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PubMed1988

Determination of environmental levels of peptidoglycan and lipopolysaccharide using gas chromatography with negative-ion chemical-ionization mass spectrometry utilizing bacterial amino acids and hydroxy fatty acids as biomarkers.

D-Alanine and diaminopimelic acid originating from bacterial peptidoglycans and hydroxy fatty acids from lipopolysaccharides (endotoxins) were analysed by gas chromatography using a chiral column (Chirasil-Val as stationary phase) and selected-ion monitoring detection with negative-ion chemical-ionization mass spectrometry. The amino acids were analysed as N-heptafluorobutyryl isobutyl esters after rapid hydrolysis of peptidoglycan followed by isolation of the amino acids with disposable ion-exchange columns. Racemization of amino acid enantiomers was controlled by using deuterium chloride in the hydrolysis. The hydroxy acids were analysed as O-pentafluorobenzoyl methyl esters. Most of the bacteria present in airborne dust from a poultry confinement building were found to be Gram-positive according to the analytical chemical method whereas the Limulus amoebocyte lysate test suggested the presence of appreciable amounts of lipopolysaccharides of Gram-negative bacteria. Further studies are required to compare the utility of these two methods for determining endotoxins in complex environments.

Amino Acids↗
PubMed1968

Fatty-acid composition of Mycoplasma lipids: biomembrane with only 1 fatty acid.

Mycoplasma strain Y grew well when elaidate was the only fatty acid added to the medium, and this acid then comprised over 97 percent of the lipid fatty acids. It also grew well when elaidate was supplied together with any one of a series of straight-chain saturated fatty acids, and the lipids then contained both in approximately equimolar proportions. The ratio of cholesterol to phospholipid remained constant.

Cell Membrane↗
PubMed1992

Fatty acid profiles of brain phospholipid subclasses of rats fed n - 3 polyunsaturated fatty acids of marine or vegetable origin. A two generation study.

The effects of dietary n - 3 polyunsaturated fatty acids (PUFA) on fatty acid profiles of rat brain phospholipid subclasses as well as on heart phosphatidylethanolamine through two generations were examined: Three groups of rats were fed 20 weight% fat diets in which approx. 30% of the fatty acids were polyunsaturated, either 17% linoleic acid + 13% C20(-) + C22 polyunsaturates from fish oil or 17% linoleic + 13% alpha-linolenic acid from linseed oil or 30% linoleic acid. The rats of the two generations were killed as adults at 18 weeks of age. The results demonstrated that fish oil was a better source than alpha-linolenic acid for incorporation of n - 3 PUFA into the examined phospholipids. This was seen both in brain and heart tissue and in both generations of rats. In the brain phosphatidylethanolamine (PE) and phosphatidylserine (PS) similar fatty acid profiles were found in 1st and 2nd generation, but fish oil was more efficient than 18:3(n - 3) in increasing the levels of 22:6(n - 3), 20:5(n - 3), 22:5(n - 3) and reducing 20:4(n - 6) and 22:5(n - 6). Fatty acid profiles of phosphatidylinositol (PI), phosphatidylinositol-4-phosphate (PIP) and phosphatidylinositol-4,5-bisphosphate (PIP2) were affected by dietary fats. In PIP and PIP2 of 2nd generation rats 20:4(n - 6) was reduced from 36 to 29% following fish oil intake, whereas alpha-linolenic acid had no effects. The cholesterol/phospholipid ratio was not affected in the brain, neither was the degree of unsaturation of the phospholipids. In heart PE the highest levels of 20:5(n - 3)(2%) and 22:6(n - 3) (36%) were observed following fish oil intake. However, in rats fed alpha-linolenic acid a considerable increase in the level of 22:6(n - 3) was observed from the 1st (21%) to the 2nd generation (26%).

Animals↗
PubMed1995

Inclusion/exclusion of fatty acids in amylose complexes as a function of the fatty acid chain length.

