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1.
Food Res Int ; 157: 111025, 2022 07.
Article En | MEDLINE | ID: mdl-35761513

The unique geographical characteristics and food culture of Tibet can affect the nutrition of human milk lipids. But little has been done in the comparison of the lipids between Tibet and other areas. This study gives in-depth analysis of the species, concentration and composition of lipid subclasses at the molecular level of the Tibetan human milk. There were averagely 132 ± 30 species of lipids, among which triglycerides (TAGs), phosphatidylethanolamine (PE) and sphingomyelin (SM) accounted for 79.78% of the total species number in the Tibetan human milk samples. The contents of TAG, SM, phosphatidylcholine (PC), and PE in the Tibetan human milk were 85.84%, 17.79%, 25.94% and 55.81% of those in the comparative human milk of China, respectively. The contents of TAGs and diglycerides (DAGs) with PUFAs in Tibetan human milk were significantly lower than those in the comparative group. However, the content and percentage of TAGs and DAGs with odd-chain saturated fatty acids were both higher in the Tibetan human milk than those in the comparative human milk. In total, 18 molecular species of lipids were downregulated and 5 ones were upregulated in the Tibetan human milk compared with those in the comparative human milk of China. The profile of lipids in the Tibetan human milk at the molecular level provided the scientific basis for maternal diet and supplemented the Chinese human milk lipids database.


Milk, Human , Phospholipids , Diglycerides , Fatty Acids/analysis , Glycerides/analysis , Humans , Milk, Human/chemistry , Phospholipids/analysis , Tibet , Triglycerides/analysis
2.
Nutrients ; 13(7)2021 Jul 03.
Article En | MEDLINE | ID: mdl-34371807

The endocannabinoid system is involved in the regulation of a variety of physiological and cognitive processes. While the endocannabinoids 2-arachidonoylglycerol (2-AG) and anandamide (N-arachidonoylethanolamine, AEA) have been found in breast milk, their role(s) have yet to be determined. This study determined the normal concentration ranges of endocannabinoids (2-AG and AEA) in breast milk and the influences, if any, of obesity and diurnal rhythms on their levels. Milk samples were collected from 36 breastfeeding mothers at 4-8 weeks postpartum at each feed over a 24-h period, and further stratified into three groups based on body mass index (BMI). The samples were analyzed using liquid chromatography mass spectrometry. AEA was below the limit of detection and 2-AG levels averaged 59.3 ± 18.3 ng/mL (± SD) in women with normal BMI. Wide-ranging 2-AG concentrations in the overweight (65.5 ± 41.9 ng/mL) /obese (66.1 ± 40.6 ng/mL) groups suggest BMI may be a contributing factor influencing its levels. Following a diurnal pattern, there was a significantly higher 2-AG concentration observed during the day, as compared to night time samples. In conclusion, our study clearly suggests that appropriate milk collection and storage conditions are critical. Further, body weight and diurnal rhythm appear to influence levels of 2-AG. Based on these results, future studies are underway to determine what specific roles endocannabinoids may play in human milk and how elevated levels of 2-AG may modulate infant appetite and health.


Arachidonic Acids/analysis , Circadian Rhythm/physiology , Endocannabinoids/analysis , Glycerides/analysis , Milk, Human/chemistry , Obesity/metabolism , Polyunsaturated Alkamides/analysis , Adult , Body Mass Index , Chromatography, Liquid , Female , Humans , Longitudinal Studies , Mass Spectrometry , Maternal Nutritional Physiological Phenomena , Overweight/physiopathology
3.
Sensors (Basel) ; 21(2)2021 Jan 12.
Article En | MEDLINE | ID: mdl-33445599

In this study, a novel approach was developed to quantify endocannabinoids (eCBs), and was based on the liquid biosensor BIONOTE. This device is composed of a probe that can be immersed in a solution, and an electronic interface that can record a current related to the oxy-reductive reactions occurring in the sample. The two most representative members of eCBs have been analysed in vitro by BIONOTE: anandamide (N-arachidonoylethanolamine, AEA) and 2-arachidonoylglycerol (2-AG). Bovine serum albumin was used to functionalize the probe and improve the sensibility of the whole analytical system. We show that BIONOTE is able to detect both AEA and 2-AG at concentrations in the low nanomolar range, and to discriminate between these eCBs and their moieties arachidonic acid, ethanolamine and glycerol. Notably, BIONOTE distinguished these five different molecules, and it was also able to quantify AEA in human plasma. Although this is just a proof-of-concept study, we suggest BIONOTE as a cheap and user-friendly prototype sensor for high throughput quantitation of eCB content in biological matrices, with an apparent diagnostic potential for tomorrow's medicine.


