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To determine the performance of a sophorolipid biosurfactant production process, it is important to have accurate and specific analytical techniques in place. Among the most popular are the anthrone assay, gravimetric quantification (hexane:ethyl acetate extraction), and high-performance liquid chromatography (HPLC). The choice of analytical tool varies depending on cost, availability, and ease of use; however, these techniques have never been compared directly against one another. In this work, 75 fermentation broths with varying product/substrate concentrations were comprehensively tested with the 3 techniques and compared. HPLC-ultraviolet detection (198 nm) was capable of quantifying C18:1 subterminal hydroxyl diacetylated lactonic sophorolipid down to a lower limit of 0.3 g/L with low variability (<3.21%). Gravimetric quantification of the broths following liquid:liquid extraction with hexane and ethyl acetate showed some linearity (R2 = .658) when compared to HPLC but could not quantify lower than 11.06 g/L, even when no sophorolipids were detected in the sample, highlighting the non-specificity of the method to co-extract non-sophorolipid components in the final gravimetric measure. The anthrone assay showed no linearity (R2 = .129) and was found to cross-react with media components (rapeseed oil, corn steep liquor, glucose), leading to consistent overestimation of sophorolipid concentration. The appearance of poor biomass separation during sample preparation with centrifugation was noted and resolved with a novel sample preparation method with pure ethanol. Extensive analysis and comparisons of the most common sophorolipid quantification techniques are explored and the limitations/advantages are highlighted. The findings provide a guide for scientists to make an informed decision on the suitable quantification tool that meets their needs, exploring all aspects of the analysis process from harvest, sample preparation, and analysis., (© The Author(s) 2024. Published by Oxford University Press on behalf of Society of Industrial Microbiology and Biotechnology.)

Background: Armeniaca sibirica seed kernel oil is rich in oleic acid and linoleic acid, thus holding potential value as a source of high-quality edible oils. However, some regulatory factors involved in fatty acids accumulation in A. sibirica seed kernels remain largely elusive. Thus, the aim of this study was to elucidate the regulatory mechanisms underlying fatty acids biosynthesis in A. sibirica developing seed kernels., Methods: Seed kernels from six plants from a single A. sibirica clone were taken at five different developmental stages (days 30, 41, 52, 63, and 73 after anthesis). Fatty acid composition in seed kernel oil was determined by gas chromatography-mass spectrometry (GC-MS). In addition, transcriptome analysis was conducted using second-generation sequencing (SGS) and single-molecule real-time sequencing (SMRT)., Results: Rapid accumulation of fatty acids occurred throughout the different stages of seed kernels development, with oleic acid and linoleic acid as the main fatty acids. A total of 10,024, 9,803, 6,004, 6,719 and 9,688 unigenes were matched in the Nt, Nr, KOG, GO and KEGG databases, respectively. In the category lipid metabolism, 228 differentially expressed genes (DEGs) were annotated into 13 KEGG pathways. Specific unigenes encoding 12 key enzymes related to fatty acids biosynthesis were determined. Co-expression network analysis identified 11 transcription factors (TFs) and 13 long non-coding RNAs (lncRNAs) which putatively participate in the regulation of fatty acid biosynthesis. This study provides insights into the molecular regulatory mechanisms of fatty acids biosynthesis in A. sibirica developing seed kernels, and enabled the identification of novel candidate factors for future improvement of the production and quality of seed kernel oil by breeding., Competing Interests: The authors declare there are no competing interests., (©2022 Wu et al.)

This study aimed to determine the association between the seed coat color of two chia seed genotypes for their composition, protein content, amino acid, and fatty acid profiles. The optimal pH for protein isolation for both genotypes (BCPI and WCPI) was 10, based on protein purity and solubility. Fatty acid profiling indicated, overall, 18 different fatty acids higher in BCPI10 with linolenic acid domination (∼66%) followed by linoleic acid (∼19%) and oleic acid (∼6%), contributing PUFAs (∼86%). Optimized protein isolates, black (BCPI10) and white (WCPI10) chia, had shown purity, L*-value, solubility, and yields of 90.65%, 75.86%, 77.75%, 11.30%, and 90.00%, 77.83%, 76.07%, 10.69%, respectively. BCPI10 depicted higher EAA (33.19 g/100 g N) and EEA indices (57.676%) compared to WCPI10 (32.14 g/100 g N) and 56.360%, respectively. Amino acid profiling indicated higher, PER, TAA, TEAA, TNEAA, TAAA, TBA, acidic AA values for BCPI10, and higher leucine/isoleucine ratio for WCPI10 having leucine and sulfur amino acids as limiting amino acids. BCPI10 had higher sulfur-containing amino acid contents, as the main contributor to the albumin a water-soluble fraction, leading to its higher in vitro digestibility (71.97%) than WCPI10 (67.70%). Both isolates exhibited good WHC and OHC of 3.18, 2.39 and 3.00, 2.20, respectively. Both protein isolates had similar ∆Td (°C) values with some variation in FTIR spectrum from 1000 cm -1 to 1651 cm -1 having more peak intensity for BCPI10. SDS-PAGE indicated bands at 150 kDa, representing globulin and mild bands at 25-33 kDa for glutelin and albumin. A significant (p < 0.05) variation reported in this study for protein and lipid profiles of both genotype attributes to genetic differences between the seeds. PRACTICAL APPLICATION: Based on the nutritional profile, both chia seed isolates (black and white) are suitable for consumption with an edge for black seed when supplemented with their limiting amino acids. The high values of the functional properties and structural characteristics combined with high nutritional values make the chia protein isolate an excellent source of raw material for various food formulations. Fatty acid profile of the oils from the genotypes showed the presence of high amounts of unsaturated fatty acids, especially the PUFAs with more number of fatty acids in black chia seed. The excellent lipid profile of chia seed oil indicates the benefit of using chia seed oil as a source of essential fatty acids in the human diet for optimal health., (© 2022 Institute of Food Technologists®.)

For indirect determination of 3-chloro-1,2-propanediol fatty acid esters (3-MCPDEs) and glycidyl fatty acid esters (GEs) in thermally processed foodstuffs distributed in Japan, we modified two published methods, an enzymatic method (later approved as JOCS Standard Method for the Analysis of Fats, Oils, and Related Materials 2.4.14 -2016 and Joint JOCS/AOCS Official Method Cd 29d-19) and EFSA method developed by the Joint Research Centre of the European Commission. The performance of these methods was demonstrated to be satisfactory. The partially modified enzymatic method showed mean recoveries of 93.7-98.5% for 3-MCPDEs, 94.4-98.4% for GEs, and HorRat (r) values of 0.06-0.78 in analyses of 6 types of foods including Japanese specific foods (fried rice cracker, fried instant noodle, biscuit, karinto, vegetable tempura, and frozen deep-fried chicken) spiked with 3-MCPD dioleate and glycidyl oleate at 0.02-0.04 mg/kg or 0.2-0.4 mg/kg. The partially modified EFSA method showed mean recoveries of 96.6-99.4% for 3-MCPDEs, 95.7-100.1% for GEs, and HorRat (r) values of 0.14-1.05 in analyses of 5 types of foods (not including karinto) spiked simultaneously with 3-MCPD dioleate and glycidyl oleate at either 0.02-0.04 mg/kg or 0.2-0.4 mg/kg. The results of analyses of 9 samples (fried rice cracker, biscuit, 2 potato crisps, fried potato snack, baked cracker, cracker dough, seafood tempura, and frozen deep-fried chicken) using these 2 methods were comparable. The 95% confidence intervals determined with weighted Deming regression analysis between the results of 3-MCPDEs or GEs in the same samples analyzed by the 2 methods showed: the slope around 1 (3-MCPDEs, 0.982-1.025; GEs, 0.887-1.078); and intercept close to 0 (3-MCPDEs, －0.002-0.003; GEs, －0.011-0.015). These data confirmed that the concentrations of 3-MCPDEs and GEs in food samples determined by 2 independent analytical methods were equivalent.

To determine Industrially-Produced Trans fatty acids (IP-TFAs) distribution of Lebanese traditional foods, especially regarding Elaidic acid (EA; 9t18:1) and Linolelaidic acid (LEA; 9t12t18:2), a mapping exercise was enrolled between January 2019 and April 2021 in which 145 food samples of three categories (traditional dishes, Arabic sweets, and market food products) were analyzed using Gas chromatography methods. Results showed that about 93% of the products tested in Lebanon, between 2019 and 2021, met the World Health Organization recommendations, while about 7% exceeded the limit. The mean level of the IP-TFAs Elaidic and Linolelaidic acid in most Traditional dishes (0.9%), Arabic sweets (0.6%), butter and margarine (1.6%), and market foods (0.52%) were relatively low compared with other countries. Despite that, the relative impact of IP-TFAs on heart diseases mortality in Lebanon is limited but unambiguously still substantial. The persistence of food products with high IP-TFAs levels threatens the health of Lebanese people. Fortunately, this problem is fairly easy to solve in Lebanon via proper legislation.