Structural models are proposed for amylose-fatty acid complexes depending on the respective chain lengths of their constituents. The three studied fatty acids induce the Vh amylose crystalline type. However, in contrast to lauric and palmitic acids, caprylic acid is not present in crystals. On the basis of the relative amounts of amylose and fatty acid determined in complexes and previous results of molecular modelling, inclusion of lauric and palmitic acids inside the amylose helices is proposed; the acyl chains are included in crystalline areas and the carboxylic groups in amorphous areas. The absence of caprylic acid in crystals could be due to the solubility of this compound in the crystallization medium.

Amylose↗
PubMed1993

Interaction of dietary protein and alpha-linolenic acid on polyunsaturated fatty acid composition of liver microsomal phospholipids and eicosanoid production in streptozotocin-induced diabetic rats.

The effect of dietary protein, either casein (CAS) or soybean protein (SOY), on the polyunsaturated fatty acid (PUFA) composition of liver microsomal phospholipids and eicosanoid production was compared in normal and streptozotocin-induced diabetic rats fed diets containing perilla oil rich in alpha-linolenic acid. In normal rats the linoleic acid desaturation index in liver microsomal phospholipids was significantly higher in the CAS group than in the SOY group, whereas it was reversed in diabetic rats. The proportion of eicosapentaenoic acid (EPA) decreased in diabetic rats, in particular those fed SOY, whereas it was vice versa for arachidonic acid (AA). The ratio of aortic prostacyclin production to platelet thromboxane A2 production decreased only in diabetic rats fed SOY reflecting a reduction of the EPA/AA ratio. Thus, dietary protein differently modified the PUFA composition and eicosanoid balance even in the diabetic rat. In this respect, alpha-linolenic acid seemed to be less influential than linoleic acid.

Animals↗
PubMed1980

[The relation between polyunsaturated fatty acids and cardio-vascular accidents. I. Study of fatty acid components phospholipids].

Blood plasma lipids of women about seventy years old who had suffered from cardiovascular diseases (AVC) were studied and compared with the plasma lipids of women of about the same age without cardiac troubles. A great difference appears in the unesterified fatty acids of the phospholipids from cardiac women: we have observed a decreasing level of polyunsaturated fatty acids with a carbon chain of more than 18 carbons, and a decreasing ratio between the total concentration of the two precursors (linoleic acid omega and alpha-linolenic acid omega 3) and the total concentration of their long chain polyunsaturated derived fatty acids. On the contrary, we did not observe any significant variation of the unesterified fatty acid level in the plasma. The triglyceride and cholesterol levels also were not different between the two groups of patients. The hypothesis of a lack of elongation and of desaturation of linoleic and alpha-linolenic acids by competitive inhibition with oleic acid seems improbable, since the plasmatic concentration of oleic acid was not statistically different.

Aged↗
PubMed1990

Suppression of interleukin 2-dependent human T cell growth in vitro by prostaglandin E (PGE) and their precursor fatty acids. Evidence for a PGE-independent mechanism of inhibition by the fatty acids.

PGE represent oxygenation products of polyunsaturated essential fatty acids and are important regulators of cell-mediated immune responses. Because oils enriched in such fatty acids reduce inflammation and tissue injury in vivo, we examined the effects of these PGE precursors on IL-2-driven growth of human T lymphocytes. Dihomogamma linoleic acid (DGLA), AA, and their metabolites (PGE1 and PGE2, respectively) strongly inhibited short- and long-term growth of IL-2-dependent T cell cultures; EPA was much less inhibitory and its product, PGE3, failed to suppress IL-2 responses. Short-term pretreatment of the cells with DGLA or AA and removal of the fatty acids before the proliferation assay resulted in a smaller reduction in [3H]TdR incorporation. PGE and fatty acids did not alter the number of high affinity IL-2 binding sites on the T cell cultures but reduced the percentage of cells expressing CD25 and HLA class II molecules. No PGE was detected in supernatants from the fatty acid-treated cultures. Moreover, indomethacin, a cyclooxygenase inhibitor, did not reverse the antiproliferative effects of the fatty acids. Together, these findings indicate that fatty acids can inhibit IL-2-driven T cell growth via a PGE-independent mechanism and might be relevant to inflammatory diseases associated with persistent T cell activation.

