Effect of essential fatty acid deficiency on the fatty acid composition, morphology, and electroretinographic response of the retina.
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Animals↗
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Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I.
The effects of low extracellular pH and intracellular accumulation of weak organic acids were compared with respect to fatty acid synthesis by whole cells of Mycobacterium tuberculosis and Mycobacterium smegmatis. The profile of fatty acids synthesized during exposure to benzoic, nicotinic, or pyrazinoic acids, as well as that observed during intracellular hydrolysis of the corresponding amides, was not a direct consequence of modulation of fatty acid synthesis by these compounds but reflected the response to inorganic acid stress. Analysis of fatty acid synthesis in crude mycobacterial cell extracts demonstrated that pyrazinoic acid failed to directly modulate the fatty acid synthase activity catalyzed by fatty acid synthase I (FAS-I). However, fatty acid synthesis was irreversibly inhibited by 5-chloro-pyrazinamide in a time-dependent fashion. Moreover, we demonstrate that pyrazinoic acid does not inhibit purified mycobacterial FAS-I, suggesting that this enzyme is not the immediate target of pyrazinamide.
Antitubercular Agents↗
Interactions of long-chain fatty acids and albumin: determination of free fatty acid levels using the fluorescent probe ADIFAB.
Equilibrium binding of long-chain fatty acids (FA) with albumin from human serum (HSA), bovine serum (BSA), and murine serum (MSA) has been studied by measuring the equilibrium levels of free fatty acids (FFA). FFA levels were measured directly, using a new fluorescent probe composed of acrylodan-derivatized intestinal fatty acid binding protein (ADIFAB). Measurements of [FFA] were done as a function of the ratio of total FA to total albumin (v) for v values between 0 and 6, at pH 7.4 and 37 degrees C. Under conditions observed in normal human physiology (v < or = 2), [FFA] values of the most abundant serum FA (palmitate, stearate, oleate) in equilibrium with human or bovine albumin are less than 15 nM. These values are considerably smaller than the generally quoted values of [FFA] in equilibrium with albumin: more than 20-fold for palmitate and more than 50-fold for oleate. FFA levels were found to increase monotonically with for all three albumins and all FA. In most cases [FFA] increased, for the same chain length, with increasing degree of acyl chain unsaturation, suggesting that FA aqueous solubility may play a significant role in the equilibrium between FA association with albumin and the aqueous phase. [The highest FFA levels (approximately 3000 nM), for example, were observed for linoleate (18:3) at the maximum v value (6).] Although aqueous-phase solubility of the FA may be important in understanding the interaction between FA and albumin, protein structure, as reflected in differences among the three albumins, also significantly affects the equilibrium.(ABSTRACT TRUNCATED AT 250 WORDS)
Animals↗
The quality properties and saturated and unsaturated fatty acid profiles of quail egg: the alterations of fatty acids with process effects.
The nutritional composition (moisture, ash, crude protein, available carbohydrates, total lipids), energy value, some quality characteristics (yolk weight, albumen weight and shell weight), cholesterol level and fatty acid profiles of quail egg were determined (p<0.01). The protein content of quail egg was higher than laying hen's egg. The fatty acid composition of quail egg yolk consisted of 24 fatty acids including saturated fatty acids (C14:0, C16:0, C17:0, C18:0, C20:0, C22:0, C24:0), monounsaturated fatty acids (C15:1, C16:1, C17:1, C18:1n9, C18:1n7, C22:1n9, C24:1) and polyunsaturated fatty acids (C18:2n6t , C18:2n6c , C18:3n6, C18:3n3, C20:2, C20:3n6, C20:3n3, C20:4n6, C22:2, C20:5n3, C22:6n3). The total cholesterol level of quail egg was found to be 73.45+/-1.07 mg/100 g. Linoleic acid (C18:2n6c) (10.28%), arachidonic acid (C20:4n6) (1.92%) and cis-5,8,11,14,17-eicosapentaenoic acid (C20:5n3) (0.63%) were the major polyunsaturated fatty acids in the fatty acid content of quail egg yolk, whereas oleic acid (C18:1n9c) was the major monounsaturated fatty acid comprising 26.71% in the yolk. The palmitic acid (C16:0) and stearic acid (C18:0) levels were 16.62% and 6.89%, respectively. Total omega-3 was detected as 1.16% in raw egg whereas it was 0.82% in soft-boiled (rafadan) egg. The polyunsaturated fatty acid/saturated fatty acid proportion was 0.58 and 0.64 for raw and processed yolk, respectively.