The human milk fatty acid, including trans fatty acid, composition is predominantly affected by the maternal diet. The aim of this research was to determine the trans fatty acid level in human milk among lactating women in Latvia, and to evaluate how maternal dietary habits affect the trans fatty acid composition of human milk. In total, 70 lactating women participated in this cross-sectional study. A 72-hour food diary and food frequency questionnaire were used to evaluate maternal dietary habits. Different trans fatty acids in human milk samples were determined using gas chromatography (Agilent 6890N, Agilent Technologies Incorporated, the United States). Overall, the dietary intake of trans fatty acids among the participants was 0.54 ± 0.79 g per day. The total trans fatty acid level in the human milk samples was 2.30% ± 0.60%. The composition of trans fatty acids found in human milk was associated with maternal dietary habits. Higher elaidic acid, vaccenic acid and total trans fatty acid levels in human milk were found among participants with a higher milk and dairy product intake. Meat and meat product intake were associated with a higher vaccenic acid and total trans fatty acid levels in human milk. A moderate association was also established between maternal trans fatty acid intake and the total trans fatty acid level in human milk. The obtained correlations indicate that maternal dietary habits during lactation can impact the composition of trans fatty acids found in human milk.

We developed an alternative whipping cream fat using shea butter but with low saturation. Enriched stearic-oleic-stearic (SOS) solid fat was obtained from shea butter via solvent fractionation. Acyl migration reactant, which mainly contains asymmetric SSO triacylglycerol (TAG), was prepared through enzymatic acyl migration to obtain the creaming quality derived from the β'-crystal form. Through enzymatic acyl migration, we obtained a 3.4-fold higher content of saturated-saturated-unsaturated (SSU) TAG than saturated-unsaturated-saturated (SUS) TAG. The acyl migration reactant was refined to obtain refined acyl migration reactant (RAMR). An alternative fat product was prepared by blending RAMR and hydrogenated palm kernel oil (HPKO) at a ratio of 4:6 ( w / w ). The melting points, solid fat index (SFI), and melting curves of the alternative products were similar to those of commercial whipping cream fat. The alternative fat had a content of total unsaturated fatty acids 20% higher than that of HPKO. The atherogenic index (AI) of alternative fat was 3.61, much lower than those of whipping cream fat (14.59) and HPKO (1220.3), because of its low atherogenic fatty acid content and high total unsaturated fatty acids. The polymorphic crystal form determined by X-ray diffraction spectroscopy showed that the β'-crystal form was predominant. Therefore, the alternative fat is comparable with whipping cream that requires creaming quality, and has a reduced saturated fat content.

Biosurfactants have been investigated as potential alternatives for synthetic surfactants in several areas, for example, in environmental and pharmaceutical fields. In that regard, extensive research has been carried out with sophorolipids and rhamnolipids that also present various biological properties with therapeutic significance. These biosurfactants are obtained as complex mixtures of slightly different molecules, and thus when studying these microbial glycolipids, the ability to identify and purify the produced compounds is of extreme importance. This study aimed to develop improved methodologies for the identification, separation, and purification of sophorolipids and rhamnolipids. Therefore, an ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method was modified to ensure faster characterization of both sophorolipids and rhamnolipids, enabling the identification and fragmentation pattern description of 10 and 13 congeners, respectively. The separation and purification of these biosurfactants was achieved with novel reversed-phase solid-phase extraction methods guaranteeing the isolation of different glycolipids, including those considered for their significant biological activity (e.g. antimicrobial, anticancer). It was possible to isolate sophorolipids and rhamnolipids with purity of 94% and 99%, respectively. The methods presented herein can be easily implemented and are expected to make purification of these biosurfactants easier, facilitating the study of their individual properties in further works.

Oleoylethanolamide is an endogenous molecule with neuroprotective effects. It has been reported that exogenous oleoylethanolamide can be administered therapeutically, but the confounding presence of the endogenous molecule has led to conflicting reports regarding the mechanisms of the effects and highlights a need for an adequate methodology to differentiate them. We have developed a liquid chromatography-tandem mass spectrometry method to study oleoylethanolamide in rat plasma and brain using a 13 C-labeled isotope, 13 C-oleoylethanolamide. 13 C-oleoylethanolamide was extracted using a liquid-liquid extraction employing acetonitrile and tert-butyl methyl ether (1:4). Analysis was performed using a gradient with a total run time of 12 min. 13 C-oleoylethanolamide, d 4 -oleoylethanolamide (internal standard), and 12 C-oleoylethanolamide (endogenous background) eluted simultaneously at 1.64 min. The method was validated for specificity, sensitivity, accuracy, and precision and found to be capable of quantification within acceptable limits of ±15% over the calibration range of 0.39-25 ng/mL for the plasma and 1.17-75 ng/g for the brain. It was then applied to quantify 13 C-oleoylethanolamide over 90 min after intravenous administration of a solution (1 mg/kg) in rats. Results suggest that 13 C-oleoylethanolamide does not reach therapeutic concentrations in the brain, despite a relatively prolonged plasma circulation, suggesting that rapid degradation in the brain remains an obstacle to its clinical application to neurological disease., (© 2021 Wiley-VCH GmbH.)

Endogenous cannabinoids are an increasingly intriguing target for biological research, given the changing legal status of medicinal cannabinoid-based products throughout the world. However, studying the endogenous cannabinoid system is a relatively new field, with few research teams attempting to develop quantitative methods for these important modulatory analytes in human matrices, other than blood. Here we develop and validate simultaneous methods for quantifying arachidonoyl-ethanolamide, 2-arachidonoyl glycerol, oleoylethanolamide, cortisol and progesterone in human plasma and saliva using liquid-liquid extraction combined with ultra-high performance liquid chromatography coupled to tandem mass spectrometry. The method was fully validated over the linear concentration range 1-20 ng/mL for each analyte in plasma (R 2  = 0.98-0.99) and saliva (R 2  = 0.99). We find that salivary endogenous cannabinoids and cortisol are acutely responsive to exercise, suggesting that targeting the saliva system may present a convenient way for future research of endogenous cannabinoids. This finding also encourages a broader understanding of the endogenous cannabinoid system during stress responses, and our method may consequently lead to a better understanding of the role of endogenous cannabinoids in peripheral tissues., Competing Interests: Declaration of Competing Interest The authors declared that there is no conflict of interest., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Microbial production of hydroxy fatty acids (HFAs) was widely studied because of important biological properties of HFAs. Among microorganisms producing HFAs, Pseudomonas aeruginosa PR3 was well known to produce various HFAs from different unsaturated fatty acids. Recently, a new variant species of P. aeruginosa PR3 was isolated and characterized, showing improved efficiency for producing 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid. In this study, we report the production of 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD) from ricinoleic acid by the newly isolated P. aeruginosa KNU-2B. TOD was efficiently produced from ricinoleic acid by KNU-2B with the maximum conversion yield of 56.7% under the optimum reaction conditions of pH 8.0 and 48-h incubation at 27 °C, 150 rpm. Under optimized reaction conditions, maximum TOD production reached 340.3 mg/100 mL of the culture. However, requirement of nutritional factors by KNU-2B for production of TOD were considerably different from those by PR3 strain.