Antigens, CD↗
PubMed1970

The mobilization of free fatty acids in relation to adipose tissue triglyceride fatty acids in the rat.

Three diets, consisting respectively of formulations high in oleic and stearic acid, linolenic acid, and lauric acid, were fed to rats until the adipose tissue TGFA largely reflected the dietary pattern of fatty acids. The composition of the serum FFA under basal conditions and following noradrenaline-stimulated lipolysis, were examined in relation to the respective adipose tissue TGFA. It was found in both in vivo and in vitro studies that lauric acid appeared to be less easily mobilized than longer chain acids. The in vitro studies indicated that this could not be explained either by positional preference of the shorter chain acids for the alpha-position of esterification or by increased reesterification of the shorter chain acids. The possibility remains that the difference is due to some specificity of tissue lipases for certain ester linkages.

Adipose Tissue↗
PubMed2001

Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.

Trypanosoma brucei is the protozoan parasite that causes African sleeping sickness. Its surface is packed with 10(7) copies of the glycosyl phosphatidylinositol (GPI)-anchored variant surface glycoprotein (VSG). This GPI anchor is unusual in that it contains two myristates (14:0) in its lipid moiety. This fatty acid specificity is achieved through myristoylation of the GPI precursor, and the acyltransferases involved in the GPI remodeling were presumed to be specific for myristate. However, their specificity had never been fully evaluated. Here we found as expected that the remodeling acyltransferases completely excluded palmitate (16:0) and stearate (18:0) in a cell-free fatty acid remodeling system. In contrast, we found surprisingly that one of these enzymes was permissive to shorter fatty acids such as laurate (12:0) and octanoate (8:0). However, the rates of incorporation of shorter fatty acids were lower than that of myristate at low substrate concentration. Since shorter fatty acids are virtually absent in the parasite and in the host bloodstream, it is unlikely that shorter fatty acids compete effectively with myristate as remodeling substrates under physiological conditions. Even if they were present in small quantities, a recently identified specialized fatty acid synthetase efficiently elongates shorter fatty acids to myristate prior to incorporation into GPIs (Morita et al., Science 288 (2000) 140-3.). Therefore, even though a remodeling acyltransferase is permissive with regard to substrate chain length, the myristate specificity in GPI anchors is very high.

Acyltransferases↗
PubMed1978

The relative contribution of propionate, and long-chain even-numbered fatty acids to the production of long-chain odd-numbered fatty acids in rumen bacteria.

1. The relative contribution of propionate, and long-chain even-numbered fatty acids to the production of long-chain odd-numbered fatty acids in six pure cultures of rumen bacteria were studied, using single and double isotope procedures. 2. Both propionate and even-numbered fatty acids were converted to odd-numbered fatty acids, presumably by elongation of 2-C atoms and alpha-oxidation reactions, but even-numbered fatty acids were much more effective. 3. The occurrence of alpha-oxidation was further confirmed by relatively large quantities of 14CO2 produced when [1-14C]palmitate was used in the incubation medium. 4. The incorporation of propionate into odd-numbered fatty acids was markedly reduced in the presence of palmitate, or stearate. 5. The significance of the operation of alpha-oxidation is discussed in relation to the energy conservation in rumen bacteria.

Animals↗
PubMed1998

Comparison of the fatty acid compositions in intraepithelial and infiltrating lesions of the cervix: part III, saturated and unsaturated fatty acid profiles.