Animals↗
Nephrotoxicity and hepatotoxicity of 5,6-dichloro-4-thia-5-hexenoic acid: evidence for fatty acid beta-oxidation-dependent bioactivation.
5,6-Dichloro-4-thia-5-hexenoic acid (DCTH) is toxic to rat liver and kidney mitochondria and is cytotoxic to isolated rat hepatocytes. The object of this investigation was to test the hypothesis that DCTH is bioactivated in vivo by the enzymes of mitochondrial fatty acid beta oxidation and that the observed mitochondrial dysfunction is a consequence of this bioactivation. DCTH was a potent nephrotoxin and hepatotoxin in Long-Evans rats, whereas the odd-chain-length analog 6,7-dichloro-5-thia-6-heptenoic acid was not toxic. DCTH produced morphological changes in renal proximal convoluted tubules and the liver. The increases in urinary protein, glucose and blood urea nitrogen concentrations were consistent with the renal lesions. Hepatic lesions were associated with an increase in plasma glutamate-pyruvate transaminase activity, a marked infiltration of lipid and depletion of glycogen concentrations. A pronounced decrease in plasma glucose concentrations was also observed. DCTH decreased fatty acid beta oxidation by 75% and 40% in liver and kidney mitochondria, respectively, isolated from DCTH-treated rats. In addition, medium-chain acyl-coenzyme A dehydrogenase activity was reduced by 25% in rat liver mitochondria incubated with DCTH. The data presented are consistent with the hypothesis that DCTH is bioactivated by the mitochondrial fatty acid beta-oxidation system and that mitochondria are a critical cellular target in DCTH-induced toxicity.
2-Methyl-4-chlorophenoxyacetic Acid↗
Studies on acid oils and fatty acids for chickens III. Effect of chemical composition on metabolisable energy of by-products of vegetable oil refining.
1. Fourteen by-products of oil refining, selected for their variability in free fatty acid and unsaponifiable contents, were analysed chemically with the objective of relating the determined ME values of the products to chemical composition by means of multiple linear regression analysis. Refined sunflower oil was included as a reference fat. 2. Twenty-one 2-week-old chicks were used to determine fat digestibilities and AMEn values of diets, using the total collection method. Fats were included in a wheat-soyabean meal diet at 100 g/kg. Multiple linear regression analysis was used to express the ME values of fats as functions of the parameters measured (moisture, gross energy, impurities, unsaponifiables, non eluted material, free fatty acid content, unsaturated: saturated ratio, peroxide value, TBA test). 3. The ME of the fat products lay in the range l2.62 to 24.35 MJ/kg, and 29.26 MJ/kg for refined sunflower oil. Free fatty acid content of the fats was shown to be a poor predictor of their ME values, whereas non eluted material (NEM) of the fat products showed a good correlation with their ME. A regression equation could be derived (R2 0.6548; SEE 2.0064) with the unsaturated: saturated ratio (U:S) and NEM. An ME prediction equation based on the U:S, NEM and unsaponifiable content is also proposed (R2= 0.7l68; SEE= 1.9058).
Animal Feed↗
Stimulation of fatty acid oxidation by a 3-thia fatty acid reduces triacylglycerol secretion in cultured rat hepatocytes.
The present work shows that when mitochondrial beta-oxidation is stimulated by the hypolipemic, non-beta-oxidizable fatty acid analogue tetradecylthioacetic acid, there is a decrease in the secretion of triacylglycerol in cultured rat hepatocytes. In order to study the effects of tetradecylthioacetic acid in cells with different fatty acid oxidation rates, cells were grown without or with L-carnitine supplement or with addition of the beta-oxidation inhibitor L-aminocarnitine. In cells grown without and with L-carnitine in the medium, the oxidation of [1-14C]oleic acid was stimulated by tetradecylthioacetic acid, whereas it was not significantly changed by palmitic acid. In cells grown with L-aminocarnitine, oxidation of [1-14C]oleic acid was almost abolished both in the absence and in presence of tetradecylthioacetic acid. The effect of tetradecylthioacetic acid and palmitic acid on incorporation of [1-14C]oleic acid into triacylglycerol was similar under all conditions. In the presence of L-carnitine, secretion of oleic acid-labeled triacylglycerol was reduced significantly more by tetradecylthioacetic acid than by palmitic acid. The effects of tetradecylthioacetic acid and palmitic acid on secretion of oleic acid-labeled triacylglycerol were reversed in cells grown with L-aminocarnitine, where palmitic acid was the stronger inhibitor. These results were substantiated by determination of mass of triacylglycerol secreted. It is concluded that tetradecylthioacetic acid reduces secretion of triacylglycerol from rat hepatocytes mainly by acutely stimulating fatty acid oxidation.