Triacylglycerols (TAGs) containing less common fatty acids (FAs) were isolated from the seeds of three plants (Santalum album, Crepis foetida, and Leucas aspera). These FAs had allenic (laballenic acid, Lb) and acetylenic (crepenynic, C; ximenynic acids, Xi) bonds. TAGs were analyzed on reversed-phase and chiral columns. High-resolution tandem mass spectrometry identified TAGs by positive electrospray ionization (ESI + ). Twenty-two molecular species of TAGs isolated from the seed oil of Santalum album were separated by RP-HPLC and chiral HPLC methods and identified by positive electrospray ionization tandem MS detection (ESI + -MS). Two major enantiomers, i.e., sn-OOLb and sn-LLLb (O represents oleic acid; and L represents linoleic acid), were synthesized from the appropriate phosphatidylcholines. This allowed the identification of enantiomers after separation by chiral chromatography by tandem mass spectrometry. Similarly, TAGs from the seeds of Crepis foetida, and Leucas aspera were analyzed by reversed-phase chromatography and identified by mass spectrometry. Four enantiomers (sn-OOC, sn-LLC, sn-OOXi, and sn-LLXi) were synthesized. A total of six and three enantiomers of TAGs containing crepenynic and ximenynic acids, respectively, were identified by chiral column analysis. The retention times of TAGs containing allenic and acetylenic bonds were always greater on the reversed-phase column than TAGs with the same number of carbon atoms and the same unsaturation (e.g., LLL versus LLLb). From the chiral column, the regioisomers and enantiomers were eluted in the order of symmetric-asymmetric-asymmetric (i.e., sn-OCO, sn-COO, and sn-OOC). Through tandem mass spectrometry, we were able to identify and distinguish regioisomer [DAG] + -type ions, i.e., [MNH 4 NH 3 RCOOH] + , that can be considered diagnostic. Unfortunately, enantiomers and TAGs with the same numbers of carbon atoms and the same unsaturation levels have identical mass spectra, such as LLL and LLLb., Competing Interests: Declaration of Competing Interest The authors declare no competing financial interest., (Copyright © 2020 Elsevier B.V. All rights reserved.)

The fatty acid (FA) composition and content of whole milk (3.25% fat) from organic, omega-3 (n-3) FA fortified, and conventional retail brands available in the northeastern U.S. were assessed monthly via gas chromatography. Among the retail labels, organic milk stood out as it contained a distinct and more healthful FA profile, consistently comprising a higher content of unique bioactive FAs (short-chain FAs, odd- and branched-chain FAs, vaccenic acid, and conjugated linoleic acids) per serving, particularly during the warm season. The total content of saturated FAs did not differ by retail label. While organic and n-3 fortified milk contained a similar content of total n-3 FAs, the proportion of individual n-3 FAs differed significantly (organic milk: 18:3 n-3; n-3 fortified milk: 20:6 n-3) as a result of the production system and process, respectively. Overall, per serving, the FA profile of organic milk may provide added nutritional and health benefits.

Obesity has become a severe public health problem worldwide. An endogenous fatty acid ethanolamine oleoyl ethanolamine (OEA) is reported to be capable of reducing body weight and food intake by increasing striatal extracellular dopamine concentration. However, association between obesity and striatal OEA level remains unknown. As such, it is necessary to develop a sensitive and reliable method to quantitate OEA concentration in striatum. Because true endogenous analytes free blank matrix is not available, surrogate analyte, surrogate matrix and background subtraction methods are often employed for the analysis of endogenous compounds. In this study, three liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods were developed and validated for the determination of OEA concentration in mouse brain homogenate. Interestingly, stability results found that OEA-d4 degraded in brain homogenate under room temperature, while OEA level remarkably increased with time. Since lowering temperature could observably decelerate the endogenous transformation of OEA, sample collection and preparation were carried out under ice-bath condition. Hexane: isopropanol (9:1, v/v) was employed as an extractant for liquid-liquid extraction. After method validation, three methods were applied to quantify OEA in striatum homogenate from C57B6/L mice following normal and high fat diet feeding for 4 months. Results from three methods all showed the striatal OEA level in obesity group was significantly higher than control group and obesity-resist group, which indicated that obesity might be associated with elevated striatal OEA level., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Trihydroxyoctadecenoic acids (TriHOMEs) are linoleic acid-derived lipid mediators reported to be dysregulated in obstructive lung disease. In contrast to many other oxylipins, TriHOME biosynthesis in humans is still poorly understood. The association of TriHOMEs with inflammation prompted the current investigation into the ability of human granulocytes to synthesize the 16 different 9,10,13-TriHOME and 9,12,13-TriHOME isomers and of the TriHOME biosynthetic pathway. Following incubation with linoleic acid, eosinophils and (to a lesser extent) the mast cell line LAD2, but not neutrophils, formed TriHOMEs. Stereochemical analysis revealed that TriHOMEs produced by eosinophils predominantly evidenced the 13(S) configuration, suggesting 15-lipoxygenase (15-LOX)-mediated synthesis. TriHOME formation was blocked following incubation with the 15-LOX inhibitor BLX-3887 and was shown to be largely independent of soluble epoxide hydrolase and cytochrome P450 activities. TriHOME synthesis was abolished when linoleic acid was replaced with 13-HODE, but increased in incubations with 13-HpODE, indicating the intermediary role of epoxy alcohols in TriHOME formation. In contrast to eosinophils, LAD2 cells formed TriHOMEs having predominantly the 13(R) configuration, demonstrating that there are multiple synthetic routes for TriHOME formation. These findings provide for the first-time insight into the synthetic route of TriHOMEs in humans and expand our understanding of their formation in inflammatory diseases., (Copyright © 2020 Elsevier B.V. All rights reserved.)

No data are available on whether a diet deficient of the essential fatty acids is able to modulate tissue levels of endocannabinoids and congeners. Male rats fed for 12 weeks a diet deficient of essential fatty acids, palmitic and oleic acids (EFAD), replaced with saturated fatty acids (SAFA), showed lowered n-3 and n-6 PUFAs levels in plasma, liver and adipose tissue, with concomitant steep increase of oleic and mead acids, while in hypothalamus no changes in PUFA concentration were detected and only palmitoleic acid was found increased. We found a reduction of anandamide and palmitoylethanolamide in liver and brain, while oleoylethanolamide increased significantly in liver and adipose tissue, associated to a 50 % body weight decrease. Changes in N-acylethanolamide profile may contribute to body weight reduction distinctive of EFA deficiency., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

Objective: The endocannabinoid (eCB) system is involved in diverse aspects of human physiology and behavior but little is known about the impact of circadian rhythmicity on the system. The two most studied endocannabinoids, AEA (ananamide) and 2-AG (2-arachidonoylglycerol), can be measured in peripheral blood however the functional relevance of peripheral eCB levels is not clear. Having previously detailed the 24-h profile of serum 2-AG, here we report the 24-h serum profile of AEA to determine if these two endocannabinoids vary in parallel across the biological day including a nocturnal 8.5-h sleep period. Further, we assessed and compared the effect of a physiological challenge, in the form of sleep restriction to 4.5-h, on these two profiles., Methods: In this randomized crossover study, we examined serum concentrations of AEA across a 24-h period in fourteen young adults. Congeners of AEA, the structural analogs oleoylethanolamide (OEA) and palmitoylethanolamide (PEA) were simultaneously assayed. Prior to 24-h blood sampling, each participant was exposed to two nights of normal (8.5 h) or restricted sleep (4.5 h). The two sleep conditions were separated by at least one month. In both sleep conditions, during the period of blood sampling, each individual ate the same high-carbohydrate meal at 0900, 1400, and 1900., Results: Mean 24-h concentrations of AEA were 0.697 ± 0.11 pmol/ml. A reproducible biphasic 24-h profile of AEA was observed with a first peak occurring during early sleep (0200) and a second peak in the mid-afternoon (1500) while a nadir was detected in the mid-morning (1000). The 24-h profiles for both OEA and PEA followed a similar pattern to that observed for AEA. AEA, OEA, and PEA levels were not affected by sleep restriction at any time of day, contrasting with the elevation of early afternoon levels previously observed for 2-AG., Conclusions: The 24-h rhythm of AEA is markedly different from that of 2-AG, being of lesser amplitude and biphasic, rather than monophasic. These observations suggest distinct regulatory pathways of the two eCB and indicate that time of day needs to be carefully controlled in studies attempting to delineate their relative roles. Moreover, unlike 2-AG, AEA is not altered by sleep restriction, suggesting that physiological perturbations may affect AEA and 2-AG differently. Similar 24-h profiles were observed for OEA and PEA following normal and restricted sleep, further corroborating the validity of the wave-shape and lack of response to sleep loss observed for the AEA profile. Therapeutic approaches involving agonism or antagonism of peripheral eCB signaling will likely need to be tailored according to time of day., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

New cultivars of Camellia oleifera have been developed and planted in southern China. However, lipid characteristics of their seed oils were still unclear. In this study, nine C. oleifera fruits were collected from different cultivars in different planting regions, and the lipid characteristics, such as oil content, fatty acid composition, triacylglycerol composition, tocopherol content and sterol composition were investigated for their seed oils. The oil content in Yuekexia-2 was the lowest (11.6%), while those in other cultivars ranged from 22.3% to 29.6%. The major fatty acids of C. oleifera seed oils (COSOs) were palmitic acid (16:0, 8.4-11.5%), oleic acid (18:1, 76.3-80.5%), and linoleic acid (18:2, 7.9-12.2%), respectively. Trioleoylglycerol (OOO) was the most abundant triacylglycerol specie (more than 50%) in the COSOs. COSOs contained 21.2-36.4 mg/100 g of α-tocopherol. Seven sterols and squalene were found in all COSOs, while the COSOs showed significant differences in their contents of unsaponifiable matters. The planting region and the cultivar type significantly affected some of the lipid characteristics with the C. oleifera seeds.