The purpose of the third part of this study is to construct a basic lipid model (this includes information regarding total and free saturated, monounsaturated and polyunsaturated fatty acid contents, as well as total and free fatty acid saturation and double bond indexes, and comparisons of total and free n-3, n-6, n-7 and n-9 fatty acids in normal epithelial tissue, and intraepithelial and infiltrating lesions of the cervix) which, together with the individual total and free fatty acid profiles given in parts I and II of this study, should provide an understanding of the turnover of total and free acids, especially essential fatty acids, during cervical carcinogenesis. Such information can serve as a sound basis for further studies in an attempt to access this disease process. We observed an increase in monounsaturated fatty acid values in cancer tissue compared with normal tissue and a decrease of saturated fatty acid values in cancer tissue compared with normal tissue. Based on our observations, we speculate that because of the depletion of polyunsaturated fatty acids, monounsaturated fatty acid are synthesized to compensate for this loss; a possible source for the monounsaturated fatty acids are the saturated fatty acids via elongation and/or desaturation. Of particular interest is the n-3 fatty acid docosahexaenoic acid, the most unsaturated lipid in the biological systems, detected in very small amounts only in cancer cells of the cervix.

Cervix Uteri↗
PubMed1989

Characterization and quantitation of fatty acids covalently bound to erythrocyte membrane proteins: anion transporter contains 1 mol of fatty acid thiol ester.

Human erythrocyte membranes which had been thoroughly extracted with organic solvents contained 20 nmol of fatty acids/mg dry wt. The major fatty acids were palmitic and stearic with their monoethenoic derivatives as minor constituents. No other fatty acids were detected. When solvent-extracted membranes were digested with Pronase about 90% of the original content of fatty acids was retained in the insoluble residue. Fatty acids were linked to membrane proteins through alkali-labile bonds of which 30% were of a thiol ester and the remainder of an O-ester type. This conclusion is based on differential liberation of fatty acids by hydroxylamine at pH 7.0 and pH 11.0. Two extracts of membranes enriched in peripheral proteins (bands 1, 2, 5 and 2.1, 4.1, 4.2, 6) were prepared and extracted with organic solvents but each contained about six times less fatty acids than the parent solvent-extracted membranes. Glycophorin A contains little if any covalently bound fatty acids. Anion transporter (band 3) contains about 1 mol of thiol ester of fatty acid. This accounts for about half of the thiol ester-linked fatty acids in the parent solvent-extracted membranes. Most of the O-ester-linked fatty acids are linked to an undisclosed membrane protein.

Anion Transport Proteins↗
PubMed1994

Fatty acids as determinants of triglyceride and cholesteryl ester synthesis by isolated hepatocytes: kinetics as a function of various fatty acids.

Triglyceride synthesis by hepatocytes is currently thought to be the rate-limiting step for lipoprotein formation. In order to determine whether triglyceride and cholesteryl ester syntheses in hepatocytes are sensitive to physiological fluctuations of serum fatty acids, the fatty acid dependence of these pathways was examined. Uptake of various fatty acids and incorporation into triglyceride and cholesteryl esters were studied in isolated rat hepatocytes. Rates were determined under conditions of linear incorporation and related to the concentrations of total and unbound fatty acid in a mixture of fatty acids and albumin. The findings were: pathways for triglyceride and cholesteryl ester synthesis saturated at unbound fatty acid concentrations (or fatty acid albumin ratios) within the range of serum values and thus would be acutely modulated by fluctuations in serum fatty acids. Addition of cholesterol to the medium increased cellular cholesterol, but did not alter rates of cholesterol esterification, suggesting that endogenous cholesterol synthesis provided the needed substrate. Oleate, palmitate, and linoleate were comparable in their saturation kinetics and ability to support triglyceride and cholesteryl ester synthesis. Consequently, their binding affinity for serum albumin would determine their lipid-incorporation rates. On this basis, in humans, oleate would yield the lowest rates as it has the lowest unbound fatty acid at each fatty acid-albumin ratio. Stearate, in contrast to the other fatty acids, was poorly esterified into neutral lipids by hepatocytes. Poor hepatic metabolism of stearate most likely explains previous findings of a hypocholesteremic effect of diets high in stearate as compared to other saturated fatty acids.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1991

Effects of diets high in saturated fatty acids, canola oil, or safflower oil on platelet function, thromboxane B2 formation, and fatty acid composition of platelet phospholipids.

