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PubMed1966

The oxidation of fatty acids combined with albumin by isolated rat liver mitochondria.

Long chain fatty acids at concentrations inhibiting mitochondrial respiration were, in the presence of serum albumin, found to produce almost as high a rate of oxygen uptake as alpha-ketoglutarate, succinate, or acetate. This oxidation was characterized in terms of its coupling to phosphorylation, need for cofactors, and production of different metabolites during the reactions. Fatty acids were oxidized to carbon dioxide, acetoacetate, beta-hydroxybutyrate, and other water-soluble metabolites, tentatively identified as intermediates of the citric acid cycle. An agent to spark the citric acid cycle and adenosine tri- or monophosphate were necessary for optimal oxidation rate, as described for other fatty acid oxidation systems. Balance experiments with different amounts of malate were performed with incubations lasting as long as oxygen uptake took place. In the presence of 1 mumole of malate, practically all added palmitic acid was used up and found to be converted primarily to carbon dioxide, acetoacetate, and other water-soluble metabolites of which the major part was tentatively identified as succinate. A significant portion was found in mitochondrial phospholipids. With 10 mumoles of malate some palmitic acid remained in the system, while a comparatively small amount was converted to carbon dioxide, and a major part was found as succinate. Here also incorporation into phospholipids occurred. With no malate added, fatty acid oxidation was much smaller than with malate, although significant conversion to carbon dioxide took place. Only a little succinate and phospholipid were found. Oxygen uptake was greater than a theoretical value calculated from radioactive balance experiments. It was concluded that albumin contains oxidizable material even after extraction and dialysis. Albumin at high concentrations inhibited both fatty acid and alpha-ketoglutarate oxidation. The oxidation of long chain fatty acids in high concentrations in the form of albumin-fatty acid complex was coupled to phosphorylation. Thus P:O ratios above 2 were found as well as evidence for respiratory control. It was concluded that oxidation of long chain fatty acids by isolated mitochondria occurs from their albumin complex. This process can also be studied at high concentrations of fatty acids, where high rates of oxygen uptake are obtained from oxidation which is coupled to phosphorylation.

Animals↗
PubMed1997

Fatty acids and retinoids bind independently and simultaneously to beta-lactoglobulin.

beta-Lactoglobulin (Big) binds 1 mol of a fatty acid spin-label analog, 5-doxylstearic acid (5-DSA), per mole of protein with a dissociation constant Kd = 0.8 microM for the strongest binding site. There are also several weaker sites for this ligand. Blg saturated with either retinol or retinoic acid binds 5-DSA with essentially equal affinity (Kd = 0.6 and 1 microM, respectively). Palmitic acid and SDS displace bound 5-DSA from Blg. However, unlike palmitic acid, 5-DSA binding does not enhance the structural stability of Blg to urea denaturation. The spin-labeled fatty acid also binds to the protein at low pH, presumably at secondary fatty acid binding sites. These results suggest that Blg binds at least two different types of hydrophobic ligands simultaneously.

Binding, Competitive↗
PubMed1968

The incorporation of acetate and palmitate into lipids by human platelets.

The optimal conditions for the incorporation of acetate-1-(14)C and palmitic acid-1-(14)C into platelet lipids have been described. In buffer incubations with acetate there was a sharp pH optimum at 6.8; in plasma incubations, there was a broad pH optimum between 6.8-7.4. Maximal incorporation of acetate occurred at a final concentration of 1.5 mmoles/liter. In buffer, no labeled lipids were released from platelets into the medium. In plasma, 40% of newly formed lipids was recovered in the plasma. 75% of the incorporated acetate could be recovered in ceramide, lecithin, and free fatty acids. Platelet fatty acids were formed both by de novo synthesis and chain elongation. The fatty acids formed by de novo synthesis exchanged with plasma free fatty acids. In buffer incubations no turnover of newly labeled lipids occurred, but in the plasma incubations exchange of newly labeled lecithin with plasma lipids was demonstrable. Palmitic acid-1-(14)C added to plasma was incorporated into platelet lipids. The distribution among the lipid classes of palmitate taken up from plasma was the same as that of palmitate formed intracellularly by de novo synthesis.

