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An increase in energy consumption and the extended use of nonrenewable fossil fuels raises the need to develop alternative fuels as an energy supply that can protect the environment from unwanted emissions of pollutants. One alternative renewable fuel is biodiesel. Currently, most biodiesel feed sources are edible oils, but using them leads to the dilution of global food sources. The present study aims to find an effective method of biodiesel production using food industry fatty wastes called brown grease (BG). BG contains fats, mainly linoleic and oleic free fatty acids (FFAs), that can serve as raw materials for biodiesel production using esterification reactions. The esterification and transesterification reactions for biodiesel production were studied using commercial FFAs, commercial glyceryl trilinoleate (trilinolein), soybean oil, and BG. The reactions were carried out under ultrasonic activation using BF3 and AlCl3 Lewis acids as catalysts in both free and immobilized forms when immobilization was performed in silica matrices using the sol-gel synthesis route. Biodiesel production was examined in batch and continuous flow reactors. The BF3 catalyst was more efficient at the initial stages of the continuous operation, reaching a maximum conversion of 90%, with a gradual decrease in efficiency after 15 h of the process. The AlCl3 catalyst showed better stability, reaching maximum yields of 97% and maintaining efficiency until the end of the experiment. The proposed method offers an efficient and easy way to produce biodiesel from a variety of lipids sources, including fatty wastes (BG). [ABSTRACT FROM AUTHOR]

Cerebrovascular disease is one of the leading causes of disability and death worldwide, and seeking a potential treatment is essential. Trilinolein (TriL) is a natural triacylglycerol presented in several plants. The effects of TriL on cerebrovascular diseases such as cerebral ischemia and carotid stenosis have never been studied. Accordingly, we investigated the protection of TriL on cerebral ischemia/reperfusion (I/R) and vascular smooth muscle cell (VSMC) migration in vivo and in vitro. The cerebral infarction area, the intima to media area (I/M ratio), and proliferating cell nuclear antigen (PCNA)-staining of the carotid artery were measured. Platelet-derived growth factor (PDGF)-BB-stimulated A7r5 cell migration and potential mechanisms of TriL were investigated by wound healing, transwell, and Western blotting. TriL (50, 100, and 200 mg/kg, p.o.) reduced: the cerebral infarction area; neurological deficit; TUNEL-positive apoptosis; intimal hyperplasia; and PCNA-positive cells in rodents. TriL (5, 10, and 20 µM) significantly inhibited PDGF-BB-stimulated A7r5 cell migration and reduced matrix metalloproteinase-2 (MMP-2), Ras, MEK, and p-ERK protein levels in PDGF-BB-stimulated A7r5 cells. TriL is protective in models of I/R-induced brain injury, carotid artery ligation-induced intimal hyperplasia, and VSMC migration both in vivo and in vitro. TriL could be potentially efficacious in preventing cerebral ischemia and cerebrovascular diseases. [ABSTRACT FROM AUTHOR]

• The 12 main compounds of Cannabis fructus were identified using HPLC-ESI-MS/MS. Trilinolein was extracted and shown to have anti-inflammatory and antioxidant effects both in vitro and in vivo. • Trilinolein prevents dinitrochlorobenzene (DNCB)-induced atopic dermatitis (AD)-like lesions and restores the skin barrier in BALB/c mice. • Trilinolein attenuates IL-4- and TNF-α-induced mitochondrial DNA (mtDNA) release and ROS production in HaCaT cells via the AhR-Nrf2 pathway. Atopic dermatitis (AD) is a common skin condition that causes chronic and recurring eczema lesions. Prior research has indicated that Cannabis fructus , the mature fruit of Cannabis sativa, has an antioxidant effect. Historically, Cannabis fructus has been used in cosmetics and medicine. However, there is limited knowledge regarding its biological components and the mechanisms by which it prevents and treats AD. HPLC-ESI-MS/MS analysis was utilized to identify the main compounds of Cannabis fructus , and trilinolein was extracted using chromatographic techniques. The potential of trilinolein in the prevention of AD was assessed, and its underlying mechanisms of action were elucidated. The distribution of distinct cellular subpopulations and the principal biological processes implicated in the pathogenesis of AD were assessed through a comparative study involving chronic AD patients and healthy controls (HCs). Differential gene expression was validated in clinical samples from the lesions of AD patients and the healthy skin of controls. The pharmacodynamic activity of trilinolein was validated in dinitrochlorobenzene (DNCB)-induced BALB/c mice and in IL-4- and TNF-α-induced HaCaT cells. Proteomics analyse was employed to investigate its mechanisms. Single-cell transcriptome analysis revealed that chronic AD is characterized by abnormal keratinocyte differentiation and oxidative stress damage. When topically applied, trilinolein can effectively improve AD-like skin lesions induced by DNCB. It increases the expression of terminal differentiation proteins and decreases the expression of NADPH oxidase 2 (NOX2), with a therapeutic effect comparable to that of the positive control drug crisaborole. Additionally, trilinolein reduced ROS fluorescence intensity, restored mitochondrial morphology and membrane potential, and decreased mitochondrial DNA (mtDNA) release in keratinocytes stimulated with IL-4 and TNF-α. Moreover, trilinolein increased the protein expression of AhR, CYP1A1, and Nrf2 in a dose-dependent manner. The effect of trilinolein on keratinocyte terminal differentiation proteins and ROS levels was blocked by the addition of an AhR inhibitor. The study suggests that trilinolein from Cannabis fructus alleviates NOX2-dependent mitochondrial dysfunction and repair the skin barrier via AhR-Nrf2 pathway, making it a promising agent for the prevention and treatment of AD. [Display omitted] [ABSTRACT FROM AUTHOR]

