the apparent extent of absorption of the triglyceride, glycerol trioleate. Using murine skin samples it was found that the addition of albumin to the receptor fluid resulted in an increase in the apparent extent of absorption, while the presence of the bacteriostatic agent thiomersal resulted in a decrease. The viability of the skin samples had no effect on absorption. It was determined that the chemical species in the receptor fluid was the free fatty acid. Albumin presumably bound the fatty acid, thereby creating a sink which enabled the fatty acid to partition from the skin into the receptor fluid.

Properties of Porous Si3N4/BN Composites Fabricated by RBSN Technique

Reaction bonding of silicon nitride (RBSN) technique combined with slip‐casting shaping process was used to fabricate porous Si3N4/BN ceramic composites. Si/BN slurry with chemical stability, good dispersibility, and viscosity was prepared using glycerol trioleate (GTO) covering on Si surface and poly(acrylic acid) (PAA) as dispersant. The hydrolysis of Si was strongly prevented by GTO coating. The dispersibility of covered Si and BN suspensions were improved by PAA dispersant. Twenty volume percent covered Si/BN slurries with low viscosity were successfully casted. The cast bodies were dried at room temperature, debindered at 750°C and nitrided below 1450°C. The nitrided samples mainly consist of α‐Si3N4, β‐Si3N4, and h‐BN. The composites exhibit homogeneous microstructure consisting of faceted particles, α‐Si3N4 nanowires and a large amount of pores. The porosity is 52.64% and the pore size is in the range of 60–300 nm. The composites show compressive strength of 16.6±1.5 MPa. The dielectric constant of the composite is about 3.1 and the dielectric loss is below 0.5% under different frequencies.

Damage of guinea pig heart and arteries by a trioleate-enriched diet and of cultured cardiomyocytes by oleic acid.

BackgroundMono-unsaturated fatty acids (MUFAs) like oleic acid have been shown to cause apoptosis of cultured endothelial cells by activating protein phosphatase type 2C α and β (PP2C). The question arises whether damage of endothelial or other cells could be observed in intact animals fed with a trioleate-enriched diet.Methodology/Principal FindingsDunkin-Hartley guinea pigs were fed with a trioleate-enriched diet for 5 months. Advanced atherosclerotic changes of the aorta and the coronary arteries could not be seen but the arteries appeared in a pre-atherosclerotic stage of vascular remodelling. However, the weight and size of the hearts were lower than in controls and the number of apoptotic myocytes increased in the hearts of trioleate-fed animals. To confirm the idea that oleic acid may have caused this apoptosis by activation of PP2C, cultured cardiomyocytes from guinea pigs and mice were treated with various lipids. It was demonstrable that oleic acid dose-dependently caused apoptosis of cardiomyocytes from both species, yet, similar to previous experiments with cultured neurons and endothelial cells, stearic acid, elaidic acid and oleic acid methylester did not. The apoptotic effect caused by oleic acid was diminished when PP2C α and β were downregulated by siRNA showing that PP2C was causally involved in apoptosis caused by oleic acid.Conclusions/SignificanceThe glycerol trioleate diet given to guinea pigs for 5 months did not cause marked atherosclerosis but clearly damaged the hearts by activating PP2C α and β. The diet used with 24% (wt/wt) glycerol trioleate is not comparable to human diets. The detrimental role of MUFAs for guinea pig heart tissue in vivo is shown for the first time. Whether it is true for humans remains to be shown.

Nanostructured lipid carriers constituted from high-density lipoprotein components for delivery of a lipophilic cardiovascular drug