Animals↗
Influence of dietary volatile fatty acids on the fatty-acid composition of lamb triglycerides, with special reference to the effect of propionate on the presence of branched-chain components.
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Acetates↗
The 1st Congress of the International Society for the Study of Fatty Acids and Lipids (ISSFAL): fatty acids and lipids from cell biology to human disease.
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Clinical Trials as Topic↗
The first total synthesis of the marine fatty acid (+/-)-9-methoxypentadecanoic acid: a synthetic route towards mid-chain methoxylated fatty acids.
The marine fatty acid (+/-)-9-methoxypentadecanoic acid was synthesized for the first time in seven steps (7.8% overall yield) starting from commercially available 9-decen-1-ol. The key step in the synthesis was the coupling of pentylmagnesium bromide with 1-benzyloxy-9,10-epoxydecane under 1,5-cyclooctadiene copper (I) chloride catalysis. Nuclear magnetic resonance data are provided for the first time for this type of methoxylated fatty acids and the synthetic approach utilized is of general applicability since it can be used in the synthesis of other mid-chain methoxylated fatty acids. This synthetic methodology should afford sufficient quantities of these fatty acids for biological evaluation. The spectral data obtained for the title compound will also be helpful in subsequent characterizations of other mid-chain methoxylated fatty acids using nuclear magnetic resonance spectroscopy.
Fatty Acids↗
Inhibition of binding to fatty acid binding protein reduces the intracellular transport of fatty acids.
Male livers, containing lesser amounts of fatty acid binding protein (FABP), utilize fatty acids more slowly than female livers. Conventional wisdom dictates that FABP stimulates fatty acid use by increasing cytoplasmic transport rates. Previously, we showed that the cytoplasmic diffusion of a fatty acid analogue [12-N-methyl-7-nitrobenzo-2-oxa-1,3-diazol-amino stearate (NBD-stearate)] is faster in female hepatocytes, paralleling the larger amounts of FABP. Sex differences in other cytoplasmic factors could also lead to faster diffusion, independent of FABP levels. The aim of this study was to determine the effect of inhibition of fatty acid binding to FABP on the directly measured intracellular transport rate of NBD-stearate. The binding of NBD-stearate to FABP was reduced by incubating hepatocytes isolated from male and female rats with alpha-bromo-palmitate (0-1,500 microM), a modified long-chain fatty acid that binds to FABP. The inhibition by alpha-bromo-palmitate on NBD-stearate binding to FABP was measured with the use of centrifugation to separate cytosol from cytoplasmic membranes. Laser photobleaching (fluorescence recovery after photobleaching) was used to measure the cytoplasmic diffusion of NBD-stearate in hepatocytes. Alpha-Bromo-palmitate incubation reduced NBD-stearate binding to FABP in a dose-dependent manner. The measured diffusion rate was also reduced in proportion to the degree of binding inhibition. We conclude that cytoplasmic transport of NBD-stearate is modulated by binding to soluble proteins like FABP. FABP enhances diffusive transport by reducing binding to immobile cytosolic membranes.
4-Chloro-7-nitrobenzofurazan↗
Effects of butter high in ruminant trans and monounsaturated fatty acids on lipoproteins, incorporation of fatty acids into lipid classes, plasma C-reactive protein, oxidative stress, hemostatic variables, and insulin in healthy young men.
BACKGROUND: Evidence suggests that ruminant trans fatty acids (FAs), such as vaccenic acid, do not increase the risk of ischemic heart disease (IHD). However, the effects of ruminant trans FAs on risk markers of IHD have been poorly investigated. OBJECTIVE: The objective was to investigate the effect of butter with a naturally high content of vaccenic acid and a concomitantly higher content of monounsaturated FAs on classic and novel risk markers of IHD. DESIGN: In a double-blind, randomized, 5-wk, parallel intervention study, 42 healthy young men were given 115 g fat/d from test butter that was high in vaccenic acid (3.6 g vaccenic acid/d) or a control butter with a low content of vaccenic acid. Blood and urine samples were collected before and after the intervention. RESULTS: The intake of the vaccenic acid-rich diet resulted in 6% and 9% lower total cholesterol and plasma HDL-cholesterol concentrations, respectively, than did the intake of the control diet (P = 0.05 and 0.002, respectively), whereas the ratio of total to HDL cholesterol did not differ significantly between the groups. The FA composition of lipid classes reflected the FAs' proportion of the test butter. No other differences were observed. CONCLUSIONS: Butter high in ruminant trans and monounsaturated FAs resulted in significantly lower total and HDL cholesterol than did the control butter with higher amounts of saturated FAs. It may be that the differences were due to the greater content of monounsaturated FAs and the lesser content of saturated FAs in the butter rich in ruminant trans FAs, rather than to the content of vaccenic acid per se.
