Analysis Of Fatty Acid Esters Research Articles

Analysis of fatty acid esters of hydroxy fatty acids in edible mushrooms

Edible mushrooms are consumed worldwide. The overall amount of lipids in mushrooms is small and consists of complex lipids, such as triacylglycerols, phospholipids, and sterols. Nutritional studies have outlined the lipid compositions of mushrooms but have not analyzed their fatty acid esters of hydroxy fatty acid (FAHFA) profiles. FAHFAs are a class of anti-inflammatory and antidiabetic lipids frequently found in human food. This study aimed to characterize the FAHFA profiles of various edible mushrooms.Using a liquid chromatography-mass spectrometry-based lipidomics approach, we identified 34 FAHFAs in seven members of the fungal order Agaricales, also known as gilled mushrooms. Linoleic acid (LA)-containing FAHFAs were the most abundant among all the species. Shiitake (Lentinula edodes) and enokitake (Flammulina velutipes) mushrooms showed the most divergent FAHFA profiles, being rich in short-chain FAHFAs and very long-chain FAHFAs, respectively. The brown (Hypsizygus tessulatus) and white (Hypsizygus ulmarius) varieties of shimeji have closely related FAHFA compositions and quantities of FAHFA diversity can be used for chemotaxonomic classification of the mushroom family, similar to mitochondrial (mt)DNA information. Adding mushrooms to the diet provides several micronutrients, including FAHFAs, with minimal impact on the overall calories from fat.

Study of fatty acid esters obtained from the biomass of Hermetia illucens larvae and the prospects of their use in the food industry

In this study we carried out a physicochemical analysis of fatty acid esters (FFA) obtained from the biomass of larvae, which can be used as ingredients in the food industry and for the manufacture of feed. The acute toxicity of fatty acid esters obtained from the biomass of Hermetia illucens larvae was determined. It was revealed that the acid and peroxide values of the fat fraction obtained from the biomass of Hermetia illucens larvae are within the limits established by the norm, which indicates the high quality of this product. The fatty acid composition is represented mainly by lauric, palmitic, oleic and myristic acids. It was shown that the differences in fatty acid composition of the samples, obtained from the biomass of Hermetia illucens larvae manually and using the Soxhlet extraction apparatus, were insignificant and within the acceptable values. In the study of presence of toxic elements in fat fractions, lead, cadmium, arsenic, mercury, iron were not detected or they did not exceed the established values.

Sensitive analysis of fatty acid esters of hydroxy fatty acids in biological lipid extracts by shotgun lipidomics after one-step derivatization.

Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are an important family of endogenous lipids, possessing antidiabetic and anti-inflammatory functions. Therefore, analysis of FAHFAs in biological samples obtained under healthy and disease states can uncover underlying mechanisms of various relevant disorders (e.g., diabetes and autoimmune diseases). Up to now, due to their extremely low abundance, the determination of the changed levels of these species is still a huge challenge, even though great efforts have been made by utilizing liquid chromatography-tandem mass spectrometry with or without derivatization. Herein, we described a novel method for analysis of FAHFAs present in lipid extracts of biological examples after solid-phase extraction and chemical derivatization with one authentic FAHFA specie as an internal standard based on the principles of multi-dimensional mass spectrometry-based shotgun lipidomics. The approach possessed marked sensitivity, high specificity, and broad linear dynamic range of over 3 orders without obvious matrix effects. Moreover, after chemical derivatization, the molecular masses of FAHFAs shift from an overlapped region with ceramide species to a new region without overlaps, removing these contaminating signals from ceramides, and thereby reducing the false results of FAHFAs. Finally, this novel method was successfully applied for determining FAHFAs levels in varieties of representative biological samples, including plasma from lean and overweight/obese individuals of normoglycemia, and tissue samples (such as liver and white adipose tissue from diabetic (db/db) mice). We revealed significant alterations of FAHFAs in samples under patho(physio)logical conditions compared to their respective controls. Taken together, the developed method could greatly contribute to studying altered FAHFA levels under a variety of biological/biomedical conditions, and facilitate the understanding of these lipid species in the patho(physio)logical process.

