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The fatty acids of platelets and red blood cells in urban black South Africans with myocardial infarction.

The occurrence of myocardial infarction (MI) in Black South Africans, while poorly documented, is believed by many to be approximately one-tenth that of White South Africans. Recently, this disease has been reported to be increasing in the urban Black South African population. In order to determine if variations in dietary habit within the urban black community are contributing to the disease occurrence, the fatty acid content of whole platelets and red blood cells (RBC) were measured in 25 urban Black Africans with documented history of MI. These values were compared to an asymptomatic Black African control group. Total saturated fatty acids were increased and total polyunsaturated fatty acids (PUFA) were decreased in the patient's platelets. Stearic acid (18:0) was significantly increased and eicosapentaenoic acid (20:5 n-3) was slightly but significantly decreased in the patient's platelets. No difference was seen in the total saturated and total unsaturated fatty acid levels of red blood cells (RBCs). Only 20:5n-3 and 22:5n-3 were slightly but significantly decreased in the patient's RBCs. Similarities in RBC fatty acids indicate that the progression of MI in this population may not be related solely to changes in dietary habits.

Adult↗

[Time-course changes in the alkenyl and acyl chain composition of plasmalogens from the heart and kidneys of rats ingesting trielaidin].

Weaned rats were fed for 7 or 32 days a semi-purified diet containing 10% of fat supplement in which elaidic acid accounted for 64.5% of total fatty acids. Alkenyl groups from plasmalogens of kidney and heart mitochondria were analysed as their alkyl-substituted dioxane derivatives by gas liquid chromatography (GLC). Acyl chains of total and individual phospholipids (phosphatidylcholine: PC; phosphatidylethanolamine: PE, diacyl and alkenyl-acyl forms; phosphatidylinositol: PI; cardiolipin: CL) were also analysed by GLC. Maximum level of elaidic acid incorporation was attained after only one week on the experimental diet in either total or individual phospholipids. Heart mitochondria phospholipids contained about 40% more trans-monounsaturated acids (20.9%) than kidney mitochondria phospholipids (12.5%) after one month. trans-Monounsaturated acids (t-18: 1 plus t-16: 1 acids) were incorporated in individual phospholipids from both organs in decreasing order: PI greater than PE (total) greater than PC much greater than CL. The order of incorporation of elaidic acid seemed to be related to the content of stearic acid in these phospholipids when the diet was devoid of elaidic acid (PI greater than PE greater than PC much greater than CL). The content of elaidic acid in alkenyl-acyl-glycerophosphoethanolamine (alkenyl-acyl-GPE) was the same (6% of total fatty acids) in both organs. The time-course incorporation of trans-monounsaturated alkenyl chains was different. After one week on the elaidic acid-enriched diet, they represented only 65% (kidney) or 43% (heart) of the values reached after one month. At the end of the feeding period, the trans-monounsaturated alkenyl chains were also about 40% less in total plasmalogens from kidney mitochondria (27.8%) than from heart mitochondria (46%). trans-Monounsaturated acyl chains were incorporated at a higher rate in the 2-position of alkenyl-acyl-GPE than trans-monounsaturated alkenyl chains in their 1-position. Our results confirm the unique observation of Kramer et al. (1985) who noticed that the fatty acid composition of phospholipids was much more rapidly equilibrated than the alkenyl chain composition of plasmalogens (1 week vs 2-3 weeks) from heart of rats fed diets supplemented with different oils.

Animals↗

Radiometric measurement of differential metabolism of fatty acids by Mycobacterium lepraemurium.

An assay system has been developed based on automated radiometric quantification of 14CO2 produced through oxidation of (1--14C) fatty acids by mycobacteria. With this system, the Hawaiian strain of M. lepraemurium was studied using the K-36 buffer as a suspending solution for the organisms along with 5.0 muCi of one of the following fatty acids: acetate, butyric, hexanoic, octanoic, decanoic, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, and malonic. The 14CO2 production by this organism was greatest with lauric, decanoic, myristic, octanoic, stearic, oleic, linoleic, linolenic, and malonic. The 14CO2 production by this organism was greatest with lauric, decanoic, myristic, octanoic, and stearic acids, in decreasing order. Assimilation studies and radiochromatograms confirmed that most of the oxidized substrates were converted into by-products with no change in those from which no oxidation was found. These data suggest that the radiometric measurement of differential fatty acid metabolism may provide a basis of radiometric identification of M. lepraemurium and assessment of the growth requirements of this organism.