Acetates↗
PubMed1995

The alphavirus replicase protein nsP1 is membrane-associated and has affinity to endocytic organelles.

In alphavirus-infected cells the four virus-specific nonstructural proteins (nsP1-nsP4) are located on modified endosomes and lysosomes known as type I cytopathic vacuoles. In this paper, we show that when nsP1 was expressed alone in HeLa cells with the aid of the recombinant T7 RNA polymerase vaccinia (vTF7-3) virus system, it was tightly associated with intracellular smooth membranes. The membrane association may be due to acylation, since nsP1 could be labeled with [3H]palmitic acid in both Semliki Forest virus-infected and nsP1-transfected HeLa cells. Release of the 3H-label by alkaline methanolysis suggests that the palmitate was associated with nsP1 via an ester bond. Pulse-chase experiments done on nsP1-transfected cells revealed that this protein was rapidly associated with the membranes. After synchronizing the synthesis of the nsP1 gene product in transfected cells, nsP1 appeared first at the plasma membrane and thereafter on vesicles, many of which contained the endosomal transferrin receptor marker. Later, nsP1 appeared on large vacuoles, which contained the lysosome specific h-lamp-1 protein. Membrane association of nsP1, and its affinity to endosomes and lysosomes, suggest a role of this protein in the biogenesis of the alphavirus-specific RNA replication complex.

Acylation↗
PubMed1987

Digestibility of cocoa butter and corn oil and their influence on fatty acid distribution in rats.

The comparative bioavailability of cocoa butter (a predominantly saturated fat) and corn oil (a predominantly unsaturated fat) was determined in male Sprague-Dawley rats by analysis of total fecal lipids following ad libitum feeding of purified diets containing 5, 10 and 20% cocoa butter or corn oil for 2 wk. Fecal lipid elimination was significantly increased (P less than 0.05) in each cocoa butter group when compared with the corresponding corn oil group, resulting in lower digestibility coefficients for cocoa butter (59-72%) than for corn oil (93-97%). Body weight gain and food intake data were similar among all treatment groups. Fecal fatty acid profiles in rats fed corn oil diets consisted primarily of 27-34% palmitic acid (16:0), 22-32% stearic acid (18:0) and 25-37% oleic acid (18:1). Palmitic, oleic and linoleic acids were also the primary fatty acids stored in epididymal fat tissue from corn oil-fed rats. In contrast, fecal fatty acids in animals fed cocoa butter diets consisted of 31-37% palmitic acid and 58-64% stearic acid; oleic acid was the major fatty acid stored in epididymal fat tissue. These results indicate that the decreased digestibility of cocoa butter is largely a result of its fatty acid composition. This reduced bioavailability of cocoa butter may be at least partially responsible for its previously described neutral effect on serum cholesterol.

Adipose Tissue↗
PubMed1979

The labeling of lung phosphatidylcholine in premature rabbits.

Lung phosphatidylcholine metabolism was studied in vivo in premature rabbits delivered by cesarean section as early in gestation as compatible with prolonged viability (28.9 days). The newborn rabbits initially required supplemental oxygen and had respiratory distress. The amount of phosphatidylcholine isolated from the lung parenchyma changed little over the first 3 days of life, while phosphatidylcholine in the alveolar wash increased in 3 days from 0.05--3.1 mumol/50 g animal. The phosphatidylcholine of the lungs of the premature rabbits was pulse labeled with isotopically labeled palmitic acid, choline, and phosphate given to the pregnant does 10 min before delivery of the newborns. After the initial incorporation period, the total amount of radioactive precursor palmitic acid, choline, or 32P) incorporated into lung phosphatidylcholine did not change for a period of 4 days. Labeled phosphatidylcholine was detected initially in alveolar wash 3 hr after administration of the three precursors and continued to accumulate for many hours. The biological half-life values for lung and alveolar phosphatidylcholine indicated that phosphatidylcholine was turning over very slowly. However, if the effect of dilution on the measured specific activity caused by phosphatidylcholine accumulation was considered, virtually no labeled alveolar or lung phosphatidylcholine disappeared during the 3--4 days of these observations. These results with premature newborn rabbits were similar to those for term newborn rabbits, but different from similar measurements made in the adult rabbit.