Background: The discovery of N‑acylethanolamines (NAEs) has prompted an increase in research aimed at understanding their biological roles including regulation of appetite and energy metabolism. However, a knowledge gap remains to understand the effect of dietary components on NAE levels, in particular, heterogeneity in dietary fatty acid (DFA) profile, on NAE levels across various organs., Objective: To identify and elucidate the impact of diet on NAE levels in seven different tissues/organs of male hamsters, with the hypothesis that DFA will act as precursors for NAE synthesis in golden Syrian male hamsters., Method: A two-month feeding trial was performed, wherein hamsters were fed various dietary oil blends with different composition of 18-C fatty acid (FA)., Results: DFA directly influences tissue FA and NAE levels. After C18:1n9-enriched dietary treatments, marked increases were observed in duodenal C18:1n9 and oleoylethanolamide (OEA) concentrations. Among all tissues; adipose tissue brown, adipose tissue white, brain, heart, intestine-duodenum, intestine-jejunum, and liver, a negative correlation was observed between gut-brain OEA concentrations and body weight., Conclusion: DFA composition influences FA and NAE levels across all tissues, leading to significant shifts in intestinal-brain OEA concentrations. The endogenously synthesized increased OEA levels in these tissues enable the gut-brain-interrelationship. Henceforth, we summarize that the brain transmits anorexic properties mediated via neuronal signalling, which may contribute to the maintenance of healthy body weight. Thus, the benefits of OEA can be enhanced by the inclusion of C18:1n9-enriched diets, pointing to the possible nutritional use of this naturally occurring bioactive lipid-amide in the management of obesity., (Copyright © 2019. Published by Elsevier B.V.)

In the present work, linoleic acid and oleic acid were isolated from Indonesian corn oil and palm oil and they were used to prepare monoacylglycerol derivatives as the antibacterial agent. Indonesian corn oil contains 57.74% linoleic acid, 19.88% palmitic acid, 11.84% oleic acid and 3.02% stearic acid. While Indonesian palm oil contains 44.72% oleic acid, 39.28% palmitic acid, 4.56% stearic acid and 1.54% myristic acid. The oleic acid was purified by using Urea Inclusion Complex (UIC) method and its purity was significantly increased from 44.72% to 94.71%. Meanwhile, with the UIC method, the purity of ethyl linoleate was increased from 57.74% to 72.14%. 1-Monolinolein and 2-monoolein compounds were synthesized via two-step process from the isolated linoleic acid and oleic acid, respectively. The preliminary antibacterial assay shows that the 1-monolinolein did not give any antibacterial activity against Staphylococcus aureus and Escherichia coli, while 2-monoolein showed weak antibacterial activity against Staphylococcus aureus.

Preclinical studies have demonstrated that the endocannabinoid system (ECS) plays an important role in the protection against intestinal inflammation and colorectal cancer (CRC); however, human data are scarce. We determined members of the ECS and related components of the 'endocannabinoidome' in patients with inflammatory bowel disease (IBD) and CRC, and compared them to control subjects. Anandamide (AEA) and oleoylethanolamide (OEA) were increased in plasma of ulcerative colitis (UC) and Crohn's disease (CD) patients while 2-arachidonoylglycerol (2-AG) was elevated in patients with CD, but not UC. 2-AG, but not AEA, PEA and OEA, was elevated in CRC patients. Lysophosphatidylinositol (LPI) 18:0 showed higher levels in patients with IBD than in control subjects whereas LPI 20:4 was elevated in both CRC and IBD. Gene expression in intestinal mucosal biopsies revealed different profiles in CD and UC. CD, but not UC patients, showed increased gene expression for the 2-AG synthesizing enzyme diacylglycerol lipase alpha. Transcripts of CNR1 and GPR119 were predominantly decreased in CD. Our data show altered plasma levels of endocannabinoids and endocannabinoid-like lipids in IBD and CRC and distinct transcript profiles in UC and CD. We also report alterations for less known components in intestinal inflammation, such as GPR119, OEA and LPI.

A novel screening method for the simultaneous detection of elaidic and vaccenic trans fatty acid isomers by CZE-UV was proposed and applied to brazilian spreadable cheese analysis. Optimized background electrolyte was composed by 10 mmol L -1 heptakis (2, 3, 6-tri-o-methyl)-beta cyclodextrin, 24 mmol L -1 sodium tetraborate buffer solution, 45% methanol and 15% acetonitrile. Sample preparation comprised only a saponification reaction and dilution of sample solution before analysis. The method proved to be simple, environmental friendly and sensitive (LOD calculated for elaidic and vaccenic acid were 0.0163 mmol L -1 and 0.0169 mmol L -1 , respectively) and may be used to detect adulteration in dairy products, where the addition of hydrogenated vegetable fat to food is prohibited., (Copyright © 2018 Elsevier B.V. All rights reserved.)

High fatty acid (FA) levels are deleterious to pancreatic β-cells, largely due to the accumulation of biosynthetic lipid intermediates, such as ceramides and diglycerides, which induce ER stress and apoptosis. Toxicity of palmitate (16:0) and oleate (18:1 cis-Δ 9 ) has been widely investigated, while very little data is available on the cell damages caused by elaidate (18:1 trans-Δ 9 ) and vaccenate (18:1 trans-Δ 11 ), although the potential health effects of these dietary trans fatty acids (TFAs) received great publicity. We compared the effects of these four FAs on cell viability, apoptosis, ER stress, JNK phosphorylation and autophagy as well as on ceramide and diglyceride contents in RINm5F insulinoma cells. Similarly to oleate and unlike palmitate, TFAs reduced cell viability only at higher concentration, and they had mild effects on ER stress, apoptosis and autophagy. Palmitate increased ceramide and diglyceride levels far more than any of the unsaturated fatty acids; however, incorporation of TFAs in ceramides and diglycerides was strikingly more pronounced than that of oleate. This indicates a correlation between the accumulation of lipid intermediates and the severity of cell damage. Our findings reveal important metabolic characteristics of TFAs that might underlie a long term toxicity and hence deserve further investigation., (Copyright © 2018. Published by Elsevier Ltd.)

The yeast Starmerella bombicola is known to produce sophorolipids (SLs) by fermentation method. In the fermentative production of SLs, at least three phases i.e. hydrophilic phase of glucose, ions and acidic-form SLs; hydrophobic phase of oil and lactone-form SLs; solid phase of cell biomass and SLs crystals are present in the broth. Therefore, a rapid and real-time detection of residual oil and SLs can provide valuable information in the regulation and optimization of the process to better produce SLs effectively. Looking into the importance, in this study, a rapid, accurate and precise method to quantify the concentrations of oil and SLs using low-field nuclear magnetic resonance (LF-NMR) was developed. Compared to the traditional weighing method, all the parameters for the evaluation of accuracy, precision and relative recovery presented better performances. Moreover, the proposed LF-NMR method could completely avoid using organic solvents that are commonly employed in the weighing method, besides shortening the pre-treatment and detection times from 24 h to just <20 min. Finally, LF-NMR method has been successfully used to monitor residual oil and SLs during the fermentation of Starmerella bombicola to obtain SLs and it has been observed that the production of SLs would be effectively improved by appropriately controlling the concentration of oil in terms of titer, productivity and yield., (Copyright © 2018 Elsevier B.V. All rights reserved.)

During industrial wood drying, extractives migrate towards the wood surfaces and make the material more susceptible to photo/biodegradation. The present work provides information about the distribution, quantity and nature of lipophilic substances beneath the surface in air- and kiln-dried Scots pine (Pinus sylvestris L.) sapwood boards. Samples were taken from knot-free sapwood surfaces and the composition of lipophilic extractives, phenols and low-molecular fatty/resin acids layers at different nominal depths below the surface was studied gravimetrically, by UV-spectrometry and by gas chromatography-mass spectrometry (GC-MS). The concentration of total extractives was significantly higher in kiln-dried than in air-dried samples and was higher close to the surface than in the layers beneath. The scatter in the values for the lipophilic extractives was high in both drying types, being highest for linoleic acid and slightly lower for palmitic, oleic and stearic acids. The amount of fatty acids was low in kiln-dried boards, probably due to a stronger degradation due to the high temperature employed. The most abundant resin acid was dehydroabietic acid followed by pimaric, isopimaric, and abietic acids in both drying types. It is concluded that during kiln-drying a migration front is created at a depth of 0.25 mm with a thickness of about 0.5 mm., Competing Interests: The authors have declared that no competing interests exist.

