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PubMed1990

Cardiovascular effects of n-6 fatty acids.

N-6 fatty acids comprise linoleic, dihomo-gamma-linolenic and arachidonic acid. Each of these polyunsaturated fatty acids display an individual pattern of cardiovascular effects. Moreover, the supplementation of the diet with one of these n-6 fatty acids results in a concomitant effect on the resorption, distribution and metabolism of the other n-6 fatty acids. While linoleic acid is abundant in our diet, the other n-6 fatty acids are only found in minute amounts. Accordingly, the effects with linoleic acid are less impressive, but more complex (e.g. lowering of plasma cholesterol, inhibition of renin) than with both other n-6 fatty acids. Linoleic acid, being no direct prostaglandin precursor, displays a variety of effects on the prostaglandin cascade, while dihomo-gamma-linolenic acid gives rise to 1-series prostaglandins and arachidonic acid to prostaglandins (eicosanoids) of the 2-series. The quality and quantity of prostaglandins formed, contribute essentially to the cardiovascular effects of the individual n-6 fatty acids.

Animals↗
PubMed1979

[Unusual fatty acids in turkeys fed a diet containing "Toprina". I. Composition of the higher fatty acids in "Toprina", the diet, feces and blood].

Totals lipids (TL) phospholipids (PL) and fatty acid composition of TL and PL (the latter in blood only) were estimated in Candida lipolytica cultivated on n-alkanes by industrial method ("Toprina"), in 0%, 10% and 15% "Toprina" diets and in faeces and blood of turkeys, males and females, fed these diets. With increasing concentrations of dietary "Toprina" phospholipids and 15:0 and 17:0 fatty acids increased, 17:1 and 17:2, typical of the product, appeared and increased in diets and blood. Other lipid and fatty acids values were not affected by dietary yeast.

Alkanes↗
PubMed2006

Breast milk fatty acids may link innate and adaptive immune regulation: analysis of soluble CD14, prostaglandin E2, and fatty acids.

In addition to its role in sensing intraluminal microbial antigens, soluble (s)CD14 may regulate immune responses by its lesser known function as a lipid carrier with possible influences in the production of fatty acid-derived eicosanoids. We investigated the interrelations of fatty acids, prostaglandin E2 (PGE2), and sCD14 and their role in infant atopic eczema during the first year of life. Serum and breast milk samples from mothers and serum samples from their infants were collected at infant's age 3 mo and analyzed for sCD14 and PGE2 concentrations and for fatty acid compositions. The main correlation of sCD14 was with arachidonic acid (20:4n-6) (AA). Dihomo-gamma-linolenic acid (20:3n-6) (DHGLA) and the ratio of n-6 to n-3 fatty acids correlated positively and docosahexaenoic acid (22:6n-3) (DHA) and sum of n-3 fatty acid negatively with PGE2 in mother's serum and linoleic acid (LA) negatively with PGE2 in breast milk. Soluble CD14 tended to be higher and LA, total polyunsaturated fatty acid (PUFA), and sum of n-6 fatty acids were lower in breast milk received by infants with atopic eczema compared with those without. These results suggest that fatty acids contribute to the regulation of innate and adaptive immune responses and link intraluminal exposures, mother's diet, and microbes.

Adult↗
PubMed1999

Incorporation of dietary polyunsaturated fatty acids into pork fatty tissues.

