Trans Polyunsaturated Fatty Acids Research Articles

Rapid Prediction of Fatty Acid Content in Marine Oil Omega-3 Dietary Supplements Using a Portable Fourier Transform Infrared (FTIR) Device and Partial Least-Squares Regression (PLSR) Analysis

Using a portable field device, a Fourier transform infrared spectroscopy (FTIR) and partial least-squares regression (PLSR) method was developed for the rapid (<5 min) prediction of major and minor fatty acid (FA) concentrations in marine oil omega-3 dietary supplements. Calibration models were developed with 174 gravimetrically prepared samples. These models were tested using an independent validation set of dietary supplements. FAs analyzed included eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA); the sums of saturated, branched-chain, and monounsaturated FAs; and n-6, n-4, n-3, n-1, and trans polyunsaturated FA. The spectral ranges 650-1500 or 650-1500 and 2800-3050 cm-1 provided reliable predictions for FA components in 34 neat oil products: standard error of prediction, 0.73-1.58%; residual predictive deviation, 6.41-12.6. This simple, nondestructive quantitative method is a rapid screening tool and a time and cost-saving alternative to gas chromatography for verifying label declarations and in quality control.

A novel series of C18–C22 trans ω3 PUFA from Northern and Southern Hemisphere strains of the marine haptophyte Imantonia rotunda

A series of novel C18–C22trans ω3 polyunsaturated fatty acids (PUFA) with a single trans double bond in the ω3 position was found in Northern and Southern Hemisphere strains of the marine haptophyte Imantonia rotunda. The novel ω3 PUFA were identified as 18:3(9c,12c,15t) (0.2–1.8 % of total fatty acids), 18:4(6c,9c,12c,15t) (1.9–4.1 %), 18:5 (3c,6c,9c,12c,15t) (0.7–8.8 %), 20:5(5c,8c,11c,14c,17t) (1.2–4.1 %) and 22:6(4c,7c,10c,13c,16c,19t) (0.3–4.3 %), and were accompanied by larger proportions of the all cis isomers: 18:3ω3(9,12,15) (2.7–3.5 %), 18:4ω3(6,9,12,15) (9.3–14.3 %), 18:5ω3(3,6,9,12,15) (7.8–18.5 %), 20:5ω3(5,8,11,14,17) (3.2–3.9 %), 22:5ω3(7,10,13,16,19) (0.1–0.3 %) and 22:6ω3(4,7,10,13,16,19) (2.3–5.2 %). GC analysis of FAME using a non-polar column did not reveal the trans isomers as they coeluted with the all cis PUFA. However, GC using a polar column resolved the trans PUFA from the all cis PUFA, with the trans isomers eluting before the all cis isomers. GC-MS of FAME fractionated by argentation solid-phase chromatography confirmed the molecular ions of all components. FAME were derivatized to form 4,4-dimethyloxazoline (DMOX) derivatives, and GC-MS revealed the same double bond positions for each trans and cis FAME. The results suggest that the ω3 trans double bond originated from the Δ15/ω3 desaturation of 18:2(9c,12c), suggesting that this desaturase has dual cis/trans activity in these species. These results indicate that 18:3(9c,12c,15 t) was the precursor trans isomer produced for the trans series and further desaturation by the common Δ6 desaturase to produce the trans tetraene and successive elongations and desaturations led to the subsequent series of trans ω3 PUFA isomers. To our knowledge, this is the first report of these trans ω3 isomers occurring in strains of I. rotunda. These trans ω3 PUFA may be used as biomarkers in marine food webs for this species and with their unique structure may be biologically active.

