11-octadecenoic-acid and elaidic-acid

The definition and evaluation of trans fatty acids (TFA) with regard to foodstuffs and health hazard are not consistent. Based on the current situation, the term should be restricted only to TFA with isolated double bonds in trans-configuration. Conjugated linoleic acids (CLA) should be separately assessed. Ideally, the origin of the consumed fat should be declared, i.e., ruminant TFA (R-TFA) and industrial TFA (non-ruminant; I-TFA). In ruminant fat, more than 50% of R-TFA consists of vaccenic acid (C18:1 t11). In addition, natural CLA, i.e., c9,t11 CLA is also present. Both are elevated in products from organic farming. In contrast to elaidic acid (t9) and t10, which occur mainly in partially hydrogenated industrial fat, t11 is partially metabolized into c9,t11 CLA via Δ9-desaturation. This is the major metabolic criterion used to differentiate between t11 and other trans C18:1. t11 indicates health beneficial effects in several studies. Moreover, CLA in milk fat is associated with the prevention of allergy and asthma. An analysis of the few studies relating to R-TFA alone makes clear that no convincing adverse physiological effect can be attributed to R-TFA. Only extremely high R-TFA intakes cause negative change in blood lipids. In conclusion, in most European countries, the intake of R-TFA is assessed as being low to moderate. Restriction of R-TFA would unjustifiably represent a disadvantage for organic farming of milk.

Topics: Animals; Cardiovascular Diseases; Dietary Fats; Health Status; Humans; Linoleic Acids, Conjugated; Milk; Nutrition Policy; Oleic Acid; Oleic Acids; Organic Agriculture; Ruminants; Trans Fatty Acids; World Health Organization

The human milk fatty acid, including

Topics: Adult; Breast Feeding; Chromatography, Gas; Cross-Sectional Studies; Dairy Products; Diet; Diet Records; Eating; Feeding Behavior; Female; Humans; Lactation; Latvia; Maternal Nutritional Physiological Phenomena; Middle Aged; Milk, Human; Oleic Acids; Surveys and Questionnaires; Trans Fatty Acids; Young Adult

Topics: Animals; Anti-Inflammatory Agents; Carbon Radioisotopes; Endothelium, Vascular; Humans; Inflammation; Oleic Acids; Ruminants; Trans Fatty Acids; Tumor Necrosis Factor-alpha

There has been controversial evidence regarding the relationship between isomers of circulating trans-fatty acids (TFAs) and mortality. This study aimed to ascertain the relationships between plasma TFAs and overall or cause-specific mortality of the general population in two independent subsets from the US National Health and Nutrition Examination Survey (1999-2000 and 2009-2010 cycles).. Plasma TFA isomers (C16:1n-7t, C18:1n-7t, C18:1n-9t and C18:2n-6,9t) in 3439 adults free of cancer or severe cardiovascular disease were analyzed by gas chromatography/mass spectrometry. Overall, 259 died among 1376 individuals over a median follow-up of 15.6 years in the 1999-2000 cycle, and 105 died in the latter subset of 2063 subjects during a median of 5.9 years. Cox proportional hazards regression was conducted to estimate the hazard ratios of mortality. The main isomer of industrially derived TFAs, elaidic acid (C18:1n-9t) was considerably associated with long-term total mortality in the 1999-2000 cycle after adjusting for confounders, with a 54% increase in the top tertile compared with the bottom one. However, the association disappeared with halving C18:1n-9t by 2009-2010. In contrast, neither of the ruminant-derived TFAs (C16:1n-7t and C18:1n-7t) suggested any inverse correlations with all-cause death, mortality due to heart disease, cancer or other causes.. The major isomer of industrial TFAs, the higher circulating C18:1n-9t might be associated with increased long-term mortality. The associations with death risk turned slight with the reduction of TFAs consumption by half. However, dietary guidelines should rigorously identify the healthy effect of animal TFAs consumption.

Topics: Adult; Cause of Death; Diet; Eating; Fatty Acids, Monounsaturated; Female; Follow-Up Studies; Gas Chromatography-Mass Spectrometry; Humans; Linoleic Acid; Male; Middle Aged; Mortality; Nutrition Surveys; Oleic Acids; Proportional Hazards Models; Prospective Studies; Risk Factors; Time Factors; Trans Fatty Acids; United States

trans fatty acids (TFAs) have been reported to promote vascular diseases mainly by promoting apoptosis and inflammation of vascular endothelial cells. However, it has been reported in recent years that elaidic acid (9t18:1) and vaccenic acid (11t18:1) may have different effects on vascular health. This study investigated the effects of 9t18:1 and 11t18:1 on human umbilical vein endothelial cell (HUVEC) function and the possible mechanism of inflammation by analyzing the changes in the phospholipid composition and the relationship between phospholipase A2 (PLA2) and MAPK pathway. Here we found that the effect of 11t18:1 on cell viability, membrane damage and cellular inflammation was significantly lower than that of 9t18:1 (p < 0.05). And 9t18:1 and 11t18:1 had different effects on phospholipid composition. Both 9t18:1 and 11t18:1 significantly increased the protein expression of PLA2. Moreover, the MAPK pathway regulated the expression of PLA2, inflammatory cytokines and cyclooxygenase-2 (COX-2) and the secretion of prostaglandin E2 (PGE2) in HUVECs induced by 9t18:1 and 11t18:1. In conclusion, 9t18:1 and 11t18:1 activated the MAPK pathway which regulated the expression of PLA2 to cause inflammation in HUVECs.

