A simple method for the analysis of trans fatty acid with GC–MS and AT-Silar-90 capillary column

The study was aimed to evaluate a simplified gas chromatography method based on the AOAC method 996.06 to analyze the trans fat content in food samples. The gas chromatograph was equipped with mass spectrometer and Alltech AT^™-Silar-90 capillary column. Ten kinds of the trans fatty acid standard were separated completely from the cis standard and the chemical composition of the peaks was verified by using the mass spectrum. Under the optimized conditions, the recovery rate for triheptadecanoin was 99.0%, the correlation coefficients of trans fatty acid calibration curve was 0.9998 or higher. It demonstrated that the methylation and hexane extraction procedures used in this method was effective and the result was consistent. The major fatty acids found in the shortening sample were 16:0, 18:0, trans-18:1, cis-18:1, cis-18:2, and cis-18:3. The total trans fat content in the sample was 283.6 ± 18.2 mg/g. The current method was more convenient. It is adequate for the routine analysis of trans fat content in food products with low free fatty acid content.     

Identification and quantification of trans fatty acids in bakery products by gas chromatography–mass spectrometry after focused microwave Soxhlet extraction

Trans fatty acids have been determined in fourteen bakery products using derivatisation by ester formation, gas chromatography–mass spectrometry for individual separation and identification/quantification following total fat isolation by Soxhlet extraction accelerated by focused microwave irradiation at the cartridge zone. The detection and quantification limits between 0.98 and 3.93 and 3.23–12.98 μg g⁻¹, respectively, and the linear dynamic ranges between LOQs values and 12,000 μg g⁻¹ thus obtained, demonstrated the utility of the approach for this type of analysis thanks to the wide determination range and high information level it provides. The proposed extraction method, which was validated by comparison with the Folch reference method – extraction under very mild conditions, shows that no changes of the original fat are produced under microwave-assisted extraction. The much shorter extraction time – 35 or 60 min vs. 3.5 h of the Folch method – and similar characteristics of the extract make this method an excellent alternative for the treatment of solid samples prior to trans fatty acids analysis. The target analytes were determined in fourteen bakery products; thus supporting the validity of the overall process.     

Formation of trans fatty acids in edible oils during the frying and heating process

To assess an impact of heated edible oils on intake of trans fat, the formations of trans fatty acids (TFAs) in cooking conditions was estimated by a frying and heating model system. For the frying model, sliced raw potatoes (10% of the frying oil (w/w)) were fried in commercially available canola oil at 160, 180 and 200 °C, and the 10 frying cycles were performed. The TFAs contained both in fried potatoes and in frying oils were measured by gas chromatography (GC). Lipids content of raw potatoes was about 0.1% (w/w) and TFAs in the raw potatoes were negligible. On the other hand, fried potatoes contained lipids at the level of 8.8%–9.2% and their fatty acid composition was mostly in correspondence with that of the frying oil. The TFAs amount of potatoes fried by the tenth frying operation was at the level of 0.99–1.05 g/100 g lipids. When 100 g potatoes fried in this process were consumed, the TFAs intake was estimated at less than 0.1 g. After 10 frying operations, TFAs content, acid values and peroxide values of the frying oils were measured and compared with those of corresponding heated canola oils without food. The amounts of trans 18:1 FAs contained both in the frying oil and in heated oil were less than the quantitative limit (0.047 g/100 g oil). The increases of trans 18:2 FAs and trans 18:3 FAs of the used frying oil were 0.02 g/100 and 0.05 g/100 g, respectively, compared with those of the fresh oil. trans 18:2 FAs accumulation in the heated oil was slightly less than that in the frying oil. To elucidate TFAs accumulation in various edible oils during cooking, six kinds of commercially available edible vegetable oils were heated to 180 °C in glass test tubes. Small changes in TFAs amounts were observed after four hours heating. These results suggested that an ordinary frying process using unhydrogenated edible oils has little impact on TFAs intake from edible oils.     