The incorporation and elimination rate of dietary PUFA in pork fat was investigated in this study. Experiment 1 examined the incorporation of dietary PUFA into backfat (BF) and into the triglyceride (TG) and phospholipid (PL) fractions of the i.m. fat of the loin. Experiment 2 examined the elimination of PUFA from BF due to withdrawal of PUFA from the diet. In Exp. 1, Piétrain x Seghers Hybrid pigs (70 barrows and 70 gilts averaging 11 wk of age and 30 kg initially) were assigned to five dietary treatments in a 2 x 5 factorial arrangement during a 16-wk feeding period. Pigs received a diet containing about 2.5% tallow (T) for 8, 10, 12, 14, or 16 wk, followed by a diet containing about 15% full-fat soybeans (FFS) for 8, 6, 4, 2, or 0 wk, respectively. Additionally, BF biopsies were taken every 2 wk from eight pigs on the 8-wk FFS dietary treatment, starting from the time pigs were switched to the FFS diet. Linoleic acid [18:2(n-6)], linolenic acid [18:3(n-3)], eicosadienoic acid [20:2(n-6)], arachidonic acid [20:4(n-6)], and PUFA contents in BF increased (P < .01) with time on the FFS diet, but contents of these fatty acids were similar for pigs fed FFS for 6 or 8 wk. The PUFA content of the biopsies rose throughout the FFS treatment; the greatest increase in PUFA occurred during the first 2 wk of feeding FFS. The PUFA content of the TG and PL fractions in i.m. fat of the longissimus muscle tended to increase with time on the FFS diet. The increase was significant (P < .01) in the TG fraction for 18:3(n-3) and in the PL fraction for 20:4(n-6) and 22:6(n-3). In Exp. 2, 11-wk-old pigs (10 barrows and 10 gilts) were fed a FFS-based diet from 11 to 19 wk of age, followed by the T-diet for an additional 8 wk. During the latter period, biopsies were taken every 2 wk. The elimination of PUFA from BF was greatest during the first 2 wk after the dietary change. The PUFA reached the lowest level at the age of 25 wk. These experiments show that the PUFA: saturated fatty acid ratio of BF can be increased from .34, corresponding with a T-based diet, to .55, by feeding a FFS diet for 6 wk before slaughter.

Adipose Tissue↗
PubMedDate not supplied

Concentrations of serum albumin and nonesterified fatty acids in bovine aqueous humor with regard to the fatty acid sensitivity of bovine lens epithelial cells.

Concentrations of albumin and nonesterified fatty acids (FAs) have been determined in bovine serum and aqueous humor (AH) with regard to the FA-to-albumin molar ratio, which has been proved decisive for the FA cytotoxicity to bovine lens epithelial cells as described previously. In 6- to 7-month-old female calves the average albumin level was reduced 309-fold from 638 micromol/l in serum to 2.00 micromol/l in AH, in 72- to 84-month-old cows 405-fold from 632 to 1. 56 micromol/l, and in 12- to 18-month-old bulls 395-fold from 553 to 1.40 micromol/l. In 64% of the animals the albumin concentration in AH differed significantly between both eyes. The serum albumin values resulted in a Gaussian curve, but the frequency distribution for AH albumin values skewed to the right. Using an enzymatic method the concentrations of nonesterified FAs were determined in serum as well as in concentrated AH samples. In all animals investigated the molar FA-to-albumin ratio was higher in AH than in serum. The results are discussed in view of the assumption that unsaturated nonesterified FAs might be cataractogenic risk factors.

Aging↗
PubMed2005

The influence of n-3 polyunsaturated fatty acids and very low calorie diet during a short-term weight reducing regimen on weight loss and serum fatty acid composition in severely obese women.

Polyunsaturated fatty acids of n-3 series (n-3 PUFA) were shown to increase basal fat oxidation in humans. The aim of the study was to compare the effect of n-3 PUFA added to a very low calorie diet (VLCD), with VLCD only during three-week inpatient weight reduction. Twenty severely obese women were randomly assigned to VLCD with n-3 PUFA or with placebo. Fatty acids in serum lipid fractions were quantified by gas chromatography. Differences between the groups were determined using ANOVA. Higher weight (7.55+/-1.77 vs. 6.07+/-2.16 kg, NS), BMI (2.82+/-0.62 vs. 2.22+/-0.74, p<0.05) and hip circumference losses (4.8+/-1.81 vs. 2.5+/-2.51 cm, p<0.05) were found in the n-3 group as compared to the control group. Significantly higher increase in beta-hydroxybutyrate was found in the n-3 group showing higher ketogenesis and possible higher fatty acid oxidation. The increase in beta-hydroxybutyrate significantly correlated with the increase in serum phospholipid arachidonic acid (20:4n-6; r = 0.91, p<0.001). In the n-3 group significantly higher increase was found in n-3 PUFA (eicosapentaenoic acid, 20:5n-3, docosahexaenoic acid, 22:6n-3) in triglycerides and phospholipids. The significant decrease of palmitoleic acid (16:1n-7) and vaccenic acid (18:1n-7) in triglycerides probably reflected lower lipogenesis. A significant negative correlation between BMI change and phospholipid docosahexaenoic acid change was found (r = -0.595, p<0.008). The results suggest that long chain n-3 PUFA enhance weight loss in obese females treated by VLCD. Docosahexaenoate (22:6n-3) seems to be the active component.