Adult↗
IN VITRO ESTERIFICATION OF CHOLESTEROL BY PANCREATIC JUICE AND BY ACETONE POWDER EXTRACTS OF SMALL INTESTINE: THE EFFECT OF UNSATURATED FATTY ACIDS UPON ESTERIFICATION WITH SATURATED FATTY ACIDS.
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Acetone↗
Changes in plasma and colonic mucosa fatty acid profiles in rats with ulcerative colitis induced by trinitrobenzene sulfonic acid.
Polyunsaturated fatty acids have a key role in the pathogenesis of inflammatory bowel disease since some of the arachidonic acid-derived eicosanoids have been found to be increased in inflamed intestinal mucosa in the acute phase of human disease. The aim of this study was to prospectively assess plasma and colon mucosa fatty acid patterns in rats with experimental ulcerative colitis. Twenty rats were treated with trinitrobenzene sulfonic acid and 20 with NaCl; two groups were killed after one week and two after two weeks to evaluate colon damage. Plasma was obtained by aortic puncture and colonic mucosa was scraped off and the fatty acid pattern was determined by gas-liquid chromatography. Total, saturated, and monounsaturated plasma fatty acids were significantly higher in both periods of ulcerative colitis as compared to controls. Plasma n-6 fatty acids were increased after treatment, but no significant changes were observed concerning to n-3 fatty acids. With regard to colon mucosa, saturated and monounsaturated fatty acids did not change because of the disease; however, n-6 fatty acids decreased in the first week and increased in the second week and n-3 fatty acids were increased. Changes on the fatty acid distribution in plasma did not parallel to those of colonic mucosa except for 22:6(n-3). We have also found that experimental ulcerative colitis induced by trinitrobenzene sulfonic acid reproduces many of the features related to changes in plasma and colon mucosa fatty acids observed in the human disease.
Animals↗
Proportion of individual fatty acids in the non-esterified (free) fatty acid (FFA) fraction in the serum of laboratory rats of different ages.
In experiments on Wistar strain rats of both sexes, aged 5, 10 and 14 days and adult (90-120 days), of their own breed, the authors determined the quantitative proportion of individual fatty acids in the serum free non-esterified fatty acid (FFA) fraction, using mixed blood (obtained by decapitation) and the titration method of Trout et al. (1960). The proportion of the individual fatty acids was then determined in this fraction by gas chromatography (Base 1978) and their concentration (in mumol.1-1) was determined by simple calculation from the relative chromatogram data. Animals in the first three age groups were killed in the morning, directly from the nest; in adult rats the FFA fraction was measured after a 20 h fast. It was demonstrated that the increase in the proportion of monoenoic acids was highly statistically significant (about fivefold) during ontogenesis and that there was also a marked increase in the quantitative expression of polyenic acids, especially in group (n-6). The n-6/n-3 acid index in the FFA fraction altered during maturation (despite some fluctuation it basically rose from 4.3 in 5-day-old young to 10.0 in adult rats). It was further demonstrated that the concentration of fatty acids with a very short chain fell significantly during development, so that C 8:0, for example, could be detected only in the first two age groups, but not in 14-day-old and adult rats. The concentration of the saturated fatty acids C 15:0 to C 18:0 in the serum FFA fraction showed a statistically significant increase, while the index expressing the ratio of saturated to unsaturated fatty acids displayed a downward trend during development.
Aging↗
The effect of 3-mercaptopicolinic acid and substrate interactions on the incorporation of lipogenic precursors into glyceride-glycerol, glyceride-fatty acids and nonesterified fatty acids in bovine adipose tissue.