Oxylipins are bioactive mediators that play diverse roles in (patho)physiology. We developed a sensitive and selective ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method for the simultaneous profiling of 57 targeted oxylipins derived from five major n-6 and n-3 polyunsaturated fatty acids (PUFAs) that serve as oxylipin precursors, including linoleic (LA), arachidonic (AA), alpha-linolenic (ALA), eicosapentaenoic (EPA), and docosahexaenoic (DHA) acids. The targeted oxylipin panel provides broad coverage of lipid mediators and pathway markers generated from cyclooxygenases, lipoxygenases, cytochrome P450 epoxygenases/hydroxylases, and non-enzymatic oxidation pathways. The method is based on combination of protein precipitation and solid-phase extraction (SPE) for sample preparation, followed by UPLC-MS/MS. This is the first methodology to incorporate four hydroxy-epoxy-octadecenoic acids and four keto-epoxy-octadecenoic acids into an oxylipin profiling network. The novel method achieves excellent resolution and allows in-depth analysis of isomeric and isobaric species of oxylipin extracts in biological samples. The method was quantitatively characterized in human plasma with good linearity (R = 0.990-0.999), acceptable reproducibility (relative standard deviation (RSD) < 20% for the majority of analytes), accuracy (67.8 to 129.3%) for all analytes, and recovery (66.8-121.2%) for all analytes except 5,6-EET. Ion enhancement effects for 28% of the analytes in tested concentrations were observed in plasma, but were reproducible with RSD < 17.2%. Basal levels of targeted oxylipins determined in plasma and serum are in agreement with those previously reported in literature. The method has been successfully applied in clinical and preclinical studies.

In this study, physico-chemical properties of raw and roasted tigernut oils extracted by two different solvents were determined. Peroxide values of raw and roasted tigernut oils extracted by petroleum ether and n-hexane solvents changed between 0.83 and 0.91 meqO 2 /100g to 1.57 and 1.63 meqO 2 /100g, respectively. While oleic acid contents of raw tigernut oils extracted by petroleum ether and n-hexane are determined as 66.83 and 67.47%, oleic acid contents of roasted tigernut oils extracted by petroleum ether and n-hexane were determined as 67.08 and 68.16%, respectively. The highest δ-tocopherol content was found in raw tigernut oil extracted by petroleum ether (54.91 mg/100g), while the lowest level is determined in roasted tigernut oil by n-hexane (50.77 mg/100g). As a result, the fatty acid profiles of roasted tigernut oil extracted by n-hexane were higher compared to results of raw tigernut oils extracted by petroleum ether (p < 0.05).

Chain length and degree of saturation plays an important role for the characteristics of various products derived from fatty acids, such as fuels, cosmetics, and food additives. The seeds of Theobroma cacao are the source of cocoa butter, a natural lipid of high interest for the food and cosmetics industry. Cocoa butter is rich in saturated fatty acids that are stored in the form of triacylglycerides (TAGs). One of the major TAG species of cocoa butter, consisting of two stearic acid molecules and one oleic acid molecule (stearic acid-oleic acid-stearic acid, sn-SOS), is particularly rare in nature as the saturated fatty acid stearic acid is typically found only in low abundance. Demand for cocoa butter is increasing, yet T. cacao can only be cultivated in some parts of the tropics. Alternative means of production of cocoa butter lipids (CBLs) are, therefore, sought after. Yeasts also store fatty acids in the form of TAGs, but these are typically not rich in saturated fatty acids. To make yeast an attractive host for microbial production of CBLs, its fatty acid composition needs to be optimized. We engineered Saccharomyces cerevisiae yeast strains toward a modified fatty acid synthesis. Analysis of the fatty acid profile of the modified strains showed that the fatty acid content as well as the titers of saturated fatty acids and the titers of TAGs were increased. The relative content of potential CBLs in the TAG pool reached up to 22% in our engineered strains, which is a 5.8-fold increase over the wild-type. SOS content reached a level of 9.8% in our engineered strains, which is a 48-fold increase over the wild type., (© 2018 Wiley Periodicals, Inc.)

Trichoderma species are a rich source of metabolites, but less known for biomedical potential. This work deals with antibacterial and antioxidant potentials of intracellular non-cytotoxic metabolites, extracted from Trichoderma atroviride (KNUP001). A total of 53 fractions was collected by column chromatography and tested for cytotoxicity by MTT assay. Only one fraction (F41) was found to be non-toxic to Vero cells with 95.4 ± 0.61% of survival. The F41 was then subjected to chemical analysis, antibacterial and antioxidant assays. The F41 at 500 μg ml -1 showed the total antioxidant of 48.70 ± 2.90%, DPPH radical scavenging activity of 37.25 ± 2.25, nitric oxide (NO) radical scavenging activity of 54.55 ± 1.95 and H 2 O 2 radical scavenging activity of 43.75 ± 3.21. The F41 at 25 μg ml -1 displayed antibacterial activity against E. coli (14.25 ± 0.25 mm), Proteus mirabilis (10.40 ± 0.60 mm), and Enterobacter aerogenes (5.60 ± 0.40 mm). GC-MS analysis revealed the dominant presence of oleic acid C 18.1 (63.18%), n-hexadecanoic acid (6.17%), and ethyl oleate (4.93%) in the F41, and hence these fatty acids are likely responsible for the antioxidant and antibacterial activities of F41. Hence, further investigation deserves on purification and characterization of the active metabolites from T. atroviride strain KNUP001 towards developing molecular leads to effective antibacterial drugs, and non-toxic to host cells., (Copyright © 2018. Published by Elsevier Ltd.)

Oil content and bioactive properties of almond and walnut kernels were investigated in developing almond and walnut kernels at 10 days intervals. The oil contents of almond and walnuts after the first harvest (1.H) stage changed between 46.2% and 55.0% to 39.1% and 70.5%, respectively (p<0.05). Oleic acid contents of almond and walnut oils ranged from 71.98% (1.H) to 78.68% (5.H) and 10.51% (1.H) to 16.78% (2.H) depending on harvest (H) times, respectively (p<0.05). In addition, linolenic acid contents of walnut and almond oils were found between 62.35% and 67.78%, and 12.02% and 17.65%, respectively. The almond kernel oil after the first harvest stage contained 1.045, 1.058, 1.018, 0.995 and 0.819 mg/kg ɑ-tocopherol, respectively. γ-Tocopherol contents of walnut oil changed between 1.364 (3.H) and 2.954 mg/kg (1.H). The β-sitosterol contents of both almond and walnut oils were found between 1956.6 (5.H) and 2557.7 (1.H), and 1192.1 (3.H) and 4426.4 mg/kg (1.H). The study exhibited the presence of high percentage of oleic and linoleic for almond and walnut, respectively, and γ-tocopherol and β-sitosterol.

The objective of this study was to evaluate the effects of varying the ratio of dietary palmitic (C16:0), stearic (C18:0), and oleic (cis-9 C18:1) acids in basal diets containing soyhulls or whole cottonseed on nutrient digestibility, energy partitioning, and production response of lactating dairy cows. Twenty-four mid-lactation multiparous Holstein cows were used in a split-plot Latin square design. Cows were allocated to a main plot receiving either a basal diet with soyhulls (SH, n = 12) or a basal diet with whole cottonseed (CS, n = 12) that was fed throughout the experiment. Within each plot a 4 × 4 Latin square arrangement of treatments was used in 4 consecutive 21-d periods. Treatments were (1) control (CON; no supplemental fat), (2) high C16:0 supplement [PA; fatty acid (FA) supplement blend provided ∼80% C16:0], (3) C16:0 and C18:0 supplement (PA+SA; FA supplement blend provided ∼40% C16:0 + ∼40% C18:0), and (4) C16:0 and cis-9 C18:1 supplement (PA+OA; FA supplement blend provided ∼45% C16:0 + ∼35% cis-9 C18:1). Interactions between basal diets and FA treatments were observed for dry matter intake (DMI) and milk yield. Among the SH diets, PA and PA+SA increased DMI compared with CON and PA+OA treatments, whereas in the CS diets PA+OA decreased DMI compared with CON. The PA, PA+SA, and PA+OA treatments increased milk yield compared with CON in the SH diets. The CS diets increased milk fat yield compared with the SH diets due to the greater yield of de novo and preformed milk FA. The PA treatment increased milk fat yield compared with CON, PA+SA, and PA+OA due to the greater yield of mixed-source (16-carbon) milk FA. The PA treatment increased 3.5% fat-corrected milk compared with CON and tended to increase it compared with PA+SA and PA+OA. The CS diets increased body weight (BW) change compared with the SH diets. Additionally, PA+OA tended to increase BW change compared with CON and PA and increased it in comparison with PA+SA. The PA and PA+OA treatments increased dry matter and neutral detergent fiber digestibility compared with PA+SA and tended to increase them compared with CON. The PA+SA treatment reduced 16-carbon, 18-carbon, and total FA digestibility compared with the other treatments. The CS diets increased energy partitioning toward body reserves compared with the SH diets. The PA treatment increased energy partitioning toward milk compared with CON and PA+OA and tended to increase it compared with PA+SA. In contrast, PA+OA increased energy partitioned to body reserves compared with PA and PA+SA and tended to increase it compared with CON. In conclusion, milk yield responses to different combinations of FA were affected by the addition of whole cottonseed in the diet. Among the combinations of C16:0, C18:0, and cis-9 C18:1 evaluated, fat supplements with more C16:0 increased energy output in milk, whereas fat supplements with more cis-9 C18:1 increased energy storage in BW. The combination of C16:0 and C18:0 reduced nutrient digestibility, which most likely explains the lower performance observed compared with other treatments., (Copyright © 2018 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.)