Trilinolein (TL) is an active substance contained in traditional Chinese herbs; modern studies have shown that trilinolein has anti-inflammatory and antioxidant effects on the body. This study delves into the photoprotective effect of trilinolein on UVB-irradiated Human Skin Fibroblast (HSF) cells and the underlying mechanisms. Our findings reveal that trilinolein had a photoprotective effect on HSF cells: trilinolein enhanced cellular autophagy, restored UVB-inhibited cell proliferative viability, and curbing UVB-induced reactive oxygen species (ROS) and apoptosis. Intriguingly, after inhibition of TL-induced autophagy via wortmannin, diminished trilinolein's photoprotective effects. Meanwhile, trilinolein was shown to modulate the AMPK-mTOR signaling pathway, thus enhance cellular autophagy in HSF cells, and this tendency was suppressed after the administration of compound C (AMPK inhibitor). In a mouse model of skin photodamage, trilinolein significantly mitigated photodamage extent through morphological and histopathological analyses. This study illuminates trilinolein could inhibit the photodamaging effects of UVB irradiation by regulating cellular autophagy through the AMPK-mTOR signaling pathway, suggesting its promising application in combating UV-induced skin disorders. [Display omitted] • After inhibiting cellular autophagy, trilinolein photoprotection disappeared. • Inhibition of AMPK-mTOR signaling pathway, trilinolein pro-autophagy effect disappeared. • In the mouse model of photodamage, the application of trilinolein has good effect. [ABSTRACT FROM AUTHOR]

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℃, 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. [ABSTRACT FROM AUTHOR]

Normal-phase high-performance liquid chromatography (HPLC) is widely used in combination with evaporative light scattering detection (ELSD) for separating and detecting lipids in various food samples. ELSD responses of different lipids were evaluated to elucidate the possibilities and challenges associated with quantification by means of HPLC-ELSD. Not only the number and type of polar functional groups but also the chain length and degree of unsaturation of (free or esterified) fatty acids (FAs) had a significant effect on ELSD responses. Tripalmitin and trilinolein yielded notably different ELSD responses, even if their constituting free FAs produced identical responses. How FA structure impacts ELSD responses of free FAs is thus not predictive for those of triacylglycerols and presumably other lipids containing esterified FAs. Because ELSD responses of lipids depend on the identity of the (esterified) FA(s) which they contain, fully accurate lipid quantification with HPLC-ELSD is challenging and time-consuming. Nonetheless, HPLC-ELSD is a good and fast technique to semi-quantitatively compare the levels of different lipid classes between samples of comparable FA composition. In this way, lipid profiles of different flours from near-isogenic wheat lines could be compared.

In the present study, a novel ultra high-pressure liquid chromatography method using charged aerosol detector (UHPLC-CAD) with an inverse-gradient solvent compensation has been developed for the analysis of triacylglycerols (TAGs) in extra-virgin olive oil. Using a gradient method with a superficially porous particles column, an improved separation of TAGs was obtained, with notably shortening of both solvent consumption and analysis time, in comparison with the IOC official method for ECN 42 analysis. Furthermore, an almost baseline separation of trilinolein was obtained. CAD provides good linearity (R 2  > 0.999) in the range of 0.05–10 μg of trilinolein injected on column as well as uniformity of response factor for different TAG molecular species. Finally, the proposed UHPLC-CAD methodology has been successfully applied to the determination of trilinolein in low-linoleic acid extra-virgin olive oil mixed in different proportions with high-oleic sunflower oil, palm olein and a mix of them at different percentages of 2, 4, 6, 8 and 10% (w/w). Good linearity was achieved in all the three blends with correlation coefficients greater than 0.975 in all cases. [ABSTRACT FROM AUTHOR]

