Trilinolein

Synthesis of highly active ETS-10-based titanosilicate for heterogeneously catalyzed transesterification of triglycerides.[Pubmed:31728253]

Beilstein J Nanotechnol. 2019 Oct 28;10:2039-2061.

In this contribution, the preparation of hierarchically structured ETS-10-based catalysts exhibiting notably higher activity in the conversion of triolein with methanol compared to microporous titanosilicate is presented. Triolein, together with its unsaturated analog Trilinolein, represent the most prevalent triglycerides in oils. The introduction of mesopores by post-synthetic treatment with hydrogen peroxide and a subsequent calcination step results in the generation of an additional active surface with Bronsted basic sites becoming accessible for triolein and enhancing the rate of transesterification. The resulting catalyst exhibits a comparable triolein conversion ( approximately 73%) after 4 h of reaction to CaO ( approximately 76%), which is reportedly known to be highly active in the transesterification of triglycerides. In addition, while CaO showed a maximum conversion of 83% after 24 h, the ETS-10-based catalyst reached 100% after 8 h, revealing its higher stability compared to CaO. The following characteristics of the catalysts were experimentally addressed - crystal structure (X-ray diffraction, transmission electron microscopy), crystal shape and size (scanning electron microscopy, laser diffraction), textural properties (N2 sorption, Hg porosimetry), presence of hydroxyl groups and active sites (temperature-programmed desorption of NH3 and CO2, (29)Si magic angle spinning nuclear magnetic resonance (NMR)), mesopore accessibility and diffusion coefficient of adsorbed triolein (pulsed field gradient NMR), pore interconnectivity (variable temperature and exchange spectroscopy experiments using hyperpolarized (129)Xe NMR) and oxidation state of Ti atoms (electron paramagnetic resonance). The obtained results enabled the detailed understanding of the impact of the post-synthetic treatment applied to the ETS-10 titanosilicate with respect to the catalytic activity in the heterogeneously catalyzed transesterification of triglycerides.

Oleochemical Properties for Different Fractions of Foxtail Millet Bran.[Pubmed:31292341]

J Oleo Sci. 2019 Aug 1;68(8):709-718.

Foxtail millet (FM) is one of the oldest cultivated grain crops with a variety of nutritions, and foxtail millet bran (FMB), a by-product of FM milling process, is also rich in variety of nutrient substance. There are four classifications of FMB, namely coarse bran (FMCB), skin bran (FMSB), polished bran (FMPB) and mixed bran (FMMB). Because these nutrients are distributed within the different fractions of FMB, we compared some chemical composition and its oleochemical properties of four FMB samples. Results showed that the oil extracted from FMB is high value-added plant oil. It contains abundant unsaturated fatty acid (UFA), with the main UFAs were linoleic acid (65%~69%) and oleic acid (12~17%), which accounted for more than 80% of the lipids. The main triacylglycerols were Trilinolein (LLL) and oleodilinolein (OLL). There were no evident difference on fatty acid, triacylglycerol and sterols profiles for FMSB, FMPB and FMMB, but the contents of amino acids, tocols, squalene and oryzanol were different.

Studies on the bioactive flavonoids isolated from Azadirachta indica.[Pubmed:30835540]

Nat Prod Res. 2019 Mar 5:1-9.

Two novel natural metabolites, 3-O-butyl-(-)-epicatechin (1) and 3-O-butyl-(-)-epigallocatechin (2), as well as several known substances, (-)-epicatechin (3), (+)-gallocatechin (4), (-)-epigallocatechin (5), azadirachtin A (6), Trilinolein (7) and octadecanoic acid-tetrahydrofuran-3,4-diyl ester (8), were isolated from the bark of Azadirachta indica. The structures of all compounds were established by comprehensive and comparative spectroscopic analysis of NMR and ESI-HRMS data. The new metabolites 1 and 2 represent one of the few examples of natural compounds with a butyl ether group moiety. The acaricidal activity of the compounds was tested using a standard Shaw larval immersion assay. All the compounds, except 7, possess a LD50 value less than or equal to 7.2 mM.

Preparation of High-Purity Trilinolein and Triolein by Enzymatic Esterification Reaction Combined with Column Chromatography.[Pubmed:30651418]

J Oleo Sci. 2019 Feb 1;68(2):159-165.

