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PubMed1959

Antagonism of veratrine by calcium ion in monolayers of stearic acid.

Force-area diagrams for monolayers of stearic acid on Ringer's solution demonstrate a competition between veratrine and calcium for carboxyl groups of the films. The competition occurs at customary concentrations. Local anesthetics act quite differently. The interactions suggest those observed less directly in living cells and therefore indicate that such surface films may serve as models for the study of drug and ion effects.

Calcium↗
PubMed1976

The use of 8-anilino-1-naphthalenesulfonic acid as a reporter group molecule for circular dichroism and fluorescence measurements. The effect of stearic acid and sodium dodecylsulfate on the conformation of bovine and human serum albumin.

The fluorescence probe ANS(8-anilino-1-naphthalenesulfonic acid) was employed as a reporter group molecule for circular dichroism and fluorescence measurements in order to investigate the effects of stearic acid and sodium dodecylsulfate on the conformation of bovine and human serum albumin. Stearate as well as dodecylsulfate displaces ANS from the binding to both albumins. Besides this displacement, stearate and dodecylsulfate influence the fluorescence properties and the extrinsic Cotton effects on ANS bound to both albumins. It is suggested that the origin of these effects is a microdisorganization of the albumin structure, provoked by the binding of stearate and sodium dodecylsulfate. Each of the four extrinsic CD bands of bound ANS was influenced in a different manner by the addition of stearate and dodecylsulfate. Using the data of the fluorescence measurements and of the circular dichroism measurements it was possible to differentiate the effects of one ligand on both albumins and of both ligands on one albumin more efficiently than would have been possible using one of the two methods alone. It is suggested that the use of ANS as a reporter group molecule for fluorescence and circular dichroism measurements is a very good tool to detect small changes in the environment of ligand binding sites on protein molecules.

Anilino Naphthalenesulfonates↗
PubMed1990

ESR studies of stearic acid binding to bovine serum albumin.

The ESR spectra of a series of chain-labelled doxyl stearic acids (5-, 7-, 12- and 16-DSA) and doxyl methyl stearates (5-, 7-, 12- and 16-DMS) bound to the high-affinity binding sites of bovine serum albumin (BSA) have been analyzed using nonlinear least-squares fitting of slow-motional ESR stimulation. The motional analysis reveals that the rotational diffusion of these stearates around the axis perpendicular to the long hydrocarbon chain is greatly hindered, suggesting that they are held tightly in a channel of the protein. Comparison of the isotropic hyperfine splitting, A0, among each series shows that 5- and 16-DSA and 16-DMS have larger A0 values than the other spin labels. In addition, labels at the 16-C position of both DSA and DMS exhibit significantly increased motion relative to the other positions. These observations suggest that the channel starts at 5-C of the chain and ends somewhere between 13-C and 15-C, leading to an estimate of 11 +/- 1 A for the length of the channel. The methyl stearate labels exhibit significantly faster rotation around the chain axis than the analogous stearic acid labels, suggesting a double hydrogen-bonding mechanism for fatty acid binding to BSA. The ability of the acid to form two hydrogen bonds apparently fixes it more rigidly in the protein, preventing rotation about either single hydrogen bond. A double-hydrogen bonding mechanism is most consistent with the formation of a salt bridge between the negatively charged carboxylate of the acid and either a positively charged guanidino group of arginine, or the positively charged omega-amino groups of two lysine residues. An ESR study of the pH dependence of DSA binding indicates that salt bridge formation with lysine is responsible for at least some of the long chain fatty acid binding sites of BSA.

Amino Acid Sequence↗
PubMed1976

Identification of isomeric doxyl stearic acids by gas-liquid chromatography and mass spectrometry.

Direct probe and GC/MS spectra were determined for the isomeric 4- to 16-doxyl stearic acids and their methyl and silyl esters in pure form and in mixture with natural fatty acids and their esters. The base peak for all free and esterified doxyl stearic acids was at m/e 281. The methyl esters of all isomers gave nearly identical fragments in the high mass regions having M+ at m/e 398 with intensities of 2-3%. The isomers were identified on the basis of the fragments retaining the doxyl group, which had positive charge and were different for each compound. It was shown that the fragment m/e 281 may be used to identify and quantitate the stearate derivatives in presence of natural fatty acids. The silyl esters of the doxyl stearates gave complex mass spectra. The isomeric doxyl stearates were resolved by GLC on 3 ft. glass columns containing 1% SE-30 packing as methyl esters.