Biosensing Techniques/methods , Endocannabinoids/analysis , Arachidonic Acids/analysis , Arachidonic Acids/blood , Biosensing Techniques/instrumentation , Endocannabinoids/blood , Glycerides/analysis , Glycerides/blood , Humans , Polyunsaturated Alkamides/analysis , Polyunsaturated Alkamides/blood
4.
Int J Mol Sci ; 22(2)2021 Jan 14.
Article En | MEDLINE | ID: mdl-33466869

Raman spectroscopy (RS), a non-invasive and label-free method, has been suggested to improve accuracy of cytological and even histopathological diagnosis. To our knowledge, this novel technique tends to be employed without concrete knowledge of molecular changes in cells. Therefore, identification of Raman spectral markers for objective diagnosis is necessary for universal adoption of RS. As a model study, we investigated human mammary epithelial cells (HMEpC) and breast cancer cells (MCF-7) by RS and employed various multivariate analyses (MA) including principal components analysis (PCA), linear discriminant analysis (LDA), and support vector machine (SVM) to estimate diagnostic accuracy. Furthermore, to elucidate the underlying molecular changes in cancer cells, we utilized multivariate curve resolution analysis-alternating least squares (MCR-ALS) with non-negative constraints to extract physically meaningful spectra from complex cellular data. Unsupervised PCA and supervised MA, such as LDA and SVM, classified HMEpC and MCF-7 fairly well with high accuracy but without revealing molecular basis. Employing MCR-ALS analysis we identified five pure biomolecular spectra comprising DNA, proteins and three independent unsaturated lipid components. Relative abundance of lipid 1 seems to be strictly regulated between the two groups of cells and could be the basis for excellent discrimination by chemometrics-assisted RS. It was unambiguously assigned to linoleate rich glyceride and therefore serves as a Raman spectral marker for reliable diagnosis. This study successfully identified Raman spectral markers and demonstrated the potential of RS to become an excellent cytodiagnostic tool that can both accurately and objectively discriminates breast cancer from normal cells.


Breast Neoplasms/metabolism , Breast/metabolism , Epithelial Cells/metabolism , Spectrum Analysis, Raman/methods , Biomarkers, Tumor/analysis , Breast/cytology , Breast Neoplasms/diagnosis , Discriminant Analysis , Glycerides/analysis , Humans , Least-Squares Analysis , Linoleic Acid/analysis , MCF-7 Cells , Multivariate Analysis , Principal Component Analysis , Reproducibility of Results , Sensitivity and Specificity , Support Vector Machine
5.
J Chromatogr A ; 1636: 461766, 2021 Jan 11.
Article En | MEDLINE | ID: mdl-33316562

To evaluate the endocannabinoid system in an animal model of Parkinson's disease, in-tube solid-phase microextraction (in-tube SPME) was directly coupled to a tandem mass spectrometry (MS/MS) system for determination of the endocannabinoids anandamide (AEA) and 2-arachidonoylglycerol (2-AG) in rat brain samples. In-tube SPME-which consisted of a microtube of restricted access material (RAM) with a hydrophilic diol external surface and a hydrophobic octyl inner surface-efficiently excluded (up to 95%) macromolecules from the biological samples and selectively pre-concentrated the analytes. In-tube SPME parameters, such as sample volume, mobile phases, flow rate, and pre-concentration time, were evaluated to improve the extraction efficiency and throughput performance. The selectivity of the in-tube SPME and MS/MS (MRM mode) techniques allowed them to be directly coupled online, which dismissed the need for the chromatographic separation step. The in-tube SPME-MS/MS method was validated and shown to be linear from 6.0 to 30.0 ng mL-1 for AEA and from 10.0 to 100.0 ng mL-1 for 2-AG; the intra- and inter-assay accuracy and precision were lower than 15%. Parallelism between the calibration curves constructed in the matrix and aqueous solution confirmed that there was no matrix effect. The method allowed endogenous concentrations of AEA and 2-AG to be determined in rat brain striatum from unilaterally 6-hydroxydopamine-lesioned animals. The concentrations of these endocannabinoids in striatum ipsilateral and contralateral to the lesion differed significantly (p<0.001).