Analysis of Fatty Acid Esters of Hydroxyl Fatty Acid in Selected Plant Food.

Metabolic syndrome, characterized by obesity, low-grade inflammation, insulin resistance, hyperglycemia, dyslipidemia and hypertension, is a major risk factor for cardiovascular mortality. Preclinical studies on recently discovered classes of lipids - fatty acid esters of hydroxy fatty acids (FAHFA) have revealed their anti-inflammatory and insulin-sensitizing potential. The FAHFA levels are significantly decreased in insulin-resistant individuals, their application exhibited anti-inflammatory effects and restoring the glucose-insulin homeostasis. The aim of our research was to analyze the overall FAHFA composition in a common diet, as only a partial FAHFA composition has been revealed so far (only the PAHSA subclass was analyzed in a few foods). A new approach to the FAHFAs analysis includes nano-LC and post-column modifier followed by negative ion mass spectrometry, in order to obtain maximum sensitivity. Analysis of different foods - oat (whole grain, coarse flakes and fine flakes), apple, clementine, lemon, strawberry, blueberry, mango, kiwi, avocado, pineapple, banana, onion, garlic, cherry tomato, carrot, parsley root, pepper and radish - exhibited wide inter-food variation in the FAHFA profiles. Sixteen analyzed FAHFAs (palmitic, oleic, palmitoleic and stearic hydroxy-esters) showed microgram to low nanogram levels (0.165ng/g - 32μg/g FW), with the highest abundancy in oat, clementine, garlic and pineapple. Stearic acid hydroxy stearic acid (SAHSA) was the most abundant FAHFA, especially in the food with antioxidative, anti-inflammatory and beneficial metabolic effects. In contrary, the PAHSA - previously proven to have the strongest antihyperglycemic and insulin-sensitizing effects, was not present in some foods (radish, avocado, mango, lemon, cherry tomato, kiwi). Our study proves the importance of overall FAHFA analysis in food (especially in a functional food), because of their potential metabolic benefits and possible future incorporation in special diets.

Confirmatory and quantitative analysis of fatty acid esters of hydroxy fatty acids in serum by solid phase extraction coupled to liquid chromatography tandem mass spectrometry

A novel class of endogenous mammalian lipids endowed with antidiabetic and anti-inflammatory properties has been recently discovered. These are fatty acid esters of hydroxy fatty acids (FAHFAs) formed by condensation between a hydroxy fatty acid and a fatty acid. FAHFAs are present in human serum and tissues at low nanomolar concentrations. Therefore, high sensitivity and selectivity profiling analysis of these compounds in clinical samples is demanded. An automated qualitative and quantitative method based on on-line coupling between solid phase extraction and liquid chromatography–tandem mass spectrometry has been here developed for determination of FAHFAs in serum with the required sensitivity and selectivity. Matrix effects were evaluated by preparation of calibration models in serum and methanol. Recovery factors ranged between 73.8 and 100% in serum. The within-day variability ranged from 7.1 to 13.8%, and the between-days variability varied from 9.3 to 21.6%, which are quite acceptable values taking into account the low concentration levels at which the target analytes are found. The method has been applied to a cohort of human serum samples to estimate the concentrations profiles as a function of the glycaemic state and obesity. Statistical analysis revealed three FAHFAs with levels significantly different depending on the glycaemic state or the body mass index. This automated method could be implemented in high-throughput analysis with minimum user assistance.

Collaborative Study of an Indirect Enzymatic Method for the Simultaneous Analysis of 3-MCPD, 2-MCPD, and Glycidyl Esters in Edible Oils.

