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Stearic acid and iodo-stearic and inhibited cell growth in a cervical cancer cell line (HOG-1) in a dose-related manner, with a half maximal effect at 50 microM stearic acid. Addition of oleic acid abrogated the effect of stearic acid. EGF-stimulated DNA synthesis and growth of HOG-1 cells was inhibited in the presence of stearic acid without any apparent effect on EGF receptor number or affinity.
The effects of temperature and cholesterol on the membrane fluidity of human erythrocytes were studied using 5-nitroxide stearic acid (5NS), 12-nitroxide stearic acid (12NS), and 16-nitroxide stearic acid (16NS). Human erythrocytes and their lipid vesicles were treated in the range of 5--55 degrees C. In erythrocytes, ESR signals for 12NS and 16NS showed line broadening above 40 degrees C, whereas those for 5NS became sharper with increasing temperature as was the case with the signals of lipid vesicles for each label molecule. Lipid extraction from the heated sample caused no radical reduction. Only in 12NS-labeled erythrocytes did a weakly immobilized component and a strongly immobilized component appear. In the time course at 50 degrees C, the former decreased and the latter remained constant. From the ratio of both components, it was found that the interaction of the label molecules with the binding sites was determined by the physical state of the membrane. Furthermore, the dependence on temperature of the molecular motion of the labels in the cell membrane was irreversible above 40 degrees C. On addition of cholesterol to the membrane, the outer hyperfine splittings for 12NS and 16NS increased but that for 5NS decreased at C/P greater than 1, perhaps indicating a spread between the head groups of phospholipids by cholesterol.
Unsaturated free fatty acids such as oleic, arachidonic or linoleic at concentrations of 5-25 microgram/ml inactivate enveloped viruses such as herpes, influenza, Sendai, Sindbis within minutes of contact. At these concentrations the fatty acids are inocuous to animal host cells in vitro. Naked viruses, such as polio, SV40 or EMC are not affected by these acids. Saturated stearic acid does not inactivate any viruses at concentrations tested. Though the mode of action of unsaturated fatty acids is not understood, electronmicrographs of enveloped viruses treated by them indicate that the inactivation is associated with disintegration of the virus envelope.
Six crystalline substances were isolated from the stem of Ephedra likiangensis Florin and were identified as ephedrine (I), beta-sitosterol (II), palmitic acid (IV), stearic acid (V), cerotic acid (III) and beta-daucosterol (VI).
The effect of global cerebral ischemia and reperfusion on cerebral capillary endothelial cell membrane fluidity was examined using electron paramagnetic resonance techniques following 8 minutes of global ischemia and 15 minutes of blood reperfusion. The luminal surface of the cerebral vasculature was perfused with a series of doxyl stearic acid reporters (5-, 12-, 16-doxyl stearic acid) which differ in the site of attachment of the nitroxide free radical on the fatty acid chain. Each doxyl stearic acid reports on membrane fluidity characteristics from different depths within the membrane. Ischemia/reperfusion produced a membrane ordering that was markedly dependent on intramembrane location, and was consistent with changes previously associated with lipid peroxidation. The effect of ischemia/reperfusion on membrane fluidity was maximal in the membrane environment reported by 12-doxyl stearic acid (12-DS). The utilization of a liposomal system was shown to enhance superoxide dismutase delivery to cerebral tissues as well as attenuating the change in membrane order seen following reperfusion-induced lipid peroxidation.
The effect of salt and pH titration on the selectivity of spin-labeled analogues of phosphatidic acid, phosphatidylserine, phosphatidylcholine, and stearic acid for the nicotinic acetylcholine receptor (nAcChoR) reconstituted into dioleoylphosphatidylcholine was examined at 0 degrees C using electron spin resonance spectroscopy. The order of selectivity at pH 7.4 and 0 mM NaCl was phosphatidylserine > stearic acid > phosphatidic acid > phosphatidylcholine. The addition up to 2 M NaCl or titration of pH from 5.0 to > 9.0 did not alter the selectivity of the phospholipids for the nAcChoR. For stearic acid, conversely, titration of pH from 5.0 to 9.0 at 0 mM NaCl and titration of NaCl from 0 to 2 M at pH 9.0 both increased selectivity for the nAcChoR. It is concluded that electrostatic interactions do not account for the selectivity of the negatively charged phospholipids, phosphatidylserine, and phosphatidic acid for the nAcChoR. This is consistent with the known orientation of the transmembrane sequences M1 and M4, which predicts a balance in the number of negative and positive charges in the lipid-protein interface and suggests that the two positive charges on each M3 helix are not exposed to the lipid-protein interface.