To investigate the possibility of reconstituted protein-free high-density lipoprotein (HDL) being a carrier for delivering a lipophilic cardiovascular drug, Tanshinone IIA-loaded HDL-like nanostructured lipid carriers (TA-NLC) were prepared by a nanoprecipitation/solvent diffusion method. The physicochemical parameters of TA-NLC were characterized in terms of particle size, zeta potential, morphology, entrapment efficiency, differential scanning calorimetry (DSC) and stability. A novel two-step method has been employed to determine entrapment efficiency of TA-NLC. The binding properties of TA-NLC to apolipoproteins were investigated by in vitro incubation competition assay in the presence of native HDL and electrophoresis test. Phagocytosis and cytotoxicity was evaluated using mouse macrophage cell line RAW 264.7 with TA-NLC and incubated TA-NLC with native HDL (TA-NLC-apo). The results showed that TA-NLC had an average diameter of 8.0 ± 1.2 nm, zeta potential of −29.0 ± 0.0 mV, drug loading of 6.17 ± 0.3% and entrapment efficiency of 97.84 ± 1.2%. TA-NLC were demonstrated spheres with drug incorporated in lipid core forming a shell-core structure. DSC analysis showed that TA was dispersed in NLC in an amorphous state. The incorporation of glycerol trioleate to NLC led to crystal order disturbance. Agarose gel electrophoresis and sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-SPAGE) patterns indicated that TA-NLC could bind to apolipoprotein A-I (apoA-I) specifically in vitro. Phagocytosis studies showed significant differences in uptake between TA-NLC and TA-NLC-apo and demonstrated that TA-NLC incubated with native HDL could turn endogenous by association to apolipoproteins, which cannot trigger immunological responses and could escape from recognition by macrophages.

Highly Unsaturated Fatty Acid might Act as an Antioxidant in Emulsion System Oxidized by Azo Compound

Now it is recognized that DHA is oxidatively stable fatty acid compared with linoleic acid (LA) in emulsified system, although DHA is oxidatively unstable in a bulk system. In fact, an emulsified mixture of DHA and LA behaves as in a bulk system, namely the oxidative stability of DHA becomes lower than that of LA. Therefore, in this study, tridocosahexaenoate (DDD) and glycerol trilinoleate (LLL) were separately emulsified using TritonX-100 as an emulsifier and DDD emulsion was mixed with the oxidizing LLL emulsion using a water-soluble radical initiator, 2,2'-azobis(2-aminopropane) dihydrochloride. As a result, DHA suppressed the oxidation of LA, while DHA was not significantly oxidized. This suppression ability was examined using glycerol trieicosapentaenoate, glycerol trilinolenate, or glycerol trioleate instead of DDD and it was found that this activity was increased with the increasing number of double bonds in the structure. Furthermore, the same type of experiment was carried out using a lipid-soluble radical initiator, 2,2'-azobisisobutyronitrile and the similar result was obtained. These results indicated that a highly polyunsaturated fatty acid might act as an antioxidant in an emulsion system oxidized by an azo compound.

Boy's Death Spurs Action on Neonatal Genetic Screening

Boy's Death Spurs Action on Neonatal Genetic Screening

Oil Base Mud. Part I: Synthesis of Some Local Surfactants Used as Primary Emulsifiers for Oil Base Mud and Evaluation of Their Rheology Properties

Six oil soluble nonionic surfactants with different HLBs have been prepared. Their HLBs situate between 3.9 and 6.7. Transesterification was carried out for glycerol and triethanol amine with oleic acid at different moles to obtain six emusilifiers. They named glycerol momooleate (I), glycerol diooleate (II), glycerol trioleate (III), triethanol amine mono-, di- and tri-oleate (IV), (V,) and (VI). The chemical structure was confirmed using; the elemental analysis, FTIR and 1HNMR. They were evaluated as a primary emulsifiers (PE) for thdrilling fluids (oil base mud) comparing with a currently used primary emulsifier (Fc). The water in oil base mud (w/o emulsions) was prepared. The concentration of emulsifiers and their HLB exhibited interesting rheology properties including shear-thinning behavior, yield value, viscoelastic effects, thixtropy, gel strength, and filtration loss. The rheology properties of such emulsions strongly depended on the average size distribution of the dispersed droplets that could be varied both with the bulk concentration and HLB value of the emulsifiers. The interfacial and surface properties of these emulsifiers suggest that the droplet size of the dispersed phase and bulk concentration are strongly related to the HLB value of emulsifiers. The w/o emulsion (mud formulation) stability is sensitive to the droplet size of the dispersed phase and HLB value of the used emulsifier. The results were discussed on the light the chemical structure of the primary emulsifiers and the emulsion ingredients.