Topics: Cyclooxygenase 2; Dinoprostone; Human Umbilical Vein Endothelial Cells; Humans; MAP Kinase Signaling System; Oleic Acids; Phospholipases A2

Fundamental nutritional studies on bioactive molecules require minimizing exposure to confounding foreign elements, like solvents. Herein, aqueous formulations of lecithin nanovesicles are proposed to study three individual trans fatty acids relevant to human nutrition: elaidic acid, trans-vaccenic acid and trans-palmitoleic acid. This proof-of-concept study describes the encapsulation of fatty acids, in vivo bioavailability, and the use of nanovesicles in behavioral experiments. The oral bioavailability of the encapsulated molecules and the selective exposure of animals to each trans-fatty acid of interest were confirmed in healthy rats. Behavioral studies also evidenced that nanovesicles can be used to evaluate the palatability of the lipids and investigate food preferences in mice. Altogether this study shows that lecithin nanovesicles offer an elegant tool to efficiently deliver hydrophobic molecules to animal models. This approach paves the way for future studies deconvoluting the nutritional effects of trans-fatty acids.

Topics: Administration, Oral; Animals; Biological Availability; Diet; Fatty Acids; Female; Food Preferences; Humans; Hydrophobic and Hydrophilic Interactions; Lecithins; Lipids; Mice; Mice, Inbred C57BL; Nanostructures; Nutrients; Oleic Acids; Rats; Trans Fatty Acids

High fatty acid (FA) levels are deleterious to pancreatic β-cells, largely due to the accumulation of biosynthetic lipid intermediates, such as ceramides and diglycerides, which induce ER stress and apoptosis. Toxicity of palmitate (16:0) and oleate (18:1 cis-Δ

Topics: Animals; Apoptosis; Cell Line, Tumor; Ceramides; Dietary Fats, Unsaturated; Diglycerides; Endoplasmic Reticulum Stress; Insulin-Secreting Cells; MAP Kinase Kinase 4; Necrosis; Oleic Acid; Oleic Acids; Palmitic Acids; Phosphorylation; Rats; Trans Fatty Acids

A novel screening method for the simultaneous detection of elaidic and vaccenic trans fatty acid isomers by CZE-UV was proposed and applied to brazilian spreadable cheese analysis. Optimized background electrolyte was composed by 10 mmol L

Topics: beta-Cyclodextrins; Cheese; Electrophoresis, Capillary; Food Contamination; Limit of Detection; Molecular Dynamics Simulation; Oleic Acid; Oleic Acids; Stereoisomerism; Trans Fatty Acids

Previous studies on health effects of trans fatty acids (TFA) have focused mainly on cardiovascular health. Little is known about the association of TFA with brain or mental health. In this study, we examined the associations of objectively-measured plasma TFA concentrations with depression in a large population-based cross-sectional study among U.S. adults.. We included 2136 non-pregnant participants aged 20 years or older from the National Health and Nutrition Examination Survey 2009-2010. Four major TFAs, including palmitelaidic acid (C16:1n-7t), elaidic acid (C18:1n-9t), vaccenic acid (C18:1n-7t), and linoelaidic acid (C18:2n-6t, 9t), were measured in fasting plasma using gas chromatography/mass spectrometry. Depressive symptoms were assessed using the validated Patient Health Questionnaire-9.. Participants with depressive symptoms had a higher plasma concentration of total TFA compared with those without depressive symptoms (6.6 vs 6.0 μmol/g lipids, P = 0.046). After adjustment for other major risk factors, the odds ratio (OR) of depressive symptoms comparing the highest with lowest tertile of TFAs was 1.44 (95% CI, 0.86-2.39) for total TFAs (P for trend 0.15). For each individual type of TFA, the corresponding OR was 1.78 (1.03-3.07) for elaidic acid (P for trend 0.049), 1.23 (0.76-2.00) for linoelaidic acid (P for trend 0.37), 1.19 (0.75-1.87) for palmitelaidic acid (P for trend 0.46), and 1.20 (0.75-1.94) for vaccenic acid (P for trend 0.43).. The cross-sectional study design limited causal inferences of the findings.. In a nationally representative population, plasma elaidic acid, a major trans fatty acid, was positively associated with depressive symptoms in adults. A positive but non-significant association of depressive symptoms was observed for total TFAs, linolelaidic acid, palmitelaidic acid, and vaccenic acid.

Topics: Adult; Aged; Cross-Sectional Studies; Depression; Fasting; Fatty Acids, Monounsaturated; Female; Gas Chromatography-Mass Spectrometry; Humans; Linoleic Acid; Male; Middle Aged; Nutrition Surveys; Oleic Acids; Patient Health Questionnaire; Risk Factors; United States

Endothelial inflammation is recognized as the initial stage of a multistep process leading to coronary heart disease (CHD). Recently, the different effects of industrial trans fatty acids (elaidic acid, 9t18:1) and ruminant trans fatty acids (vaccenic acid, 11t18:1) on CHD have been reported in epidemiological and animal studies, however, the mechanism was not fully studied. Therefore, the objective of this study was to explore the underlying mechanism by which 9t18:1 and 11t18:1 affect human umbilical vein endothelial cells (HUVECs) inflammation. We found that 9c11t-CLA modulated the inflammation of HUVECs induced by 9t18:1 and 11t18:1. Fatty acid composition, pro-inflammatory factors, phosphorylation of MAPKs, and the TLR4 level in HUVECs altered by 11t18:1 induction, collectively suggest that the bio-conversion of 11t18:1 to 9c11tCLA might be the cause why 11t18:1 and 9t18:1 have distinct influences on endothelial injuries. It was concluded that it is biosynthesis of 9c11t CLA from11t18:1, and the modulation of TLR4-MAPK pathway by 9c11t CLA, which at least partially account for the slight effect of 11t18:1 on endothelial inflammation.