Carbon Dioxide↗

[Specificity in the accumulation of fatty acids in adipose tissue of mammals].

To investigate possible differences in triacylglyceride accumulation in adipose tissue, six different species have been studied (hamster, mouse, rat, rabbit, dog and pig). They were fed the same diet of high proportion of saturated fatty acids during 3 months after the lactation period. There are significant differences between the fatty acids in the diet and the studied tissue, a higher proportion of myristic, palmitoleic and linoleic acids together with a minor proportion of palmitic and stearic acids being accumulated in all studied species except in pig. The differences among species were significant in most cases being maximal in pig (57.7% of saturated fatty acids) and hamster (24.4% of saturated fatty acids). There is a direct relationship between the position of each fatty acid in the triacylglyceride and its proportion in the tissue, this proportion being maximal when the fatty acid is placed on position 2 in the triacylglycerides. There is also a relationship between the different position in the phylogenetic scale of each studied species and the differential fatty acid composition. All these data suggest that there are specific mechanisms involved in the fatty acids accumulation on the adipose tissue. The position of the different fatty acids in the triacylglyceride studied could be a part of this mechanism.

Adipose Tissue↗

[Subcutaneous fat necrosis of the newborn infant. Apropos of 2 cases].

Two cases of subcutaneous fat necrosis of the newborn are reported, an infrequent disease characterized by nodules or cutaneous endurated plaques that appears a few days after birth, which histopathologic studies shows fat necrosis with formation of giant cells granulomas strange body type and the presence of needle shaped clefts corresponding to fat crystals. This is a benign disease that has to be to differentiated from sclerema neonatorum, a serious entity which coexists with another disease so we also think it could be more a symptom than an authentic thickness. The two entities are vinculated physiopathologically by the injury of the fat tissue with a minor quantity of oleic acid and a major relative proportion of palmitic and stearic acid; than that of the adult, which conditions its easy solidification.

Fat Necrosis↗

Regulation of the composition and positioning of saturated and monoenoic fatty acids in phosphatidylcholine.

The mechanism by which polyenoic acids control the amount and positioning of monounsaturated fatty acids in choline phosphoglycerides from baby hamster kidney cells was studied. Under normal growth conditions monoenoic acids were derived from the desaturation of saturated fatty acids and comprised over 50% of the fatty acids at position 1 of the glycerol moiety. The monoene content of positions 1 and 2 decreased in response to the addition of di- and polyenoic acids to the culture medium. All the di- and polyenoic acid supplements tested inhibited the desaturation of palmitic and stearic acid and replaced monoenes at position 2. However only linoleic, linolenic, and eicosadienoic acids replaced monoenes at position 1. The results suggest that under appropriate conditions up to 25% of the choline phosphoglyceride fraction consisted of a stable molecular species containing di- or trienoic fatty acids at both the 1 and 2 positions of glycerol moiety. With eicosatrienoic or arachidonic acid supplements, on the other hand, the monoenes at position 1 were replaced with saturated fatty acids. The magnitude of these effects, particularly at position 1, was proportional to the concentration of the fatty acid supplement. The results suggest that polyenes with at least 20 carbon atoms can play a key role in determining the ultimate composition and positioning of fatty acids in baby hamster kidney choline phosphoglycerides and that this control is mediated by their ability to inhibit delta 9 desaturase and by a retailoring system specific for these polyenes.

Acetates↗

Changes in fatty acid composition of plasma, liver microsomes, and erythrocytes in liver cirrhosis induced by oral intake of thioacetamide in rats.