Arachidonic Acids/analysis , Brain/metabolism , Endocannabinoids/analysis , Glycerides/analysis , Polyunsaturated Alkamides/analysis , Tandem Mass Spectrometry/methods , Animals , Arachidonic Acids/isolation & purification , Arachidonic Acids/standards , Brain/drug effects , Calibration , Chromatography, High Pressure Liquid , Endocannabinoids/isolation & purification , Endocannabinoids/standards , Glycerides/isolation & purification , Glycerides/standards , Hydrophobic and Hydrophilic Interactions , Male , Oxidopamine/pharmacology , Polyunsaturated Alkamides/isolation & purification , Polyunsaturated Alkamides/standards , Rats , Rats, Wistar , Solid Phase Microextraction , Tandem Mass Spectrometry/standards
6.
Food Chem ; 346: 128857, 2021 Jun 01.
Article En | MEDLINE | ID: mdl-33373822

Human milk lipids are an important energy source and essential nutrients for the growth and development of infants. The UPLC/Q-TOF-MS was used to qualitatively and quantitatively analyze human milk lipids. Totally, 411 species of lipids were identified, in which the content of OPL was generally higher than that of OPO; SM (75.38 mg/L, 40.39%), PE (51.12 mg/L, 27.39%) and PC (40.10 mg/L, 21.49%) had the highest contents among polar lipids, mainly including SM42:2:2 (22.24 mg/L), PE36:2 (C18:0-C18:2, 21.39 mg/L) and PC36:2 (C18:0-C18:2, 19.80 mg/L). In human milk, TAG56:7 (137.14 mg/L), TAG56:8 (59.49 mg/L), TAG58:8 (65.90 mg/L) and TAG58:9 (49.99 mg/L) were the main sources of AA and DHA; PE was an important source of AA and DHA in polar lipids; and linoleic acyl in glycerides and phospholipids had higher contents than other polyunsaturated fatty acyls. These results provided the scientific basis for the simulation of human milk at molecular level.


Chromatography, Liquid/methods , Glycerides/analysis , Milk, Human/chemistry , Phospholipids/analysis , Spectrometry, Mass, Electrospray Ionization/methods , Sphingolipids/analysis , China , Chromatography, High Pressure Liquid/methods , Female , Humans , Lactation , Pregnancy
7.
Article En | MEDLINE | ID: mdl-32882531

A simple and reliable method was developed and validated to determine the endocannabinoids anandamide (AEA) and 2-arachidonoylglycerol (2-AG) in rat brain samples by micro salting-out assisted liquid-liquid extraction combined with ultra-high performance liquid chromatography tandem mass spectrometry (SALLLE/UHPLC-MS/MS). The SALLE parameters (brain homogenate volume, salting-out agent, salt concentration, salt solution volume, organic solvent, organic solvent volume, and centrifugation temperature) were optimized to improve sensitivity and selectivity of the method. The SALLE/UHPLC-MS/MS method presented linear ranges from 2.00 to 20.00 ng mL-1 for AEA and from 0.300 to 10.00 µg mL-1 for 2-AG, no significant matrix effect, and inter- and intra-assay precision and accuracy with CV and RSE values lower than 15%, respectively. This innovative method was successfully applied to determine AEA and 2-AG in brain hemispheres from a 6-OHDA animal model of Parkinson's disease (PD).


Arachidonic Acids/analysis , Brain Chemistry/physiology , Endocannabinoids/analysis , Glycerides/analysis , Liquid-Liquid Extraction/methods , Polyunsaturated Alkamides/analysis , Animals , Arachidonic Acids/isolation & purification , Chromatography, High Pressure Liquid/methods , Disease Models, Animal , Endocannabinoids/isolation & purification , Glycerides/isolation & purification , Limit of Detection , Linear Models , Male , Parkinson Disease/metabolism , Polyunsaturated Alkamides/isolation & purification , Rats , Rats, Wistar , Reproducibility of Results , Tandem Mass Spectrometry/methods
8.
J Biol Chem ; 295(46): 15767-15781, 2020 11 13.
Article En | MEDLINE | ID: mdl-32917725