Electron Spin Resonance Spectroscopy↗
PubMed1995

Effects of diets containing high or low amounts of stearic acid on plasma lipoprotein fractions and fecal fatty acid excretion of men.

Ten middle-aged males participated in a crossover study to determine the cholesterolemic effect of high amounts of stearic acid in a natural diet. They consumed a 20-d stabilization diet followed by two 40-d intervention diets containing either 1.5% of energy as stearic (18:0) acid and 7.3% of energy as palmitic (16:0) acid (low stearate: LS) or 2.4% of energy as 16:0 and 7.3% of energy as 18:0 (high stearate: HS). The experimental diets also contained approximately 10% of energy each as saturated and monounsaturated fatty acids and 7.2-8% of energy as polyunsaturated fatty acids. The primary source of 18:0 in the HS diet was sheanut oil (commercially referred to as shea butter) and palm oil and butter in the LS diet. Plasma total, low-density-lipoprotein, and high-density-lipoprotein cholesterol were significantly lower with the HS than with the LS diet. Total fecal fatty acid excretion was higher throughout the HS period. Apparent digestibility of the major dietary fatty acids showed that all of the selected fatty acids, except 18:0, were > or = 95% absorbed. These data demonstrate that feeding diets containing about two times the usual amount of stearic acid consumed in the United States, contributed to an increase in plasma lipoprotein concentrations at 40 d from an earlier decrease at 20 d. The time required to achieve stable cholesterol concentrations appears to vary depending on the kind of saturated fatty acids present in the diet.

Adult↗
PubMed1995

Increased norfloxacin skin permeability for fatty alcohol propylene glycol (FAPG) ointment by optimized process of preparation: behavior of stearic acid in stratum corneum lipids.

Preparation of the fatty alcohol propylene glycol (FAPG) ointment base plays an important role in controlling the physicochemical properties of ointments. These essay investigates the effects of preparative conditions such as cooling rate and stirring rate on the percutaneous absorption of norfloxacin from FAPG ointment. The influence of process-induced variation in enhancing effect of stearic acid which was incorporated into FAPG base was evaluated in vitro on rat skin. In the permeation experiment, norfloxacin penetration significantly increased with faster cooling rate. This result directly related to the increasing norfloxacin skin--vehicle partition coefficient. Histological analysis results showed no appreciable exfoliation of the stratum corneum. The differential scanning calorimetry (DSC) results show that stearic acid enriched lipid in the stratum corneum resulting from treatment with supercooling products may result in more crystalline structure and, hence preferential partitioning of the norfloxacin into the more crystalline regions of the membrane can be observed. A much greater enhancing effect can be achieved when we use stearic acid together with norfloxacin in propylene glycol (PG); but such effect cannot be found if 5 wt% stearic acid/PG suspension is used to pretreat skin before the application of norfloxacin PG solution.

Animals↗
PubMed2000

Trafficking of dietary oleic, linolenic, and stearic acids in fasted or fed lean rats.

Increasing evidence supports the notion that there are significant differences in the health effects of diets enriched in saturated, as opposed to monounsaturated or polyunsaturated fat. However, the current understanding of how these types of fat differ in their handling by relevant tissues is incomplete. To examine the effects of fat type and nutritional status on the metabolic fate of dietary fat, we administered (14)C-labeled oleic, linolenic, or stearic acid with a small liquid meal to male Sprague-Dawley rats previously fasted for 15 h (fasted) or previously fed ad libitum (fed). (14)CO(2) production was measured for 8 h after tracer administration. The (14)C content of gastrointestinal tract, serum, liver, skeletal muscle (soleus, lateral, and medial gastrocnemius), and adipose tissue (omental, retroperitoneal, and epididymal) was measured at six time points (2, 4, 8, 24, and 48 h and 10 days) after tracer administration. Plasma levels of glucose, insulin, and triglyceride were also measured. Oxidation of stearic acid was significantly less than that of either linolenic or oleic acid in both the fed and fasted states. This reduction was in part explained by a greater retention of stearic acid within skeletal muscle and liver. Oxidation of oleate and stearate were significantly lower in the fed state than in the fasted state. In the fasted state, liver and skeletal muscle were quantitatively more important than adipose tissue in the uptake of dietary fat tracers during the immediate postprandial period. In contrast, adipose tissue was quantitatively more important than skeletal muscle or liver in the fed state. The movement of carbons derived from dietary fat between tissues is a complex time-dependent process, which varies in response to the type of fat ingested and the metabolic state of the organism.

Adipose Tissue↗
PubMed1984

An electron-electron double-resonance study of interactions between [14N]- and [15N]stearic acid spin-label pairs: lateral diffusion and vertical fluctuations in dimyristoylphosphatidylcholine.