The aim of this study was to evaluate the changes in fatty acid composition of lipids of plasma, erythrocytes, and liver microsomes in rats with liver cirrhosis induced by oral intake of thioacetamide and to determine to what extent the experimental model reproduces the fatty acid tissue alterations reported in human cirrhosis. Two groups of rats were studied. The control group received water ad libitum, and the experimental group received 0.03% w/v thioacetamide in drinking water for 2, 4, and 6 months. At these times, lipids of plasma, erythrocytes, and liver microsomes were extracted, and their fatty acid compositions were determined. Thioacetamide intake led to macronodular and micronodular cirrhosis at 2 months. These alterations progressed at 4 months and eventuated in liver tumors at 6 months. Thioacetamide-treated rats showed a drop in total plasma fatty acids, higher percentages of palmitic acid in all lipid fractions, and lower levels of stearic acid in erythrocyte lipids and liver microsomal phospholipids. Oleic acid increased in plasma cholesteryl esters and phospholipids, as well as in erythrocyte lipids and liver microsomal phospholipids. In plasma lipids and liver microsomal phospholipids, the percentages of arachidonic and docosahexaenoic acids decreased. The latter also decreased in erythrocyte lipids. In addition, liver microsomes showed a higher cholesterol/lipid phosphorus molar ratio. The experimental model of cirrhosis obtained by intake of thioacetamide in drinking water for 4 months reproduces many of the fatty acid tissue alterations that appear in human cirrhosis and may serve to ascertain the biochemical mechanisms involved in these changes.

Administration, Oral↗

alpha-Hydroxylation of fatty acids in brain. Substrate specificity and deuterium isotope effect.

The alpha-hydroxylation of fatty acids with various chain length by a rat brain postnuclear preparation was investigated. The maximum velocity of the alpha-hydroxylation were higher for lignoceric (tetracosanoic), tricosanoic, docosanoic, and heneicosanoic acids and lower for hexacosanoic, pentacosanoic, eicosanoic, and nonadecanoic acids. Stearic palmitic, and phytanic (3,7,11,15-tetramethylpalmitic) acids were not hydroxylated by this preparation. Apparent Km values were lower for fatty acids with the higher Vmax and higher for those with the lower Vmax values. The relative order of alpha-hydroxylation strongly resembles the relative distribution of these fatty acids in brain cerebrosides, and we suggest that alpha-hydroxylation plays an important role in determining this distribution. An improved synthesis of [U-14C]phytanic acid is described. The rate of alpha-hydroxylation with [2-2H2]lignoceric acid was one-fifth of nondeuterated lignoceric acid and one-third of [3-2H2]lignoceric acid, while apparent Km values for these acids were similar. The reduced rate with [2-2H2]lignoceric acid indicates that the cleavage of the C-H bond is the rate-limiting step of the alpha-hydroxylation.

Animals↗

Molecular species of plant phosphatidylinositol with selective cytotoxicity towards tumor cells.

The molecular species of highly purified phosphatidylinositol from soybeans were determined as an aid in the investigation of the mechanism of their reported selective cytotoxicity towards tumor cells. Unlike the animal phosphatidylinositol, which contains predominantly stearic acid in the sn-1 and arachidonic in the sn-2 position (18:0 20:4), the soybean phosphatidylinositol was found to contain mainly linoleic acid in the sn-2 position and palmitic (16:0 18:2), stearic (18:0 18:2) and linoleic (18:2 18:2) acids in the sn-1 position of its molecular species.

Antineoplastic Agents↗

Role of lipid in sulfite-dependent propofol dimerization.

BACKGROUND: During long-term intravenous infusions, sulfite in sulfite-containing propofol emulsions can cause the peroxidation of lipid and dimerization of propofol. This study evaluated the role of lipid in sulfite-dependent propofol dimerization by determining the effects of individual fatty acids in soybean oil emulsion and peroxidized lipids in a model system. METHODS: Individual fatty acids, stearic (18:0), oleic (18:1), linoleic (18:2), linolenic (18:3), and arachidonic (20:4), were added to sulfite-containing propofol emulsion and incubated for 90 min at 37 degrees C. Model systems containing soybean oil (100 microl), water (900 microl), propofol (10 mg/ml), and sulfite (0.25 mg/ml) composed of oils with different peroxide values were allowed to react for 60 min at room temperature. After the reactions, propofol dimer and propofol dimer quinone were analyzed by reversed-phase high-pressure liquid chromatography. RESULTS: Propofol did not dimerize when added to aqueous sulfite unless soybean oil was also included. The addition of the polyunsaturated fatty acids (linoleic, linolenic, arachidonic) to sulfite-containing propofol emulsion resulted in large increases of propofol dimerization compared with stearic or oleic acid. Using biphasic mixtures of soybean oil and aqueous sulfite, propofol dimerization increased with increasing peroxide content of the oil. In propofol emulsion, lipoxidase and ferrous iron in the absence of sulfite also caused the dimerization of propofol. CONCLUSIONS: These results show that lipid can play a significant role in sulfite-dependent propofol dimerization. The relation of dimerization to polyunsaturated fatty acid and soybean oil peroxide content suggests that sulfite reacts with unsaturated lipid or peroxide-modified lipid to facilitate propofol dimerization.