This paper describes, for the first time, the development of a novel trilinolein biosensor based on the immobilisation of lipase and lipoxygenase (LOX) onto a cobalt phthalocyanine screen-printed carbon electrode (CoPC-SPCE) in conjunction with amperometry in stirred solution. The combination of enzymes, integrated into the novel biosensor, provide a selective response for polyunsaturated fatty acid (PUFA) triglycerides, in the presence of both monounsaturated (MUFA) and saturated fatty acid (SFA) triglycerides. The linear range of the trilinolein biosensor is 0.2–10 µM, and the detection limit is 45.5 nM. The biosensor was successfully applied to the measurement of trilinolein present in a pharmaceutical food supplement. The percentage recovery was 86% and the coefficient of variation of the biosensor response was 5.05%. This novel LOX-lipase biosensor is simple to manufacture for trilinolein analysis and has advantages of low cost, speed of analysis and ease of operation, thus making it commercially attractive for a range of applications including food and clinical samples. • Trilinolein was converted into free-fatty acid by the enzyme lipase. • Free fatty acid was converted to a hydroperoxide by LOX. • CoPC acts as an electrocatalyst for the hydroperoxide. • A Low operating potential (+0.5 V) led to good selectivity and sensitivity. • A simple low-cost biosensor assay was developed using amperometry in stirred solution. [ABSTRACT FROM AUTHOR]

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 °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 9 c,12 c and 9 t,12 t 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 9 c,12 c fatty acid is higher than that of the 9 t,12 t 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. © 2016 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

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-α-actin (SM-α-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-α-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. [ABSTRACT FROM AUTHOR]

In this study, the kinetics of the thermally induced isomerization of 9 c ,12 c linoleic acid was studied in order to better understand the geometric and positional isomerization of triacylglycerol and the various factors controlling isomeric ratios. Trilinolein was placed in glass ampoules and sealed in the absence or presence of air (O 2 ) and then subjected to thermal treatment at 180, 200, 220, 230 or 240 °C for regular time intervals. The glass ampoules were removed and the contents were analyzed using gas chromatography. The results indicate that the consumption of trilinolein is a second-order reaction. The formation reactions of cis , trans , trans , cis and trans , trans isomers are zero-order and dependent on both temperature and time. The presence of O 2 does not change the order of the reaction. In addition, the rate constants and activation energies involved in the isomerization reaction of linoleic acid with or without O 2 are presented. [ABSTRACT FROM AUTHOR]

Consumption of sugar-sweetened beverages promotes the development of metabolic syndrome (MetS) and type 2 diabetes mellitus in humans. One factor related to the appearance of MetS components is the dysfunction of the adrenal gland. In fact, the experimental generation of hyperglycemia has been associated with morphological and microvascular changes in the adrenal glands of rats. We hypothesized that high sucrose consumption from infancy promotes histological disruption of the adrenal glands associated with the appearance of metabolic syndrome indicators. Male Wistar rats were separated at weaning (21 days old) into two groups: free access to tap water (control group, C) or 30 % sucrose diluted in water (sugar-fed group). After 12 weeks, high sucrose consumption promoted an increase in visceral fat accumulation, adipose cell number, and insulin resistance. Also, a rise in the concentration of triglycerides, very low-density lipoprotein, insulin and leptin was observed. In control rats, a histomorphometric asymmetry between the right and left adrenal glands was found. In the sugar-fed group, sucrose consumption produced a major change in adrenal gland asymmetry. No changes in corticosterone serum level were observed in either group. Our results suggest that a high sucrose liquid-diet from early life alters the morphology of adrenocortical zones, leading to MetS indicators. [ABSTRACT FROM AUTHOR]

A herbal preparation, Shemamruthaa (SM), was formulated to investigate the molecular mechanism by which it exhibits anticancer effects in mammary carcinoma bearing rats. Female Sprague-Dawley rats were used for the study, and mammary carcinoma was induced by administration of 7,12-dimethylbenz(a)anthracene, intragastrically. After 3 months of induction period, the rats were treated with SM (400 mg/kg body weight) for 14 days. Our study shows that SM-treated mammary carcinoma rats showed regression in tumor volume with concomitant increase in p53, Bax, caspase-3, and caspase-9 mRNA and protein levels compared with mammary carcinoma–induced rats. Proliferating cell nuclear antigen and anti-apoptotic Bcl-2 were markedly increased in mammary carcinoma–induced rats, whereas the SM treatment significantly decreased the expression of these proteins. The expression pattern of apoptotic signaling molecules analyzed in the present study signifies the therapeutic efficacy of SM against breast cancer. [ABSTRACT FROM AUTHOR]

Some analytical methods for the determination of olive oil characteristics included in the European Union and International Olive Oil Council regulations lack precision data. To overcome such inconvenient a collaborative trial was set up including 22 laboratories from governmental institutions and industries. UV absorption at 232 nm, fatty acid composition, trilinolein and triglycerides with 42 equivalent carbon number were the tried methods. Repeatability and reproducibility data were obtained using the statistical method included in the International Standard ISO 5275/1986 (E).The effect of oil purification through a silica gel column on K232 and triglycerides was also studied. Finally for fatty acid determination, methylations by cold methanolic potash and by heating with methylated sodium were compared.