Vertical fluctuations of the terminal methyl groups of stearic acid acyl chains toward the surface of dimyristoylphosphatidylcholine (DMPC) bilayers have been investigated by using spin-label electron-electron double-resonance ( ELDOR ) methodology. Spin-label pairs consisting of two populations of stearic acid spin-labels were employed, each at 0.25 mol% concentration, where the nitroxides of the first population were 15N substituted and the nitroxides of the second contained 14N. Various combinations of labels with the nitroxide moieties located at carbons 5, 12, or 16 (C5, C12, C16) were used. ELDOR permits measurement of collision frequencies between the two constituents of the pair, for example, between 15N spin-labels at C5 and 14N labels at C16. Intramolecular contributions to the ELDOR effect including nitrogen nuclear relaxation are eliminated by the use of spin-label pairs. Above the main phase transition temperature, bimolecular collisions between C5 and C16 occur with about half the frequency of C16:C16 collisions. It is concluded that vertical fluctuations are very pronounced. A dependence of these fluctuations on temperature and pH has been observed. Lateral diffusion constants calculated from the bimolecular collision frequencies of C16:C16 pairs are 4.56 X 10(-8), 5.77 X 10(-8), and 8.09 X 10(-8) cm2/s at 27, 37, and 47 degrees C. These values are in good agreement with previous measurements of lipid diffusion in DMPC.

Diffusion↗
PubMed2001

Anaerobic degradation and methanogenic inhibitory effects of oleic and stearic acids.

Oleic acid, an 18 carbon acid with one double bond (C18:1) was degraded anaerobically to palmitic (C16:0) and myristic (C14:0) acid by-products at 21 C by a culture unacclimated to long-chain fatty acids. These by-products were degraded to acetate and ultimately to methane. In comparison, no long-chain fatty acid by-products were observed in unacclimated anaerobic cultures receiving stearic (C18:0) acid although slow removal of stearic acid occurred. Oleic acid concentrations above 30mg l(-1) inhibited acetate degradation but stearic acid up to 100 mg l(-1) did not inhibit aceticlastic methanogenesis. Hydrogenotrophic methanogenesis was slightly inhibited by oleic and stearic acids. A thermodynamic basis for comparing anaerobic C18 acid degradation and predicting by-products is presented.

Acetic Acid↗
PubMed2003

A novel DNA polymerase inhibitor and a potent apoptosis inducer: 2-mono-O-acyl-3-O-(alpha-D-sulfoquinovosyl)-glyceride with stearic acid.

Sulfo-glycolipids in the class of sulfoquinovosyl diacylglycerol (SQDG) including the stereoisomers are potent inhibitors of DNA polymerase alpha and beta. However, since the alpha-configuration of SQDG with two stearic acids (alpha-SQDG-C(18)) can hardly penetrate cells, it has no cytotoxic effect. We tried and succeeded in making a permeable form, sulfoquinovosyl monoacylglycerol with a stearic acid (alpha-SQMG-C(18)) from alpha-SQDG-C(18) by hydrolysis with a pancreatic lipase. alpha-SQMG-C(18) inhibited DNA polymerase activity and was found to be a potent inhibitor of the growth of NUGC-3 cancer cells. alpha-SQMG-C(18) arrested the cell cycle at the G1 phase, and subsequently induced severe apoptosis. The arrest was correlated with an increased expression of p53 and cyclin E, indicating that alpha-SQMG-C(18) induced cell death through a p53-dependent apoptotic pathway.

Antineoplastic Agents↗
PubMed2005

Small differences in the effects of stearic acid, oleic acid, and linoleic acid on the serum lipoprotein profile of humans.