Topics: Biotransformation; Cells, Cultured; Human Umbilical Vein Endothelial Cells; Humans; Immunologic Factors; Inflammation; Linoleic Acids, Conjugated; Mitogen-Activated Protein Kinases; Oleic Acid; Oleic Acids; Phosphorylation; Protein Processing, Post-Translational; Toll-Like Receptor 4

The effect of different individual TFA isomers on cardiovascular disease (CVD) has been a limited study, especially for stroke. We aimed to investigate the relationships between four major plasma TFA isomer (elaidic, vaccenic, palmitelaidic and linolelaidic acid) concentrations and the risk of CVD, stroke and non-stroke CVD. A cross-sectional study was conducted, utilising a nationally representative sample of US adults in the National Health and Nutrition Examination Survey. Among the 3504 participants, 304 participants self-reported CVD history. The highest quintile of elaidic acid intake was associated with a 233% higher CVD risk (p = .010). Adjusted for age, gender and race, palmitelaidic acid was associated with a decreased CVD risk, but the effect size was diminished in a subsequent analysis model. For stroke risk, we failed to identify any associations. In addition to elaidic acid, the health effect of palmitelaidic acid should be paid more attention in the future studies.

Topics: Adult; Aged; Aged, 80 and over; Body Mass Index; Cardiovascular Diseases; Cross-Sectional Studies; Diet; Fatty Acids, Monounsaturated; Female; Humans; Isomerism; Linoleic Acid; Male; Middle Aged; Nutrition Surveys; Oleic Acid; Oleic Acids; Risk Factors; Self Report; Trans Fatty Acids; United States; Young Adult

A diet high in trans-fatty acids (TFA) induces insulin resistance in rodent models and primates. However, previous epidemiological studies on the association between TFAs, based primarily on self-reported intake from the diet, and diabetes in humans have yielded conflicting results. Herein we examined the associations of objectively measured plasma TFA concentrations with diabetes in a large population-based study among US adults.. We included 3801 participants aged ≥20 years from the National Health and Nutrition Examination Survey 1999-2000 and 2009-10. Four major TFAs, namely palmitelaidic acid (C16:1 n-7t), elaidic acid (C18:1 n-9t), vaccenic acid (C18:1 n-7t), and linolelaidic acid (C18:2 n-6t, 9t), were measured in fasting plasma using gas chromatography-mass spectrometry. Diabetes was defined by self-reported physician diagnosis, plasma fasting glucose ≥126 mg/dL, or HbA1c ≥6.5%.. After adjustment for other major risk factors, the odds ratios (95% confidence intervals) of diabetes comparing the highest with lowest quintile of plasma TFAs was 2.19 (1.27-3.79) for total TFAs (P. In a nationally representative population, plasma TFAs, in particular elaidic acid, were positively associated with diabetes and biomarkers of glucose metabolism.

Topics: Adult; Blood Glucose; Diabetes Mellitus; Fasting; Fatty Acids, Monounsaturated; Female; Humans; Insulin; Insulin Resistance; Linoleic Acid; Male; Middle Aged; Nutrition Surveys; Oleic Acid; Oleic Acids; Risk Factors; Trans Fatty Acids; United States

To investigate the associations of organic food consumption with maternal pre-pregnancy BMI, hypertension and diabetes in pregnancy, and several blood biomarkers of pregnant women.. Prospective cohort study.. Pregnant women were recruited at midwives' practices and through channels related to consumption of food from organic origin.. Pregnant women who filled in FFQ and donated a blood sample (n 1339). Participant groups were defined based on the share of consumed organic products; to discriminate between effects of food origin and food patterns, healthy diet indicators were considered in some statistical models.. Consumption of organic food was associated with a more favourable pre-pregnancy BMI and lower prevalence of gestational diabetes. Compared with participants consuming no organic food (reference group), a marker of dairy products intake (pentadecanoic acid) and trans-fatty acids from natural origin (vaccenic and rumenic acids) were higher among participants consuming organic food (organic groups), whereas elaidic acid, a marker of the intake of trans-fatty acids found in industrially hydrogenated fats, was lower. Plasma levels of homocysteine and 25-hydroxyvitamin D were lower in the organic groups than in the reference group. Differences in pentadecanoic acid, vaccenic acid and vitamin D retained statistical significance when correcting for indicators of the healthy diet pattern associated with the consumption of organic food.. Consumption of organic food during pregnancy is associated with several health-related characteristics and blood biomarkers. Part of the observed associations is explained by food patterns accompanying the consumption of organic food.