Purification and Biochemical Characterization of an Extracellular Lipase from Pseudomonas fluorescens MTCC 2421

An extracellular lipase produced by Pseudomonas fluorescens MTCC 2421 was purified 184.37-fold with a specific activity of 424.04 LU/mg after anion exchange and gel exclusion chromatography. The enzyme is a homomeric protein with an apparent molecular mass of 65.3 kDa. The lipase exhibited hydrolytic resistance toward triglycerides with longer fatty acyl chain length containing unsaturation as evident from the lower V(max) (0.23 mM/mg/min) of the lipase toward glycerol trioleate (C(18:1n9)) compared with the fatty acid triglycerides having short to medium carbon chain lengths (C(18:0-12:0), V(max) 0.32-0.51 mM/mg/min). This indicates a preferential specificity of the lipase toward cleaving shorter carbon chain length fatty acid triglycerides. The lipase exhibited optimum activity at 40 degrees C and pH 8.0, respectively. A combination of Ca(2+) and sorbitol induced a synergistic effect on the thermostability of lipase with a significantly high residual activity (100%) after 30 min at 40 degrees C, as compared to 90.6% after incubation with Ca(2+) alone. The lipase activity was inhibited by Cu(2+) and Fe(2+) (42 and 48%, respectively) at 10 mM. The enzyme lost 31% of its initial activity by 0.001 mM EDTA and 42% by 0.1 mM EDTA. Significant reduction in lipase activity was apparent by 2-mercaptoethanol and phenylmethanesulfonyl fluoride at diluted concentration (0.001 mM), thereby indicating an important role of sulfhydryl groups in the catalytic mechanism.

Coingestion of Acylglycerols Differentially Affects Glucose-Induced Insulin Secretion via Glucose-Dependent Insulinotropic Polypeptide in C57BL/6J Mice

The precise role of fat in postprandial glycemia and insulinemia has not been thoroughly researched because postprandial blood glucose and concurrent insulin secretion are largely assumed to be proportional to carbohydrate intake. Recent studies have suggested that dietary fat differentially regulates the postprandial insulin response. To explore this, we examined the effects of coadministered fat on glucose-induced glycemia and insulinemia in C57BL/6J mice. The insulin response to glucose was augmented by the addition of glycerol trioleate (TO) in a dose-dependent manner, which was associated with enhanced glucose transport from the circulation to muscle and adipose tissues. To investigate the mechanism underlying fat-induced hyperinsulinemia, we examined the release of the incretin hormones glucose-dependent insulinotropic polypeptide (GIP) and glucagon-like peptide-1. TO increased GIP secretion, whereas glucagon-like peptide-1 secretion was unaffected. TO-induced hyperinsulinemia was significantly attenuated by the pretreatment of mice with a specific GIP antagonist. Diacylglycerol (DAG) promoted lower postprandial GIP and triglyceride responses and, when ingested with glucose, a lower insulin response compared with triacylglycerol of a similar fatty acid composition. Pluronic L-81, an inhibitor of chylomicron formation, reduced not only the triglyceride response but also TO-induced GIP secretion, indicating that the lower GIP response after DAG ingestion may be associated with retarded chylomicron formation in the small intestine. We conclude that dietary fat augments glucose-induced insulinemia via gut-derived GIP and, thereby, influences postprandial nutrient metabolism in mice. DAG promotes a lower GIP and thereby reduced insulin responses compared with triacylglycerol, which may differentially influence postprandial energy homeostasis.

Effect of water on methanolysis of glycerol trioleate catalyzed by immobilized lipase Candida sp. 99–125 in organic solvent system

In this study, hydrolysis and methanolysis of glycerol trioleate (TG) by lipase Candida sp. 99–125 were investigated under different water conditions. Both the reaction rates were relatively low without water, while increasing water content to 5 wt.% (or more, from 10–20%) based on the TG amount caused remarkable higher TG conversion for both reactions. Moreover, comparing the time course curves of the hydrolysis and methanolysis, it could be concluded that the methanolysis reaction catalyzed by this Candida sp. 99–125 appeared to accord with the successive reaction mechanism. TG was first hydrolyzed to partial glycerides and oleic acid (OA), then oleic acid methyl ester (OAME) was produced by esterification of the OA with methanol. This water effect was also confirmed by the experiments that water substitutions such as t-butanol and some surfactants added into the system did not get such high yields as that of the water included system. So these results showed that water took part in the methanolysis reaction, and successive hydrolysis–esterification process might be the catalytic mechanism of this lipase.