Endocannabinoid signaling plays a regulatory role in various (neuro)biological functions. 2-arachidonoylglycerol (2-AG) is the most abundant endocannabinoid, and although its canonical biosynthetic pathway involving phosphoinositide-specific phospholipase C and diacylglycerol lipase α is known, alternative pathways remain unsettled. Here, we characterize a noncanonical pathway implicating glycerophosphodiesterase 3 (GDE3, from GDPD2 gene). Human GDE3 expressed in HEK293T cell membranes catalyzed the conversion of lysophosphatidylinositol (LPI) into monoacylglycerol and inositol-1-phosphate. The enzyme was equally active against 1-acyl and 2-acyl LPI. When using 2-acyl LPI, where arachidonic acid is the predominant fatty acid, LC-MS analysis identified 2-AG as the main product of LPI hydrolysis by GDE3. Furthermore, inositol-1-phosphate release into the medium occurred upon addition of LPI to intact cells, suggesting that GDE3 is actually an ecto-lysophospholipase C. In cells expressing G-protein-coupled receptor GPR55, GDE3 abolished 1-acyl LPI-induced signaling. In contrast, upon simultaneous ex-pression of GDE3 and cannabinoid receptor CB2, 2-acyl LPI evoked the same signal as that induced by 2-AG. These data strongly suggest that, in addition to degrading the GPR55 LPI ligand, GDE3 can act as a switch between GPR55 and CB2 signaling. Coincident with a major expression of both GDE3 and CB2 in the spleen, spleens from transgenic mice lacking GDE3 displayed doubling of LPI content compared with WT mice. Decreased production of 2-AG in whole spleen was also observed, supporting the in vivo relevance of our findings. These data thus open a new research avenue in the field of endocannabinoid generation and reinforce the view of GPR55 and LPI being genuine actors of the endocannabinoid system.


Phosphoric Diester Hydrolases/metabolism , Signal Transduction , Amino Acid Sequence , Animals , Arachidonic Acids/analysis , Arachidonic Acids/metabolism , Arachidonic Acids/pharmacology , Endocannabinoids/analysis , Endocannabinoids/metabolism , Endocannabinoids/pharmacology , Female , Glycerides/analysis , Glycerides/metabolism , Glycerides/pharmacology , HEK293 Cells , Humans , Hydrolysis , Inositol Phosphates/metabolism , Lysophospholipids/metabolism , Male , Mice , Mice, Inbred C57BL , Mice, Knockout , Monoglycerides/metabolism , Phosphoric Diester Hydrolases/chemistry , Phosphoric Diester Hydrolases/deficiency , Receptor, Cannabinoid, CB2/genetics , Receptor, Cannabinoid, CB2/metabolism , Receptors, Cannabinoid/metabolism , Sequence Alignment , Signal Transduction/drug effects , Spleen/metabolism
9.
Life Sci ; 245: 117352, 2020 Mar 15.
Article En | MEDLINE | ID: mdl-32006527

AIMS: The depot-specific differences in lipidome of visceral adipose tissue (VAT) and subcutaneous adipose tissue (SAT) reflect heterogeneity of white adipose tissue (WAT), which plays a central role in its distinct response to outside stimuli. However, the detailed lipidome of depot-specific WAT is largely unknown, especially the minor constitutes including phospholipid and sphingolipid. MATERIALS AND METHODS: To investigate this field, we applied a high-coverage targeted lipidomics approach of VAT and SAT in male C57BL/6J mice to compare the basal level of their lipid profiles. Applying microarray and quantitative real-time polymerase chain reaction, we analyzed the transcriptome of twodepot-specific WAT and verified the differences in individual genes. KEY FINDINGS: In total, 342 lipid species from 19 lipid classes were identified. Our results showed the composition of TAG and FFA were different in length of chain and saturation. Interestingly, low abundance phospholipid, sphingolipid and cardiolipin were significantly higher in SAT. Lipid correlation network analysis vindicated that TAG and phospholipid formed distinct subnet and had more connections with other lipid species. Enriched ontology analysis of gene screened from LIPID MAPS and microarray suggested the differences were mainly involved in lipid metabolism, insulin resistance and inflammatory response. SIGNIFICANCE: Our comprehensive lipidomics and transcriptomics analyses revealed differences in lipid composition and lipid metabolism of two depot-specific WAT, which would offer new insights into the investigation of heterogeneity of visceral and subcutaneous white adipose tissue.