A collaborative study was conducted to evaluate an indirect enzymatic method for the analysis of fatty acid esters of 3-monochloro-1,2-propanediol (3-MCPD), 2-monochloro-1,3-propanediol (2-MCPD), and glycidol (Gly) in edible oils and fats. The method is characterized by the use of Candida rugosa lipase, which hydrolyzes the esters at room temperature in 30 min. Hydrolysis and bromination steps convert esters of 3-MCPD, 2-MCPD, and glycidol to free 3-MCPD, 2-MCPD, and 3-monobromo-1,2-propanediol, respectively, which are then derivatized with phenylboronic acid, and analyzed by gas chromatography-mass spectrometry. In a collaborative study involving 13 laboratories, liquid palm, solid palm, rapeseed, and rice bran oils spiked with 0.5-4.4 mg/kg of esters of 3-MCPD, 2-MCPD, and Gly were analyzed in duplicate. The repeatability (RSDr) were < 5% for five liquid oil samples and 8% for a solid oil sample. The reproducibility (RSDR) ranged from 5% to 18% for all oil samples. These RSDR values were considered satisfactory because the Horwitz ratios were ≤ 1.3% for all three analytes in all oil samples. This method is applicable to the quantification of 3-MCPD, 2-MCPD, and Gly esters in edible oils.

Optimization of an Indirect Enzymatic Method for the Simultaneous Analysis of 3-MCPD, 2-MCPD, and Glycidyl Esters in Edible Oils.

We developed a novel, indirect enzymatic method for the analysis of fatty acid esters of 3-monochloro-1,2-propanediol (3-MCPD), 2-monochloro-1,3-propanediol (2-MCPD), and glycidol (Gly) in edible oils and fats. Using this method, the ester analytes were rapidly cleavaged by Candida rugosa lipase at room temperature for 0.5 h. As a result of the simultaneous hydrolysis and bromination steps, 3-MCPD esters, 2-MCPD esters, and glycidyl esters were converted to free 3-MCPD, 2-MCPD, and 3-monobromo-1,2-propanediol (3-MBPD), respectively. After the addition of internal standards, the mixtures were washed with hexane, derivatized with phenylboronic acid, and analyzed by gas chromatography-mass spectrometer (GC-MS). The analytical method was evaluated in preliminary and feasibility studies performed by 13 laboratories. The preliminary study from 4 laboratories showed the reproducibility (RSD R ) of < 10% and recoveries in the range of 102-111% for the spiked 3-MCPD and 2-MCPD in extra virgin olive (EVO) oil, semi-solid palm oil, and solid palm oil. However, the RSDR and recoveries of Gly in the palm oil samples were not satisfactory. The Gly content of refrigerated palm oil samples decreased whereas the samples at room temperature were stable for three months, and this may be due to the depletion of Gly during cold storage. The feasibility studies performed by all 13 laboratories were conducted based on modifications of the shaking conditions for ester cleavage, the conditions of Gly bromination, and the removal of gel formed by residual lipase. Satisfactory RSDR were obtained for EVO oil samples spiked with standard esters (4.4% for 3-MCPD, 11.2% for 2-MCPD, and 6.6% for Gly).

Drinking water off-flavour caused by the formation of short-chain fatty acids in slow sand filters

A case study carried out at a municipal drinking water treatment plant in southern Sweden showed that the formation of short-chain fatty acids in slow sand filters can result in severe off-flavour problems. When an extract of the headspace of the surface layer of a sand filter was subjected to gas chromatographic analysis with sensory detection (GC sniffing), several strong, rancid odours were detected. Mass spectrometric analysis of the same extract, before and after methylation, showed that substantial amounts of butyric acid, valeric acid and isovaleric acid were present in the analysed sample. The off-flavour caused by these compounds was removed by repeated shock chlorination of the malfunctioning slow sand filter. Analysis of fatty acid esters may provide an early warning of the described off-flavour problem.