Age Factors↗
PubMed1990

Cell mass of Mycobacterium bovis BCG estimated by gas chromatography.

The presence of additives and large cellular aggregates in freeze-dried BCG vaccines precludes accurate measurement of total cell content by traditional methods. The possibility that extraction and quantitation of a cell membrane fatty acid may provide a suitable means of cell mass determination was tested. The palmitic acid methyl ester peak area determined by gas chromatography was directly proportional to the wet weight of freshly grown Tice-, Pasteur-, and Glaxo-substrain BCG, as well as the dry weight of the ampoule contents after removal of soluble material. Extraction of palmitic acid from Tice BCG vaccine was not appreciably affected by lyophilization and the calculated dry cell mass values of freeze-dried vaccine samples correlated well with particle number. This method, therefore, may be useful in measuring BCG cell mass during all stages of vaccine manufacture and storage.

BCG Vaccine↗
PubMed2005

Sulfur-substituted and alpha-methylated fatty acids as peroxisome proliferator-activated receptor activators.

FA with varying chain lengths and an alpha-methyl group and/or a sulfur in the beta-position were tested as peroxisome proliferator-activated receptor (PPAR)alpha, -delta(beta), and -gamma ligands by transient transfection in COS-1 cells using chimeric receptor expression plasmids, containing cDNAs encoding the ligand-binding domain of PPARalpha, -delta, and -gamma. For PPARalpha, an increasing activation was found with increasing chain length of the sulfur-substituted FA up to C14-S acetic acid (tetradecylthioacetic acid = TTA). The derivatives were poor, and nonsignificant, activators of PPARdelta. For PPARgamma, activation increased with increasing chain length up to C16-S acetic acid. A methyl group was introduced in the alpha-position of palmitic acid, TTA, EPA, DHA, cis9,trans11 CLA, and trans10,cis12 CLA. An increased activation of PPARalpha was obtained for the alpha-methyl derivatives compared with the unmethylated FA. This increase also resulted in increased expression of the two PPARalpha target genes acyl-CoA oxidase and liver FA-binding protein for alpha-methyl TTA, alpha-methyl EPA, and alpha-methyl DHA. Decreased or altered metabolism of these derivatives in the cells cannot be excluded. In conclusion, saturated FA with sulfur in the beta-position and increasing carbon chain length from C9-S acetic acid to C14-S acetic acid have increasing effects as activators of PPARalpha and -gamma in transfection assays. Furthermore, alpha-methyl FA derivatives of a saturated natural FA (palmitic acid), a sulfur-substituted FA (TTA), and PUFA (EPA, DHA, c9,t11 CLA, and t10,c12 CLA) are stronger PPARalpha activators than the unmethylated compounds.

Animals↗
PubMed1993

Photoreactive fatty acid analogues that bind to the rat liver fatty-acid binding protein: 11-(5'-azido-salicylamido)-undecanoic acid derivatives.

Photoreactive probes for the hydrophobic pocket of the liver fatty acid-binding protein, 11-(5'-azido-salicylamido)-undecanoic acid (5' ASU) and its acetyl ester (Ac5' ASU), were synthesized and their interaction with the protein was assessed. Fatty acid-binding proteins are closely related proteins which are abundantly expressed in tissues with active lipid metabolism. A simple model that assumes that the protein possesses a single kind of sites fitted the binding of radioiodinated 5' ASU to L-FABP satisfactorily. The apparent dissociation constant, 1.34 x 10(-7) M, evidenced a slightly higher affinity than that reported for C16-C20 fatty acids. Consistent with the binding curve, 5' ASU effectively competed with palmitic acid for the hydrophobic sites and the effect was nearly complete for concentrations of 1 microM; oleic acid, in turn, displaced the radiolabelled probe. Irradiation at 366 nm of 125I-5' ASU bound to L-FABP caused the covalent cross-linking of the reagent. The amount of radioactivity covalently bound reached a maximum after 2 min thus agreeing with the photo-activation kinetics of the unlabelled compound that evidenced a t1/2 of 31.1 sec. The yield with which probes bound to L-FABP became covalently linked to the protein, appraised after SDS-PAGE of irradiated samples, was estimated as 23 and 26 per cent for 5' ASU and Ac5' ASU respectively. In turn, irradiation of L-FABP incubated with 5' ASU or Ac5' ASU resulted in the irreversible loss of about one fourth its ability to bind palmitic acid.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1999

Requirement for omega and (omega;-1)-hydroxylations of fatty acids by human cytochromes P450 2E1 and 4A11.