1. The specific activities of long-chain fatty acid-CoA ligase (EC6.2.1.3) and of long-chain fatty acyl-CoA hydrolase (EC3.1.2.2) were measured in soluble and microsomal fractions from rat brain. 2. In the presence of either palmitic acid or stearic acid, the specific activity of the ligase increased during development; the specific activity of this enzyme with arachidic acid or behenic acid was considerably lower. 3. The specific activities of palmitoyl-CoA hydrolase and of stearoyl-CoA hydrolase in the microsomal fraction decreased markedly (75%) between 6 and 20 days after birth; by contrast, the corresponding specific activities in the soluble fraction showed no decline. 4. Stearoyl-CoA hydrolase in the microsomal fraction is inhibited (99%) by bovine serum albumin; this is in contrast with the microsomal fatty acid-chain-elongation system, which is stimulated 3.9-fold by albumin. Inhibition of stearoyl-CoA hydrolase does not stimulate stearoyl-CoA chain elongation. Therefore it does not appear likely that the decline in the specific activity of hydrolase during myelogenesis is responsible for the increased rate of fatty acid chain elongation. 5. It is suggested that the decline in specific activity of the microsomal hydrolase and to a lesser extent the increase in the specific activity of the ligase is directly related to the increased demand for long-chain acyl-CoA esters during myelogenesis as substrates in the biosynthesis of myelin lipids.
AIM: To prepare the micelles of stearic acid-grafted chitosan oligosaccharide and investigate the drug release from micelles. METHODS: Mediated by a 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), stearic acid (SA) was covalently attached to chitosan oligosaccharide (CSO), and the graft polymer (CSO-SA) was obtained. The critical aggregation concentration (CAC) of the CSO-SA was determined by measuring the fluorescence intensity of pyrene as a fluorescent probe. The effect of various pH dispersed media and concentration of tripolyphosphate sodium (TPP) on the micellar size distribution and zeta-potential measured by light scattering and electrophoretic mobility, was investigated. In buffers of different pH, the release profiles of methotrexate (MTX) from micelles were evaluated. RESULTS: The CAC value of CSO-SA in deionized water was 0.05 g x L(-1). The mean diameter of CSO-SA micelles was 26.7 nm and the zeta potential was (55.9 +/- 0.1) mV. With the increase of TPP concentration, the size and MTX encapsulation of CSO-SA micelles increased, while the zeta-potential decreased. With the decrease of pH value of dispersed media, the size and zeta-potential of CSO-SA micelles increased, and the MTX encapsulation in CSO-SA micelles decreased. While the enhancement of drug release from the micelles was observed. CONCLUSION: The graft polymer of CSO-SA provides polymeric micelles, which possessed a low CAC value in aqueous media. The drug release in vitro from CSO-SA micelles was affected by the pH of delivery media.
The effect of oleic acid (OA), stearic acid (SA) and elaidic acid (EA) on cellular and secreted apolipoprotein (apo) B was examined in McArdle RH-7777 (McArdle) hepatoma cells and in primary rat hepatocytes. ApoB secretion by McArdle cells was significantly inhibited by 20% in 8 h incubations in medium containing EA and SA and by 50% in medium containing OA. In contrast, apo B secretion and cellular apo B of primary rat hepatocytes was relatively unaffected by incubations in medium containing fatty acids. Both B100 and B48 secretion in McArdle wild type and B48 in apo B mRNA editing enzyme catalytic polypeptide transfectants expressing B48 were inhibited to a similar extent indicating an effect of OA on both apo B species. The effect of OA occurred without changes in cellular apo B or in apo B mRNA abundance suggesting a post-transcriptional mechanism. Time course studies indicate that the suppressive effect of OA requires 4 h of incubation suggesting the depletion of a limiting factor important in apoB secretion. By increasing the proportion of palmitic acid to OA in the medium, apoB secretion by McArdle cells was progressively restored to control levels implicating an unique role for newly synthesized saturated fatty acid.
Fatty acids of various chain lengths (C(1) to C(24)) were examined for their effects on growth, oxygen consumption, and in vitro reduced nicotinamide adenine dinucleotide oxidase activity of Neisseria gonorrhoeae CS-7. The growth inhibition caused by saturated fatty acids increased with increasing chain length to a maximum with palmitic acid (C(16)). Stearic acid (C(18)) and longer saturated fatty acids showed little inhibition of growth. However, unsaturated fatty acids of chain length C(16) to C(20) were inhibitory. Similar inhibition was observed with Bacillus subtilis and a deep rough mutant of Salmonella typhimurium. Wildtype S. typhimurium and Pseudomonas aeruginosa were more resistant to medium-chain (C(7) to C(10)) fatty acids and completely resistant to long-chain (C(12) to C(18)) fatty acids. Thus, sensitivity of N. gonorrhoeae to long-chain fatty acids appears to be related to the permeability of the outer membrane. Growth inhibition by short-chain (C(1) to C(6)) fatty acids was pH dependent; inhibition of growth increased with decreasing pH. Saturated fatty acids inhibited oxygen consumption by log-phase cells of N. gonorrhoeae. This inhibition increased with increasing chain length to a maximum observed with myristic acid (C(14)). Whereas stearic acid (C(18)) had little effect upon oxygen consumption, unsaturated C(18) fatty acids were inhibitory. An in vitro inhibition of reduced nicotinamide adenine dinucleotide oxidase activity by saturated (C(1) to C(12)) and unsaturated (C(16) to C(20)) fatty acids was also observed. Although the inhibitory concentrations were generally higher than those required to inhibit growth or oxygen consumption, an inhibition of electron transport may be partially responsible for the observed growth inhibition.