Fatty acids are some of the most important components of human milk. Polyunsaturated fatty acids (PUFAs) are essential nutrients required for the optimal growth and development of infants, especially the central nervous system, brain and retina., Aim: To determine the conjugated linolenic acid (CLA) and vaccenic acid (VA) content of human breast milk from mothers consuming different diets, and to compare the results with CLA and VA levels in infant formulas (IF) and follow-up formulas (FF)., Material and Methods: Fifty healthy mothers were classified according to their diet status into one of two groups: diet low in dairy products and conventional diet without limiting the intake of dairy products. Dietary intake of dairy fat was determined based on 3-day food diaries. Fatty acid (FA) composition in samples were analyzed by High Resolution Gas Chromatography (HR-GC)., Results: In the group of 20 mothers whose diets were deficient in dairy products, the average CLA content of breast milk fat was determined to be 0.27% of total FA, the VA 0.36%. In the group of 30 women consuming dairy products, the average content of CLA and VA in breast milk fat was statistically significantly higher: 0.49% and 0.69% of total FAs, respectively. In the fat of the IF and FF tested (n=11) only trace amounts of both FA were found., Conclusion: The results of the study indicate that CLA and VA concentrations of human milk can be influenced by diet. It is recommended that the source of these FAs in the diet of breastfeeding women are natural products and not dietary supplements. The majority of commercially available IF and FF do not contain sufficient amounts of CLA and VA, and that their FA composition is deficient in comparison with breast milk fat.

Background: Cannabis-based drugs have been shown to be effective in inflammatory diseases. A number of endocannabinoids including N- arachidonoylethanolamide (anandamide, AEA) and 2-arachidonyl glycerol (2-AG) with activity at the cannabinoid receptors (CBR) CBR1 and CBR2, have been identified. Other structurally related endogenous fatty acid compounds such as oleoylethanolamide (OEA) and palmitoyl ethanolamide (PEA) have been identified in biological tissues. These compounds do not bind to CBR but might be involved in facilitating the actions of directly acting endocannabinoids and thus are commonly termed "entourage" compounds due to their ability to modulate the endocannabinoid system. The aim of this study was to evaluate the presence of endocannabinoids and entourage compounds in the synovial fluid of dogs with osteoarthritis subjected to arthrotomy of the knee joint. Cytokines and cytology were studied as well., Results: AEA, 2-AG, OEA and PEA were all present in the synovial fluid of arthritic knees and in the contralateral joints; in addition, a significant increase of OEA and 2AG levels were noted in SF from OA knees when compared to the contralateral joints., Conclusion: The identification and quantification of endocannabinoids and entourage compounds levels in synovial fluids from dogs with OA of the knee is reported for the first time. Our data are instrumental for future studies involving a greater number of dogs. Cannabinoids represent an emerging and innovative pharmacological tool for the treatment of OA and further studies are warranted to evaluate the effectiveness of cannabinoids in veterinary medicine.

The objective of the present experiment was to determine if carcass quality and fatty acid profiles of longissimus thoracis (LT) and hamburger would be affected by feeding steers extruded flaxseed on its own followed by hay (non-TMR) compared to when hay and extruded flaxseed were fed together (TMR). Forty-eight steers in six pens were assigned to TMR or non-TMR for an average of 242days. Dry matter intake was lower for non-TMR versus TMR steers (10.56 vs. 11.42kg/d; P=0.02), but final live weight (610±0.50kg) and average daily gain (1.18±0.02kg/d) did not differ. Compared to TMR, feeding non-TMR enriched LT and hamburger with α-linolenic acid (ALA; 18:3n-3) by 14%, vaccenic acid (VA; t11-18:1) by 44%, rumenic acid (RA; c9,t11-18:2) by 40%, and conjugated linolenic acid (CLnA) by 58%. Overall, feeding extruded flaxseed separately from hay in a non-TMR was more effective at enhancing deposition of ALA, VA, RA and CLnA in beef., (Crown Copyright © 2017. Published by Elsevier Ltd. All rights reserved.)

The regulation of lipid synthesis in oil seeds is still not fully understood. Oilseed rape ( Brassica napus ) is the third most productive vegetable oil crop on the global market; therefore, increasing our understanding of lipid accumulation in oilseed rape seeds is of great economic, as well as intellectual, importance. Matrix-assisted laser/desorption ionization-mass spectrometry imaging (MALDI-MSI) is a technique that allows the mapping of metabolites directly onto intact biological tissues, giving a spatial context to metabolism. We have used MALDI-MSI to study the spatial distribution of two major lipid species, triacylglycerols and phosphatidylcholines. A dramatic, heterogenous landscape of molecular species was revealed, demonstrating significantly different lipid compositions between the various tissue types within the seed. The embryonic axis was found to be particularly enriched in palmitic acid, while the seed coat/aleurone layer accumulated vaccenic, linoleic, and α-linoleic acids. Furthermore, the lipid composition of the inner and outer cotyledons differed from each other, a remarkable discovery given the supposed identical functionality of these two tissues. Triacylglycerol and phosphatidylcholine molecular species distribution was analyzed through a developmental time series covering early seed lipid accumulation to seed maturity. The spatial patterning of lipid molecular species did not vary significantly during seed development. Data gathered using MALDI-MSI was verified through gas chromatography analysis of dissected seeds. The distinct lipid distribution profiles observed imply differential regulation of lipid metabolism between the different tissue types of the seed. Further understanding of this differential regulation will enhance efforts to improve oilseed rape productivity and quality., (© 2017 The author(s). All Rights Reserved.)

Hair testing for alcohol biomarkers is an important tool for monitoring alcohol consumption. We propose two methods for assessing alcohol exposure through combined analysis of ethyl glucuronide (EtG) and fatty acid ethyl esters (FAEEs) species (ethyl myristate, palmitate, stearate and oleate) in hair (30 mg). EtG was analysed by liquid chromatography-tandem mass spectrometry, while FAEEs were analysed by gas chromatography-tandem mass spectrometry using electron impact ionization. Both methods were validated according to internationally accepted guidelines. Linearity was proven between 3 and 500 pg/mg for EtG and 30-5000 pg/mg for FAEEs, and the limits of quantification were 3 pg/mg for EtG and 30 pg/mg for each of the four FAEEs. Precision and accuracy were considered adequate, processed EtG samples were found to be stable for up to 96 h left in the injector and processed FAEEs samples for up to 24 h. Matrix effects were not significant. Both methods were applied to the analysis of 15 authentic samples, using the cut-off values proposed by the Society of Hair Testing for interpretation. The results agreed well with the self-reported alcohol consumption in most cases, and demonstrated the suitability of the methods to be applied in routine analysis of alcohol biomarkers, allowing monitoring consumption using low sample amounts., (Copyright © 2016 John Wiley & Sons, Ltd.)