In this study, we have investigated the anti-inflammatory effects of trilinolein (TL) using a lipopolysaccharide (LPS)-stimulated mouse macrophage (RAW264.7) and carrageenan (Carr)-induced mouse paw edema model. When RAW264.7 macrophages were treated with different concentrations of TL together with LPS, a significant concentration-dependent inhibition of nitric oxide (NO), tumor necrosis factor (TNF-α), interleukin-1 (IL-1β), and IL-6 production was detected. Western blotting revealed that TL blocked the protein expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), nuclear factor-κB (NF-κB), IκBα, and mitogen-activated protein kinases (MAPKs). In the anti-inflammatory test, TL decreased the paw edema at the 5th h after λ-Carr administration in paw edema. We also demonstrated TL significantly attenuated the malondialdehyde (MDA) level in the edema paw at the 5th h after Carr injection. TL decreased the NO and TNF-α levels on the serum level at the 5th h after Carr injection. Western blotting revealed that TL decreased Carr-induced iNOS and COX-2 expressions at the 5th h in the edema paw. The anti-inflammatory mechanisms of TL might be related to the decrease in the level of iNOS, COX-2, IκBα, and MAPK pathway through the suppression of TNF-α, IL-1β, and IL-6. [ABSTRACT FROM AUTHOR]

Abstract: Objective: To investigate the bioactive constituents of Shemamruthaa (SM), a herbal combination and its therapeutic effects on the mitochondrial functions with reference to lipid peroxidation (LPO), antioxidant status, citric acid cycle enzymes and electron transport chain enzymes in mammary tissues of 7,12-dimethylbenz(a)-anthracene (DMBA) induced mammary carcinoma in rat model. Methods: Adult female Sprague-Dawley rats were used for the study and were divided into four groups. Group I served as control and Group II rats were induced mammary carcinoma by administration of DMBA (25 mg/kg b.w.) orally. The normal and cancer-induced rats (Group III) were treated with SM (400 mg/kg b.w./day) orally by gastric incubation for 14 days. Group IV rats served as SM-treated control animals. Results: Cancer-induced rats showed a considerably increased level of LPO with concomitant decreased levels of antioxidants, citric acid cycle enzymes, electron transport chain enzymes and cytochrome contents in the mammary tissue. Treatment with SM brought back the aforementioned biochemical parameters to near normal. Conclusions: From the results, it can be inferred that Shemamruthaa possesses significant anticancer effect through its role in attenuation of LPO, prevention of membrane damage and restoring membrane integrity. [Copyright &y& Elsevier]

Abstract: Mixtures of sitosterol (S) and lecithin (L) are able to prepare food-grade organogel by structuring liquid edible oil. In this paper, various S to L mass ratios (i.e., S0L10 to S10L0) in the sunflower oil (SO) high in trilinolein were used to develop organogels at three storage temperatures (T s: 5, 15 and 25°C). Influences of mass ratio and storage temperature on the rheological properties of organogels after ten days of storage were evaluated in detail, and the corresponding microstructures of the crystal network in these organogels were studied by microscopy. At each storage temperature, the rheological properties of the organogels formed by sitosterol and lecithin were different from organogels formed from sitosterol alone. The crystal microstructure in organogels also revealed a dependence on structurant composition and T s. By increasing T s, the elasticity and thermal stability of the organogel developed by mixed structurant were enhanced, and the length of microplatelet units was increased along with a decrease in mesh size, leading to the formation of higher ordered networks, and therefore, the most typical example (S8L2 organogel at T s =25°C) had a higher elasticity than other organogels. The observed rheological behavior is likely to be associated with the composition of structurant, the storage temperature, the viscosity of liquid oil and the microstructure of crystal network. [Copyright &y& Elsevier]

Trilinolein has been identified as one of the active constituents isolated from Panax notoginseng used widely in traditional Chinese medicine. Protective actions of Panax notoginseng against cerebral ischemia, beneficial effects on the cardiovascular system, and hemostatic, antioxidant, hypolipidemic, hepatoprotective, renoprotective and estrogen-like activities have been illustrated. In the present study, the effects of trilinolein on the growth of non-small cell lung carcinoma A549 were investigated. It was found that the exposure of A549 cells to trilinolein resulted in the growth inhibition and the induction of apoptosis in a dose- and time- dependent manner. Trilinolein treatment induced the upregulation of pro-apoptotic Bax, downregulation of anti-apoptotic Bcl-2 expression, which was associated with the proteolytic activation of caspases and the concomitant degradation of poly(ADP-ribose) polymerase (PARP) protein. Intracellular reactive oxygen species seem to play a role in the trilinolein-induced apoptosis, since ROS were produced early in the trilinolein treatment. Moreover, the activity of PI3K/Akt was downregulated in trilinolein-treated cells. Our results demonstrated that the most important regulators of trilinolein-induced apoptosis are Bcl-2 family and caspase-3, which are associated with cytochrome c release and dephosphorylation on the Akt signaling pathway. [ABSTRACT FROM AUTHOR]