Determination of Thermally Induced trans-Fatty Acids in Soybean Oil by Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy and Gas Chromatography Analysis

The intake of edible oil containing trans-fatty acids has deleterious effects mainly on the cardiovascular system. Thermal processes such as refining and frying cause the formation of trans-fatty acids in edible oil. This study was conducted to investigate the possible formation of trans-fatty acids because of the heat treatment of soybean oil. The types of trans-fatty acids in heated soybean oil are determined by attenuated total reflectance Fourier transform infrared spectroscopy and gas chromatography-mass spectrometry methods. The effects of the heating temperature on the trans-fatty acids in soybean oil were evaluated using gas chromatography flame ionization detection analysis. Results show that heat treatment at 240 °C causes the formation of trans-fatty acids in soybean oil and the amount of trans-fatty acids increases with heating time. The only peak observed at 966 cm(-1) of the samples indicates the formation of nonconjugated trans isomers in the heated soybean oil. The major types of trans-fatty acids formed were trans-polyunsaturated fatty acids. Significant increases (P < 0.05) in the amounts of two trans-linoleic acids (C18:2-9c,12t and C18:2-9t,12c) and four trans-linolenic acids (C18:3-9c,12c,15t, C18:3-9t,12c,15c, and C18:3-9t,12t,15c/C18:3-9t,12c,15t) in soybean oil heated to temperatures exceeding 200 °C were compared with those of the control sample. The heating temperature and duration should be considered to reduce the formation of trans-fatty acids during thermal treatment.

Effect of replacing calcium salts of palm oil distillate with incremental amounts of conventional or high oleic acid milled rapeseed on milk fatty acid composition in cows fed maize silage-based diets

Based on potential benefits to human health, there is increasing interest in altering the composition of ruminant-derived foods. Including rapeseeds in the dairy cow diet is an effective strategy for replacing medium-chain saturated fatty acids (SFA) with cis-monounsaturated fatty acids (MUFA) in bovine milk, but there is limited information on the optimum level of supplementation. Decreases in SFA due to plant oils are also accompanied by increases in milk trans fatty acid (FA) content and it is possible that high oleic acid rapeseeds may result in a higher enrichment of cis-9 18:1 and lower increases in trans FAs in milk compared with conventional varieties. Seven multiparous lactating Holstein–Friesian cows were allocated to one of seven treatments in an incomplete Latin square design with five 28-day experimental periods, to evaluate the effect of replacing calcium salts of palm oil distillate (CPO; 41 g/kg diet dry matter, DM) with 128, 168 or 207 g/kg diet DM of conventional (COR) or a high oleic acid (HOR) rapeseed fed as a supplement milled with wheat. Rapeseed variety and inclusion level had no effect (P > 0.05) on DM intake, milk yield and composition. Both rapeseed varieties decreased linearly (P < 0.001) milk fat SFA content, which was partially compensated for by a linear increase (P < 0.001) in cis-9 18:1 concentration. Reductions in milk SFA were also associated with increases (P < 0.05) in trans 18:1 and total trans FA content, with no difference (P > 0.05) between rapeseed varieties. Replacing CPO in the diet with milled rapeseeds had no effect (P > 0.05) on total milk conjugated linoleic acid (CLA) concentration. Relative to a COR, inclusion of a high oleic acid variant in the diet increased (P = 0.01) the ratio of trans-MUFA : trans-polyunsaturated fatty acids in milk that may have implications with respect to cardiovascular disease risk in humans. In conclusion, data indicated that replacing CPO with milled rapeseeds at levels up to 1150 g oil/day could be used as a nutritional strategy to lower milk SFA content without inducing adverse effects on DM intake and milk production. HOR reduced milk fat SFA content to a greater extent than a conventional variety, but did not minimise associated increases in trans FA concentrations. However, the high oleic acid variant did alter the relative abundance of specific trans 18:1, CLA and trans 18:2 isomers compared with conventional rapeseeds.