Topics: Biomarkers; Body Mass Index; Dairy Products; Diet, Healthy; Fatty Acids; Female; Food, Organic; Fruit; Homocysteine; Humans; Linoleic Acids, Conjugated; Meat; Micronutrients; Netherlands; Oleic Acid; Oleic Acids; Pregnancy; Principal Component Analysis; Prospective Studies; Socioeconomic Factors; Surveys and Questionnaires; Trans Fatty Acids; Vegetables; Vitamin D

High calcium intake may increase hip fracture (HF) incidence. This phenomenon, known as the calcium paradox, might be explained by vaccenic acid (18:1t n-7, VA), the highly specific trans fatty acid (TFA) present in dairy products. First, we ecologically investigated the relationship between 18:1 TFA intake and HF incidence using data from 12 to 13 European countries collected before 2000; then we measured the effects of VA and elaidic acid (18:1t n-9, EA) on osteoblasts from goldfish scales (tissues very similar to mammalian bone), with alkaline phosphatase as a marker; and finally we measured the effect of VA on mRNA expression in the scales for the major bone proteins type I collagen and osteocalcin. HF incidence was significantly correlated with 18:1 TFA intake in men (r=0.57) and women (r=0.65). Incubation with 1μmol/L VA and EA for 48h significantly decreased alkaline phosphatase activity by 25% and 21%, respectively. Incubation of scales with 10μmol/L VA for 48h significantly decreased mRNA expression for type I collagen and osteocalcin (by about 50%). In conclusion, VA may be causatively related to HF and could explain the calcium paradox. It may be prudent to reduce 18:1 TFA intake, irrespective of trans positions, to prevent HF.

Topics: Aged, 80 and over; Animals; Calcium; Collagen Type I; Female; Gene Expression Regulation; Goldfish; Hip Fractures; Humans; Incidence; Male; Oleic Acid; Oleic Acids; Osteoblasts; Osteocalcin; Trans Fatty Acids

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

Topics: Adolescent; Brazil; Breast Feeding; Chromatography, Gas; Colostrum; Cross-Sectional Studies; Fatty Acids, Omega-3; Female; Humans; Linoleic Acids, Conjugated; Milk, Human; Oleic Acid; Oleic Acids; Pregnancy; Trans Fatty Acids; Young Adult

The studies suggest that trans fatty acids are the most harmful type of fatty acids, and their ingestion leads to an increase in oxidative stress, changes in the plasma levels of LDL cholesterol, and a reduction in n-6 and n-3 fatty acids utilization. The objective of this study was to determine the concentration profiles of elaidic and vaccenic acids in maternal blood plasma in the perinatal period, and in the plasma of blood collected from the umbilical vein. The article deals with the issue of the correlation between the levels of trans-unsaturated fatty acids in maternal and neonatal blood, which could suggest the transplacental transport of these acids. The potential correlations between the levels of trans-unsaturated fatty acids in maternal and umbilical blood and birth weight and body length in neonates was also verified.. The study group comprised 53 pregnant patients of the Clinic of Obstetrics and Perinatology of the Pomeranian Medical University in Szczecin, aged 18-39 years, together with their newborn babies. Elaidic and vaccenic acid levels were determined in maternal and umbilical plasma. Fatty acid methyl esters were injected onto the capillary column of the Agilent 6890M gas chromatography system integrated with an autosampler. The content of individual fatty acids was determined from the reference curves and expressed in mg/mL.. The lowest levels of both acids were observed in umbilical blood plasma. The level of elaidic acid was 0.0019 mg/mL ± 0.0013 mg/mL, while the level of vaccenic acid was 0.0007 mg/mL ± 0.0011 mg/mL. A statistically significant negative correlation was observed between maternal vaccenic acid levels and umbilical vaccenic acid levels.. The presence of trans-unsaturated fatty acids (elaidic acid and vaccenic acid) in umbilical plasma is evidence of the transplacental transport of these acids. The significantly higher levels of elaidic acid compared to vaccenic acid in umbilical plasma suggests that vaccenic acid is more extensively metabolized in placenta. The levels of trans-unsaturated fatty acids had no effect on birth weight and body length in neonates.

Topics: Adult; Biomarkers; Chromatography, Gas; Female; Fetal Blood; Humans; Infant, Newborn; Oleic Acid; Oleic Acids; Pregnancy; Pregnancy Complications; Prenatal Exposure Delayed Effects; Prenatal Nutritional Physiological Phenomena; Risk Assessment; Umbilical Cord; Young Adult

The structure of trans unsaturated fatty acids (TFAs) includes at least one double bond with a trans configuration. Numerous studies have shown that TFAs influence negative changes in blood lipid profile, may initiate or accelerate the course of many inflammatory diseases, and reduce n-6 and n-3 fatty acids' utilization. Their presence in tissues and systemic fluids is mainly the result of ingestion of TFA-containing foods. The objective of this study was to determine the concentration profiles of elaidic and vaccenic acids in human milk, and the existence of potential correlations between the levels of trans-unsaturated fatty acids and long chain polyunsaturated fatty acids.. The study group consisted of 53 lactating women, aged 18-39 years, 5-6 weeks after delivery. Elaidic and vaccenic acid levels were determined in human milk. Fatty acid methyl esters were injected onto the capillary column of an Agilent 6890M gas chromatography system integrated with an autosampler. Geometrical and positional isomers of fatty acids were identified by comparing their retention times with those of the fatty acid standards from Sigma-Aldrich. The content of individual fatty acids was determined from the reference curves and expressed in mg/mL.. The level of elaidic acid was 0.2572 ± 0.1811 mg/mL, and the level of vaccenic acid was 0.2736 ± 0.1852 mg/mL. No negative correlations between the levels of the analyzed TFAs and PUFAs were observed in human milk.. The levels of elaidic and vaccenic acid were similar and had no negative influence on the levels of arachidonic acid and docosahexaenoic acid.