High-purity Trilinolein and triolein were prepared by Novozym 435-catalyzed esterification reaction combined with column chromatography purification in this study. Firstly, linoleic acid and oleic acid were respectively extracted from safflower seed oil and camellia seed oil by urea adduct method. Secondly, Trilinolein and triolein were synthesized through Novozym 435 catalyzed esterification of glycerol and fatty acids. The best synthesis conditions were obtained as follows: reaction temperature 100 degrees C, residual pressure 0.9 kPa, enzyme dosage 6%, molar ratio of glycerol to linoleic acid 1:3 and reaction time 8 h. Crude Trilinolein and triolein were further purified by silica gel column chromatography. Finally, highpurity Trilinolein (95.43+/-0.97%) and triolein (93.07+/-1.05%) were obtained.

Quantitative determination of major oxidation products in edible oils by direct NP-HPLC-DAD analysis.[Pubmed:29559268]

J Chromatogr A. 2018 Apr 27;1547:62-70.

The objective of the present study was to explore the possibilities of the direct analysis of vegetable oils by normal-phase HPLC-DAD to evaluate the amounts of the main oxidation products of triacylglycerols containing linoleate, i.e. hydroperoxy-, keto- and hydroxy-dienes. A follow-up of oxidation at 40 degrees C of Trilinolein, used as a simplified model lipid system, high-linoleic sunflower oil and high-oleic sunflower oil was performed to evaluate samples with different fatty acid compositions and different oxidation levels. The results showed that the HPLC-DAD method proposed allows for determining the concentrations of mono-hydroperoxydienes in edible oils without applying any isolation or derivatization step. The method was found to be direct, sensitive (LOQ 0.06mmol/kg oil), precise (CV

Fermentation-Guided Natural Products Isolation of a Grape Berry Triacylglyceride that Enhances Ethyl Ester Production.[Pubmed:29329227]

Molecules. 2018 Jan 12;23(1). pii: molecules23010152.

A full understanding of the origin, formation and degradation of volatile compounds that contribute to wine aroma is required before wine style can be effectively managed. Fractionation of grapes represents a convenient and robust method to simplify the grape matrix to enhance our understanding of the grape contribution to volatile compound production during yeast fermentation. In this study, acetone extracts of both Riesling and Cabernet Sauvignon grape berries were fractionated and model wines produced by spiking aliquots of these grape fractions into model grape juice must and fermented. Non-targeted SPME-GCMS analyses of the wines showed that several medium chain fatty acid ethyl esters were more abundant in wines made by fermenting model musts spiked with certain fractions. Further fractionation of the non-polar fractions and fermentation of model must after addition of these fractions led to the identification of a mixture of polyunsaturated triacylglycerides that, when added to fermenting model must, increase the concentration of medium chain fatty acid ethyl esters in wines. Dosage-response fermentation studies with commercially-available Trilinolein revealed that the concentration of medium chain fatty acid ethyl esters can be increased by the addition of this triacylglyceride to model musts. This work suggests that grape triacylglycerides can enhance the production of fermentation-derived ethyl esters and show that this fractionation method is effective in segregating precursors or factors involved in altering the concentration of fermentation volatiles.

Changes in Acylglycerols Composition, Quality Characteristics and In vivo Effects of Dietary Pumpkin Seed Oil upon Thermal Oxidation.[Pubmed:28798910]

Front Chem. 2017 Jul 26;5:55.

This study was aimed to determine the acylglycerols composition, quality characteristics, and protective role of dietary pumpkin seed oil (PSO) in rabbits. PSO was thermally oxidized and analyzed for quality characteristics and acylglycerols composition using reversed phase high performance liquid chromatography with diode array detection (HPLC-DAD). Oxidized and un-oxidized oil samples were fed to the rabbits in different doses for 2 weeks. The changes in the serum biochemistry, hematology, and liver histology were studied. The levels of quality parameters such peroxide value (PV), anisidine value (AV), total phenolic contents (TPC), thiobarbituric acid reactive substances (TBARS), conjugated dienes (CD) and conjugated trienes (CT) significantly increased with thermal treatment. HPLC analyses revealed 10 individual triacylglycerols (TAGs), total di-acylglycerols (DAGs), mono-acylglycerols (MAGs), and total oxidized TAGs. Trilinolein (LLL), 1-oleoyl-2,3-dilinolinoyl glycerol (OLL), triolein (OOO) and 1,2-distearoyl-3-palmitoyl glycerol (SSP) were present in higher amounts and decreased with thermal treatment. Animal's studies showed that oxidized oils decreased the whole body weight, which was ameliorated by the co-administration of un-oxidized oils. The levels of serum biochemical parameters were improved by co-administration of pumpkin seed oils. There were no significant effects of both oxidized and un-oxidized PSO on the hematological and histological parameters of rabbits. In conclusion, nutritionally important triacylglycerols were present in PSO with protective role against the toxicity of its corresponding oxidized oils.