Trans-Fatty Acid Isomers in Two Sesame (Sesamum indicum L.) Seed Byproducts under Processing

The present study has been inspired by the growing need for rigorously controlling the nutritional quality and safety of food products. The impact of application in the food industry on fatty acids composition, trans-fatty acids (TFAs), and conjugated linoleic acid (CLA) profiles were investigated in a highly consumed candy byproduct of sesame seed (chamia) in comparison to fresh sesame seed oil (SSO) and heated SSO under simulated frying experiments. The effect of treatment on SSO was studied by determining the TFA and CLA changes. Results showed significant differences between the two byproducts in TFA and CLA amounts. Total TFAs were found to be significantly higher in chamia than fresh SSO (1.31 versus 0.066%, respectively; p < 0.05) and even higher than all heated SSO from 2 to 10 h at 180 °C (1.31 versus 0.33%, respectively; p < 0.05). A significant linear relationship was found between trans-monounsaturated fatty acid (MUFA), trans-polyunsaturated fatty acid (PUFA), and total TFA and the time of processing, with a correlation coefficient (R(2)) greater than 0.9 for TFA and PUFA, with a higher correlation assigned to PUFA (r = 0.988; p < 0.001), followed by TFA (r = 0.959; p < 0.01) and MUFA (r = 0.844; p < 0.05). Principal component analysis of the fatty acid (FA) profiles showed discrimination between chamia and both fresh and heated SSO. A high stability of SSO against isomerization reactions as compared to their chamia sample counterpart has been noted. These findings suggest that the food industry engenders relatively higher changes in fatty acid configurations than the frying process.

Optimization of the selectivity of a cyanopropyl stationary phase for the gas chromatographic analysis of trans fatty acids

The quantification of monounsaturated and polyunsaturated trans fatty acids in partially hydrogenated fats by gas–liquid chromatography on a CP-Select CB-FAME capillary column was optimized using equivalent chain length values of fatty acids methyl esters that could coelute in the temperature range from 155 to 200 °C. The most appropriate temperature for the simultaneous determination of these trans isomers is around 197 °C. It is proposed a system to discriminate trans from cis octadecenoic fatty acid methyl esters based on the angular coefficient values of the equivalent chain length curves. The limits of detection and quantification were 0.28 and 0.93 mg g −1. Quantification was performed in the range from 0.93 to 280 mg g −1. Quantification accuracy was estimated by spike recovery of elaidic and trans-13-octadecenoic acids in hydrogenated fat samples. The obtained levels were from 97.60 to 103.28% for elaidic acid and from 98.12 to 99.27% for trans-13-octadecenoic acid. These results indicate that the accuracy of the methodology proposed for the quantification of monounsaturated and polyunsaturated trans fatty acids in hydrogenated fats is adequate.

Opposing roles of omega‐3 and trans polyunsaturated fatty acids in sudden cardiac death and vascular remodeling

Omega‐3 polyunsaturated fatty acids (n‐3 PUFAs) have well‐recognized cardio‐beneficial effects. In contrast, premature coronary deaths are associated with consuming high levels of trans polyunsaturated fatty acids (TFAs). We studied effects of n‐3 PUFAs and TFAs on cardiac health using sudden cardiac death and compensatory vascular remodeling models. Male rats were subjected to coronary ligation and were randomly assigned to diets high in n‐3 PUFAs or TFAs. Feeding an n‐3 PUFA‐enriched diet caused an increase in plasma n‐3 PUFAs by 7 fold compared to that of TFA fed group whereas TFA‐enriched diet caused an increase in plasma TFAs by 2.5 fold compared to n‐3 PUFA group. A diet high in TFAs was associated with a lower survival rate (6‐month post MI) due to sudden cardiac death. Animals on a TFA diet also exhibited variable degrees of aortic atherosclerotic lesions. For compensatory vascular remodeling, male mice were subjected to femoral artery ligation. After 3 months on the diets, animals on TFA diet did not exhibit any collateral vascular growth whereas animals on n‐3 PUFA diet exhibited compensatory vascular growth around ligated regions. In conclusion our data suggest that TFAs decrease whereas n‐3 PUFAs improve animal survival after Myocardial Infarction. TFAs induce whereas n‐3 PUFAs prevent development of atherosclerotic lesions and TFAs prevent whereas n‐3 PUFAs stimulate compensatory vascular remodeling.