Biocompatible Water-in-Oil Emulsion as a Model to Study Ascorbic Acid Effect on Lipid Oxidation

A biocompatible water-in-oil (W/O) emulsion has been used as a model to study the effect of ascorbic acid (AA) on the oxidation of the oil (glycerol trioleate, GTO) continuous phase. The model system consisted of 3 wt % water dispersed in GTO containing 0.5 wt % sodium oleate (NaO)/oleic acid (OA) mixture (NaO/OA = 20/80 mol/mol %) as a stabilizer. To study the ascorbic acid effect on GTO light-promoted oxidation, we added aqueous solutions of ascorbic acid to GTO in place of distilled water. Results obtained as peroxide values show that ascorbic acid activity depends on its concentration and it is affected by the characteristics of the W/O interface. In the presence of ascorbyl palmitate (AP) or sorbitan trioleate (Span 85) in the continuous phase, ascorbic acid activity increases in the first few hours of oxidation. The effect of ascorbic acid has been related to emulsion structure by calculating characteristic parameters of the droplet size distributions by means of optical microscopy.

Immobilized lipase Candida sp. 99-125 catalyzed methanolysis of glycerol trioleate: Solvent effect

The immobilized lipase Candida sp. 99-125 catalyzed methanolysis of glycerol trioleate was studied in twelve different solvents in order to deduce the solvent effect through an attempt to correlate the highest yield with such solvent properties as hydrophobicity (log P), dielectric constant ( ε), and Hildebrand solubility parameter ( δ). The results showed that the conversion of glycerol trioleate and yield of oleic acid methyl ester were quite dependent on the solvent. The catalyst lipase in various solvents also needed different optimum amount of water to keep its maximum activity, and generally this lipase in more hydrophobic solvents required more water. The correlation between the highest yield and log P value was found to be reasonable except deviation of data points of certain solvents, while no obvious correlation existed between the other two parameters, dielectric constant ( ε) and Hildebrand solubility parameter ( δ), and the enzyme activity. The study revealed that more hydrophobic solvents such as n-hexane or cyclohexane were more suitable solvents for Candida sp. 99-125 catalyzed transesterification of glycerol trioleate to oleic acid methyl ester.

Uptake and metabolism of plasma-derived erucic acid by rat brain

We examined the ability of erucic acid (22:1n-9) to cross the blood-brain barrier (BBB) by infusing [14-14C]22:1n-9 (170 microCi/kg, iv and icv) into awake, male rats. [1-14C]arachidonic acid (20:4n-6) [intravenous (i.v.)] was the positive control. After i.v. infusion, 0.011% of the plasma [14-14C]22:1n-9 was extracted by the brain, compared with 0.055% of the plasma [1-14C]20:4n-6. The [14-14C]22:1n-9 was extensively beta-oxidized (60%), compared with 30% for [1-14C]20:4n-6. Although 20:4n-6 was targeted primarily to phospholipid pools, 22:1n-9 was targeted to cholesteryl esters, triglycerides, and phospholipids. When [14-14C]22:1n-9 was infused directly into the fourth ventricle of the brain [intracerebroventricular (i.c.v.)] for 7 days, 60% of the tracer entered the phospholipid pools, similar to the distribution observed for [1-14C]20:4n-6. This demonstrates plasticity in the ability of the brain to esterify 22:1n-9 in an exposure-dependent manner. In i.v. and i.c.v. infused rats, a significant amount of tracer found in the phospholipid pools underwent sequential rounds of chain shortening and was found as [12-14C]20:1n-9 and [10-14C]oleic acid. These results demonstrate for the first time that intact 22:1n-9 crosses the BBB, is incorporated into specific lipid pools, and is chain-shortened.

Kinetic study on the prooxidative effect of vitamin C on the autoxidation of glycerol trioleate in micelles