Analysis of trans–cis fatty acids in fatty acid steryl esters isolated from soybean oil deodoriser distillate

The characterisation of the isolated natural product from soybean oil deodoriser distillate (SODD) has gained increasing importance due to health concerns. The purpose of the present work was to characterise fatty acids steryl esters (FASEs) composition and to determine the trans fatty acids (TFAs) contents in FASEs obtained from SODD by using simple and accurate method. Isolation of FASEs with saturated fatty acids moieties from FASEs mixture was also developed. It was found that the fatty acids composition of the isolated FASEs were 31.74% palmitate acid (C16:0), 9.99% stearic acid (C18:0), 0.46% elaidic acid (C18:1 trans-9), 27.51% oleic acid (C18:1 cis-9), 0.19% linoleaidic acid (C18:2 cis-9, trans-12), and 29.19% linoleic acid (C18:2 cis-9, cis-12). TFAs, which account for about 0.65% of the total fatty acids, were detected in the isolated FASEs. Palmitate and stearate steryl esters isolated from SODD are promising natural product because they are free of trans-isomers.     

Trans fatty acids in a range of UK processed foods

A survey to determine the trans fatty acid content of a range of processed foods was carried out in response to recent reformulation work by the food industry to lower the artificial trans fatty acid content of processed products. Sixty two composite samples, made up of between 5 and 12 sub-samples, were collected in 2010 and were analysed for fatty acids, and a range of nutrients. The foods analysed included pizza, garlic bread, breakfast cereals, quiche, fat spreads, a range of fish and meat products, chips, savoury snacks, confectionery and ice cream. Levels of trans fatty acids were reduced considerably compared with previous UK analyses of similar foods where comparisons are possible. Concentrations of trans elaidic acid (t9-C18:1) from hydrogenated oils in all samples were <0.2 g/100 g food. These results confirm information provided by the food industry in 2007 on the levels of trans fats in key processed food sectors.     

毛细管气相色谱法测定精炼和氢化大豆油中的反式脂肪酸

采用CP—Sil88强极性毛细管柱气相色谱法对精炼和氢化大豆油中的顺、反异构和位置异构的脂肪酸进行定性、定量分析。结果表明，精炼和氢化大豆油中主要顺、反式脂肪酸实现了很好地分离，各种位置异构的反式脂肪酸也实现了较好地分离。采用归一化法对各种脂肪酸进行定量分析，结果表明，精炼大豆油中反式脂肪酸为总脂肪酸含量的3．45％，以△9c，12t—C18：2、△9t，12c—C18：2和△9c，12c，15t—C18：3、△9t，12c，15c—C18：3 4种形式为主；氢化大豆油中反式脂肪酸为总脂肪酸含量的38．73％，以△9t—C18：1、△10t—C18：1、△11t—C18：1 3种形式为主的反式十八碳单烯酸（t—C18：1）占反式脂肪酸总量的90．81％。     

Application of transmission FT-IR spectroscopy for the trans fat determination in the industrially processed edible oils

The amount of trans fatty acids (TFA) in fourteen industrially hydrogenated and deodorized oils was determined. To achieve better sensitivity 200 μm KCl cell was used in transmission Fourier transform infrared (FT-IR) spectroscopy. The results of transmission FT-IR spectroscopy were evaluated by gas chromatography (GC) with flame ionization detector (FID), and found to be comparable. All analyzed cooking oil samples had a lower trans content of 0.4–1.8%. Trans fatty acid contents of partially hydrogenated oil samples were relatively higher as comparable to those of the cooking oils. Among the samples examined, the highest level was found to be at 26.5% and 25.7% by the GC–FID and FT-IR spectroscopy, respectively. Due to harmful effects, high amounts of trans fatty acids in partially hydrogenated oils is an alarming issue for the consumer’s health and quality control authorities.     