Fatty acid contents of Brazilian soybean oils with emphasis on trans fatty acids

The fatty acid composition of the main soybean oil brands consumed by the Brazilian has been determined. The mean trans fatty acids (TFA) levels ranged between 0.8 and 2.6% of the total fatty acids and comprised 18:1, 18:2, and 18:3 isomers. 18:1 TFA levels were lower than 0.1% in all the studied brands. Among the polyunsaturated TFA, 18:3 predominated, with levels ranging from 0.5 to 1.4%. This group comprised mono and di-trans fatty acids and the main acid was 18:3 9c,12c,15t. The amounts of 18:2 TFA ranged from 0.3 to 1.1% with a predominance of acid 18:2 9c,12t . Alpha-linolenic acid contents ranged from 3.5 to 5.4%, with a mean value of 4.1%. The degree of isomerization of linoleic and alpha-linolenic acids ranged from 0.5 to 2.1% and from 9.1 to 27.2%, respectively. This study probably indicates that the thermal treatment applied to soybean oil during the deodorization step in the last years is too intense and that it results in a significant decrease in oil alpha-linolenic acid content and an increase in the n-6/n-3 ratio in the Brazilian diet.

Trans geometric isomers of EPA decrease LXRα-induced cellular triacylglycerol via suppression of SREBP-1c and PGC-1β

Dietary mono- or di-trans fatty acids with chain lengths of 18-22 increase the risk of cardiovascular diseases because they increase LDL cholesterol and decrease HDL cholesterol in the plasma. However, the effects of trans isomers of PUFAs on lipid metabolism remain unknown. Dietary PUFAs, especially eicosapentaenoic acid (EPA) in marine oils, improve serum lipid profiles by suppressing liver X receptor alpha (LXRalpha) activity in the liver. In this study, we compared the effects of trans geometric isomers of eicosapentaenoic acid (TEPA) on triacylglycerol synthesis induced by a synthetic LXRalpha agonist (T0901317) with the effects of EPA in HepG2 cells. TEPA significantly decreased the amount of cellular triacylglycerol and the expression of mRNAs encoding fatty acid synthase, stearoyl-CoA desaturase-1, and glycerol-3-phosphate acyltransferase induced by T0901317 compared with EPA. However, there was no significant difference between the suppressive effect of TEPA or EPA on the expression of sterol-regulatory element binding protein-1c (SREBP-1c) induced by T0901317. We found that TEPA, but not EPA, decreased the mRNA expression of peroxisome proliferator-activated receptor gamma coactivator 1beta (PGC-1beta), which is a coactivator of both LXRalpha and SREBP-1. These results suggest that the hypolipidemic effect of TEPA can be attributed to a decrease not only in SREBP-1 but also in PGC-1beta expression.

Formation of trans PUFA during deodorization of canola oil: A study through computational simulation

This article presents the application of an improved differential distillation model for the study of the formation of trans linoleic acid and trans linolenic acid during batch deodorization of canola oil, combining computational simulation and response surface methodology. The effects of four factors (temperature, duration of the batch and the initial contents of cis linoleic acid and cis linolenic acid) in the final content of trans polyunsaturated fatty acids of the deodorized oil were investigated. Following previous works, group contribution equations were used in the prediction of the required physical properties. To exemplify the usefulness of our modeling and evaluate its performance, the simulation results were compared with experimental values reported in the literature. The inclusion of kinetic models in the simulation program and the careful modeling of the reaction features allowed a good agreement between the results of the experimental work and the values estimated by our RSM equations.

The retina is more susceptible than the brain and the liver to the incorporation oftransisomers of DHA in rats consumingtransisomers of alpha-linolenic acid

Trans polyunsaturated fatty acids are formed during heat treatments of vegetable oils from polyunsaturated fatty acids containing cis double bonds. After dietary intake, they are distributed in the body and are incorporated into nervous tissues including the retina. Since nervous tissues are known to be rich in n-3 fatty acids such as docosahexaenoic acid (DHA), we studied the ability of the retina and the brain to incorporate trans isomers of DHA formed in vivo from the dietary precursor trans alpha-linolenic acid. Wistar rats were fed with trans isomers of alpha-linolenic acid for 21 months. A linear incorporation of trans DHA and a decrease in cis DHA was observed in the retina, whereas no major changes were observed in the brain. In parallel to the modifications in retinal cis and trans DHA levels, the retinal functionality evaluated by the electroretinogram showed defects in animals that consumed trans alpha-linolenic acid. These results suggest that the mechanisms leading to the incorporation of cis and trans fatty acids are quite different in the retina when compared to the brain and the liver, the retina being more susceptible to changes in the dietary lipid contribution.