Adipose Tissue, White/metabolism , Intra-Abdominal Fat/metabolism , Lipidomics , Subcutaneous Fat/metabolism , Transcriptome , Adipose Tissue, White/chemistry , Animals , Cardiolipins/analysis , Cardiolipins/metabolism , Ceramides/analysis , Ceramides/metabolism , Fatty Acids/analysis , Fatty Acids/metabolism , Glycerides/analysis , Glycerides/metabolism , Intra-Abdominal Fat/chemistry , Lipid Metabolism , Lipids/analysis , Male , Mice , Mice, Inbred C57BL , Phospholipids/analysis , Phospholipids/metabolism , Real-Time Polymerase Chain Reaction , Subcutaneous Fat/chemistry
10.
Prep Biochem Biotechnol ; 50(4): 401-407, 2020.
Article En | MEDLINE | ID: mdl-31829798

In the present study, we report a reverse-phase high-performance liquid chromatography (RP-HPLC) method for separation of the regio-isomers of Glyceryl MonoRicinoleate (GMR) identified using position specificity of lipases. The approaches explored to identify these regio-isomers include LC-mass spectrometry, UV spectroscopy, and selective hydrolysis with lipases. A distinct UV absorption spectrum and λmax values for each isomer were noted, and mass spectral analysis further revealed their molecular weight. Lastly, the purified regio-isomers were subjected to hydrolysis with two distinctive regio-specific lipases to identified as sn-2 and sn-1(3) GMR. The current methodology of using analytic tool and enzyme specificity provides a useful platform for identifying regio-isomers for structured lipid synthesis.


Glycerides/analysis , Lipase/chemistry , Ricinoleic Acids/analysis , Castor Oil/chemistry , Chromatography, High Pressure Liquid , Chromatography, Reverse-Phase , Glycerides/chemistry , Hydrolysis , Isomerism , Ricinoleic Acids/chemistry , Ricinus/chemistry
11.
Elife ; 82019 10 08.
Article En | MEDLINE | ID: mdl-31591965

Sleep deprivation has marked effects on food intake, shifting food choices toward energy-dense options. Here we test the hypothesis that neural processing in central olfactory circuits, in tandem with the endocannabinoid system (ECS), plays a key role in mediating this relationship. We combined a partial sleep-deprivation protocol, pattern-based olfactory neuroimaging, and ad libitum food intake to test how central olfactory mechanisms alter food intake after sleep deprivation. We found that sleep restriction increased levels of the ECS compound 2-oleoylglycerol (2-OG), enhanced encoding of food odors in piriform cortex, and shifted food choices toward energy-dense food items. Importantly, the relationship between changes in 2-OG and food choices was formally mediated by odor-evoked connectivity between the piriform cortex and insula, a region involved in integrating feeding-related signals. These findings describe a potential neurobiological pathway by which state-dependent changes in the ECS may modulate chemosensory processing to regulate food choices.


Cerebral Cortex/physiology , Food Preferences , Olfactory Pathways/physiology , Piriform Cortex/physiology , Sleep , Adult , Female , Glycerides/analysis , Humans , Male , Neuroimaging , Sleep Deprivation , Smell , Young Adult
12.
Nutrients ; 11(9)2019 Sep 11.
Article En | MEDLINE | ID: mdl-31514309

There is mounting evidence that the consumption of fermented dairy products such as cheese and yoghurt is associated with a reduced risk of type II diabetes. This effect is greater than in fresh milk and differs between cheese and yoghurt. However, the molecular components responsible for the effect are not known. We tested the hypothesis that the lipid and/or glyceride profiles of yoghurts and cheeses are distinct from one another and fresh milk. We developed a novel sample preparation technique for high-fat samples that can be used with Direct Infusion-Mass Spectrometry. We found that the lipid and glyceride profiles of cheddars from the UK, Ireland and France, and hard cheeses from Sweden and Italy were similar to one another but distinct from unfermented dairy products. The lipid and glyceride profile of yoghurts was varied and included types that may be similar to fresh milk. Several odd-chain-containing triglycerides were more abundant, while a variety of others were less abundant, in fermented milk samples. Phosphatidylcholines and phosphatidylethanolamines were more abundant in cheeses, with evidence that the phosphatidylethanomine profile is re-modelled in a way that reflects the bacterial cell envelope. We concluded that a combination of microorganismal metabolism, concentration of the lipid/glyceride fraction and oxidation during fermentation contribute to the observed lipid profile if fermented dairy foods. These differences in the lipid and glyceride profile provide a new avenue for understanding why different fermented dairy foods show a different association with reduced disease risk compared to unfermented dairy.