GC-MS quantification of fatty acid profile including trans FA in the locally manufactured margarines of Pakistan

Ten margarine brands of Pakistan were analyzed for their fatty acid composition with emphasis on trans fatty acids (TFA) using GC-MS. Saturated, cis-monounsaturated and polyunsaturated fatty acids were present at 24.2–58.1, 5.7–35.4 and 3.8–37.4% of total fatty acids, respectively. Among the saturated fatty acids, palmitic acid (16.9–33.8%) was dominant in all analyzed margarine brands and its higher amount indicates that palm oil was a major contributor in the margarine manufacturing. Among samples tested only one contained a low level of TFA (2.2%) while the rest contained very high amounts of TFA (11.5–34.8%) which clearly shows that hydrogenated oils were used in the formulation of margarines. Fatty acid profiles demonstrated that all samples belong to the hard margarine category containing high amounts of trans and saturated fatty acids which is an alarming issue for the health of consumers.     

黑豆油理化指标及脂肪酸组成分析

黑豆系为食药两用植物种籽,为更好开发和利用黑豆资源,分别对南北黑豆油理化指标、脂肪酸组成及甘油三酯组成进行测定。结果表明,黑豆含油量为17%左右,粗蛋白含量达46%左右,粗纤维含量为4.5%左右;黑豆油富含油酸和亚油酸,不饱和脂肪酸含量高达80%以上。     

Effects of antioxidants on heat-induced trans fatty acid formation in triolein and trilinolein

To elucidate the relation between heat-induced cis/trans isomerisation and thermal oxidative degradation of double bonds in unsaturated lipids, we investigated the effects of several edible antioxidants on these two molecular structural changes of double bonds in triolein (cis-9, 18:1) and trilinolein (cis-9, cis-12, 18:2), which were heated at 180 °C. trans Isomerisation and oxidative degradation of each cis double bond in the triacylglycerols during heating were evaluated on the basis of the increase in the amount of trans isomers and decrease in the amount of cis isomers by gas chromatography analysis. The synchronous suppression in trans isomerisation and cis deterioration of double bonds in these triacylglycerols were found by addition of antioxidants, whose inhibitory effects were associated with their kinds and concentrations. When triolein was heated in the presence of antioxidant, suppression of heat-induced trans isomerisation was directly proportional to that of cis deterioration. The results of our analysis suggested that the appropriate addition of antioxidants to edible oils during processing and cooking would facilitate the control of not only thermal oxidative degradation but also heat-induced trans isomerisation of double bonds in unsaturated lipids.     

固体超强酸催化大豆油和大豆油脂肪酸酯化与酯交换制备单甘酯的研究

采用固体超强酸催化大豆油和大豆油脂肪酸与甘油酯化和酯交换制备单甘酯,通过二级分子蒸馏纯化单甘酯。通过响应面优化得到的最佳条件为：大豆油30.0 g,大豆油脂肪酸20.0 g,反应温度200℃,固体超强酸催化剂添加量0.26%（占大豆油和大豆油脂肪酸质量）,甘油添加量12.66 g和反应时间4.81 h。在最佳条件下,反应得到的甘油酯混合物中,单甘酯含量达到69.82%。甘油酯混合物在Ⅰ级135℃分子蒸馏除去游离脂肪酸和甘油,在Ⅱ级185℃分子蒸馏蒸出单甘酯,得到产品中单甘酯含量为96.54%。     

Antioxidant activity and chemical constituents of essential oil and extracts of Rhizoma Homalomenae

Antioxidant activity and composition of essential oil and extracts of Rhizoma Homalomenae were determined. The extracts, especially the ethyl acetate extract (QJ4 fraction) of the aqueous residue after oil distillation, had considerable antioxidant potency which was significantly associated with their total phenolic and flavonoid contents, but the essential oil showed only weak or moderate activity. GC–MS analysis of the essential oil (yield: 0.82%, v/w) resulted in the identification of 77 compounds, accounting for 96.5% of the content of the oil. The major components, epi-α-cadinol (14.8%), α-cadinol (14.8%), α-terpineol (13.8%), linalool (11.1%), terpinen-4-ol (4.92%), and δ-cadinene (4.91%) constituted 64.3% of it. LC–MS/MS and HPLC analyses showed seven phenolic compounds (protocatechuic acid, vanillic acid, syringic acid, caffeic acid, p-coumaric acid, ferulic acid and apigenin) with a great amount in the ethyl acetate extract (QJ4 fraction). The strong antioxidant properties of the plant extracts may be attributed to the presence of these phenolics.     