OBJECTIVE: To study the chemical constituents of fat oil from root of Polygala tenuifolia Willd. METHOD: The components were separated and identified by gas chromatograpy-mass spectrometry and elucidated on the standard mass spectral data and the percentages were determined by gas chromatographic area normalization method. RESULT: Eighteen constituents were separated and sixteen of them were identified. CONCLUSION: The major components of the fat oil were established first time as oleic acid, linoleic acid, palmitic acid, eicosenoic acid and stearic acid, which make up 87.0%, 7.31%, 3.27%, 1.07%, 0.91% of fat oil respectively.
The psychological effects on cortisol, human growth hormone (HGH), free fatty acids and lactate were investigated in 10 healthy students using a one hour television game. To insure that only the psychological aspects of the game were being measured, hematocrit, creatininkinase, CK-MB and myoglobin were used as controls. The game began 60 minutes after venapuncture of a lower arm vein with an indwelling catheter. Blood samples were taken 30 and 60 minutes after venapuncture, at intervals of 20 minutes during the game and 30, 60 and 120 minutes after the end of the game. After an initial rise, plasma cortisol levels sank steadily and significantly (alpha = 1%). The HGH level initially fell, but as the game progressed, rose and remained at a high level for a considerable period after the game had ended. These variations however were not statistically significant. The three free fatty acids under investigations, myristinic acid (C14), palmitic acid (C16), and stearic acid (C18), all showed similar levels over the course of the experiment. During the first 20 minutes of the play, free fatty acid levels rose, with stearic acid levels rising the most (52%). The free fatty acid levels then sank as the game progressed, with the palmitinic acid level showing a significant decline (alpha = 1%). The other parameters remained relatively constant during the experiment, with the exception of the CK-MB level, which showed severe, hard-to-interpret variations.
The distribution of fatty acids, proteins, polysaccharides and antigens in subcellular fractions of Mycobacterium avium is described. Significant qualitative differences in the chemical composition of the various fractions have been used to further characterize the tripartite structure of the cell wall. In the outer dense layer (POL), in addition to previously described complex amphiphatic lipids, new oligosaccharides (lipooligosaccharides?) and a major glycoprotein were located; and it was found that tuberculostearic acid (TSA) esterified the phospholipids of this outerlayer. Judging from the data, it was proposed that the phospholipids formed a basic matrix monolayer in which other compounds of the POL intercalated. It was suggested that in an aqueous environment the hydrophobic ends of the phospholipids oriented to face the mycolic acid residues of the cell wall skeletons (or CWS) to form the 12 nm thick electron transparent layer. The purified CWS contained alpha-, keto-, and dicarboxylic mycolic acids; alanine, glutamic acid and diaminopimelic acid; and arabinose and galactose. Two additional nonidentified amino acids and an unidentified sugar were found in the CWS. Also, in the CWS the fatty acids: palmitic acid (21.8%), oleic acid (4.3%), stearic acid (9.2%) and TSA (4.3%), were detected. The main fatty acids detected in the cytoplasmic membrane (CM) were palmitic (20%), oleic (14.5%) and stearic (8.6%) acids. Mycolic acids and TSA were absent in the CM phospholipids. The major proteins of the CM (86, 40, and 26 Kd proteins) were distinct from the major proteins detected in the cytosol (CYT) fraction (43, 36, and 19 Kd proteins). A 58 Kd protein was present in both the CM and the CYT. The CYT and CM antigens were found absent in surface antigens extracted using sodium dodecyl sulphate (SDS).
Because of their reported antiviral and anti-inflammatory activities, cream formulations containing n-docosanol (docosanol) or stearic acid were tested for effects on chemically-induced burns in mice. In this model, injury was induced by painting the abdomens of mice with a chloroform solution of phenol. This was followed by the topical application of test substances 0.5, 3, and 6 h later. Progression of the wounds was assessed by a single evaluator after 8 h, using a numerical score of gross morphology. Docosanol- and stearic acid-containing creams substantially and reproducibly lessened the severity and progression of skin lesions compared to untreated sites with a 76% and 57% reduction in mean lesion scores, respectively. Untreated wounds appeared red and ulcerated; docosanol cream-treated wounds showed only slight erythema.