Cheese/analysis , Fermentation , Glycerides/analysis , Lipids/analysis , Milk/chemistry , Nutritive Value , Yogurt/analysis , Animals , Cheese/microbiology , Diabetes Mellitus, Type 2/metabolism , Diabetes Mellitus, Type 2/prevention & control , Food Microbiology , Humans , Lipidomics/methods , Mass Spectrometry , Milk/microbiology , Yogurt/microbiology
13.
Food Chem ; 297: 124976, 2019 Nov 01.
Article En | MEDLINE | ID: mdl-31253293

Milk fat is arguably one of the most complex fats found in nature and varies widely between animal species. Analysis of its digestion products is tremendously challenging, due to the complexity, diversity, and large range of concentrations of triacylglycerols (TAGs) and their digestion products (i.e. diacylglycerols (DAGs), monoacylglycerols (MAGs), and free fatty acids (FFAs)). Therefore, a method combined the solid phase extraction (SPE), high-performance liquid chromatography (HPLC) and multi-dimension mass spectrometry (MDMS) was developed to identify and semi-quantify the TAGs, DAGs and MAGs in milk fat after in vitro digestion. Up to 105, 64, 14 and 30 species of TAGs, DAGs, MAGs, and FFAs were determined with their concentrations of 0.01-22.3, 0.01-39.2, 0.01-47.8, and 0.04-191.0 mg/g fat, respectively, during the in vitro digestion of cow and sheep milk. The validation of the method shows that this method was precise and reliable.


Cattle/metabolism , Glycerides/analysis , Milk/chemistry , Sheep/metabolism , Solid Phase Extraction/veterinary , Animals , Chromatography, High Pressure Liquid/veterinary , Diglycerides/analysis , Fatty Acids, Nonesterified/analysis , Female , Glycolipids/chemistry , Glycoproteins/chemistry , Lipid Droplets , Mass Spectrometry/veterinary , Monoglycerides/analysis , Triglycerides/analysis
14.
Nutrients ; 11(5)2019 May 20.
Article En | MEDLINE | ID: mdl-31137537

We tested the hypothesis that the lipid composition of infant formula is consistent between manufacturers, countries and target demographic. We developed techniques to profile the lipid and glyceride fraction of milk and formula in a high throughput fashion. Formula from principal brands in the UK (2017-2019; bovine-, caprine-, soya-based), the Netherlands (2018; bovine-based) and South Africa (2018; bovine-based) were profiled along with fresh British animal and soya milk and skimmed milk powder. We found that the lipid and glyceride composition of infant formula differed by region, manufacturer and date of manufacture. The formulations within some brands, aimed at different target age ranges, differed considerably where others were similar across the range. Soya lecithin and milk lipids had characteristic phospholipid profiles. Particular sources of fat, such as coconut oil, were also easy to distinguish. Docosahexaenoic acid is typically found in triglycerides rather than phospholipids in formula. The variety by region, manufacturer, date of manufacture and sub-type for target demographics lead to an array of lipid profiles in formula. This makes it impossible to predict its molecular profile. Without detailed profile of the formula fed to infants, it is difficult to characterise the relationship between infant nutrition and their growth and development.


Food Analysis , Glycerides/analysis , Infant Formula/analysis , Lipids/analysis , Age Factors , Child Development , High-Throughput Screening Assays , Humans , Infant , Infant Formula/standards , Infant Nutritional Physiological Phenomena , Infant, Newborn , Nutritive Value , Quality Control
15.
Food Chem ; 286: 29-37, 2019 Jul 15.
Article En | MEDLINE | ID: mdl-30827609