Tobacco seeds can give oil and meal. It is a by-product of leaves production in several countries. Tobacco seed oil (TSO) is considered as a renewable potential energy source and almost 38% of seed is oil. Remaining parts are protein, crude fibre, carbohydrate and inorganic material. Trilinolein and palmitodilinolein are main TSO triglycerides (90%). Major fatty acids (FA) are linoleic acid (66-76%), oleic acid (17-27%), palmitic acid (7-10%) and stearic acid (3.1%). TSO drying index and iodine values are 55-75 & 135-147 respectively. Hence, TSO is classified as semi-drying linoleic oil, is also free from nicotine and is comparable to edible oils. Because of low proportion of saturated FA, could be considered as nutritionally appropriate, compared to high-saturated-fat vegetable oils. Vegetable oils are common raw materials in coating industry, especially for alkyd resins. Besides, TSO is shown to be a feedstock for biodiesel production. The biodiesel obtained had fuel properties within the limits prescribed by American and European standards. A comparison different extraction methods of TSO in N. tabacum was done. The physical, chemical and fuel related properties of tobacco seed oil were investigated. These properties were comparable to those of other vegetable oils and to current European specifications. This study suggests that TSO is non edible may be an appropriate substitute for diesel fuel. Environmental advantages of TSO as a fuel can be exploited for specific niche markets. TSO represents a possible hope for "healthy" tobacco use and for future tobacco agriculture. [ABSTRACT FROM AUTHOR]

The products formed by thermally induced isomerization of trilinolein and trilinoelaidin at 250 °C were studied by infrared spectroscopy and gas chromatography. The triglycerides of the 9c12c and 9t12t fatty acids, linoleic and linoelaidic acid respectively, were subjected to thermal treatment under nitrogen in glass. The products were removed at regular intervals and analysed by infrared spectroscopy using a single reflectance attenuated total internal reflectance crystal accessory. Trans-esterification of the products provided the corresponding fatty acid methyl esters which were studied by gas chromatography. The results show that the samples undergo decomposition and isomerization. Thermally induced 9c12c fatty acid (linoleic acid) molecules in the trilinolein molecules isomerize into 9c12t, 9t12c and 9t12t isomers. Thermally induced 9t12t fatty acid (linoelaidic acid) molecules in the trilinoelaidin molecules isomerize into 9c12t, 9t12c and 9c12c isomers. However, the concentration profiles are different for these two triglyceride samples. The rates of formation of isomers from linoleic acid are higher than the rates of formation of isomers from linoelaidic acid. In addition, these two fatty acids also isomerize into conjugated linoleic acids (CLAs). The profiles of the CLAs are identical in both cases. [ABSTRACT FROM AUTHOR]

Sterol regulatory element binding proteins (SREBPs) are key transcription proteins that bind to sterol regulatory elements (SRE) of genes essential for cellular cholesterol and fatty acid homeostasis. Polyunsaturated fatty acids (PUFA) strongly inhibit SREBP processing at post-transcriptional levels. We questioned if delivering PUFA as part of a triglyceride (TG) molecule would have similar effects and efficiency as free non-esterified PUFA. CHO cells stably transfected with an SRE-promoter linked to the luciferase reporter gene were incubated for 8–24 h with linoleic acid (LA) complexed to BSA (molar ratios 0.5–4:1), VLDL-sized trilinolein emulsions (TL, 25–200 μg/ml), and chylomicron-sized soy oil emulsions in the presence and absence of apoE. Effects of LA and TL on decreasing SRE-luciferase activity were similar and dose and time dependent. Both TL and LA significantly and rapidly (≤2–12 h) reduced SRE-mediated gene expression by up to 75%. At equal fatty acid concentrations, SRE inhibition by TL was as effective as LA. ApoE addition increased inhibition by TL. Inhibition of gene expression was highly correlated to cell TG accumulation. We conclude that TG like fatty acids are rapid and efficient modulators of SRE-mediated gene expression. [ABSTRACT FROM AUTHOR]

The enzymatic transesterification of selected phenolic acids with TAG, including trilinolein (TLA) and trilinolenin (TLNA), was investigated in an organic solvent medium. Maximal bioconversion of 66% was obtained with a dihydrocaffeic acid (DHCA) to TLA ratio of 1:2 after 5 d of reaction. Similarly, the highest bioconversion of 62% was obtained with a DHCA to TLNA ratio of 1:2, but after 12 d of reaction. However, a ratio of 1:4 DHCA/TLA decreased the bioconversion to 53%. Transesterification reactions of ferulic acid with both TAG, using a ratio of 1:2, resulted in low bioconversion of 16 and 14% with TLA and TLNA, respectively. The overall results indicated that bioconversion of phenolic MAG was higher than that of phenolic DAG. The structures of mono- and dilinoleyl dihydrocaffeate as well as those of mono- and dilinolenyl dihydrocaffeate were confirmed by LC-MS analyses. The phenolic lipids demonstrated moderate radical-scavenging activity. [ABSTRACT FROM AUTHOR]