Topics: Adult; Breast Feeding; Female; Gas Chromatography-Mass Spectrometry; Humans; Infant Nutritional Physiological Phenomena; Infant, Newborn; Lactation; Milk, Human; Oleic Acid; Oleic Acids; Young Adult

Few studies have explored whether fetal exposure to trans fatty acids (TFAs) influences the inception of atopic diseases. The aim of this study was to investigate the relationship between the concentration of specific TFAs (elaidic, vaccenic, and rumenic acids) in maternal plasma and the risk of developing atopic manifestations in the first year of life.. A subsample from a population-based pregnancy cohort of the INMA Project was analyzed. Maternal intake of fatty acids was assessed by a food-frequency questionnaire (75.5% of the cohort). TFAs and n-3 and n-6 long-chain polyunsaturated fatty acids were measured in samples of plasmatic phospholipids at 12 wk of pregnancy. Information regarding eczema and wheeze in offspring was obtained through questionnaires at ages 6 and 14 mo.. Elaidic acid correlated negatively with n-3 long-chain polyunsaturated fatty acids (total, eicosapentaenoic acid, and docosahexaenoic acid), and rumenic acid positively with both n-3 and n-6 long-chain polyunsaturated fatty acids in maternal plasma. Neither of these two fatty acids was associated with the risk of atopic eczema or wheeze in offspring in the first year of life. However, a higher vaccenic acid level was found to be linked to a lower risk of atopic eczema.. High vaccenic acid concentrations in maternal plasma may protect offspring against atopic eczema in infancy.

Topics: Adult; Age Factors; Animals; Biomarkers; Dermatitis, Atopic; Diet; Docosahexaenoic Acids; Eicosapentaenoic Acid; Female; Humans; Infant; Linoleic Acids, Conjugated; Male; Nutrition Assessment; Nutritional Status; Oleic Acid; Oleic Acids; Pregnancy; Prenatal Exposure Delayed Effects; Prenatal Nutritional Physiological Phenomena; Protective Factors; Respiratory Hypersensitivity; Respiratory Sounds; Risk Assessment; Risk Factors; Surveys and Questionnaires

Consumption of trans fatty acids (TFA) increase cardiovascular risk more than do saturated FA, but the mechanisms explaining their atherogenicity are still unclear. We investigated the impact of membrane incorporation of TFA on cholesterol efflux by exposing J774 mouse macrophages or human monocyte-derived macrophages (HMDM) to media enriched or not (standard medium) with industrially produced elaidic (trans-9 18:1) acid, naturally produced vaccenic (trans-11 18:1) acid (34 h, 70 μM) or palmitic acid. In J774 macrophages, elaidic and palmitic acid, but not vaccenic acid, reduced ABCA1-mediated efflux by ~23% without affecting aqueous diffusion, SR-BI or ABCG1-mediated pathways, and this effect was maintained in cholesterol-loaded cells. The impact of elaidic acid on the ABCA1 pathway was weaker in cholesterol-normal HMDM, but elaidic acid induced a strong reduction of ABCA1-mediated efflux in cholesterol-loaded cells (-36%). In J774 cells, the FA supplies had no impact on cellular free cholesterol or cholesteryl ester masses, the abundance of ABCA1 mRNA or the total and plasma membrane ABCA1 protein content. Conversely, TFA or palmitic acid incorporation induced strong modifications of the membrane FA composition with a decrease in the ratio of (cis-monounsaturated FA+polyunsaturated FA):(saturated FA+TFA), with elaidic and vaccenic acids representing each 20% and 13% of the total FA composition, respectively. Moreover, we demonstrated that cellular ATP was required for the effect of elaidic acid, suggesting that it contributes to atherogenesis by impairing ABCA1-mediated cholesterol efflux in macrophages, likely by decreasing the membrane fluidity, which could thereby reduce ATPase activity and the function of the transporter.

Topics: Adenosine Triphosphate; Animals; ATP Binding Cassette Transporter 1; ATP-Binding Cassette Transporters; Biological Transport; CD36 Antigens; Cell Membrane; Cholesterol; Diffusion; Gene Expression Regulation; Humans; Macrophages; Mice; Monocytes; Oleic Acid; Oleic Acids; Phospholipids; RNA, Messenger

Elaidic acid (trans-9-C₁₈:₁ or trans-9) is assumed to exert atherogenic effects due to its double bond configuration. The possibility that trans-9 and vaccenic acid (trans-11-C₁₈:₁ or trans-11), its positional isomer, were biochemically equivalent and interchangeable compounds, was investigated by reference to their cis-isomers through esterification-related activities using rat liver cells and subcellular fractions. In hepatocytes, both trans-C₁₈:₁ were incorporated to the same extent in triacylglycerols, but trans-9 was more esterified than trans-11 into phospholipids (P < 0.05). Glycerol-3-phosphate acyltransferase activity in microsomes was lower with trans-11 than with trans-9, while this activity in mitochondria was ~40% greater with trans-11 than with trans-9 (P < 0.05). Activity of 2-lysophosphatidic acid acyltransferase in microsomes was of comparable extent with both trans isomers, but activity of 2-lysophosphatidylcholine acyltransferase was significantly greater with trans-9 than with trans-11 at P < 0.01. Lipoproteins secreted by hepatocytes reached equivalent levels in the presence of any isomers, but triacylglycerol production was more elevated with trans-11 than with trans-9 at P < 0.05. Cholesterol efflux from previously labelled hepatocytes was lower with trans-11 than with trans-9. When these cells were exposed to either trans-C₁₈:₁, the gene expression of proteins involved in fatty acid esterification and lipoprotein synthesis was unaffected, which indicates that the biochemical differences essentially depended on enzyme/substrate affinities. On the whole, vaccenic and elaidic acid were shown to incorporate cell phospholipids unequally, at least in vitro, which suggests they can differently affect lipid metabolic pathways in normal cells.