Chemical composition of Lycium europaeum fruit oil obtained by supercritical CO2 extraction and evaluation of its antioxidant activity, cytotoxicity and cell absorption.[Pubmed:28407975]

Food Chem. 2017 Sep 1;230:82-90.

We studied the total phenols and flavonoids, liposoluble antioxidants, fatty acid and triacylglycerol profiles, and oxidative status of oil obtained from Lycium europaeum fruits following supercritical CO2 extraction (at 30MPa and 40 degrees C). Linoleic (52%), palmitic (18%), oleic (13%), and alpha-linolenic (6%) were the main oil fatty acids, while Trilinolein and palmitodilinolein/oleodilinolein represented the main triacylglycerols. The oil was characterized by high levels of all-trans-zeaxanthin and all-trans-beta-carotene (755 and 332mug/g of oil, respectively), alpha-tocopherol (308mug/g of oil), total phenols (13.6mg gallic acid equivalents/g of oil), and total flavonoids (6.8mg quercetin equivalents/g of oil). The oil showed radical scavenging activities (ABTS and DPPH assays) and inhibited Caco-2 cell growth. Moreover, the incubation of differentiated Caco-2 cells with a non-toxic oil concentration (100mug/mL) induced a significant intracellular accumulation of essential fatty acids. The results qualify L. europaeum oil as a potential source for food/pharmaceutical applications.

Effects of Different Simple Triglycerides on Cell Fatty Acid Compositions, Proliferation-Related Protein, and Gene Expressions Induced by Oxidized-LDL in HUVSMCs.[Pubmed:28135401]

J Food Sci. 2017 Feb;82(2):529-535.

The proliferating effects of 3 different simple triglycerides (tristearin, triolein, and Trilinolein) on the human umbilical vein smooth muscle cells (HUVSMCs) induced by oxidized-LDL (ox-LDL) were investigated in this study. The protein and mRNA gene expressions of proliferating cell nuclear antigen (PCNA), smooth muscle-alpha-actin (SM-alpha-actin), and monocyte chemoattractant protein-1 (MCP-1) in HUVSMCs were measured by Western blotting and real-time quantitative polymerase chain reaction (PCR). It was shown that in tristearin (SSS) treated HUVSMCs, the saturated fatty acid content was increased, and the compositions of polyunsaturated fatty acid (PUFA) and monounsaturated fatty acid were decreased significantly. On the other hand, triolein (OOO) and Trilinolein (LLL) significantly increased the levels of some typical PUFA such as arachidonic acid, eicosapentaenoic acid, and docosahexaenoic acid. Moreover, LLL and OOO could upregulate the protein and mRNA expressions of PCNA, MCP-1 as well as downregulate the expression of SM-alpha-actin. The results also showed that, SSS had significant promotion effects on the proliferation of HUVSMCs induced by ox-LDL. Although both LLL and OOO could inhibit the proliferation of HUVSMCs induced by ox-LDL, and might have certain inhibition of the atherosclerotic process.

Non-invasive Quantitative Analysis of Specific Fat Accumulation in Subcutaneous Adipose Tissues using Raman Spectroscopy.[Pubmed:27845402]

Sci Rep. 2016 Nov 15;6:37068.

Subcutaneous adipose tissue (SAT), visceral adipose tissue (VAT), and fat beneath the dermis layer were investigated using a ball lens top hollow optical fiber Raman probe (BHRP). Hamsters were fed with Trilinolein (TL) and tricaprin (TC) for six weeks and measurements were carried out every two weeks. The BHRP with an 800 mum diameter fused-silica ball lens was able to obtain information on the subcutaneous fat in a totally non-invasive manner. Changes in the concentration of TL and TC during the treatment were analyzed, and the relationship between fat accumulation and dietary fat was studied. It was found that SAT had, in general, a higher degree of unsaturation than VAT. The accumulation rate of TC found in SAT and VAT was 0.52 +/- 0.38 and 0.58 +/- 0.4%, respectively, while the TL accumulation rate was 4.45 +/- 1.6 and 4.37 +/- 2.4%, respectively. The results suggest different metabolic pathways for TC, a typical medium-chain fatty acid, and TL, a long-chain unsaturated fatty acid. Raman subsurface spectra were successfully obtained and used to analyze the subcutaneous fat layer. The accumulation rates of TL and TC found in skin fat were 5.01 +/- 3.53% and 0.45 +/- 0.36%, respectively. The results demonstrate the high feasibility of Raman spectroscopy for non-invasive analysis of adipose tissue.