3-Hydroxybutyric Acid↗
PubMed1988

Effect of salicylic acid on mitochondrial-peroxisomal fatty acid catabolism.

To understand the possible role of salicylic acid in the pathogenesis of Reye's syndrome, we examined its effect on the oxidative metabolism of fatty acids in the rat liver mitochondrial-peroxisomal fraction. Fatty acids of different chain lengths are oxidized in different organelles. Octanoic acid is oxidized in mitochondria, lignoceric acid in peroxisomes, and palmitic acid in both mitochondria and peroxisomes. Salicylic acid (up to 1 mM concentration) had no effect on the oxidation of [1-14C]lignoceric acid. However, at the same concentration it inhibited the oxidation of [1-14C]palmitic acid by 26% and [1-14C] octanoic acid by 42%. The apparent Ki for the oxidation of [1-14C] octanoic acid, [1-14C]palmitic acid and [1-14C]lignoceric acid were 0.27, 6.0, and 14.8 mM, respectively. This selective inhibition of mitochondrial oxidation of medium-chain (octanoic acid) and long-chain (palmitic acid) fatty acids by salicylic acid may potentiate the accumulation of fatty acids in plasma in Reye's syndrome patients.

Animals↗
PubMed2003

The effect of feeding structured triacylglycerols enriched in eicosapentaenoic or docosahexaenoic acids on murine splenocyte fatty acid composition and leucocyte phagocytosis.

The effects of altering the type of n-3 polyunsaturated fatty acid (PUFA) in the mouse diet on the ability of monocytes and neutrophils to perform phagocytosis were investigated. Male weanling mice were fed for 7 d on one of nine diets which contained 178 g lipid/kg and which differed in the type of n-3 PUFA and in the position of these in dietary triacylglycerol (TAG). The control diet contained 4.4 g alpha-linolenic acid/100 g total fatty acids. In the other diets, eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) replaced a proportion (50 or 100 %) of the alpha-linolenic acid, and were in the sn-2 or the sn-1(3) position of dietary TAG. There were significant increases in the content of n-3 PUFA in spleen-cell phospholipids when EPA or DHA was fed. These increases were largely independent of the position of EPA or DHA in dietary TAG except when EPA was fed at the highest level, when the incorporation was greater when it was fed in the sn-2 than in the sn-1(3) position. There was no significant effect of dietary DHA on monocyte or neutrophil phagocytic activity. Dietary EPA dose-dependently decreased the number of monocytes and neutrophils performing phagocytosis. However, when EPA was fed in the sn-2 position, the ability of active monocytes or neutrophils to engulf bacteria was increased in a dose-dependent fashion. This did not occur when EPA was fed in the sn-1(3) position. Thus, there appears to be an influence of the position of EPA, but not of DHA, in dietary TAG on its incorporation into cell phospholipids and on the activity of phagocytic cells.

Animals↗
PubMed1996

Contribution of de novo fatty acid synthesis to very low density lipoprotein triacylglycerols: evidence from mass isotopomer distribution analysis of fatty acids synthesized from [2H6]ethanol.