Trilinolein, isolated from the traditional Chinese herb Sanchi ( Panax notoginseng), has been shown to have myocardial protective effects via its antioxidant ability. However, the cellular and molecular mechanisms of the protective effect of trilinolein in the heart remain to be elucidated. Oxidative mechanisms have been implicated in neonatal cardiomyocyte hypertrophy. We previously reported that ET-1 induces ROS generation via the ETA receptor and ROS modulates c-fos gene expression. We have therefore examined whether trilinolein attenuates ROS production and ET-1-induced c-fos gene expression in cardiomyocytes. Cultured neonatal rat cardiomyocytes were stimulated with ET-1 (10 nM), and c-fos gene expression was examined. Trilinolein (1 and 10 μM) inhibited ET-1-induced c-fos gene expression in cardiomyocytes. We also examined the effects of trilinolein on ET-1- increased NADPH oxidase activity and superoxide formation. Trilinolein inhibited ET-1-increased NADPH oxidase activity and superoxide formation in a concentration-dependent manner. This increase in superoxide production by ET-1 was significantly inhibited by trilinolein, diphenyleneiodonium, or N-acetylcysteine. Trilinolein also decreased ET-1- or H2O2-induced extracellular signal-regulated kinase (ERK) phosphorylation, c-Jun NH2-terminal kinase (JNK) phosphorylation, and activator protein-1 activation. These data indicate that trilinolein inhibits ET-1-induced ERK phosphorylation, JNK phosphorylation, and c-fos gene expression via attenuating superoxide production in cardiomyocytes. [ABSTRACT FROM AUTHOR]

After swarming, reproductive dealates of the Formosan subterranean termite, Coptotermes formosanus, run together in tandem. The tandem running is an age-related behavioral activity in C. formosanus. This behavior was not evoked in pre-flight alates less than 6-d-old that were artificially dealated. Female age was more important than male age for evoking tandem behavior. Females and males, older than 35 days, did not exhibit this behavior. Mating status was not important for female and male dealates to form the tandem pairs. The titers of the major tergal gland component, trilinolein, did not decline significantly and remained high, not only in virgin females, but also in mated females for a period of time after swarming. On the other hand, increasing amounts of the female-specific compound trilinolein were detected in male dealates 7, 14, and 42 days after pairing. This suggests that trilinolein in the females might be transferred to the males as a nuptial gift in C. formosanus. In addition, females have structurally different lateral setae that may constitute a morphological factor involved in the tandem behavior in this species. Covering the setae with dimethyl sulfoxide prevented the tandem behavior. [Copyright &y& Elsevier]

The myocardial protective effects of trilinolein, isolated from the Chinese herb Sanchi (Panax notoginseng), may be related to its antioxidant effects. In the present study, we investigated the effects of trilinolein on angiotensin II-induced cardiomyocyte hypertrophy. Cultured neonatal rat cardiomyocytes were stimulated with angiotensin II, [3H]leucine incorporation and the β-myosin heavy chain promoter activity were examined. We also examined the effects of trilinolein on angiotensin II-induced intracellular reactive oxygen species generation. Trilinolein significantly inhibited angiotensin II-increased protein synthesis, β-myosin heavy chain promoter activity, and intracellular reactive oxygen species generation. Antioxidant N-acetylcysteine also decreased angiotensin II-increased protein synthesis and β-myosin heavy chain promoter activity. Furthermore, trilinolein and N-acetylcysteine decreased angiotensin II- or hydrogen peroxide (H2O2)-activated mitogen-activated protein kinases (MAPKs) phosphorylation, and activator protein-1 (AP-1)- [or nuclear factor-κB (NF-κB)]-reporter activities. These data indicate that trilinolein inhibits angiotensin II-induced cardiomyocyte hypertrophy and β-myosin heavy chain promoter activity via attenuation of reactive oxygen species generation. [Copyright &y& Elsevier]

The myocardial protective effects of trilinolein, isolated from the traditional Chinese herb Sanchi (Panax notoginseng), are thought to be related to its antioxidant activity. However, the intracellular mechanism underlying the protective effect of trilinolein in the heart remains unclear. In the present study, we investigated the effect of trilinolein on norepinephrine (NE)-induced protein synthesis in cardiomyocytes. Cultured neonatal rat cardiomyocytes were stimulated with NE, then protein content, [[sup 3] H]-leucine incorporation, and β-myosin heavy chain (β-MyHC) promoter activity were examined. The effect of trilinolein on NE-induced intracellular reactive oxygen species (ROS) generation was measured with a redox- sensitive fluorescent dye (2′,7′-dichlorofluorescin diacetate) and extracellular signal-regulated kinase (ERK) phosphorylation by Western blotting. Trilinolein inhibited NE-increased protein synthesis, β-MyHC promoter activity, and intracellular ROS. Both trilinolein and the antioxidant, N-acetyl-cysteine, decreased NE- and H[sub 2] O[sub 2] -induced protein synthesis, β-MyHC promoter activity, and ERK phosphorylation. These data indicate that trilinolein inhibits NE-induced protein synthesis via attenuation of ROS generation in cardiomyocytes. Copyright © 2004 National Science Council, ROC and S. Karger AG, Basel [ABSTRACT FROM AUTHOR]