Rice bran wax (RBW) is a traditional plant based natural wax and an increasingly popular component in textiles, fruit coatings and cosmetics. Properties of RBW can be modified by acyglycerols, and the resulting products can possess features with great potential in different applications. In this study, RBW was interesterified with palm olein (POL) catalyzed by Lipozyme TL IM, and the effects of RBW on the crystallization rate, solid fat content (SFC) and thermodynamic properties were investigated. The crystallization rates of RBW-based enzymatically interesterified (EIE) products were significantly higher than both the starting mixture and fully hydrogenated rapeseed oil (FHRSO). The EIE RBW-based samples were predominantly crystallized in ß' form, and presented a much smoother SFC profile as compared to physically blended raw materials. The SFC values were significantly decreased, conversely increased, and remained constant, and at 10 °C, 20-30 °C, and 35-40 °C as the wax ester and acylglycerols compositions changes. Overall, RBW-based samples after EIE showed an increased hardness and good surface properties, which make it a potential plastic fats substitute.


Lipase/metabolism , Palm Oil/metabolism , Rice Bran Oil/metabolism , Biocatalysis , Chromatography, Gas , Crystallization , Esterification , Fatty Acids/analysis , Fatty Acids/chemistry , Glycerides/analysis , Glycerides/chemistry , Oryza/chemistry , Oryza/metabolism , Palm Oil/chemistry , Rice Bran Oil/chemistry , Temperature
16.
Sci Rep ; 9(1): 2358, 2019 02 20.
Article En | MEDLINE | ID: mdl-30787385

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.


Colorectal Neoplasms/metabolism , Endocannabinoids/metabolism , Inflammatory Bowel Diseases/metabolism , Adult , Aged , Aged, 80 and over , Arachidonic Acids/analysis , Arachidonic Acids/blood , Colitis, Ulcerative/metabolism , Colonic Neoplasms/metabolism , Colorectal Neoplasms/physiopathology , Crohn Disease/metabolism , Endocannabinoids/analysis , Endocannabinoids/blood , Female , Glycerides/analysis , Glycerides/blood , Humans , Inflammation , Inflammatory Bowel Diseases/physiopathology , Male , Middle Aged , Oleic Acids/analysis , Oleic Acids/blood , Polyunsaturated Alkamides/analysis , Polyunsaturated Alkamides/blood , Receptor, Cannabinoid, CB1/metabolism , Receptors, G-Protein-Coupled/metabolism
17.
Food Res Int ; 116: 276-282, 2019 02.
Article En | MEDLINE | ID: mdl-30716946

Black soldier fly (BSF, Hermetia illucens) represents a valuable source of biomolecules and it also constitutes an economic way to valorise residual biomasses. BSF prepupae contain high amounts of lipids (37% DM basis). The present investigation aimed at studying the composition of BSF lipids and the effect of killing/storage on their quality. The main fatty acid was lauric acid, sterols were represented primarily by beta-sitosterol and campesterol. Global fatty acid and sterol profiles, determined by GC-MS, were only slightly affected by the killing procedure, while lipid classes distribution, determined by 1H NMR, strongly changed. Prepupae killed by freezing showed a drastic reduction of acylglycerols during storage and a relevant release of free fatty acids, likely due to activation of lipases. On the contrary, prepupae killed by blanching have a stable lipid fraction constituted mainly by triacylglycerols. Therefore, killing procedure strongly influences BSF oil composition and the potential applications.


Food Handling/methods , Homicide , Lipids/analysis , Simuliidae/chemistry , Animals , Body Composition , Diptera , Fatty Acids/analysis , Freezing , Glycerides/analysis , Larva/chemistry , Sterols/analysis
18.
Article En | MEDLINE | ID: mdl-30652962

The effects of the presence of chloride on the formation of 3-monochloro-1,2-propanediol fatty acid esters (3-MCPDEs) and glycidol fatty acid esters (GEs) in saltwater fish, meats and acylglycerols (diacylglycerol and triacylglycerol) during heating were investigated in this study. Five saltwater fish species (salmon, saury, yellowtail, mackerel and Spanish mackerel) were grilled with a fish griller. 3-MCPDEs and GEs were detected in all of the grilled fish samples. The total amount of GEs was higher than 3-MCPDEs. Beef and pork patties with or without sodium chloride (1.5%) were cooked using gaseous fuel. The formation of 3-MCPDEs was significantly increased by the addition of sodium chloride to the meat patties, whereas the concentration of GEs in the cooked meat patties was not changed by the content of sodium chloride. Hexadecane solutions of diacylglycerol or triacylglycerol containing FeCl3 were heated at 240°C. The formation of 3-MCPDEs was greatly increased by adding FeCl3 to the solutions of triacylglycerol. The amounts of 3-MCPDEs decreased with the extension of the heating time. From these results, it is suggested that 3-MCPDEs and GEs are formed in saltwater fish and meats by cooking, and that the formation of 3-MCPDEs was affected by chloride in foodstuffs.