Human liver microsomes and recombinant human P450 have been used as enzyme source in order to better understand the requirement for the optimal rate of omega and (omega;-1)-hydroxylations of fatty acids by cytochromes P450 2E1 and 4A. Three parameters were studied: alkyl chain length, presence and configuration of double bond(s) in the alkyl chain, and involvement of carboxylic function in the fatty acid binding inside the access channel of P450 active site. The total rate of metabolite formation decreased when increasing the alkyl chain length of saturated fatty acids (from C12 to C16), while no hydroxylated metabolite was detected when liver microsomes were incubated with stearic acid. However, unsaturated fatty acids, such as oleic, elaidic and linoleic acids, were omega and (omega;-1)-hydroxylated with an efficiency at least similar to palmitic acid. The (omega;-1)/omega ratio decreased from 2.8 to 1 with lauric, myristic and palmitic acids as substrates, while the reverse was observed for unsaturated C18 fatty acids which are mainly omega-hydroxylated, except for elaidic acid showing a metabolic profile quite similar to those of saturated fatty acids. The double bond configuration did not significantly modify the ability of hydroxylation of fatty acid, while the negatively charged carboxylic group allowed a configuration energetically favourable for omega and (omega;-1)-hydroxylation inside the access channel of active site.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

[The effect of a structural analog of gamma-butyrobetaine, mildronate, [3-2,2,2-trimethylhydrazine)propionate] on dynamic carnitine-dependent metabolism].

Inhibitor of carnitine-dependent metabolism mildronate, 3-(2,2,2-trimethylhydrazinium) propionate, administered into rats at a dose of 200 mg/kg, per os, within 10 days, caused a decrease in concentration of free carnitine and of long-chain acylcarnitine in myocardium as well as contributed to accumulation of free fatty acids in blood serum. Besides, the rate of I-14C-palmitic acid turnover to 14CO2 was decreased in myocardium homogenate. The drug inhibitory effect on carnitine biosynthesis from gamma-butyrobetaine was responsible for the phenomenon observed. Content of the metabolites studied was altered gradually both during treatment of rats with mildronate and after the drug abolition, thus demonstrating an opportunity of gentle influence on carnitine-dependent metabolism by means of the drug treatment and its abolition.

Animals↗
PubMed1990

The cell cycle modulated glycoprotein GP115 is one of the major yeast proteins containing glycosylphosphatidylinositol.

The cell cycle modulated protein gp115 (115 kDa, isoelectric point about 4.8-5) of Saccharomyces cerevisiae undergoes various post-translational modifications. It is N-glycosylated during its maturation along the secretory pathway where an intermediary precursor of 100 kDa (p100), dynamically related to the mature gp115 protein, is detected at the level of endoplasmic reticulum. Moreover, we have shown by the use of metabolic labeling with [35S]methionine, [3H]palmitic acid and myo-[3H]inositol combined with high resolution two-dimensional gel electrophoresis and immunoprecipitation with a specific antiserum, that gp115 is one of the major palmitate- and inositol-containing proteins in yeast. These results, and the susceptibility of gp115 to phosphatidylinositol-specific phospholipase C treatment strongly indicate that gp115 contains the glycosylphosphatidylinositol (GPI) structure as membrane anchor domain. The two-dimensional analysis of the palmitate- and inositol-labeled proteins has also allowed the characterization of other polypeptides which possibly contain a GPI structure.

Acetylglucosaminidase↗
PubMed1983

Synthesis and metabolism of arachidonyl- and eicosapentaenoyl-CoA in rat aorta.