Reaction pathway mechanism of thermally induced isomerization of 9,12-linoleic acid triacylglycerol.[Pubmed:27507439]

J Sci Food Agric. 2017 Apr;97(6):1861-1867.

BACKGROUND: To clarify the formation mechanism of trans linoleic acid isomers in edible oils during the heating process, Trilinolein and trilinoelaidin, as representative oils, were placed in glass ampoules and sealed before heating at 180, 240 and 320 degrees C. The glass ampoules were removed at regular time intervals, and the contents were analyzed by infrared spectroscopy. The samples were then subjected to derivatization into their methyl esters for gas chromatographic analysis. RESULTS: Analysis results show that 9c,12c and 9t,12t fatty acids from Trilinolein and trilinoelaidin molecules undergo chemical bond rotation, migration and degradation, leading to the formation of non-conjugated linoleic acids (NLAs), conjugated linoleic acids (CLAs) and aldehydes. The formation rate of isomers from the 9c,12c fatty acid is higher than that of the 9t,12t fatty acid. The production of aldehydes increases with heating temperature and time. The isomerization pathways involved in the formation of NLAs and CLAs during heating are clearly presented. CONCLUSION: These findings suggest possible pathways of NFA and CFA formation from heated Trilinolein and trilinoelaidin, complement the mechanistic studies previously published in the literature, and provide a theoretical basis for future control of the quality and safety of fats and oils. (c) 2016 Society of Chemical Industry.

Microscopic study of the morphology and metabolic activity of Fusarium oxysporum f. sp. gladioli treated with Jatropha curcas oil and derivatives.[Pubmed:30023207]

J Microsc Ultrastruct. 2016 Jan-Mar;4(1):28-35.

The fungus Fusarium oxysporum f. sp. gladioli is one of the main pathogenic microorganisms of the ornamental genus Gladiolus. The attack of this microorganism includes corms and different plant phenological stages. In this study, different microscopic techniques and fluorochromes were used to evaluate the effect of J. curcas oil and acylglycerides, namely Trilinolein, triolein, monomyristin and dimyristin, on the morphology, membrane integrity (%), viability (%) and germination (%) of F. oxsporum f sp. gladioli. Phase-contrast optical photomicrographs and scanning microscopy showed that J. curcas oil and the triglycerides triolein and Trilinolein caused the formation of numerous vacuoles, alterations in the morphology of the outer covering of the mycelium and conidia, and inhibition of membrane activity in the fungus during 24 h of incubation. The fluorochromes used detected no permanent damage to the viability of the conidia. The high germination percentage of the conidia of Fusarium oxysporum f. sp. gladioli indicates that the damage caused by the application of the treatments was fungistatic rather than fungicidal and did not cause cell death.

Shemamruthaa, a Herbal Formulation Induces Apoptosis in Breast Cancer Cells and Inhibits Tumor Progression in Rats.[Pubmed:26416955]

J Evid Based Complementary Altern Med. 2016 Oct;21(4):NP1-NP10.

Phytochemicals present in plants are more effective than their individual constituents in preventing cancer through synergetic effects. From this perspective, Shemamruthaa, a herbal formulation was evaluated with a view to potentiate more intense anticancer property. This study investigates the anticancer activity of Shemamruthaa in breast cancer (MDA-MB 231) cell lines and its cancer therapeutic potential in 7,12-dimethylbenz[a]anthracene induced breast cancer rats. Results of MTT, trypan blue, and apoptotic marker assays suggested that Shemamruthaa can induce cytotoxicity in cancer cells, in a concentration- and time-dependent manner. Oral administration of Shemamruthaa effectively suppressed the tumor progression as evidenced by decrease in tumor volume and modulation of oxidant-antioxidant status and resulted in extended life span. Gas chromatography-mass spectrometry and high-performance liquid chromatography analysis of Shemamruthaa revealed the presence of pyrogallol, 5-hydrxoymethylfurfural, Trilinolein, and flavonoids. Finally, we show that Shemamruthaa contains potential anticancer agents acting either singly or in combination against breast cancer cell proliferation.