Chlorides/chemistry , Epoxy Compounds/analysis , Esters/analysis , Fatty Acids/analysis , Glycerides/analysis , Heating , Propanols/analysis , alpha-Chlorohydrin/analysis , Animals , Fishes , Food Contamination/analysis , Meat/analysis
19.
J Chromatogr A ; 1584: 165-178, 2019 Jan 11.
Article En | MEDLINE | ID: mdl-30551941

Triacyl-, diacyl- and monoacylglycerols (TAGs, DAGs, MAGs) along with monocarboxylic acids (MCAs) are intermediate products in many triacylglycerol oil-to-biofuel conversion pathways. Accumulation of these compounds leads to poor biofuel characteristics and may result in fuel system damage. We developed a method for simultaneous identification and quantification of a wide range of MCAs (C4-C18), MAGs, DAGs, and TAGs. The method is based on trimethylsilylation followed by high temperature GC with programmed temperature vaporizer (PTV) injection coupled to parallel FID and MS detectors (HTGC-FID/MS). To minimize the discrimination of both low and high molecular weight species typically occurring on the injector, we optimized injection conditions using a central composite design. The critical variables were the time at initial temperature (40 °C), splitless time, and the interaction between these two parameters. Among three tested electron ionization source/quadrupole analyzer temperatures, a 350/200 °C setting provided the highest response and signal-to-noise ratio for TAGs and did not have an effect on MAGs and DAGs. Similar results were obtained when quantifying target analytes in intermediate products of soybean oil cracking with FID and MS (using specific acylglycerol fragmentation ions). The instrumental FID limits of detection (LODs) were 0.07-0.27 ng for most of the target analytes. Selected ion monitoring (SIM) LODs were 0.01-0.05 ng for MCAs and 0.03-0.14 ng for acylglycerols. For the total ion current (TIC), LODs observed increased with acyl chain length and degree of unsaturation, resulting in an increase from 0.05 to 0.18 ng for MCAs (C5 to C18) and from 0.03 to 1.8 ng for acylglycerols (TAGs C8 to C22). Deviations in the repeatability of sample preparation, intra- and inter-day analyses, including sample stability over an eight-day time period, did not exceed 10% variance. These results demonstrate that the developed method is accurate and robust for the determination of acylglycerols and MCAs produced during the processing of TAGs into biofuels.


Biofuels/analysis , Carboxylic Acids/analysis , Flame Ionization/methods , Gas Chromatography-Mass Spectrometry/methods , Glycerides/analysis , Hot Temperature , Limit of Detection , Soybean Oil/chemistry
20.
Article En | MEDLINE | ID: mdl-30476796

Fatty acids and glycerides are globally accepted quality and nutrition indicators of oils. Schisandra chinensis (S. chinensis) is a good functional oil source, with an oil content of 10-50% (dry weight). In this study, the UPLC-Q/TOF-MSE technique was developed to profile FFA and glycerides in the S. chinensis oils directly. The results showed that all of the 36 FFA calibration equations of the mixture standard had good linear relationships (R2 > 0.99). The limit of detection for the tested compounds ranged from 0.0001 to 0.0200 µg/mL, while the limit of quantification ranged from 0.0005 to 0.1300 µg/mL. In total, seventeen FFAs, six diglycerides and 20 triglycerides were identified. Linoleic, oleic, stearic and palmitic acids were the most abundant FFAs in the S. chinensis oils. It was also found that S. chinensis oil is rich in the L-L, L-L-L, O-L-L and O-L-O glycerides. These results will be helpful for the use of this technique in physicochemical evaluation and for further application development.


Chromatography, High Pressure Liquid/methods , Fatty Acids/analysis , Glycerides/analysis , Plant Oils/chemistry , Schisandra/metabolism , Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization/methods , Chromatography, Supercritical Fluid , Limit of Detection , Linear Models , Plant Oils/analysis , Reproducibility of Results , Tandem Mass Spectrometry
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