In studies on the metabolism of polyunsaturated fatty acids, acyl-CoA synthetase for 5,8,11,14-20:4 (arachidonic acid) and 5,8,11,14,17-20:5 (eicosapentaenoic acid) and the incorporation of these fatty acids into complex lipids and their conversion to CO2 were investigated in rat aorta. The activity of acyl-CoA synthetase was 35.9 for arachidonic acid and 63.0 for eicosapentaenoic acid (nmol/mg protein per 10 min) and the apparent Km values were 45 microM for arachidonic acid and 56 microM for eicosapentaenoic acid. Inhibition of eicosapentaenoyl-CoA synthesis by arachidonic acid was stronger than that of arachidonyl-CoA synthesis by eicosapentaenoic acid. Arachidonic acid and eicosapentaenoic acid were mostly incorporated into phospholipids. The incorporation of these fatty acids into cholesterol ester and their conversion to CO2 were less than those of palmitic acid, but their incorporation into triacyglycerol was greater. The incorporation of these fatty acids into phosphatidylserine + phosphatidylinositol and phosphatidylethanolamine was also greater than that of palmitic acid. The patterns of incorporation of arachidonic acid and eicosapentaenoic acid were similar. The physiological roles of these polyunsaturated fatty acids and the interference of eicosapentaenoic acid in arachidonic acid metabolism are discussed on the basis of these results.

Animals↗
PubMed1998

Some aspects of beta-lactoglobulin structural properties in solution studied by fluorescence quenching.

The technique of protein fluorescence quenching by acrylamide and sodium nitrite (NO2-) was used to study some structural aspects of beta-lactoglobulin in solution. The degree of exposure and the micro-environments of the two tryptophanyl residues (Trp-19 and Trp-61) present in this ruminant milk protein were sensed, and the influence of the pH and the binding of palmitic acid in their accessibilities were analyzed. The results obtained showed that Trp-19 has an accessibility to the quenchers higher than could be supposed from its structural location. The binding of palmitic acid, on the other hand, increases the accessibility of both tryptophanyl residues, a fact that could be associated with a slight conformational change of the protein.

Acrylamide↗
PubMed1990

Importance of blood glucose concentration in regulating lipolysis during fasting in humans.

The importance of the decline in blood glucose concentration on lipolysis and the lipolytic effect of epinephrine was evaluated during short-term fasting. Lipolytic rates were determined by infusing [2H5]glycerol and [1-13C]palmitic acid. Five volunteers were studied after 12 h of fasting before and during epinephrine infusion and after 84 h of fasting, before and during glucose infusion when plasma glucose was restored to postabsorptive values, and during glucose plus epinephrine infusion. In another protocol, five volunteers were given glucose intravenously throughout fasting to maintain plasma glucose at postabsorptive levels and isotopic studies were performed after 12 and 84 h of fasting before and during epinephrine infusion. Glucose infusion after 84 h of fasting restored glucose and insulin concentrations and lipolytic rates toward 12-h fasting values. When euglycemia was maintained throughout fasting, plasma insulin still declined (P less than 0.05) and lipolytic rates still increased (P less than 0.05). Despite similar glucose concentrations, the lipolytic response to epinephrine infusion was greater after 84 h than after 12 h of fasting in both protocols (P less than 0.05). These studies demonstrate that the decline in plasma glucose contributes to, but is not required for, the increase in lipolysis during fasting. The increase in epinephrine-stimulated lipolysis that occurs during fasting is not dependent on a decrease in plasma glucose concentration.

Adult↗
PubMed2006

Effect of fatty acids, glucose, and insulin on hepatic glucose uptake and glycolysis.

OBJECTIVE: There is evidence from in vitro studies that fatty acids can inhibit glucose uptake in liver. However, it is uncertain whether this happens in vivo when the liver is exposed to high levels of glucose and insulin, in combination with fatty acids, after a mixed meal. This study determined the effects of a combination of fatty acids and insulin on glucokinase (GK) activity and glycolysis in primary rat hepatocytes. METHODS: Hepatocytes were cultured with 15 mM glucose and 2 or 10 nM insulin in combination with the fatty acids palmitate, oleate, linoleate, eicosapentaenoic acid, or docosahexaenoic acid. Total GK activity and the proportion of GK in the active, unbound state were measured to determine the effect of fatty acid on the activity and cellular localization of GK. Glucose phosphorylation and glycolysis were measured in intact cells. Lactate and pyruvate synthesis and the accumulation of ketone bodies were also estimated. RESULTS: Palmitate and eicosapentaenoic acid lowered total GK activity in the presence of 2 nM insulin, but not with 10 nM insulin. In contrast, oleate, linoleate, and docosahexaenoic acid did not alter GK activity. None of the fatty acids tested inhibited glucose phosphorylation or glycolysis in intact rat hepatocytes. In addition, GK activity was unaffected by insulin concentration. CONCLUSION: Some fatty acids can act to inhibit GK activity in primary hepatocytes. However, there was no evidence that this decrease in GK activity impaired glucose phosphorylation or glycolysis. Glucose and high concentrations of insulin, which promote glucose uptake, appear to counteract any inhibitory action of fatty acids. Therefore, the presence of fatty acids in a normal mixed meal is likely to have little effect on the capacity of the liver to take up, phosphorylate, and oxidize glucose.