A detailed comparison of the structures of plasma very low density lipoprotein (VLDL) and liver triacylglycerols (TG) (Yang et al. 1995. J. Lipid Res. 36: 125-136) has demonstrated that a minimum of 60% of the secreted TG could have been derived from partial lipolysis and reesterification of stored TG and a maximum of 40% could have been derived from direct secretion of newly made TG. To investigate the processes involved in the transfer of TG to VLDL in vivo, we have determined the distribution of deuterium among the molecular species of the liver-TG and VLDL-TG during the infusion of perdeuterated ethanol along with fructose or glucose and during the provision of either glucose or fructose in the drinking water for 2 weeks. The deuterium labeling (percent excess and percent replacement) of the total fatty acids was determined by GC/MS of the methyl esters while the labeling of the glycerol and the glycerol plus fatty acids of the enantiomeric diacylglycerol moieties of TG was determined by LC/MS with on-line mass spectrometry. Supplementation of the diet for 2 weeks with either glucose and fructose stimulated the synthesis of TG containing new fatty acids and glycerol. The proportion of the newly made to preexisting TG differed in VLDL from that in the liver. The 2H % replacement in glycerol and in total fatty acids was greater in VLDL-TG than in the liver-TG. On the basis of the mass isotopomer distribution analysis it was estimated that a maximum of 30% of the VLDL-TG could have been derived directly from TG that was made de novo and did not equilibrate with the liver-TG stores. The transfer of the stored TG to VLDL was best accounted for by a degradation to 2-monoacylglycerols and resynthesis via the 2-monoacylglycerol pathway with addition of an excess of newly synthesized fatty acids to the resynthesized TG.

Animals↗
PubMed1999

Eicosapentaenoic and docosahexaenoic acid affect mitochondrial and peroxisomal fatty acid oxidation in relation to substrate preference.

Decreased triacylglycerol synthesis within hepatocytes due to decreased diacylglycerol acyltransferase (DGAT) activity has been suggested to be an important mechanism by which diets rich in fish oil lower plasma triacylglycerol levels. New findings suggest that eicosapentaenoic acid (EPA), and not docosahexaenoic acid (DHA), lowers plasma triacylglycerol by increased mitochondrial fatty acid oxidation and decreased availability of fatty acids for triacylglycerol synthesis. To contribute to the understanding of the triacylglycerol-lowering mechanism of fish oil, the different metabolic properties of EPA and DHA were studied in rat liver parenchymal cells and isolated rat liver organelles. EPA-CoA was a poorer substrate than DHA-CoA for DGAT in isolated rat liver microsomes, and in the presence of EPA, a markedly lower value for the triacyl[3H]glycerol/diacyl[3H]glycerol ratio was observed. The distribution of [1-14C]palmitic acid was shifted from incorporation into secreted glycerolipids toward oxidation in the presence of EPA (but not DHA) in rat liver parenchymal cells. [1-14C]EPA was oxidized to a much greater extent than [1-14C]DHA in rat liver parenchymal cells, isolated peroxisomes, and especially in purified mitochondria. As the oxidation of EPA was more effective and sensitive to the CPT-I inhibitor, etomoxir, when measured in a combination of both mitochondria and peroxisomes, we hypothesized that both are involved in EPA oxidation, whereas DHA mainly is oxidized in peroxisomes. In rats, EPA treatment lowered plasma triacylglycerol and increased hepatic mitochondrial fatty acid oxidation and carnitine palmitoyltransferase (CPT)-I activity in both the presence and absence of malonyl-CoA. Whereas only EPA treatment increased the mRNA levels of CPT-I, DHA treatment increased the mRNA levels of peroxisomal fatty acyl-CoA oxidase and fatty acid binding protein more effectively than EPA treatment. In conclusion, EPA and DHA affect cellular organelles in relation to their substrate preference. The present study strongly supports the hypothesis that EPA, and not DHA, lowers plasma triacylglycerol by increased mitochondrial fatty acid oxidation.

Acyl-CoA Oxidase↗
PubMed1999

Fatty acid uptake by cultured human keratinocytes grown in medium deficient in or supplemented with essential fatty acids.