Laccase enzymes were investigated for their potential to catalyze the oxidation of trilinolein and methyl linoleate. This study demonstrates that laccase enzymes can oxidize unsaturated fatty acid esters and their associated lipids. The reaction products resulting from laccase-catalyzed reactions with trilinolein were analyzed using combined reversed-phase high-performance liquid chromatography and mass spectrometry via an atmospheric pressure chemical ionization source. The dominant oxidation products detected were monohydroperoxides, bishydroperoxides, and epoxides. This paper presents the first detailed investigation into the interaction between laccase enzymes and lipids containing unsaturated fatty acids. [Copyright &y& Elsevier]

Trilinolein, a triacylglycerol with linoleic acid, was found to inhibit Ca[sup 2+] influx in cardiomyocytes. The purpose of this study was to evaluate the effects of trilinolein on ventricular arrhythmia induced by intravenous strophanthidin in guinea pigs anesthetized with intraperitoneal urethane. After strophanthidin- induced ventricular tachycardia, treatment with trilinolein (0.1, 1, 10 and 100 µg/kg) or control (0.04% propylene glycol) did not terminate ventricular tachycardia. However, 1, 10 and 100 µg/kg trilinolein could narrow the width of the QRS complex during ventricular tachycardia. Pretreatment with trilinolein before strophanthidin administration did not prevent the occurrence of ventricular tachycardia; the doses of strophanthidin required to induce arrhythmias (ventricular extrasystole and ventricular tachycardia) were similar in guinea pigs pretreated with trilinolein or control. However, there were fewer ventricular extrasystoles in guinea pigs pretreated with trilinolein than in the control group (ANOVA, p < 0.01). Moreover, the ventricular extrasystoles were fewer in guinea pigs pretreated with higher doses of trilinolein (100 µg/kg, 103 ± 60; 10 µg/kg, 188 ± 86) than lower doses of trilinolein (1 µg/kg, 366 ± 102; 0.1 µg/kg, 436 ± 145). This study demonstrated that trilinolein was not effective in terminating or preventing strophanthidin-induced ventricular tachycardia. However, trilinolein could improve ventricular depolarization and suppress ventricular extrasystoles. [ABSTRACT FROM AUTHOR]

Chemoenzymatic conversion of trilinolein to (+)-coriolic acid was investigated in this work. Lipase-catalyzed hydrolysis of trilinolein and lipoxygenation of liberated linoleic acid were coupled in a two-phase medium that consisted of a pH 9 borate buffer and a water-immiscible organic solvent (octane). High concentrations of trilinolein could be dissolved in the organic phase (up to 340 mM). Linoleic acid, liberated after hydrolysis, transferred to the aqueous phase and was enzymatically converted to the preferred 13( S)-hydroperoxy-9 Z,11 E-octadecadienoic acid with soybean lipoxygenase-1. This product, which remained in the aqueous phase, could be recovered by centrifugation and then chemically reduced to (+)-coriolic acid (purity >95%). Recovery of this compound by liquid-liquid extraction was easy. The structure of (+)-coriolic acid has been confirmed by 1H nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy. High yields were obtained with pure trilinolein or sunflower oil as initial substrates. [ABSTRACT FROM AUTHOR]

Four oils [triolein, trilinolein, oleic acid-esterified propoxylated glycerol (EPG-08 oleate), and linoleic acid-esterified propoxylated glycerol (EPG-08 linoleate)], each without added antioxidants, were heated for 12 h/d at approximately 190°C in a small deep-fat fryer until the polymer concentration exceeded 20%, as determined by high-performance size-exclusion chromatography. Increases in the free fatty acid content, total acid value, food oil sensor value, and p-anisidine value during heating indicated that significant thermal oxidation had occurred in each oil. Capillary supercritical fluid chromatography (SFC) was used to determine the substrate concentration of each oil after each heating interval. The average, apparent first-order reaction rate constant (as determined by SFC) for trilinolein was 0.0348±0.0034 h−1, while the rate for EPG-08 linoleate was 0.0253±0.0032 h−1. The average apparent reaction rate constant for triolein was 0.0256±0.0011 h−1, while the rate for EPG-08 oleate was 0.0252±0.0008 h−1. Triolein contained >20% polymer after 60 h of heating, EPG-08 oleate contained >20% polymer after 36 h of heating, and both trilinolein and EPG-08 linoleate contained >20% polymer after 24 h of heating. [ABSTRACT FROM AUTHOR]

Two immobilized lipases, IM60 from Mucor miehei and SP435 from Candida antarctica, were used as biocatalysts for the modification of trilinolein with n-3 polyunsaturated fatty acids (PUFA), such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), by using their ethyl esters as acyl donors (EEPA and EDHA, respectively). Transesterification (ester-ester interchange) reactions were carried out in organic solvent. The products were analyzed according to their equivalent carbon number and polarity by reverse-phase high-performance liquid chromatography, and the fatty acid profiles were determined by gas-liquid chromatography. Modified triacylglycerol products contained 1 or 2 molecules of n-3 PUFA. With EEPA as the acyl donor, the total EPA product yields with IM60 and SP435 as biocatalysts were 79.6 and 81.4%, respectively. However, with EDHA as the acyl donor and IM60 and SP435 as biocatalysts, the total DHA product yields were 70.5 and 79.7%, respectively. Effects of reaction parameters, such as type of solvent, enzyme load, time course, and molar ratio of substrates on the n-3 PUFA incorporation, were followed with SP435 as the biocatalyst. High yields were obtained, even in the absence of organic solvent. These lipids do hold promise for specialty nutrition and other therapeutic uses. [ABSTRACT FROM AUTHOR]