Topics: Animals; Cell Culture Techniques; Cholesterol; Esterification; Gene Expression; Glycerol-3-Phosphate O-Acyltransferase; Hepatocytes; Isomerism; Lipoproteins; Liver; Male; Microsomes; Mitochondria; Oleic Acid; Oleic Acids; Phospholipids; Rats; Rats, Wistar; Therapeutic Equivalency; Triglycerides

Trans fatty acids (TFAs) are present in meat and dairy products as m ruminant animals and in vegetable fats due to partial hydrogenation. This study aimed to discriminate between natural (N-TFA) and hydrogenated trans fatty (H-TFA) acids by GC×GC-flame ionization detection (GC×GC-FID) and comprehensive GC×GC-time-of-flight mass spectrometry (GC×GC-TOFMS). The separation of two kinds of trans fats, vaccenic acid (18:1 trans-11) and elaidic acid (18:1 trans-9), was performed using GC×GC-FID and GC×GC-TOFMS. A 100 m×0.25 mm I.D.×0.2 μm (film thickness) SP-2560 (bis-cyanopropyl polysiloxane) fused capillary column (first separation dimension, 1D) was coupled to a 1.5 m×0.18 mm I.D.×0.18 μm (film thickness) RTX-5 (5% diphenyl/95% dimethyl polysiloxane) fused capillary column (second separation dimension, 2D). The RSD of the intra-day repeatability by both GC×GC-FID and GC×GC-TOFMS for elaidic and vaccenic acids was ≤9.56% and ≤9.97%, and the RSD of the inter-day repeatability was ≤8.49 and ≤9.06%, respectively. It was found that the V/E value (vaccenic acid to elaidic acid ratio) could be used to distinguish H-TFA from N-TFA and to evaluate the quality of the fatty foods.

Topics: Food Analysis; Gas Chromatography-Mass Spectrometry; Oleic Acid; Oleic Acids; Quality Control; Reproducibility of Results; Trans Fatty Acids

Vaccenic acid (trans-11-C(18:1)) chemically resembles elaidic acid (trans-9-C(18:1)) which is assumed to increase the risk of cardiovascular diseases, and thus could exert similar effects. Possible different oxidation rates of vaccenic versus elaidic acid were checked in muscles and liver, and through related gene expression in normal rat liver cells. In hepatic mitochondria, carnitine palmitoyltransferase (CPT) I exhibited comparable activity rates with both trans-isomers. CPT II activity was 30% greater (P < 0.05) with vaccenic than with elaidic acid as nonesterified fatty acids (NEFAs) or acyl-CoAs. Activity of the first beta-oxidation step was similar between the isomers in all the tissue slices and liver extracts assayed. Respiration rates were comparable with both trans-isomers as NEFAs in various liver extracts, but were 30% greater (P < 0.05) with vaccenoyl-CoA than with elaidoyl-CoA in liver mitochondria. Vaccenic acid was oxidised 25% more (P < 0.05) by liver peroxisomes than elaidic acid. In hepatocytes cultured with trans- and corresponding cis-C(18:1) isomers, gene expression of CPT I, hydroxyacyl-CoA dehydrogenase and hydroxymethylglutaryl-CoA synthase was at least 100% increased (P < 0.05), but was unchanged with vaccenic acid, relative to controls. In conclusion, the position and geometry of the double bonds in acyl chains are suggested to confer on vaccenic and elaidic acid specific biochemical properties that might differently affect their fates in tissues.

Topics: Acyl Coenzyme A; Animals; Carnitine O-Palmitoyltransferase; Fatty Acids, Nonesterified; Gene Expression Regulation; Liver; Male; Oleic Acid; Oleic Acids; Oxidation-Reduction; Rats; Rats, Wistar

This study assessed the long-term effects of dietary vaccenic acid (VA) and elaidic acid (EA) on plasma and splenocyte phospholipid (PL) composition and related changes in inflammation and splenocyte phenotypes and cytokine responses in obese/insulin resistant JCR:LA-cp rats. Relative to lean control (Ctl), obese Ctl rats had higher serum haptoglobin and impaired T-cell-stimulated cytokine responses. VA and EA diets improved T-cell-stimulated cytokine production; but, only VA normalized serum haptoglobin. However, EA- and VA-fed rats had enhanced LPS-stimulated cytokine responses. The changes elicited by VA were likely due changes in essential fatty acid composition in PL; whereas EA-induced changes may due to direct incorporation into membrane PL.

Topics: Animals; Case-Control Studies; Cytokines; Diet; Disease Models, Animal; Fatty Acids; Haptoglobins; Insulin Resistance; Mitogens; Obesity; Oleic Acid; Oleic Acids; Phospholipids; Rats; Spleen

In the present study, the effects of trans-MUFA, elaidic acid (EA; 18 : 1-9t) and vaccenic acid (VA; 18 : 1-11t) on rat neutrophil functions were compared with those of cis-monounsaturated oleic acid (OA) (18 : 1-9c) and saturated stearic acid (SA; 18 : 0) (10-150 microm). Trans-fatty acids enhanced neutrophil phagocytic capacity, superoxide (O2-) and hydrogen peroxide production, and candidacidal activity. The same effects were observed for OA. Cells treated with trans-MUFA showed reduced production of NO, whereas those treated with OA showed an increase in production. Treatment with SA did not provoke significant effect on the parameters investigated. The increase in O2- production induced by MUFA was not observed when diphenyleneiodonium, an NADPH oxidase inhibitor, was added to the medium. This finding suggests that MUFA stimulate neutrophil NADPH oxidase activity. The addition of 3-[1-[3-(dimethylamino)propyl]-1H-indol-3-yl]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione, a protein kinase C (PKC) inhibitor, and wortmannin, a phosphatidylinositol-3 kinase (PI3K) inhibitor, did not affect O2- production induced by MUFA. Therefore, the mechanisms by which MUFA stimulate NADPH oxidase are not dependent on PKC and do not seem to involve PI3K. Experiments using Zn2+, an inhibitor of NADPH oxidase H+ channel, indicated that MUFA activate the NADPH oxidase complex in rat neutrophil due to opening of H+ channel.