Essential oil composition of Salvia miltiorrhiza flower

Hydrodistillation of the flower of seven populations of Salvia miltiorrhiza Bge. collected in different locations in China afforded a pale yellowish oil in a yield of approximately 0.2%. A total of 82 compounds were identified across all the samples, accounting for 98–100% of the total compositions of each sample. Components were mainly monoterpenes, sesquiterpenes, fatty acids and alkanes. GC and GC–MS analysis indicated that the predominant components of the essential oils are β-caryophyllene (12.2–31.7%), β-caryophyllene oxide (1.4–11.6%), α-caryophyllene (4.8–10.6%), cadinadiene (7.4–29.3%), and hexadecanoic acid (3.9–18.8%).     

Silphium L. extracts – composition and protective effect on fatty acids content in sunflower oil subjected to heating and storage

The influence of ethanol and hexane extracts from leaves, inflorescences, and rhizomes of Silphium perfoliatum, Silphium trifoliatum, Silphium integrifolium on fatty acid content changes in sunflower oil subjected to heating and storage was studied in comparison to the synthetic antioxidant – butylated hydroxyanisole (BHA). A positive effect of extracts made of above-ground and underground organs of Silphium on the durable quantitative composition of fatty acids was proven. Tested extracts elevated the value of change inhibition with reference to linoleic acid to a level comparable with BHA, and sometimes, in appropriate systems, they were characterized by better values (for oil stored for 180 days at room temperature, the inhibition coefficient for linoleic acid changes reached 4.6% for 0.04% BHA, and 7.09% for hexane extract made of S. trifoliatum inflorescences, 400 μl/2 g; for oil heated for 120 h, the inhibition coefficient of linoleic acid changes amounted to 11.32% for 0.06% BHA, and 15.69% for hexane extract made of S. perfoliatum rhizomes, 600 μl/2 g). It was found that active substances groups such as phenolic acids, flavonoids and terpenes were present in tested extracts.     

Effects of the heating process of soybean oil and seeds on fatty acid biohydrogenation in vitro

Heating fat is an efficient way to alter ruminal biohydrogenation (BH) and milk fat quality. Nevertheless, results are variable among studies and this could be due to various heating conditions differently affecting BH. The objectives of this study were to determine the effect of type and duration of heating of soybean oil or seeds on BH in vitro. Ruminal content cultures were incubated to first investigate the effects of roasting duration (no heating, and 0.5- and 6-h roasting) at 125°C and its interaction with fat source (soybean seeds vs. soybean oil), focusing on linoleic acid BH and its intermediates: conjugated linoleic acid (CLA) and trans-C18:1. Additionally, we compared the effects of seed extrusion with the 6 combinations of unheated and roasted oils and seeds. None of the treatments was efficient to protect linoleic acid from BH. Soybean oil resulted in higher trans-11 isomer production than seeds: 5.7 and 1.2 times higher for cis-9,trans-11 CLA and trans-11 C18:1, respectively. A 125°C, 0.5-h roasting increased trans-11 isomer production by 11% compared with no heating and 6-h roasted fat. Extrusion of seeds was more efficient to increase trans-11 C18:1 production than seed roasting, leading to values similar to oils. For other fatty acids, including cis-9,trans-11 CLA, extrusion resulted in similar balances to seeds (mainly 0.5-h-roasted seeds). Extruded oilseeds would be more efficient than roasted seeds to produce trans-11 C18:1; nevertheless, effects of conditions of extrusion need to be explored.     