Normal-phase high-performance liquid chromatography (HPLC) is widely used in combination with evaporative light scattering detection (ELSD) for separating and detecting lipids in various food samples. ELSD responses of different lipids were evaluated to elucidate the possibilities and challenges associated with quantification by means of HPLC-ELSD. Not only the number and type of polar functional groups but also the chain length and degree of unsaturation of (free or esterified) fatty acids (FAs) had a significant effect on ELSD responses. Tripalmitin and trilinolein yielded notably different ELSD responses, even if their constituting free FAs produced identical responses. How FA structure impacts ELSD responses of free FAs is thus not predictive for those of triacylglycerols and presumably other lipids containing esterified FAs. Because ELSD responses of lipids depend on the identity of the (esterified) FA(s) which they contain, fully accurate lipid quantification with HPLC-ELSD is challenging and time-consuming. Nonetheless, HPLC-ELSD is a good and fast technique to semi-quantitatively compare the levels of different lipid classes between samples of comparable FA composition. In this way, lipid profiles of different flours from near-isogenic wheat lines could be compared. [ABSTRACT FROM AUTHOR]

The dichloromethane extract of the leaves of Aglaia loheri afforded spinasterol (1), trilinolein (2) and phytyl fatty acid ester (3). The structures of 1-2 were identified by comparison of their 1°C NMR data with those reported in the literature. Compounds 1, 2 and 3 were evaluated for cytotoxicity against the colon carcinoma (HCT 116) using the MTT assay. They exhibited moderate cytotoxicity against HCT 116 with IC50 values of 40.52, 46.73 and 40.06, respectively. [ABSTRACT FROM AUTHOR]

Static headspace and capillary gas chromatography/infrared spectroscopy-mass spectrometry were used to collect, separate, detect and quantitate the oxidative and thermal decomposition products in heated trilinolein. Trilinolein without added antioxidants was heated in a deep-fat fryer at 190°C for 12 h each day for a total of 24 h until the amount of polymeric material in the oil exceeded 20%. The concentration of the volatile compounds in trilinolein, as well as the p-anisidine values and polymer content, increased with an increase in heating time. After 24 h of heating, the concentrations of the major volatile compounds (>10 ppm) had increased as follows: pentane (33.4-398.7 ppm), pentanal (11.7-73.5 ppm), 1-pentanol (5.2-46.7 ppm), hexanal (67.6-346.1 ppm), ( E)-2-hexenal (12.9-87.6 ppm), ( E)-2-heptenal (309.6-894.1 ppm), 1-octen-3-ol (35.2-150.2 ppm), formic acid (0-18.7 ppm), hexanoic acid (0-83.8 ppm), heptanal (2.5-29.5 ppm), 2-pentylfuran (29.2-146.9 ppm), ( E)-2-octenal (26.4-347.2 ppm), ( E)-2-octenal (26.4-347.2 ppm), ( E)-2-nonenal (31.6-163.2 ppm), ( E,Z)-2,4-decadienal (15.0-320 ppm) and ( E,E)-2,4-decadienal (43.1-1137.5 ppm). [ABSTRACT FROM AUTHOR]

• MW-HPLC has been successfully applied for the determination of triacylglycerols. • Shorter retention times have been achieved with MW-HPLC respect to conventional HPLC. • Non-volatile mobile phases are advisable to be used in MW-HPLC. Microwave (MW) radiation was applied to perform the separation of triacylglycerols (TGs) in oil samples. The novelty of the work lies in the application of MW radiation to assist the separation of several non-polar compounds employing a totally organic mobile phase. Once the influence of the evaporative light scattering detector (ELSD) variables on the sensitivity was optimized, the TGs separation was compared conditioning the column with either a conventional HPLC or a MW oven. Contrary to previous applications in which the mobile phase contained water, the improvement in sensitivity using MW was not as significant in comparison with conventional heating but it allowed a shortening in the retention times of several TGs in about 50% respect elution at room temperature. The method was finally applied for the quantification of most common TGs in almond, tiger nut, and argan oil. [ABSTRACT FROM AUTHOR]

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°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.

The article presents information on a study involving the isolation and identification of the chemical constituents of the dichloromethane extracts from the plant species Cinnamomum trichophyllum found in the Philippines. In the study, silica gel chromatography was conducted on the dichloromethane extracts of the leaves of Cinnamomum trichophyllum. The chemicals isolated from Cinnamomum trichophyllum included polyprenols, trilinolein, and stigmasterol.