Platelet function and fatty acid composition were investigated in 30 healthy male subjects who ate a controlled-saturated-fatty-acid (baseline) diet for 3 wk and then consumed either safflower oil or canola oil as a major fat source for 8 wk. Fatty acid composition of platelet phospholipids reflected changes in dietary fatty acid composition. Compared with baseline a 35% decrease (P less than 0.05) in arachidonic acid was observed in platelet phospholipids of the canola-oil diet group while long chain n-3 fatty acids rose 7-26% (P greater than 0.05). Compared with baseline both unsaturated-fatty-acid diets reduced platelet aggregation at 3 wk of oil-based diet feeding (P less than 0.01) whereas only canola oil influenced platelet function (lowered ATP secretion) at 8 wk (P less than 0.01). No significant difference was observed in thromboxane B2 concentrations between oil-treatment groups at 8 wk. Both oil-based diets had short-term beneficial effects on platelet function but the effect of canola oil persisted longer.

Adenosine Triphosphate↗
PubMed1978

Fatty acid metabolism in L1210 murine leukemia cells: differences in modification of fatty acids incorporated into various lipids.

L1210 leukemia cells can utilize all of the main fatty acids that normally are present in the ascites fluid in which they grow. This finding is consistent with the view that L1210 cells derive most of their fatty acids from the ascites fluid. From 80--90% of each fatty acid was incorporated into cell lipids without structural modification, suggesting that the lipid composition of these cells can be altered by changing the type of fatty acids to which they are exposed. Most importantly, the palmitate that was subsequently incorporated into total cell phospholipids was elongated and desaturated somewhat more than that incorporated into triglycerides. This difference was due primarily to more extensive modification of the palmitate incorporated into the ethanolamine phosphoglycerides fraction. Although there was no difference between total phospholipids and triglycerides with linoleate, more of the linoleate incorporated into ethanolamine phosphoglycerides was elongated and further desaturated than that incorporated into choline phosphoglycerides and triglycerides. These findings indicate fatty acids incorporated into various cell lipid fractions are not structurally modified to the same extent. There appears to be greater modification of fatty acid used for ethanolamine phosphoglyceride synthesis as compared with triglyceride and choline phosphoglyceride synthesis.

Animals↗
PubMed2003

Dietary conjugated linoleic acids as free fatty acids and triacylglycerols similarly affect body composition and energy balance in mice.

The objective of this study was to compare the effects of conjugated linoleic acid (CLA) as triacylglycerols (TAG) or free fatty acids (FFA) on body composition and energy balance in mice. We fed four groups of 5-wk-old Balb-C mice (n = 9) semipurified diets containing either CLA (0.5 g CLA/100 g of diet) or high oleic sunflower oil (HOSF) in the form of FFA or TAG for 42 d. Body composition was determined and the energy in the carcasses, excreta and food was measured in a bomb calorimeter. The amount of body fat was 4.72 +/- 0.95 g (17.9 +/- 2.8%) in the HOSF-FFA group, 2.36 +/- 0.29 g (9.4 +/- 1.0%) in the CLA-FFA mice (mean +/- SD, P < 0.05), 4.76 +/- 0.74 g (18.2 +/- 2.2%) in the HOSF-TAG group and 2.32 +/- 0.38 g (9.3 +/- 1.1%) in the CLA-TAG mice (P < 0.05). The percentage of energy intake that was stored in the body was 3.5 +/- 1.2% in the HOSF-FFA group, 0.6 +/- 0.3% in the CLA-FFA group (P < 0.05), 3.5 +/- 1.1% in the HOSF-TAG group and 0.5 +/- 0.4 in the CLA-TAG mice (P < 0.05). Conversely, the percentage of energy intake that was expended as heat was 89.4 +/- 1.2% in the HOSF-FFA group, 92.4 +/- 0.8% in the CLA-FFA mice (P < 0.05), 89.47 +/- 1.23% in the HOSF-TAG group and 92.2 +/- 0.4% in the CLA-TAG group (P < 0.05). Thus, CLA in the form of FFA or TAG had similar effects on body composition and energy balance.