Trans Polyunsaturated Fatty Acid Contents in Brazilian Refined Soybean Oil

This study examined the concentration (mg/g) of trans polyunsaturated fatty acid (TPFA) in five soybean oil brands by gas-liquid chromatography. Tricosanoic acid methyl ester was used as the internal standard. All samples analyzed presented trans 18:2 fatty and trans 18:3 acids in detectable amounts. The concentration of TPFA ranged from 5.8 to 30.2 mg/g, with a mean concentration value of 18.4 mg/g. Trans 18:3 fatty acids had the highest TPFA group concentrations, which ranged from 3.9 to 16.3 mg/g. The main isomer of this group presented the 9c, 12c, 15t configuration. For trans 18:2 fatty acids, concentrations ranged from 1.9 to 14.0 mg/g with a mean value of 8.1 mg/g. Alpha-linolenic acid (all cis) concentrations ranged from 30.7 to 60.6 mg/g and their degree of isomerization ranged from 6.0 to 31.5, indicating that the deodorization process varies from one producer to another. From per capita consumption of soybean oil brands in Brazil and their TPFA concentrations, it is possible to conclude that their contribution to the average TPFA intake per person in Brazil is 0.4 g/d.

Modulation of native T-type calcium channels by ω-3 fatty acids

Low voltage-activated, rapidly inactivating T-type Ca 2+ channels are found in a variety of cells where they regulate electrical activity and Ca 2+ entry. In whole-cell patch clamp recordings from bovine adrenal zona fasciculata cells, cis-polyunsaturated ω-3 fatty acids including docosahexaenoic acid (DHA), eicosapentaenoic acid, and α-linolenic acid inhibited T-type Ca 2+ current ( I T-Ca) with IC 50s of 2.4, 6.1, and 14.4 μM, respectively. Inhibition of I T-Ca by DHA was partially use-dependent. In the absence of stimulation, DHA (5 μM) inhibited I T-Ca by 59.7 ± 8.1% ( n = 5). When voltage steps to −10 mV were applied at 12 s intervals, block increased to 80.5 ± 7.2%. Inhibition of I T-Ca by DHA was accompanied by a shift of −11.7 mV in the voltage dependence of steady-state inactivation, and a smaller −3.3 mV shift in the voltage dependence of activation. ω-3 fatty acids also selectively altered the gating kinetics of T-type Ca 2+ channels. DHA accelerated T channel recovery from inactivation by approximately 3-fold, but did not affect the kinetics of T channel activation or deactivation. Arachidonic acid, an ω-6 polyunsaturated fatty acid, also inhibited T-type Ca 2+ current at micromolar concentrations, while the trans polyunsaturated fatty acid linolelaidic acid was ineffective. These results identify cis polyunsaturated fatty acids as relatively potent, new T-type Ca 2+ channel antagonists. ω-3 fatty acids are essential dietary components that have been shown to possess remarkable neuroprotective and cardioprotective properties that are likely mediated through suppression of electrical activity and associated Ca 2+ entry. Inhibition of T-type Ca 2+ channels in neurons and cardiac myocytes could contribute significantly to their protective actions.

Modulation of native TREK-1 and Kv1.4 K+ channels by polyunsaturated fatty acids and lysophospholipids.