Background: Crude camellia seed oil is rich in free fatty acids, which must be removed to produce an oil of acceptable quality. In the present study, we reduced the free fatty acid content of crude camellia seed oil by lipophilization of epicatechin with these free fatty acids in the presence of Candida antarctica lipase B (Novozym 435), and this may enhance the oxidative stability of the oil at the same time., Results: The acid value of crude camellia seed oil reduced from 3.7 to 2.5 mgKOH g -1 after lipophilization. Gas chomatography-mass spectrometry analysis revealed that epicatechin oleate and epicatechin palmitate were synthesized in the lipophilized oil. The peroxide, p-anisidine, and total oxidation values during heating of the lipophilized oil were much lower than that of the crude oil and commercially available camellia seed oil, suggesting that lipophilized epicatechin derivatives could help enhance the oxidative stability of edible oil., Conclusion: The enzymatic process to lipophilize epicatechin with the free fatty acids in crude camellia seed oil described in the present study could decrease the acid value to meet the quality standards for commercial camellia seed oil and, at the same time, obtain a new edible camellia seed oil product with good oxidative stability. © 2016 Society of Chemical Industry., (© 2016 Society of Chemical Industry.)

A method was developed for analyzing broad spectrum small molecule metabolites in the serum of hepatocellular carcinoma (HCC) patients based on ultrafast liquid chromatography-ion trap-time of flight tandem mass spectrometry (UFLC-IT-TOF MS). Serum samples were collected from 80 HCC patients and healthy persons. After pretreatment process for protein precipitation, the supernatant was analyzed with the UFLC-IT-TOF MS to obtain information on the metabonomics of small molecules. The eight compounds of glycocholic acid, choline glycerophosphate, acetyl-L-phenylalanine, oleamide, tetradecanamide, acetylcarnitine, lysolecithin and glycochenodeoxycholic acid in the HCC group were identified with significant differences from those in the health group (P <0.01). By using multidimensional analysis of variation coefficient and principal component analysis for the repeatability and 48 h stability, the method was demonstrated to have good repeatability, excellent precision, and high stability, which can satisfy the metabonomics research requirement. The high throughput and practical usability of the method further shows perspective for metabonomic analysis of large-batch serum samples.

The purpose of this study was to investigate the trans fatty acids (TFA) content and distribution in colostrum, mature milk, and diet of adolescent mothers, after TFA declaration in food labels became mandatory in Brazil. Participants were healthy adolescents (n 54, 15-19 years, 1-90 days postpartum) practicing exclusive breastfeeding. Milk samples were collected 3 days after delivery (colostrum) and in the third month postpartum (mature milk) by hand expression. The fatty acid composition of the milk samples was determined by gas chromatography. TFA intake corresponded to 1.23 % of total energy value. Total 18:2 TFA accounted for less than 0.5 % of the energy intake. The amount of total 18:1 TFA (mean ± SEM) was 1.9 % ± 0.14 in colostrum and 1.5 % ± 0.2 in mature milk. The total content of n-3 PUFA was inversely correlated with the total content of 18:1 TFA in colostrum. Both in colostrum and in mature milk, vaccenic acid (11t-18:1) was found to be the most abundant 18:1 trans isomer, followed by elaidic acid (9t-18:1), whereas rumenic acid (9c,11t-18:2 CLA) was the predominant 18:2 trans isomer. In conclusion, the levels of TFA of industrial sources found in the mother's diet and breast milk (colostrum and mature milk) showed a decrease in relation to those observed in studies conducted prior to the TFA labeling resolution in Brazil. However, the current low intake levels of n-3 LCPUFA and DHA content in the milk of lactating adolescents may be insufficient for supporting adequate neurological development of the infants.

This study compared the productive and nutritional parameters of milk from crossbred lactating cows managed on Panicum maximum Jacq. cv. Tanzania and with a diet supplemented with different pressed oilseed cakes. The supplements used were as follows: peanut cake, sunflower cake and palm kernel cake for replacement of soybean meal. Sixteen cows with an average weight of 544 ± 57 kg and producing 8 ± 1.4 L of milk per day were used in this study. The animals were randomly assigned to the treatments according to a Latin square design repeated over time, with four treatments, 16 animals and four experimental periods. Supplementation of the diet with peanut cake, sunflower cake and palm kernel cake compared with soybean meal in the diet of cows did not affect the average daily production or composition of the milk. The palm kernel cake promoted an increase in lauric fatty acids (C 12:0 ) and palmitoleic acids (C 16:1 ) (5.02 and 1.65%, respectively) compared with peanut cake and sunflower cake (4.13 and 4.01%, respectively). The levels of oleic fatty acids (C 18:1 ) were higher for the sunflower cake and palm kernel cake supplements (26.01 and 25.01%, respectively) compared with peanut cake (23.11%). The replacement of soybean meal with sunflower cake and palm kernel cake improved the nutritional quality of the milk, with lower concentrations of saturated fatty acids and higher concentrations of unsaturated fatty acids, without compromising the production or nutritional composition of the milk. © 2015 Japanese Society of Animal Science., (© 2015 Japanese Society of Animal Science.)

This article reviews opportunities for enriching the lipids of meat with n-3 fatty acids and conjugated linoleic acids (CLAs), both considered beneficial to human health. Special focus is put on feeds available and research carried out in Thailand. A differentiated consideration concerning the value of different n-3 fatty acids and isomers of CLAs is necessary. In ruminants, it is difficult to enrich the meat with n-3 fatty acids due to the extensive ruminal biohydrogenation of unsaturated fatty acids, but several possibilities to enhance the proportion of the most desired CLA isomer, rumenic acid, exist. By contrast, pork and poultry meat can be easily enriched with n-3 fatty acids. With purified CLA sources, CLAs also can be enhanced, but it is difficult to achieve this exclusively for rumenic acid. An interesting approach might consist in supplementing the CLA precursor vaccenic acid instead. Possible constraints for meat quality and in the fatty acid levels achieved are outlined., (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Coriander vegetable oil was extracted from fruits of French origin in a 23% yield. The oil was of good quality, with a low amount of free fatty acids (1.8%) and a concurrently high amount of triacylglycerols (98%). It is a rich source of petroselinic acid (C18:1n-12), an important renewable building block, making up 73% of all fatty acids, with also significant amounts of linoleic acid (14%), oleic acid (6%), and palmitic acid (3%). The oil was characterized by a high unsaponifiable fraction, comprising a substantial amount of phytosterols (6.70 g/kg). The main sterol markers were β-sitosterol (35% of total sterols), stigmasterol (24%), and Δ⁷-stigmastenol (18%). Squalene was detected at an amount of 0.2 g/kg. A considerable amount of tocols were identified (500 mg/kg) and consisted mainly of tocotrienols, with γ-tocotrienol as the major compound. The phospholipid content was low at 0.3%, of which the main phospholipid classes were phosphatidic acid (33%), phosphatidylcholine (25%), phosphatidylinositol (17%), and phosphatidylethanolamine (17%). About 50% of all phospholipids were non-hydratable. The β-carotene content was low at 10 mg/kg, while a significant amount of chlorophyll was detected at about 11 mg/kg. An iron content of 1.4 mg/kg was determined through element analysis of the vegetable oil. The influence of fruit origin on the vegetable oil composition was shown to be very important, particularly in terms of the phospholipids, sterols, and tocols composition.

The endocannabinoid system is important in various physiological pathways, especially the regulation of food intake. It consists of endocannabinoids like 2-arachidonoyl-glycerol (2-AG) or the fatty acid ethanolamide archachidonoyl-ethanolamide (AEA) with binding affinity to cannabinoid receptors. Further, fatty acid ethanolamides (FAEAs) influence the endocannabinoid system without affecting cannabinoid receptors by using independent physiological pathways. Among FAEAs, oleic acid ethanolamide (OEA) gained importance because of its promising ability to reduce food intake. By ultrahigh-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UHPLC-ESI-MS/MS), we detected a chromatographically separated molecule in plasma samples from rats and humans with identical mass and fragmentation patterns as those of OEA. Via synthesis and extensive analysis of ethanolamides of different cis/trans- and position isomers of oleic acid (cis9-18:1), we could identify the unknown molecule as vaccenic acid (cis11-18:1) ethanolamide (VEA). In this study we identified VEA as the most abundant 18:1 FAEA in rat plasma and the second most abundant 18:1 FAEA in human plasma.