Drinking water off-flavour caused by the formation of short-chain fatty acids in slow sand filters

A case study carried out at a municipal drinking water treatment plant in southern Sweden showed that the formation of short-chain fatty acids in slow sand filters can result in severe off-flavour problems. When an extract of the headspace of the surface layer of a sand filter was subjected to gas chromatographic analysis with sensory detection (GC sniffing), several strong, rancid odours were detected. Mass spectrometric analysis of the same extract, before and after methylation, showed that substantial amounts of butyric acid, valeric acid and isovaleric acid were present in the analysed sample. The off-flavour caused by these compounds was removed by repeated shock chlorination of the malfunctioning slow sand filter. Analysis of fatty acid esters may provide an early warning of the described off-flavour problem.

Quantitative and non-destructive analyses of fatty acid esters and cholesterol in brain tissues by Fourier transform infrared spectroscopy

Brain tissues obtained from rats were examined with Fourier transform infrared spectroscopy using a beam condenser apparatus to determine quantitatively and non-destructively the amount of fatty acid esters and cholesterol in the small specimens. For the analysis of fatty acid esters we calculated the ratio between the peak intensities of the fatty ester C  O (1730 cm −1) or methylene CH (2850 cm −1) stretches and amide II band (1550 cm −1), and compared it with the amount of fatty acid esters per mg protein determined chemically by a routine method. For analysis of cholesterol we measured the second derivative spectra between 1300 and 1400 cm −1 and the intensity of a band at 1366 cm −1 in the second derivative spectrum was compared with that of the amide II band in the normal absorption spectrum. This infrared analysis of cholesterol was compared and showed good correlations with the chemically defined data. These results suggest that the infrared technique can provide non-destructively quantitative data for the content of fatty acid esters and cholesterol in biological tissues.

Stereospecific analysis of fatty acid esters of chloropropanediol isolated from fresh goat milk.

The fatty acid esters of chloropropanediol isolated from goat milk fat in small quantities were subjected to a stereospecific analysis via phospholipase C and phosphocholine esters as intermediates. Synthetic rac-1-chloro-2,3-dioleoyl-propanediol was prepared by standard methods and was used as a control. The stereospecific analyses were performed following a release of the fatty acids from the primary positions of each chloropropanediol diester with pancreatic lipase. The resulting X-1-chloro-2-acylpropanediols were then converted into the corresponding phosphocholine derivatives by a stepwise reaction with phosphorus oxychloride and choline chloride. The X-1-chloro-2-acyl-3-phosphocholinepropanediols were subjected to hydrolysis with phospholipase C (C. perfringens), which hydrolyzed 50% of the phosphatide within two min and the rest of it in two hr. From previous experience with glycerol esters, it was assumed that the more rapidly hydrolyzed molecules were the sn-1-chloro-2-acyl-propanediol derivatives and the more slowly hydrolyzed ones the sn-2-acyl-3-chloropropanediol derivatives. A hydrolysis with phospholipase A2 (Crotalus adamanteus) released 50% of the total fatty acid along with the corresponding lyso compound within 10 min, after which there was no further reaction. The hydrolysis products were assayed directly by gas liquid chromatography (GLC) or were isolated by thin layer chromatography (TLC) prior to quantitation by GLC. Both naturally occurring and synthetic chloropropanediol diesters behaved similarly on stereospecific analysis and were therefore concluded to be racemic.

A comparison of methods for the high-performance liquid chromatographic and capillary gas-liquid chromatographic analysis of fatty acid esters

A reversed-phase high-performance liquid chromatographic (RP-HPLC) method for the analysis of free fatty acids in plasma was compared with a method usi In an application of the methods, the free fatty acid concentrations in the plasma of a group of diabetic patients and their age-matched controls were

Analysis of fatty acid esters in processed raisins by gas chromatography

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAnalysis of fatty acid esters in processed raisins by gas chromatographyAllan E. Stafford, Glenn. Fuller, Harold R. Bolin, and Bruce E. MackeyCite this: J. Agric. Food Chem. 1974, 22, 3, 478–479Publication Date (Print):May 1, 1974Publication History Published online1 May 2002Published inissue 1 May 1974https://doi.org/10.1021/jf60193a019RIGHTS & PERMISSIONSArticle Views84Altmetric-Citations8LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (271 KB) Get e-Alerts Get e-Alerts