Dimerization↗

Starvation depresses acylglycerol biosynthesis in bovine subcutaneous but not intramuscular adipose tissue homogenates.

The primary objective of this study was to document the effects of starvation on acylglycerol biosynthesis in homogenates of intramuscular and subcutaneous adipose tissues. Adipose tissue samples were obtained from 8th-13th thoracic rib sections from 12 Angus cattle (six steers plus six heifers). Three steers and three heifers were starved for 72 h prior to slaughter while the remainder were slaughtered 4 h after food was withheld. Fat-free 700 x g centrifugal fractions were used to measure the esterification of radiolabeled sn-glycerol 3-phosphate (G-3-P) into acylglycerols at 1.0 mM palmitic or stearic acid, or 0.2 mM oleic, linoleic, or alpha-linolenic acid. There were significant tissue x fatty acid interactions for rates of incorporation into diacylglycerols and triacylglycerols; in subcutaneous, but not intramuscular homogenates, palmitic > stearic = oleic = linoleic = alpha-linolenic acid. Subcutaneous homogenates incorporated a greater percentage of G-3-P into triacylglycerols, and a lesser percentage into phospholipid, than intramuscular homogenates (P < 0.05). In intramuscular homogenates, the primary product of G-3-P esterification to saturated fatty acids was phospholipids. When unsaturated fatty acid served as substrates, triacylglycerols and phospholipids were produced in equal proportions in intramuscular homogenates, and triacylglycerols were the predominant product in subcutaneous homogenates. Intramuscular adipose tissue homogenates exhibited no response to starvation, whereas triacylglycerol and diacylglycerol synthesis was depressed by approximately 50% in subcutaneous adipose tissue homogenates. Similarly, phosphatidic phosphohydrolase activity, initially greater in subcutaneous than in intramuscular adipose tissue, was decreased by approximately 50% by starvation in subcutaneous adipose tissue, but not in intramuscular adipose tissue. We conclude that differences in rates of diacylglycerol and triacylglycerol biosynthesis, and response to starvation, between intramuscular and subcutaneous adipose tissues were due to dissimilarities in the activity of phosphatidic phosphohydrolase.

Adipose Tissue↗

Oleic acid transfer from microsomes to egg lecithin liposomes: participation of fatty acid binding protein.

Oleic acid transfer from microsomes or mitochondria to egg lecithin liposomes was stimulated by fatty acid binding protein. By gel filtration, it could be demonstrated that this protein incorporates oleic acid into liposomes. Fatty acid binding protein transfer activity was higher using microsomes rather than mitochondria, which suggests a selective interaction with different kinds of membranes. Transfer of oleic acid by this soluble protein is greater than that of stearic acid. The results indicate that fatty acid binding protein may participate in the intracellular transport of fatty acids.

Animals↗

Comparison of C18-, C20- and C22-unsaturated fatty acids in reducing fatty acid synthesis in isolated rat hepatocytes.