Epidermal linoleic acid, i.e. essential fatty acid (EFA), is essential for cutaneous barrier function. Cultured human keratinocytes, routinely used for studies of lipid metabolism, are grown in a keratinocyte serum-free medium (KSFM), under conditions that reveal EFA-deficient cells. Here, fatty acid (FA) uptake was analysed in human adult keratinocytes grown either under EFA-deficient conditions [KSFM supplemented with 10% FCS (A) or 1% UltroserG (B)] or EFA-supplemented conditions [KSFM supplemented with a devised FA cocktail (C) or evening primrose oil (D)]. The FA composition of the total cellular lipid and major lipid fractions was analysed by gas chromatography. Cells grown with supplements A or B balanced their EFA-deficient state primarily with oleic acid. Cells grown with supplements C or D normalized to the epidermal FA composition in vivo with raised linoleic and lower oleic acid contents. When cells were grown longer than 48 h with supplements C or D decreased cell growth was observed. FA uptake was curvilinear with preference for linoleic over oleic acid under all culture conditions. The uptake of linoleic acid by cells cultured with supplement B was twice the uptake of those cultured with supplement A, while the uptake of oleic acid was similar under both culture conditions. Oleic acid uptake of cells cultured with supplement C or D was lower. These results show that the uptake of linoleic, but not that of oleic acid, is influenced by the extracellular FA composition, and that EFA-supplemented keratinocytes compared to EFA-deficient cells might serve as an in vitro model for the study of EFA metabolism.

Adult↗
PubMed2003

Fatty acids bound to Fasciola hepatica 12 kDa fatty acid-binding protein, a candidate vaccine, differ from fatty acids in extracts of adult flukes.

The FA composition of Fasciola hepatica 12 kDA purified native FA-binding protein (nFh12), a candidate vaccine against fascioliasis, is described. The FA chain lengths ranged between 12 and 24 carbons. The principal FA were 16:0, 18:1n-9, 18:0, 20:4n-6, and 20:1n-9. The acids 16:0, 18:1n-9, and 18:0 comprised over half the FA that were bound to the whole FA-binding protein. Small amounts (1.0-2.8%) of iso-anteiso methyl-branched FA also were characterized. Forty-one different FA were identified in extracts of the adult flukes, with the three most abundant FA also being 16:0, 18:1n-9, and 18:0. A similar proportion of saturated vs. unsaturated FA was observed between the whole extract from F. hepatica and the nFh12 protein. However, the n-3/n-6 ratio of PUFA was significantly different, being 1.2 in the whole extract vs. 9.6 in the nFh12 protein complex. The nFh12 protein binds more n-5, n-6, and n-7 PUFA and less n-3 and n-9 PUFA than the whole extract. In addition, cholesterol (56%), sitosterol (36%), and fucosterol (8%) also were bound to the nFh12 protein complex.

Animals↗
PubMed2003

Extracellular secretion of free fatty acids by disruption of a fatty acyl-CoA synthetase gene in Saccharomyces cerevisiae.

To elucidate the molecular mechanism governing fatty acid transport across the cell membrane, we first isolated a Saccharomyces cerevisiae mutant, B-1, that exhibits a reduced acyl-CoA oxidase activity and an increase in free fatty acid accumulation. Following mutagenesis of B-1, a mutant, YTS51, which secretes free fatty acids, was isolated. The concentration of free fatty acids in the YTS51 culture medium was about 17 times higher than that in B-1. The mutation that causes the fatty acid secretion phenotype occurred at a single allele, and this phenotype was suppressed by the introduction of a single copy of FAA1, a gene for acyl-CoA Synthetase, to the mutant. Although the mutation expressing this phenotype was not within FAA1 in YTS51, the disruption of FAA1 in the wild-type strain resulted in fatty acid secretion even though the level of fatty acid secretion was less than that in YTS51. We consider that YTS51 is a suitable model to elucidate the molecular basis of the fatty acid transport process.

Journal Article↗