Recombinant glutathione S-transferase P (GST-P) was purified in a homogeneous state. Fatty acid analysis of the enzyme revealed that the final enzyme preparation endogenously bound fatty acids, mostly palmitic acid or stearic acid, which were difficult to dissociate from the complex. Temperature-dependent analysis by 1H NMR indicated that the molecular motion of fatty acids was strongly restrained under physiological conditions, which was significantly different from that of serum albumin. On the other hand, there existed another hydrophobic ligand-binding region in GST-P, to which 1-amino-8-naphthalenesulfonic acid and bilirubin would bind with relatively lower affinity than the endogenously bound fatty acid. The hydrophobic ligand-binding region was determined to be around 141-156 residues from the N-terminus by procedures including association of the enzyme to fatty acid-linked Sepharose and affinity labeling with fluorescent fatty acid. Furthermore, circular dichroism analysis showed that the binding of hydrophobic ligand to GST-P produced a remarkable conformational change of the enzyme, which led to states devoid of transferase activity. In addition, the hydrophobic ligand binding caused a significant fluorescence quenching of tryptophan 38, which was assumed to be located at the active center of GST-P. It could be the result of a conformational change of the active center of the enzyme.
Interferon-gamma (IFN-gamma) specifically induced the uptake of the unsaturated fatty acid [14C]linoleic acid into membrane phospholipids of the murine macrophage-like P388D cell lineage, but did not alter the incorporation of the saturated fatty acid [14C]stearic acid. Spin label ESR spectroscopy was used to examine any effects of these IFN-gamma-induced changes on membrane fluidity and the results revealed significant increases in plasma membrane fluidity. This alteration in membrane fluidity may have important consequences in the dynamic properties of cellular physiochemical interactions and some of the stimulatory effects of IFN-gamma on macrophages might be attributed to its effects on the plasma membrane composition.
Tetrahymena species contain relatively prominent glycosylphosphatidylinositol (GPI)-anchored proteins as well as their putative precursor phosphatidylinositol (PI) glycans. We have characterized the lipid components of the two principal T. mimbres PI glycans. Following their purification by preparative TLC, the PI glycans were hydrolysed in methanolic HCl or NaOH, and resulting lipids were analysed by chromatography and mass spectrometry. The two PI glycans contained nearly identical lipid moieties having long-chain bases with N-linked fatty acids. The predominant long-chain base, 3-O-methylsphinganine, was first assumed to be O-methylated as an artifact of hydrolysis, but subsequently, on the basis of control experiments, it was shown to be naturally occurring. PI glycans from cells grown at 28 degrees C contained primarily palmitic acid (79%) and some stearic acid (11%), whereas the principal PI glycan from 38 degrees C-grown T. mimbres contained 65% stearic acid. In 15 degrees C-grown cells stearic acid accounted for only 2% of ceramide-bound fatty acids and was almost totally replaced by palmitic acid (95%). The distributions of fatty acids bound to T. mimbres GPI-anchored proteins [Ko, Hung and Thompson (1995) Biochem. J. 307, 115-121] were similar but not identical to those of the PI glycans described here. Temperature-induced specification of the lipid components of mature T. mimbres GPI-anchored proteins appears to be established both at the level of PI-glycan synthesis and the level of PI-glycan utilization for protein attachment.
We report the results of an investigation on stratum corneum lipids, which present the main barrier of the skin. Molecular dynamics simulations, thermal analysis and FTIR measurements were applied. The primary objective of this work was to study the effect of cholesterol on skin structure and dynamics. Two molecular models were constructed, a free fatty acid bilayer (stearic acid, palmitic acid) and a fatty acid/cholesterol mixture at a 1:1 molar ratio. Our simulations were performed at constant pressure and temperature on a nanosecond time scale. The resulting model structures were characterized by calculating surface areas per headgroup, conformational properties, atom densities and order parameters of the fatty acids. Analysis of the simulations indicates that the free fatty acid fraction of stratum corneum lipids stays in a highly ordered crystalline state at skin temperatures. The phase behavior is strongly influenced when cholesterol is added. Cholesterol smoothes the rigid phases of the fatty acids: the order of the hydrocarbon tails (mainly of the last eight bonds) is reduced, the area per molecule becomes larger, the fraction of trans dihedrals is lower and the hydrophobic thickness is reduced. The simulation results are in good agreement with our experimental data from FTIR analysis and NIR-FT Raman spectroscopy.