Topics: Animals; Candida albicans; Cells, Cultured; Dietary Fats, Unsaturated; Dose-Response Relationship, Drug; Fatty Acids, Monounsaturated; Hydrogen Peroxide; Indicators and Reagents; Male; Neutrophils; Nitroblue Tetrazolium; Oleic Acid; Oleic Acids; Phagocytosis; Rats; Rats, Wistar; Superoxides

Male hamsters (30 per group) were fed five different semi-purified diets ad libitum. The diets, containing 30% of energy (en%) as fat, differed in their dietary fat composition (specified fatty acids exchanged at 10 en%) and were fed for 4 weeks. The five fatty acids compared in mixed triglycerides were elaidic acid (C18:1 9t), vaccenic acid (C18:1 11t), their cis-counterpart oleic acid (C18:1 9c), medium-chain fatty acids (MCFA; C8:0 and C10:0), and palmitic acid (C16:0). Compared with oleic acid, dietary MCFA and palmitic acid tended to increase blood cholesterol levels in the hamsters. The effect of elaidic and vaccenic acid on blood cholesterol did not differ from that of oleic acid. When elaidic acid and vaccenic acids were compared directly, the ratio of LDL/HDL-cholesterol in plasma was significantly higher in hamsters fed vaccenic acid than in those fed elaidic acid, and elaidic acid was incorporated at low levels, but more efficiently than vaccenic acid at the sn-2 position of platelet phospholipids. Biological consequences of this low incorporation are considered unlikely as levels of arachidonic acid (C20:4 n-6) and docosohexaenoic acid (C22:6 n-3) in the platelet phospholipids of all dietary groups did not differ. With respect to the effect on the LDL/HDL-cholesterol ratio, elaidic acid may be preferable to vaccenic acid. We conclude that this animal study does not provide evidence for the suggestion, based on epidemiological observations, that elaidic acid would be more detrimental to cardiovascular risk than vaccenic acid.

Topics: Animals; Coronary Disease; Cricetinae; Dietary Fats, Unsaturated; Lipids; Liver; Male; Oleic Acid; Oleic Acids

The degradation of unsaturated fatty acids was examined in fibroblasts from 16 patients with very-long-chain acyl-CoA dehydrogenase (VLCAD) deficiency. Analysis of acylcarnitine intermediates following incubation of intact human cells with these compounds revealed that the milder clinical phenotypes could be distinguished from the severe cardiomyopathic phenotype. These findings may reflect more effective contributions of alternate pathways in the milder forms of the disease. Incubation of VLCAD-deficient cells with cis-9 or trans-9 unsaturated fatty acids indicate that VLCAD is largely responsible for the 2,3-dehydrogenation of cis-5 or trans-5 intermediates in fibroblasts. The first two cycles of beta-oxidation with oleic and linoleic acids occur in the absence of VLCAD activity suggesting the presence of an additional acyl-CoA dehydrogenase or alternate pathway for the oxidation of these unsaturated fatty acids. These observations have clinical relevance for determining diagnosis, prognosis and strategies for dietary treatment of these patients.

Topics: Acyl-CoA Dehydrogenase, Long-Chain; Acyl-CoA Dehydrogenases; Adult; Carnitine; Case-Control Studies; Cells, Cultured; Child; Child, Preschool; Fatty Acids, Unsaturated; Female; Fibroblasts; Humans; Infant, Newborn; Isomerism; Lipid Metabolism, Inborn Errors; Oleic Acid; Oleic Acids; Oxidation-Reduction; Substrate Specificity

In vitro and in vivo studies in animals have shown that elevated levels of free fatty acids (FFAs) induce impaired beta-cell function corresponding to the abnormalities observed in non-insulin-dependent diabetes mellitus (NIDDM). Previously, it was demonstrated that the chain length and degree of unsaturation are of importance for the insulinotropic effect of fatty acids. However, it is not known if the spatial configuration of the fatty acid influences beta-cell function. The present study examines whether cis and trans fatty acids acutely influence insulin release and glucose oxidation in isolated mouse islets in the same way and to the same extent. Thus, we studied the impact of both cis and trans forms of C 18:1 fatty acids. We found that cis and trans vaccenic acid (cis and trans C 18:1 delta11), as well as oleic acid (cis C 18:1 delta9) and elaidic acid (trans 18:1 delta9), caused a dose-dependent increase in glucose (16.7 mmol/L)-stimulated insulin secretion during static islet incubations. The maximal stimulatory effect for cis and trans vaccenic acid and for oleic and elaidic acid was observed at concentrations of 2.0 and 3.0 mmol/L, respectively. The trans isomers, trans vaccenic and elaidic acid, elicited a higher maximal insulin output than the respective cis isomers, cis vaccenic and oleic acid. In the presence of another insulin secretagogue, L-leucine, trans vaccenic but not elaidic acid caused a higher response than their cis isomeric fatty acids. The higher potency of trans fatty acids compared with the cis forms was confirmed in perifusion experiments. Both cis and trans C 18:1 fatty acids stimulated insulin secretion in a glucose-dependent manner. Also, glucose oxidation was influenced differentially by the isomers of fatty acids. Glucose oxidation at 16.7 mmol/L glucose was significantly inhibited by oleic and cis vaccenic acid compared with elaidic and trans vaccenic acid, respectively. In summary, our results demonstrate that the fatty acid spatial configuration modulates glucose oxidation and insulin secretion in mouse beta cells.