A developed pre-column derivatization method for the determination of free fatty acids in edible oils by reversed-phase HPLC with fluorescence detection and its application to Lycium barbarum seed oil

Free fatty acids (FFAs) in edible oils are one of the most frequently determined quality indices during production, storage, and marketing. In this study, a simple, stable and sensitive method for the simultaneous determination of saturated and unsaturated FFAs from edible oils using 2-(11H-benzo[a]carbazol-11-yl)-ethyl-4-methylbenzenesulphonate (BCETS) as labelling reagent with fluorescence detection has been established. FFAs are derivatized by BCETS and separated on a reversed-phase Eclipse XDB-C₈ column with a gradient elution. The results indicated that all FFAs were found to be given an excellent linear response with correlation coefficients of >0.9994. The detection limits at a signal-to-noise ratio of 3 were in the range of 0.22–1.06 ng/mL. When applied to Lycium barbarum seed oils, the developed method showed good reproducibility. The effect of extraction methods including supercritical CO₂ and organic solvent extraction on the FFAs composition has also been investigated. Meanwhile, this method exhibits powerful potential for the trace analysis of short- and long-chain free fatty acids from edible oils, foodstuff and other complex samples.     

Direct quantification of fatty acids in dairy powders with special emphasis on trans fatty acid content

In this study a validated procedure for accurate determination of fatty acids in dairy products, with special emphasis on total trans fatty acids (TFA) content is presented. Dairy fat naturally contains 4–6% of trans fatty acids, mainly trans-octadecenoic acids (i.e. vaccenic acid), and 0.3–1.5% of conjugated linoleic acids (CLA). The proposed procedure does not require lipid extraction, and transesterification of lipids could be carried out directly on dairy products. Optimal analytical conditions have been developed to allow accurate determination of TFA content without prior fractionation of cis/trans FAME isomers by thin-layer chromatography. The methodology requires the use of a highly polar open tubular capillary column having at least 100 m length. CLA and other fatty acids from C4:0 (butyric) acid to long-chain polyunsaturated fatty acids (LC-PUFAs) could also be analyzed. Therefore, the methodology presented is versatile and could be used for both targeted analysis (e.g. determination of TFA in dairy products) and determination of the broad fatty acid profile in dairy products.     

Characterisation of furan fatty acids in Adriatic fish

Furan fatty acids (F-acids) were characterised in the fillet of European hake (Merluccius merluccius), horse mackerel (Trachurus trachurus), common sole (Solea solea), European anchovy (Engralius encrasicolus), Atlantic mackerel (Scomber scombrus), European pilchard (Sardina pilchardus) was harvested in Adriatic Sea during the spring and the summer. The main F-acids were of the saturated series: 12,15-epoxy-13-methyleicosa-12,14-dienoic acid [MonoMe(11,5)] in European hake and 12,15-epoxy-13,14-dimethyleicosa-12,14-dienoic acid [DiMe(11,5)] in all the other fish species; 12,15-epoxy-13,14-dimethyloctadeca-12,14-dienoic acid, 10,13-epoxy-11-methyloctadeca-10,12-dienoic acid and 14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic acid were present in all fish species in trace amounts. Other identified F-acids were the olefinic congeners 12,15-epoxy-13,14-dimethyleicosa-12,15,16-trienoic acid and 12,15-epoxy-13,14-dimethyleicosa-10,12,14-trienoic acid. European pilchard had the highest F-acids content (30 mg/100 g fillet), whereas horse mackerel showed the lowest content (less than 0.1 mg/100 g fillet). Eicosapentaenoic acid (EPA) was positively correlated with MonoMe(11,5) and DiMe(11,5), showing that the biosynthesis of docosapentaenoic acid (DPA) and docosahexaenoic acid (DHA) is presumably competitive with that of F-acids.     

Essential oil composition of Pterospartum tridentatum grown in Portugal

The essential oils, isolated by hydrodistillation and distillation-extraction, from the aerial parts of different populations of Pterospartum tridentatum collected during the flowering phase, at different locations in Portugal, were analysed by GC and GC–MS. All the P. tridentatum populations studied afforded a yellowish oil in a yield <0.05% (v/w). cis-Theaspirane (2–14%), trans-theaspirane (2–17%) and octen-3-ol (2–37%) were, in variable amounts, the dominant components of the oils. Cluster analysis of the essential oil compositions from the nine populations studied, confirmed a major chemical variability.