The modulation of TREK-1 leak and Kv1.4 voltage-gated K+ channels by fatty acids and lysophospholipids was studied in bovine adrenal zona fasciculata (AZF) cells. In whole-cell patch-clamp recordings, arachidonic acid (AA) (1-20 microM) dramatically and reversibly increased the activity of bTREK-1, while inhibiting bKv1.4 current by mechanisms that occurred with distinctly different kinetics. bTREK-1 was also activated by the polyunsaturated cis fatty acid linoleic acid but not by the trans polyunsaturated fatty acid linolelaidic acid or saturated fatty acids. Eicosatetraynoic acid (ETYA), which blocks formation of active AA metabolites, failed to inhibit AA activation of bTREK-1, indicating that AA acts directly. Compared to activation of bTREK-1, inhibition of bKv1.4 by AA was rapid and accompanied by a pronounced acceleration of inactivation kinetics. Cis polyunsaturated fatty acids were much more effective than trans or saturated fatty acids at inhibiting bKv1.4. ETYA also effectively inhibited bKv1.4, but less potently than AA. bTREK-1 current was markedly increased by lysophospholipids including lysophosphatidyl choline (LPC) and lysophosphatidyl inositol (LPI). At concentrations from 1-5 microM, LPC produced a rapid, transient increase in bTREK-1 that peaked within one minute and then rapidly desensitized. The transient lysophospholipid-induced increases in bTREK-1 did not require the presence of ATP or GTP in the pipette solution. These results indicate that the activity of native leak and voltage-gated K+ channels are directly modulated in reciprocal fashion by AA and other cis unsaturated fatty acids. They also show that lysophospholipids enhance bTREK-1, but with a strikingly different temporal pattern. The modulation of native K+ channels by these agents differs from their effects on the same channels expressed in heterologous cells, highlighting the critical importance of auxiliary subunits and signaling. Finally, these results reveal that AZF cells express thousands of bTREK-1 K+ channels that lie dormant until activated by metabolites including phospholipase A2 (PLA2)-generated fatty acids and lysophospholipids. These metabolites may alter the electrical and secretory properties of AZF cells by modulating bTREK-1 and bKv1.4 K+ channels.

Modification of the dopaminergic neurotransmitters in striatum, frontal cortex and hippocampus of rats fed for 21 months with trans isomers of α-linolenic acid

Deficiency in n−3 fatty acids is known to disturb the release of dopaminergic neurotransmitters in rat brain. Since isomerization reduces the bioavailability of dietary fatty acids, the effect of the conversion of α-linolenic acid into trans α-linolenic acid on the dopaminergic neurotransmission was studied. Rats were fed for 21 months with a control diet, a diet unbalanced in cis α-linolenic acid and containing trans α-linolenic acid or the same diet in which the imbalance was corrected by increasing the levels of cis α-linolenic acid. After 6 and 21 months of diet, the fatty acid composition and the amounts of endogenous dopaminergic neurotransmitters was assessed in the striatum, the frontal cortex and the hippocampus. The isomerization of a part of dietary α-linolenic acid induced some modifications of the levels of endogenous dopaminergic neurotransmitters in all brain areas but was related to a very low incorporation of trans polyunsaturated fatty acids. Increasing the dietary levels of cis α-linolenic acid succeeded in correcting the endogenous neurotransmitter concentrations only in the frontal cortex but not in the striatum and the hippocampus. Thus, the levels of dopamine were lowered by 95% in the hippocampus. These results suggest that in addition to the imbalance generated by their presence, trans fatty acids may directly act on the concentration of dopaminergic neurotransmitters.

Long-Term Intake of trans (n-3) Polyunsaturated Fatty Acids Reduces the b-Wave Amplitude of Electroretinograms in Rats

Weanling rats were fed three diets differing in their concentrations of the cis- and trans-isomers of alpha-linolenic acid [18:3(n-3)] for 12 mo to study the long-term effects of these fatty acids on the electroretinogram (ERG). The diets contained 18:3(n-3) in its natural form at 2.0 g/100 g total fatty acids (C group), partially isomerized 18:3(n-3) [1.3 g/100 g cis 18:3(n-3) + 0.7 g/100 g trans 18:3(n-3); cT group] and the control level of cis 18:3(n-3) with trans 18:3(n-3) [2.0 g/100 g cis 18:3(n-3) + 0.7 g/100 g trans 18:3(n-3); CT group]. The ERG and the levels of trans-isomers of the polyunsaturated fatty acids (PUFA) of retinal and hepatic phospholipids were determined after 3, 6, 9 and 12 mo of feeding the experimental diets. Dietary trans alpha-linolenic acid altered the fatty acid composition of retinal and hepatic phospholipids by significantly increasing the Delta19trans-isomer of docosahexaenoic acid. Moreover, dietary trans-isomers of alpha-linolenic acid significantly decreased the b-wave amplitude of the ERG by 9 mo of feeding. We conclude that long-term intake of small amounts of trans-isomers of alpha-linolenic acid could disturb visual function. However, further studies are required to determine the mechanisms responsible for this phenomenon.