Topics: Animals; Calcium; Fatty Acids; Female; Glucose; In Vitro Techniques; Insulin; Insulin Secretion; Islets of Langerhans; Leucine; Mice; Oleic Acid; Oleic Acids

The metabolic course of four isomeric epoxyfatty acids derived from oleic-, elaidic-, (Z)-, and (E)-vaccenic acids in the lactone-producing yeast, Sporidiobolus salmonicolor, was studied by using the deuterium-labeled precursors. Dihydroxy-, hydroxyoxo-, and hydroxy fatty acids as well as gamma-lactones were identified as metabolic intermediates. Quantitative analysis of the label content and estimation of the enantiomeric composition of the lactones established that, in the first step, the racemic epoxyfatty acids were enantiospecifically hydrolyzed by an epoxide hydrolase. During the subsequent metabolism, the stereochemical orientation of the hydroxy groups of the dihydroxyfatty acids were modified by an oxidation/reduction step.

Topics: Basidiomycota; Deuterium; Epoxy Compounds; Fermentation; Gas Chromatography-Mass Spectrometry; Kinetics; Lactones; Mass Spectrometry; Oleic Acid; Oleic Acids; Stearic Acids; Stereoisomerism; Structure-Activity Relationship

The incorporation of [14C]elaidic acid (trans18:1(n-9)) in phosphatidylcholine and phosphatidylethanolamine molecular species in isolated rat liver cells has been studied, and the results compared with the incorporation, previously published (B. Woldseth et al. Biochim Biophys Acta 1993; 1167: 296-302), of [14C]palmitic acid (16:0) and [14C]stearic acid (18:0) and with that of [14C]oleic acid (cis18:1(n-9)). The pattern of incorporation in phospholipid molecular species is similar to that of [14C]stearic acid and different from that of [14C]palmitic acid. In phosphatidylcholine [14C]trans18:1-18:2 and [14C]trans18:1-20:4 were the most abundant species, and in phosphatidylethanolamine [14C]trans18:1-20:4 was the predominant species. With increasing concentration of [14C]elaidic acid increasing amounts of [14C]trans18:1-[14C]trans18:1 were found. The total incorporation in phospholipids was less than that of [14C]stearic acid, but more than that of [14C]palmitic acid. The distribution in percent of [14C]elaidic acid in phospholipid classes was 8.8% in phosphatidylinositol, 1.8% in phosphatidylserine, 59.1% in phosphatidylcholine and 30.3% in phosphatidylethanolamine with 0.1 mmol l-1 substrate concentration. More [14C]elaidic acid than [14C]palmitic acid or [14C]stearic acid was oxidized. The incorporation in phospholipids of [14C]elaidic acid was very different from that of [14C]oleic acid. The main species with [14C]oleic acid were 16:0-[14C]cis18:1 in phosphatidylcholine, and [14C]cis18:1-20:4 in phosphatidylethanolamine. In some experiments [14C]18:2(n-6) was incubated together with unlabelled elaidic or unlabelled trans-vaccenic acid (trans18:1(n-7)). In these experiments, more trans18:1-18:2 was formed from elaidic acid than from trans-vaccenic acid, especially in phosphatidylethanolamine.

Topics: Animals; Carbon Radioisotopes; Chromatography, Gas; Esterification; Fatty Acids, Monounsaturated; Linoleic Acid; Liver; Male; Oleic Acid; Oleic Acids; Oxidation-Reduction; Palmitic Acid; Phosphatidylcholines; Phosphatidylethanolamines; Rats; Rats, Wistar; Stearic Acids

Topics: Animals; Butter; Catalysis; Cattle; Coronary Disease; Dietary Fats, Unsaturated; Fatty Acids, Unsaturated; Humans; Hydrogenation; Isomerism; Margarine; Oleic Acid; Oleic Acids; Plant Oils; Rumen; Selection, Genetic; Sheep

Octadecenoic (18:1) trans-fatty acid fractions from margarine, butter and plasma phospholipids (PL) were isolated by silver ion TLC, and nine positional isomers (n-11-n-3) were identified by GC-MS based on their ozonolysis products. The GC analysis of the isolated fractions gave similar peak profiles and separated seven trans-isomers (n-11-n-6 and n-3). Without a preceding isolation step, the reproducibility of the GC method for plasma PL elaidic (18:1 n 9 trans) and trans-vaccenic acids (n-7) was 3.4 and 2.7% (R.S.D.), respectively. These trans-isomers were rapidly incorporated and cleared in plasma PL and they closely reflected both increased and decreased intake of 18:1 trans-fatty acids during moderate fat substitutions. Significant associations between high-density lipoprotein cholesterol (HDL-C) and PL elaidic and trans-vaccenic acids appeared in habitual margarine users only.

Topics: Adult; Butter; Chromatography, Thin Layer; Dietary Fats; Female; Gas Chromatography-Mass Spectrometry; Humans; Male; Margarine; Oleic Acid; Oleic Acids; Olive Oil; Phospholipids; Plant Oils