Animals↗
PubMed1988

The antipsoriatic drug metabolite etretin (Ro 10-1670) alters the metabolism of fatty acids in human keratinocytes in culture.

We have studied the effect of etretin (Ro 10-1670), the active metabolite of the widely used antipsoriatic drug etretinate (Ro 10-9359), on the incorporation and release of arachidonic acid in human skin keratinocytes. During 24-h culture, radioactive 14C-arachidonic acid was avidly incorporated into the cellular lipids of the keratinocytes. When the cells were cultured for another 48 h in fresh medium, 8.8% +/- 0.3% of the incorporated radioactivity was released from the cells. The presence of etretin (10(-8) M to 10(-5) M) in the medium stimulated the release of radiolabel. With 10(-5) M etretin in the culture medium, 13.0% +/- 0.4% of the incorporated radioactivity was released, and this was accompanied by decreased labelling of phosphatidylethanolamine. This suggests that phosphatidylethanolamine may be an important source of the released arachidonic acid. Etretin pretreatment reduced the incorporation of 14C-arachidonic acid into diacylglycerols, triacylglycerols, and cholesteryl esters. Pretreatment for 48 h with 10(-5) M etretin reduced subsequent 14C-arachidonic acid incorporation into nonphosphorus lipids from a mean total of 8.2% +/- 0.2% to 3.2% +/- 0.1% (p less than 0.001). These findings suggest that etretin interferes with the esterification of arachidonic acid into nonphosphorus lipids. Etretin was also found to cause changes in the fatty acid composition of keratinocytes. Following 48 h culture with etretin, the percentage amount of the fatty acids belonging to the n3 series was increased whereas that of palmitic acid (16:0) and palmitoleic acid (16:1n7) was decreased. In conclusion, our study suggests that etretin in therapeutical concentrations affects fatty acid metabolism in human keratinocytes in culture.

Acitretin↗
PubMed1999

Fatty acid metabolism in human breast cancer cells (MCF7) transfected with heart-type fatty acid binding protein.

The human breast cancer cell line MCF7 does not express heart-type fatty acid binding protein (H-FABP), a marker protein for differentiated mammary gland. MCF7 cells transfected with the bovine H-FABP cDNA expressed the corresponding protein and were characterized by growth inhibition and lower tumorgenicity in nude mice [22]. By enzyme linked immunoassay we now determined the amount of bovine H-FABP in these cells as 638 +/- 80 ng/mg protein and used the transfected cells to study the role of H-FABP in fatty acid metabolism. Compared to control cells the uptake of radioactively labelled palmitic acid and oleic acid into MCF7 cells after 30 or 60 min was increased by 67% in H-FABP expressing transfectants, demonstrating a stimulatory role for this FABP-type in fatty acid metabolism. However, preferential targeting of [14C]oleic acid into neutral or phospholipid classes was not observed by the criterion of high performance thin layer chromatography followed by autoradiography. A reason for the modest increase of fatty acid uptake in H-FABP transfected MCF7 cells may be the basal expression of epidermal-type FABP, which was detected for the first time in these cells. It appears that the small amount of E-FABP expressed in MCF7 cells fulfils the need of the cells for a cytosolic fatty acid carrier under culture conditions and that even high concentrations of another FABP do only slightly increase the uptake due to limitations of fatty acid transport through the plasma membrane or of metabolism.

Animals↗