C18-, C20- and C22-unsaturated acids were tested for inhibition of fatty acid synthesis in hepatocytes isolated from essential fatty acid-deficient rats. Fatty acid synthesis was measured by incorporation of radioactivity from [1-14C-A1-acetate or 3H2O into fatty acids. C20-polyunsaturated fatty acids included arachidonic acid (20 : 4 (n-6)) and 4 other fatty acids formed from linoleic acid (18 : 2 (n-6)) or linolenic acid (18 : 3 (n-3)). These were (11,14)-icosadienoic acid (20 : 2 (n-6)), (8,11,14)-icosatrienoic acid (20 : 3 (n-6)), (11,14,17)-icosatrienoic acid (20 : 3 (n-3)) and (5,8,11,14,17)-icosapentaenoic acid (20 : 5 (n-3). All of these have essential fatty acid activity. The fatty acid (5,8,11)-icosatrienoic acid (20 : 3 (n-9)) was also tested. This fatty acid is formed from oleic acid (18 : 1 (n-9)) and is not an essential fatty acid or a prostaglandin precursor. C20-unsaturated fatty acids and (22 : 6 (n-3)) were as effective as stearic acid in inhibiting fatty acid synthesis and were more inhibitory than their precursor C18-unsaturated fatty acids. These results are evidence that C20-unsaturated fatty acids of the linoleic and linolenic acid series can act in short-term inhibition as well as in adaptive inhibition of fatty acid synthesis (Bloch, K. and Vance, D. (1977) Annu. Rev. Biochem. 46, 263--298). The effectiveness of (5,8,11)-icosatrienoic acid indicates that short-term inhibition by C20-unsaturated fatty acids is not limited to those fatty acids which have essential fatty acid activity.

Animals↗

Fatty acid and prostaglandin composition of left ventricular myocardium from dexamethasone-treated dogs with severe low output syndrome (LOS).

The effects of dexamethasone (DEX) administration on the left ventricular myocardial content of fatty acids and prostaglandins E1, E2 and F2alpha were studied. Following a complete right and left cardiac catheterization, either DEX (8 mg/kg) or an equivalent volume of its vehicle was given intravenously 30 minutes prior to low output syndrome (LOS induction, and supplemental doses of DEX (4 mg/kg) or vehicle administered at 15 and 75 minutes post-LOS induction. Low output syndrome was induced by intravenous administration of a myocardial depressor protein (MDP) which has been isolated from the venom of the Western diamondback rattlesnake, Crotalus atrox. Neither DEX nor its vehicle had a significant effect during the entire experiment, that is, in the normal or low cardiac output state in most of the hemodynamic parameters investigated. The three hour mortality rate for the DEX-treated animals was 22% (n=10) while that of the control group was 41% (n=26) indicating that the beneficial effects of this corticosteroid are not really apparent from hemodynamic evaluation alone. Since DEX only had a significant post-LOS induction effect in maintaining a lower left ventricular end-diastolic and pulmonary capillary wedge pressures, a higher arterio-venous oxygen saturation difference, and a more efficient contractile state of myocardial fibers (Vmax), an indirect correlation to coronary arterial blood flow at the subcellular level was sought. To this effect, prostaglandins and specific lipid classes of left ventricular myocardium (LVM) from control and LOS animals receiving either vehicle or DEX were analyzed. Low output state induction alone raised myocardial PG levels above those of sham-catheterized animals; on the other hand, dexamethasone induced a significant decrease in the three prostaglandins studied when administered to control (no LOS) animals. In the presence of LOS, however, dexamethasone overrode in part the increase in PGE1 and PGE2 brought about by LOS while in the case of PGF2alpha the LOS effect was totally prevented and its concentration was not significantly higher than in control animals receiving dexamathasone. LOS induction led to an increase in myristic and arachidonic acids and a decrease in palmitic and linolenic acids. Dexamethasone administration to control animals increased the concentration of stearic acid above all the other groups but decreased the concentration of linolenic acid when compared to DEX-treated animals with LOS or sham-catheterized animals. There were no significant differences in the total myocardial lipid among the four groups of animals studied. It is suggested that the potentially beneficial effects of corticosteroid administration to animals with low output syndrome are related to their effects on fatty acid and prostaglandin content of myocardium.

Animals↗

Ethanol effects on synaptic glutamate receptor function and on membrane lipid organization.

The enhancement of L-glutamic acid binding activity of brain synaptic membranes by low concentrations of ethanol (less than 50 mM) and the decrease in binding at high concentrations (greater than 100 mM) was not due to a direct action by ethanol on the glutamate binding protein. Biphasic effects of ethanol on membrane protein complexes such as the glutamate binding sites might be the result of biphasic changes in membrane lipid organization. Low ethanol concentrations (0.1-4.0 mM) were shown to decrease fatty acid chain motion detected by the EPR probe 5-doxyl stearic acid, whereas high concentrations (greater than 400 mM) increased lipid motion in egg phosphatidylcholine liposomes. The function of the L-glutamate receptor-ion channel complex in the presence of ethanol was also determined by measuring the changes in thiocyanate (SCN-) influx brought about by L-glutamate or ethanol. A low concentration of ethanol (9.4 mM) diminished the L-glutamate-induced depolarization of synaptic membranes, while a high concentration (93.7 mM) increased the passive SCN-influx and produced a transient overshoot in glutamate-stimulated SCN-flux.