Animals↗
PubMed1983

Short-term regulation of fatty acid synthesis in isolated alveolar type II cells from adult rat lung. Effects of free fatty acids and hormones.

We measured the total rate of fatty acid synthesis in alveolar type II cells freshly isolated from the lungs of adult rats. The rate of incorporation of 3H from 3H2O into cellular fatty acids was linear during 3-hr incubations and was very brisk [18 ng-atoms 3H/10(6) cells/hr +/- 2 (mean +/- SD, n = 23)]. When the nutrient medium (Minimum Essential Medium) was supplemented with various hormones or free fatty acids, the long-chain fatty acids (C14-C20) caused a decrease in the rate of 3H incorporation to a variable degree depending on the species of fatty acid. Stearate (10(-4) M) and palmitate (10(-4) M) caused the greatest inhibition of de novo cellular fatty acid synthesis, followed by myristate, arachidonate, and oleate. Insulin (10(-7) M), glucagon (10(-8) M), terbutaline (10(-5) M), 8-bromo-cyclic AMP (10(-3) M), the essential fatty acid linoleate (10(-4) M), and the medium-chain-free fatty acids laurate and octanoate (10(-4) M) did not alter the rate of fatty acid synthesis in type II cells. We demonstrated that the alveolar type II cell is a major lipogenic cell type in the rat. We also demonstrated that the availability of preformed fatty acids in the extracellular milieu is one factor regulating the rate of fatty acid synthesis in these cells.

Animals↗
PubMed1980

Studies on cyclopropane fatty acid synthesis. Effect of carbon source and oxygen tension on cyclopropane fatty acid synthetase activity in Pseudomonas denitrificans.

The cyclopropane fatty acid, methylene hexadecanoic acid, constituted from 1% to upwards of 30% of the total lipid fatty acids of the bacterium, Pseudomonas denitrificans. The amount of this component varied along with the levels of the enzyme, cyclopropane synthetase (unsaturated-phospholipid methyltransferase, EC 2.1.1.16). When P. denitrificans was grown on succinate in a culture medium saturated with oxygen, cyclopropane synthetase remained repressed while cell densities were low. As cell densities increased, the enzyme was induced and the activity rose to a maximum over a period of 4-6 h. Cyclopropane synthetase could also be induced by rapidly limiting the oxygen supply to cells growing in conditions where oxygen was in excess. This phenomenon was independent of the phase of growth and could be prevented by addition of chloramphenicol to the medium. Growth on glucose was also shown to repress the synthesis of cyclopropane synthetase under similar conditions. However, once maximum levels of cyclopropane synthetase were reached, they remained constant for at least the following 15 h irrespective of the source of carbon in the medium. Methylene hexadecanoic acid accumulated in a linear manner throughout this period until a maximum level was achieved, the rate of accumulation being related to the activity of cyclopropane synthetase detected in vitro. The rate of conversion of total fatty acid to methylene hexadecanoic acid was approximately 1.3-1.5% per h, the methylene hexadecanoic acid being metabolically stable - the relative percentage of methylene hexadecanoic acid to total fatty acid in repressed cells, falling linearly with increase in cell number. Repression of enzyme synthesis was further investigated by growing cells on various sources of carbon other than glucose. The results indicated that succinate was unique amongst tricarboxylic acid cycle intermediates in depressing cyclopropane synthetase under limited oxygen conditions.

Carbon↗