AbstractVitamin C (L‐ascorbic acid) protects human health by scavenging toxic free radicals and other reactive oxygen species formed in cell metabolism. The surplus supplementation of vitamin C, however, may be harmful to health because the level of 8‐oxoguanine and 8‐oxoadenine in lymphocyte DNA varies remarkably. In the process of the kinetic investigation on the 2,2′‐azobis(2‐amidinopropane dihydrochloride) (AAPH)‐induced autoxidation of glycerol trioleate (GtH) in the micelles of cetyl trimethyl ammonium bromide (CTAB), sodium dodecyl sulfate (SDS) and Triton X‐100, the addition of vitamin C accelerates the autoxidation of GtH even in the absence of the free radical initiator, AAPH. The initiating rate, Ri, of vitamin C (VC)‐induced autoxidation of GtH is related to the micelle charge, i.e. Ri = 14.4 × 10−6 [VC] s−1 in SDS (anionic micelle), Ri = 1961 × 10−6 [VC] s−1 in Triton X‐100 (neutral micelle) and Ri is a maximum in CTAB (cationic micelle) when the vitamin C concentration is ∼300 µM. Thus, vitamin C can initiate autoxidation of GtH in micelles, especially in the neutral one. Moreover, the attempt to explore whether α‐tocopherol (TocH) could rectify vitamin C‐induced autoxidation of GtH leads us to find that the rate constant of TocH reacting with the anionic radical of vitamin C (VC.−), k−inh, is ∼103M−1 s−1, which is less than that of the α‐tocopherol radical (Toc.) with vitamin C (kinh = ∼105 M−1 s−1). Thus, the equilibrium constant of the reaction Toc.+VC−⇌TocH+VC.− is prone strongly to the regeneration of Toc. by vitamin C rather than the reverse reaction. Copyright © 2006 John Wiley & Sons, Ltd.

Biocompatible Lipidic Formulations: Phase Behavior and Microstructure

Biocompatible systems formulated for use in the food, cosmetic, and pharmaceutical fields are characterized. Ternary phase diagrams of mixtures of natural lipids (glycerol trioleate, glycerol monooleate, diglycerol monooleate, and lecithin) and water were investigated by means of optical microscopy in polarized light and by multinuclear NMR spectroscopy. All systems showed a microemulsion region at high oil content and a large area of coexistence of two liquid crystalline (hexagonal and lamellar) phases. 1H and 13C NMR self-diffusion measurements were used to characterize microstructural features of the microemulsions. On water dilution, the two-phase liquid crystalline region transforms into a creamy emulsion area where the droplets of water are stabilized by both the lamellar and the hexagonal phases, as indicated by 2H NMR measurements. Due to the very effective dispersing action of the two liquid crystalline phases, these emulsions show a high stability toward phase separation.

Studies on a novel carbon source and cosolvent for lipase production by Candida rugosa.

Oleic acid esters were shown to be the best carbon source for both cell growth and lipase production by Candida rugosa. Use of a cosolvent, dodecane, in fermentations improved the solubility of solid substrates and increased oxygen solubility. This resulted in the highest lipase activity in batch fermentation with glycerol trioleate and dodecane. Lipase activity reached 77.1 units ml(-1).

Anaerobic digestion of manure and mixture of manure with lipids: biogas reactor performance and microbial community analysis

Anaerobic digestion of cattle manure and a mixture of cattle manure with glycerol trioleate (GTO) was studied in lab-scale, continuously stirred tank reactors (CSTR) operated at 37 degrees C. The reactor codigesting manure and lipids exhibited a significantly higher specific methane yield and a higher removal of VS than the reactor treating manure. Microbial population analysis done by cultivation--most probable number (MPN) test and specific methanogenic activity (SMA) measurement, revealed higher MPN and increased SMA of methanogenic populations of biomass from the reactor codigesting manure and lipids. Spatial microbial distribution and activity was studied in digested materials fractionated into size of particles > 200 microm, 50-200 microm and 0.45-50 microm. With manure, the main pool of methanogenic activity from propionate, butyrate and hydrogen was associated with the particles > 200 microm, while the activity of acetotrophic methanogens was uniformly distributed in all fractions. When digesting manure and lipids, an enhanced methanogenesis was detected both for particles > 200 microm and the 50-200 microm fraction. The molecular methods--temperature gradient gel electrophoresis (TGGE), cloning library and sequencing of 16S rDNA--showed presence of a restricted number of archaeal species in both reactors. The vast majority of clones was phylogenetically most closely related to Methanosarcina siciliae.

Optimization of non-aqueous nickel slips for manufacture of MCFC electrodes by tape casting method

Tape casting is a powerful method for the manufacture of carbonyl nickel green tape, which is sintered at a given condition and then used as the electrode for molten carbonate fuel cells. In this work, the rheological behaviors of non-aqueous carbonyl nickel slips for tape casting was investigated considering different solvent and binder systems, by controlling the total binder and plasticizer content and the binder to plasticizer ratio. Glycerol trioleate was used as the dispersant and its content in the slip was also optimized. The characteristics of the green tapes obtained in different conditions were studied in terms of densities, tensile strength and microstructure, and related with the rheological properties of the slips.