Animals↗

Comparative levels of arachidonic acid and eicosapentaenoic acid in Malaysian fish.

Total lipids were extracted from 22 species of Malaysian fish and the constituent fatty acids were analysed by gas chromatography. Malaysian fish generally contained high levels of saturated fatty acids (range 36-55% total fatty acids) and contained variable amounts of monounsaturates, chiefly palmitic and stearic acids, but only trace levels of 20:1 and 22:1. Unlike fish caught in colder northern hemisphere waters, Malaysian fish were found to contain arachidonic acid (20:4 omega 6, range 2-12%) in addition to the expected eicosapentaenoic acid (20:5 omega 3, range 1-13%) and docosahexaenoic acid (22:6 omega 3, range 6.6-40.4%).

Animals↗

Regulation of membrane lipid bilayer structure during seasonal variation: a study on the brain membranes of Clarias batrachus.

(1) A significant seasonal variation in the membrane fluidity (as sensed by DPH-fluorescence polarization), membrane lipid components (phospholipid and neutral lipid), fatty acid composition of membrane phospholipid (phosphatidylcholine, phosphatidylethanolamine and sphingomyelin), positional distribution of fatty acids at Sn-1 and Sn-2 position of phosphatidyl-choline and -ethanolamine is noticed in the brain membranes (myelin, synaptosomes, and mitochondria) of a tropical air breathing teleost, Clarias batrachus. (2) A 'partial compensation' of membrane fluidity during seasonal adaptation is observed in myelin and mitochondria membrane fractions. Synaptosomes membrane fraction exhibits a different response. Depletion (about 15-70%) of membrane lipid components (phospholipid, cholesterol, diacylglycerol and triacylglycerol) per unit of membrane protein is the characteristic feature of summer adaptation. An increase (about 20-100%) in the level of oleic acid and decrease (about 20-60%) in the level of stearic acid are almost common features in membrane phospholipid fractions of winter-adapted Clarias (3) From the tissue slice experiment it is evident that there is an activation of cellular phospholipase A2 at lower growth temperature and of cellular phospholipase A1 at higher growth temperature and this suggests the reorganization of molecular architecture of the membrane during seasonal adaptation. (4) Accumulation of oleic acid in Sn-1 position and polyunsaturated fatty acids in Sn-2 position of phosphatidylcholine and -ethanolamine during winter indicates an increase in the concentration of 1-monoenoic, 2-polyenoic molecular species of phospholipid in order to maintain the stability of membrane lipid bilayer.

Acclimatization↗

Lipase catalyzed synthesis of organic acid esters of lactic acid in non-aqueous media.

Lipases from Rhizomucor miehei (Lipozyme IM20) and porcine pancreas (PPL) were employed as catalysts for the esterification reaction between the hydroxyl group of lactic acid and the carboxyl group of organic acids. Reactions were carried out at both shake-flask and bench-scale levels. Various parameters, such as solvent, temperature, substrate and enzyme concentrations, effect of buffer volume, buffer pH and water volume, were investigated for optimization of yields. While ethylmethyl ketone (EMK) was found to be the best solvent for shake-flask reactions, chloroform gave higher yields at bench-scale level. Detailed studies were carried out with respect to the synthesis of palmitoyl and stearoyl lactic acids. At shake-flask level, maximum yields of 37.5 and 40% were observed in case of palmitoyl and stearoyl lactic acids, respectively, with Lipozyme IM20; at bench-scale level, the maximum yields were 85.1 and 99% respectively, when PPL was employed. Of all the organic acids employed (C(2)--C(18)), only lauric, palmitic and stearic acids gave yields above 50%. At bench-scale level, PPL could be reused for up to three cycles with yields above 40%. Esters prepared were found to conform to Food Chemical Codex (FCC) specifications in terms of acid value, ester value, sodium and lactic acid contents.

Biotechnology↗