BACKGROUND: Studies have suggested that oleic and stearic acids, as well as oleic and linoleic acids, have comparable effects on the serum lipoprotein profile. If so, then substituting these three 18-carbon fatty acids for each other would result in similar effects on the serum lipoprotein profile. OBJECTIVE: The aim of this study was to compare simultaneously the effects of stearic, oleic, and linoleic acids on the serum lipoprotein profile of healthy subjects. DESIGN: Forty-five subjects (27 women and 18 men) consumed in random order 3 experimental diets, each for 5 wk. The diets provided 38% of energy from fat, of which 60% was supplied by the experimental fats. The dietary compositions of the diets were the same, except for 7% of energy, which was provided by stearic, oleic, or linoleic acid. At the end of each intervention period, serum lipid and lipoprotein concentrations were measured. In addition, LDL, HDL, and VLDL particle sizes and particle concentrations of lipoprotein subclasses were analyzed by nuclear magnetic resonance spectroscopy. RESULTS: No significant diet-induced changes in serum lipids and lipoproteins were found. Mean (+/-SD) serum LDL-cholesterol concentrations were 3.79 +/- 0.91, 3.71 +/- 0.79, and 3.65 +/- 0.91 mmol/L with the high-stearic acid, high-oleic acid, and high-linoleic acid diets, respectively (P = 0.137 for diet effects). Mean (+/-SD) HDL-cholesterol concentrations were 1.45 +/- 0.43, 1.46 +/- 0.45, and 1.46 +/- 0.44 mmol/L (P = 0.866). LDL, HDL, and VLDL particle sizes and lipoprotein subclass distributions also did not differ significantly between the 3 diets. CONCLUSIONS: With realistic intakes of stearic, oleic, and linoleic acids, differences between their effects on the serum lipoprotein profile are small.

Adult↗
PubMed1986

The 73 kilodalton heat shock cognate protein purified from rat brain contains nonesterified palmitic and stearic acids.

A protein related to the 71 kilodalton inducible rat heat shock protein was purified to electrophoretic homogeneity in milligram amounts from brain tissue of nonheat-stressed rats. The protein has been designated as a stress cognate protein based on previous studies and data presented herein that this protein cross-reacted with a monoclonal antibody originally raised against the Drosophila 70 kilodalton heat shock protein. The purified protein had an apparent molecular mass of 73 kilodaltons when analyzed by sodium dodecyl sulfate polyacrylamide gel electrophoresis and an apparent mass of 150 kilodaltons as determined by nondissociative gel chromatography, suggesting that the purified protein is a homodimer. The purified protein had isoelectric points of 5.0 under nondissociative conditions and 5.6 when exposed to protein denaturants, suggesting loss of bound anionic molecules and/or net exposure of basic residues upon denaturation. Chloroform/methanol extraction of the purified protein and subsequent analyses by thin layer and gas-liquid chromatography resulted in the identification of palmitic and stearic acids noncovalently bound to the protein. Approximately four molecules of fatty acids were bound per dimer with palmitic and stearic acids present in a one-to-one ratio. The purified protein did not bind exogenously added radioactive palmitate, indicating that the fatty acid-binding sites of the cognate protein were fully occupied and that the associated fatty acids were too tightly bound to exchange readily. The possible significance of the fatty acids associated with the 73 kilodalton stress cognate protein is discussed.

Animals↗
PubMed1975

Oxidative desaturation of alpha-linoleic, linoleic, and stearic acids by human liver microsomes.

The desaturation of stearic, linoleic, and alpha-linolenic acids by human liver microsomes were studied. The microsomes were isolated from liver biopsies obtained during operation. It was shown that human liver microsomes are able to desaturate 1-14-C-alpha-linoleic acid to octadeca-6,9,12,15,-telraenoic acid: 1-15-C-linoleic acid to gammalinolenic acid; and 1-14-C-stearic acid to oleic acid in the same system described in the rat. However, the desaturation activity obtained was low compared to other mammals. This effect was attributed to fasting, pre-medication, or the anaesthesia.

Adult↗
PubMed1998

Stearic acid oxidation in the Alaskan red-backed vole: effects of cold and norepinephrine.

Saturated fatty acids constitute a considerable energy reserve that could convey survival value under chronic cold exposure. It was investigated whether acclimation to cold was associated with a change in the ability of a small microtine rodent, the red-backed vole (Clethrionomys rutilis), to increase the use of saturated fatty acids during thermogenesis. The C-14 labeled stearic acid, a typical saturated fatty acid (FA), was used to determine the rate of utilization through oxidation. In warm acclimated (WA, 20 degrees C) and cold acclimated (CA, 5 degrees C) voles, acute cold exposure (WA at 5 degrees C, -2 degrees; CA at -5 degrees C) and norepinephrine (NE) injection increased metabolic rate (VO2, VCO2) and mobilization of lipid reserves. Acute cold exposure increased percent blood stearate oxidized in a linear fashion with both metabolic rate and stearate concentration in both WA and CA voles. The CA voles at 5 degrees C had increased stearate irreversible loss (1.5x) and oxidation rate (2x) compared to WA voles at 20 degrees C. The CA voles at -5 degrees C increased stearate irreversible loss and oxidation linearly with metabolic rate and blood stearate concentration. In CA voles the contribution made by stearate oxidation to VCO2, increased with the level of cold exposure and NE injection. In contrast, for WA voles stearate irreversible loss and the contribution made by stearate oxidation to VCO2 were unaffected by acute cold exposure. Thus, cold acclimation involves: (1) a modest increase (1.5x) in the use of stearate as a fuel substrate; and (2) a greater stearate oxidation and contribution to overall metabolism during acute cold exposure (-5 degrees C).