The effects of 3-mercaptopicolinic acid, an inhibitor of phosphoenolpyruvate carboxykinase, were studied in bovine subcutaneous adipose tissue slices in vitro. Lactate and glucose stimulated the incorporation of [U-14C]acetate into total lipids and nonesterified fatty acids. 3-Mercaptopicolinic acid abolished the stimulatory effect of lactate on total synthesis but had no effect on that from glucose. The inhibitor decreased glyceride-glycerol and glyceride-fatty acid synthesis from L-[U-14C]lactate by 90 and 30%, respectively; glyceride-glycerol synthesis from D-[U-14C]glucose was refractory to inhibition by 3-mercaptopicolinic acid, whereas the inhibitor tended to increase glyceride-fatty acid synthesis from glucose. The presence of lactate plus glucose in the incubation media elicited a greater than additive stimulation of acetate incorporation into total lipids. Glucose doubled the incorporation of lactate into glyceride-fatty acids, but had no effect on the net incorporation of lactate into nonesterified fatty acids. Lactate, but not glucose, stimulated the incorporation of [1-14C]palmitate into glyceride-fatty acids; 3-mercaptopicolinic acid increased this rate for all substrate combinations studied, although this was opposite to expected results. As determined with 3H2O, lactate and glucose stimulated the synthesis of total lipids, and 3-mercaptopicolinic acid decreased the stimulatory effects of lactate and glucose on 3H2O incorporation. The results suggest that lactate, and possibly glucose, stimulate the incorporation of acetate into fatty acids by increasing the availability of alpha-glycerophosphate.
Adipose Tissue↗
Effect of a vegetable oil formula rich in linoleic acid on tissue fatty acid accretion in the brain, liver, plasma, and erythrocytes of infant piglets.
The effect of feeding sow-milk formula (SMF) or a vegetable-oil infant formula (FF) with minimal n-6 and n-3 long-chain polyenoic fatty acids (LCPs) but high linoleic acid (18:2n-6) and a high ratio of 18:2n-6 to linolenic acid (18:3n-3) on the fatty acids of brain lipid and liver, plasma, and red cell phospholipids was studied in piglets fed from birth for 5, 10, 15, or 25 d. Compared with SMF, FF reduced the concentrations of 18:1 and n-3 LCPs, especially 22:6n-3, in all tissues and increased 22:4n-6 in brain, liver, plasma, and red cell phosphatidylethanolamine. FF also increased 22:5n-6 in brain lipid, liver, and plasma but not in red cell phospholipids. Thus, changes in tissues capable of in situ desaturation were not completely reflected in the red cell phospholipids. The increased liver and brain n-6 LCP accretion in the FF piglets may suggest competent desaturation and possible inhibition of n-3 desaturation and/or acylation by dietary n-6 fatty acids.
Animals↗
Effect of 6 dietary fatty acids on the postprandial lipid profile, plasma fatty acids, lipoprotein lipase, and cholesterol ester transfer activities in healthy young men.
BACKGROUND: There is increasing evidence that postprandial triacylglycerol-rich lipoproteins may be related to atherogenic risk. OBJECTIVE: The objective was to investigate the effect of individual fatty acid intakes on postprandial plasma lipoprotein triacylglycerol and cholesterol concentrations, plasma fatty acids, and preheparin lipoprotein lipase and cholesterol ester transfer protein (CETP) activities. DESIGN: Six test fats high (approximately 43% by wt) in stearic acid, palmitic acid, palmitic + myristic acid, oleic acid, elaidic acid (trans 18:1), and linoleic acid were produced by interesterification. After having fasted for 12 h, 16 healthy young men were served the individual test fats incorporated into meals (1 g fat/kg body wt) in random order on different days separated by washout periods. Blood samples were drawn before and 2, 4, 6, and 8 h after the meals. RESULTS: Different responses to the test-fat meals were observed for plasma lipoprotein triacylglycerol and cholesterol concentrations, plasma fatty acid concentrations, and lipoprotein lipase and CETP activities (diet x time interaction: 0.001 < P < 0.05). Intake of the long-chain saturated fatty acids stearic and palmitic acids resulted in a relatively lower lipemic response than did intake of the unsaturated fatty acids, probably because the saturated fatty acids were absorbed less and at a lower rate; therefore, the lipemic response took longer to return to postabsorptive values. CONCLUSIONS: Fatty acid chain length and degree of saturation appear to affect the extent and duration of lipemia and affect hepatic output indirectly. These effects may not be mediated via effects on lipoprotein lipase and CETP activities.
Adult↗