Modification of the monoaminergic neurotransmitters in frontal cortex and hippocampus by dietary trans α-linolenic acid in piglets

The effect of partial isomerization of dietary α-linolenic acid on the monoaminergic neurotransmitters in piglets was studied. After feeding the animals for 14 days with diets containing or not trans α-linolenic acid, neurotransmitters related to the monoaminergic function were quantified in the frontal cortex and in the hippocampus. The partial isomerization of dietary α-linolenic acid resulted in increasing endogenous monoamine levels in the frontal cortex (+55% for dopamine) and was related to a very low incorporation of trans polyunsaturated fatty acids. However, feeding animals with a diet in which the imbalance generated by the isomerization of α-linolenic acid was corrected succeeded in reducing the levels of monoamine in the frontal cortex but not in the hippocampus. These results suggest that the dietary trans fatty acids may act on the endogenous neurotransmitter levels during the brain development. Further work is needed to clarify the molecular mechanisms involved.

Trans Polyunsaturated Fatty Acids Have More Adverse Effects than Saturated Fatty Acids on the Concentration and Composition of Lipoproteins Secreted by Human Hepatoma HepG2 Cells

The objective of this study was to assess the relative long-term effects of linoleic (cis, cis 18:2), linolelaidic (trans, trans 18:2), and palmitic (16:0) acids on hepatic lipoprotein production in HepG2 cells. All fatty acids increased the mass of triglycerides (TG) in the medium and the incorporation of [(3)H]-glycerol into secreted TG; the increase was more pronounced with linoleic acid than with linolelaidic and palmitic acids. The net accumulation in the medium of apolipoprotein (apo) A-I was not affected by the fatty acids tested and moderate changes in that of apoB resulted in apoB/apoA-I mass ratios of 1.05, 1.27 and 0.86 with linoleic, linolelaidic and palmitic acids, respectively. The incorporation of [(14)C]-acetate into cellular plus secreted total sterols was 9.1%, 33.6% and 17.4% of total [(14)C]-labeled lipids with linoleic, linolelaidic and palmitic acids, respectively. Relative to linoleic acid, palmitic acid, and to a greater extent (P < 0.05) linolelaidic acid, increased the secretion and cellular accumulation of [(14)C]-labeled free cholesterol (FC) and cholesteryl esters and decreased those of TG and phospholipids (PL). Compared with linoleic acid, linolelaidic acid increased LDL-cholesterol (C) and HDL-C by 154% (P < 0.001) and 50% (P = 0.016), respectively, whereas palmitic acid increased LDL-C by 17% (P > 0.1) and did not affect HDL-C. The LDL-C to HDL-C ratios were 0.70, 1.18 and 0.96 with linoleic, linolelaidic and palmitic acids, respectively. These differences were not due to altered LDL receptor activity. The PL to C ratios of HDL particles were 1.61, 0.40 and 0.77 with linoleic acid, linolelaidic acid and palmitic acid, respectively. These results suggest that relative to cis polyunsaturated and saturated fatty acids, trans PUFA more adversely affect the concentration and composition of apoA-I- and apoB-containing lipoproteins secreted by HepG2 cells.