Fatty acid amides from plant root exudates, such as oleamide and erucamide, have the ability to participate in strong plant-microbe interactions, stimulating nitrogen metabolism in rhizospheric bacteria. However, mechanisms of secretion of such fatty acid amides, and the nature of their stimulatory activities on microbial metabolism, have not been examined. In the present study, collection, pre-treatment, and determination methods of oleamide and erucamide in duckweed root exudates are compared. The detection limits of oleamide and erucamide by gas chromatography (GC) (10.3ngmL(-1) and 16.1ngmL(-1), respectively) are shown to be much lower than those by liquid chromatography (LC) (1.7 and 5.0μgmL(-1), respectively). Quantitative GC analysis yielded five times larger amounts of oleamide and erucamide in root exudates of Spirodela polyrrhiza when using a continuous collection method (50.20±4.32 and 76.79±13.92μgkg(-1) FW day(-1)), compared to static collection (10.88±0.66 and 15.27±0.58μgkg(-1) FW day(-1)). Furthermore, fatty acid amide secretion was significantly enhanced under elevated nitrogen conditions (>300mgL(-1)), and was negatively correlated with the relative growth rate of duckweed. Mechanistic assays were conducted to show that erucamide stimulates nitrogen removal by enhancing denitrification, targeting two key denitrifying enzymes, nitrate and nitrite reductases, in bacteria. Our findings significantly contribute to our understanding of the regulation of nitrogen dynamics by plant root exudates in natural ecosystems., (Copyright © 2016 Elsevier GmbH. All rights reserved.)

This study evaluated the effect of dietary inclusion of grape seed and linseed, alone or in combination, on sheep milk fatty acids (FA) profile using 24 Sarda dairy ewes allocated to 4 isoproductive groups. Groups were randomly assigned to 4 dietary treatments consisting of a control diet (CON), a diet including 300 g/d per animal of grape seed (GS), a diet including 220 g/d per animal of extruded linseed (LIN), and a diet including a mix of 300 g/d per animal of grape seed and 220 g/d per animal of extruded linseed (MIX). The study lasted 10 wk, with a 2-wk adaptation period and an 8-wk experimental period. Milk FA composition was analyzed in milk samples collected in the last 4 wk of the trial. The milk concentration of saturated fatty acids (SFA) decreased and that of unsaturated, monounsaturated, and polyunsaturated fatty acids (UFA, MUFA, and PUFA, respectively) increased in GS, LIN, and MIX groups compared with CON. The MIX group showed the lowest values of SFA and the highest of UFA, MUFA, and PUFA. Milk from ewes fed linseed (LIN and MIX) showed an enrichment of vaccenic acid (VA), oleic acid (OA), α-linolenic acid (LNA), and cis-9,trans-11 conjugated linoleic acid (CLA) compared with milk from the CON group. The GS group showed a greater content of milk oleic acid (OA) and linoleic acid (LA) and tended to show a greater content of VA and cis-9,trans-11 CLA than the CON group. The inclusion of grape seed and linseed, alone and in combination, decreased the milk concentration of de novo synthesized FA C10:0, C12:0, and C14:0, with the MIX group showing the lowest values. In conclusion, grape seed and linseed could be useful to increase the concentration of FA with potential health benefits, especially when these ingredients are included in combination in the diet., (Copyright © 2016 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.)

A new vacuum ultraviolet (VUV) detector for gas chromatography was recently developed and applied to fatty acid methyl ester (FAME) analysis. VUV detection features full spectral acquisition in a wavelength range of 115-240nm, where virtually all chemical species absorb. VUV absorption spectra of 37 FAMEs, including saturated, monounsaturated, and polyunsaturated types were recorded. Unsaturated FAMEs show significantly different gas phase absorption profiles than saturated ones, and these classes can be easily distinguished with the VUV detector. Another advantage includes differentiating cis/trans-isomeric FAMEs (e.g. oleic acid methyl ester and linoleic acid methyl ester isomers) and the ability to use VUV data analysis software for deconvolution of co-eluting signals. As a universal detector, VUV also provides high specificity, sensitivity, and a fast data acquisition rate, making it a powerful tool for fatty acid screening when combined with gas chromatography. The fatty acid profile of several food oil samples (olive, canola, vegetable, corn, sunflower and peanut oils) were analyzed in this study to demonstrate applicability to real world samples., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

A method to prepare fatty acid methyl esters was developed for fatty acid analysis of triacylglycerols by gas chromatography (GC). Triacylglycerols were mixed with methanolic CH3ONa in hexane containing a mid-polar solvent for 10 s at room temperature. Under these conditions, trioleoylglycerol was converted to methyl oleate with an average yield of 99.3%. This procedure gave reliable and reproducible data on fatty acid compositions determined by GC., (Copyright © 2015 Elsevier Inc. All rights reserved.)

Cuticular hydrocarbons (CHCs) in Drosophila melanogaster represent the basis of chemical communication being involved in many important biological functions. The aim of this study was to characterize chemical composition and variation of cuticular profiles in five D. melanogaster strains. These strains were reared for approximately 300 generations on five diets: standard cornmeal medium and substrates prepared with apple, banana, tomato, and carrot. Differences in quantity and/or quality in CHCs were assumed as a result of activation of different metabolic pathways involved in food digestion and adaptations to the particular diet type. In total, independently of sex and strain, 66 chemical compounds were identified. In females of all strains, 60 compounds were identified, while, in males, 47 compounds were extracted. Certain new chemical compounds for D. melanogaster were found. MANOVA confirmed that CHC amounts significantly depend on sex and substrates, as well as on their interactions. Discriminant analysis revealed that flies belonging to 'apple' and 'carrot' strains exhibited the most noticeable differences in CHC repertoires. A non-hydrocarbon pheromone, cis-vaccenyl acetate (cVA) also contributed to the variation in the pheromone bouquet among the strains. Variability detected in CHCs and cVA may be used in the explanation of differences in mating behaviour previously determined in analyzed fly strains., (Copyright © 2016 Verlag Helvetica Chimica Acta AG, Zürich.)

This study evaluates the effect of the replacement of cereals by dried citrus pulp (DCP) in diets supplemented with 5% of soybean oil, on ewe milk yield and composition, including milk fatty acid (FA). Four Serra da Estrela multiparous ewes in the second month of lactation were used in a double 2×2 Latin square design. Ewes were individually penned and milked twice a day with an 8-h interval. Each experimental period included 14 d of diet adaptation followed by 5d of measurements and sampling. The 2 diets included on dry matter basis 450 g/kg of corn silage and 550 g/kg of either a soybean oil-supplemented concentrate meal containing barley and maize (cereal) or dried citrus pulp (DCP; citrus). Feed was offered ad libitum, considering 10% of orts, and intake was measured daily. Milk yield was higher and dry matter intake tended to be higher with the citrus diet. Milk composition and technological properties for cheese production were not affected by treatments, except for lactose, which was lower with the citrus diet. Replacement of cereals by DCP resulted in a 3-percentage-point decrease of both 18:0 and cis-9-18:1 that were mostly compensated by the 4.19- and 1.68-percentage-point increases of trans-11-18:1 and cis-9,trans-11-18:2, respectively. The intake of C18 FA tended to increase with the citrus diet compared with the cereal diet, but the apparent transfer of 18:2n-6 and of 18:3n-3 did not differ between diets. The milk output of C18 FA increased with the citrus compared with the cereal diet, mostly due to the increase of trans-11-18:1 and cis-9,trans-11-18:2 because the daily milk output of 18:0, trans-10-18:1, cis-9-18:1, 18:2n-6 and 18:3n-3 did not differ between diets. Replacing cereals with DCP in an oil-supplemented diet resulted in a selective increase of trans-11-18:1 and cis-9,trans-11-18:2 in milk, with no major effect on other biohydrogenation intermediates., (Copyright © 2016 American Dairy Science Association. Published by Elsevier Inc. All rights reserved.)

HPMC capsules are made by a dipping process and a surface lubricant for the mould pins is an essential processing aid for removing dried capsules shells. For the purpose of this study, the level was determined by quantifying methyloleate (MO) a component found in the lubricant but not in the hypromellose capsules. Here we investigated the influence of the lubricant, low (10.81 μg/capsule=60 mg/kg MO), medium (15.97 μg/capsule=90 mg/kg MO) and high (23.23 μg/capsule=127 mg/kg MO) content on powder (binary mixture of salbutamol: lactose, 1:50 w/w) aerosolization properties was investigated. Results indicated significantly lower emitted dose from capsules with 60 mg/kg MO. Furthermore, the 90 and 127 mg/kg MO level of lubricant capsules produced almost double the Fine Particle Dose & Fine Particle Fraction compared with the low level of lubricant. The data indicates that lubricant level within capsules has an influence on deposition profiles and amount of drug remaining in capsule and inhaler device after actuation. It is suggested lubricant levels greater than 60 mg/kg MO per capsule are required to minimise powder retention within capsules and maximise deposition profiles. AFM (atomic force microscopy) data suggest that internal surface roughness may be related with this phenomena., (Copyright © 2015 The Authors. Published by Elsevier B.V. All rights reserved.)