Desaturation and chain elongation of [1-14C]mono-trans isomers of linoleic and α-linolenic acids in perfused rat liver

Trans polyunsaturated fatty acids are produced during heat treatment of oils, such as deodorization and frying. The detailed metabolic pathways of these trans isomers are not fully understood. In the present work, the desaturation and chain elongation of [1-14C]linoleic acid, 9cis,12trans-18:2, 9trans,12cis-18:2, α-linolenic acid, 9cis, 12cis,15trans-18:3 and 9trans,12cis,15cis-18:3 were studied using a perfused rat liver model. After perfusion with both trans isomers of 18:2n–6, the 14C was equally distributed between phospholipids and triacylglycerols, compared to the 70:30 distribution (phospholipids:triacylglycerols) observed after infusing linoleic acid. The corresponding distribution of 14C after perfusion with both trans isomers of 18:3n–3 was comparable to what was obtained for α-linolenic acid. The products of conversion were analyzed by combination of different radio chromatographic methods. 9cis,12trans-18:2 was 16 times more converted into a C18:3n–6 fatty acid than linoleic acid into γ-linolenic acid. Trans-18:2 isomers were more elongated into “dead-end products” when compared to the conversion of linoleic acid into 20:2n–6 (from 2- to 5-times more). 9cis,12cis,15trans-18:3 and 9trans,12cis, 15cis-18:3 were 2- and 10-times less converted to trans-20:5, respectively, than α-linolenic acid into eicosapentaenoic acid. Moreover, 9cis,12cis,15trans-18:3 and 9trans,12cis, 15cis-18:3 were equally and 2.5-times more elongated into “dead-end products”, respectively, than α-linolenic acid into 20:3n–3. The partitioning of the conversion between formation of desaturated and chain elongated products on the one hand and production of “dead-end products” on the other was also calculated. Compared to their cis analogs, 9trans,12cis-18:2 and 9trans,12cis,15cis-18:3 were elongated into trans “dead-end products” rather than being converted to desaturated and chain elongated trans-metabolites. On the other hand 9cis,12cis,15trans-18:3 was more desaturated and chain elongated into 17trans 20:5 rather than elongated into 17trans-20:3. —Bretillon, L., J-M. Chardigny, J-P. Noël, and J-L. Sébédio. Desaturation and chain elongation of [1-14C]mono-trans isomers of linoleic and α-linolenic acids in perfused rat liver. J. Lipid Res. 1998. 39: 2228–2236.

Trans fatty acids in Canadian margarines: Recent trends

AbstractThe fatty acid composition and the trans fatty acid content of the top‐selling 109 Canadian margarines were determined by a combined capillary gas‐liquid chromatography/infrared spectroscopy method. The 109 brands accounted for 68% of the margarine brands sold in Canada and represented 74% of the market share. The mean level of total trans content in tub margarines (n=79) was 18.8% (g/100 g fatty acids) and ranged from 0.9 to 46.4%. The most frequent occurrence of trans in tub margarines was in the 15–20% range; 48 of the 79 tub brands were in this range but seven brands contained more than 40% trans. The trans content of hard margarines (n=30) ranged from 16.3 to 43.7% and the mean value was 34.3%. In 20 of the 109 brands, the levels of trans,trans isomers of linoleic acid exceeded the maximum level of 1% recommended for Canadian margarines. The levels of cis,trans/trans,cis isomers of linoleic acid were also high; 78 brands contained more than 1% and in 16 brands, the levels were in the 6–7% range. Linoleic acid content in the 109 brands ranged from 1.0 to 45.2% and averaged 18.3%. In 33 samples, linoleic acid was below the level of 5% recommended by an ad hoc committee of Health Canada. Moreover, in these, the total trans content exceeded 30%, and trans polyunsaturated fatty acid level was greater than 5%. There were eight margarines prepared from nonhydrogenated fat and their total trans content was below 2.5%. From the trans content and market share of each of the margarine brands, the average intake of trans fatty acids from margarine was estimated as 0.96 g/person/d. The intake of trans fatty acids in Canada from various sources was previously estimated by us as 8.4 g/person/d. Thus it is suggested that only 11% of the dietary trans fatty acids are supplied by margarines and the majority of trans fatty acids in the Canadian diet is derived from hidden fats in fast foods and bakery products.