Acclimatization↗
PubMed1984

Effect of dietary stearic acid on the genesis of spontaneous mammary adenocarcinomas in strain A/ST mice.

Strain A/ST female mice maintained on a high fat (15%) diet in which stearic acid was the major lipid component developed initial spontaneous mammary adenocarcinomas at an older age than mice fed a low fat (4.5%) stock diet. Mice placed on the SA diet at weaning developed tumors at 15.7 +/- 0.87 months compared to 12.7 +/- 0.43 months for those retained on the stock diet (p less than .05). Placing mice on the SA diet at 11.5 months resulted in a smaller but significant increase in the latency period (5.0 +/- 0.86 vs 3.0 +/- 0.57 months +/- 0.57 mo), (p less than .05). Fatty acid analyses of non-tumorous mammary tissue from mid-pregnant mice and of tumor tissues showed that feeding large amounts of 18:0 did not result in increases in the proportion of 18:0. Significant reductions in the percentages of polyunsaturated fatty acids (PUFA) was found in tissues on mice fed the SA diet. The percentage of 18:2 was reduced in both types of tissues; 20:3 and 20:4 was reduced in tumor tissues. Distribution of C18 fatty acids in plasma membranes of tumors of mice fed the two diets were similar; percentages 18:2 was higher in plasma membranes of non-tumorous tissues of mice fed the SA diet. These results suggest that dietary stearic acid interferes with the availability of certain PUFA required for tumor production.

Adenocarcinoma↗
PubMed2006

Amaranthus cruentus flour edible films: influence of stearic acid addition, plasticizer concentration, and emulsion stirring speed on water vapor permeability and mechanical properties.

Films forming solutions composed of Amaranth (Amaranthus cruentus) flour (4.0 g/100 mL), stearic acid (5-15 g/100 g of flour), and glycerol (25-35 g/100 g of flour) were prepared by an emulsification process, with varying stirring speed values (6640-13360 rpm). The influence of these parameters (stearic acid and glycerol concentrations and stirring speed) on the water vapor barrier and mechanical properties of films was evaluated using the response surface methodology (RSM). Other characterizations, including microstructure, water solubility, and oxygen permeability, were performed in optimized films. According to statistical analysis results, the optimized conditions corresponded to 10 g of stearic acid/100 g of flour, 26 g of glycerol/100 g of flour, and a stirring speed of 12 000 rpm. The films produced under these conditions exhibited superior mechanical properties (2.5 N puncture force, 2.6 MPa tensile strength, and 148% elongation at break) in comparison to those of other protein and polysaccharide composite films, low solubility (15.2%), and optimal barrier properties (WVP of 8.9 x 10(- 11) g m(- 1) s(- 1) Pa(- 1) and oxygen permeability of 2.36 x 10(- 13) cm3 m(-1) s(-1) Pa(-1)).

Amaranthus↗
PubMed2002

Dietary stearic acid alters gallbladder bile acid composition in hamsters fed cereal-based diets.

Dietary stearic acid (18:0) lowers plasma and liver cholesterol concentration by reducing intestinal cholesterol absorption. We tested the hypothesis that dietary 18:0 reduces cholesterol absorption by altering hepatic bile acid synthesis and gallbladder bile acid composition. Male Syrian hamsters were fed modified NIH-07 open formula diets, enriched (5 g/100 g diet) in one of the following fatty acids: 18:0, palmitic acid (16:0), trans fatty acids (18:1t), oleic acid (18:1c) or linoleic acid (18:2). After 18 wk, gallbladders were removed and bile acid composition determined by HPLC. The distribution of primary bile acids (mol/100 mol) was unaffected by treatment. In contrast, dietary 18:0 significantly reduced the proportion of hydrophobic secondary bile acids, resulting in a lower hydrophobicity index of the bile. These data suggest that reduced cholesterol absorption by dietary 18:0 is due, at least in part, to reduced cholesterol solubility. The data further suggest that 18:0 may have altered the microflora populations that synthesize secondary bile acids. Although cholesterol 7alpha-hydroxylase (CYP7A1) activity was significantly higher in hamsters fed 18:0 compared with 16:0, this finding is most likely due to increased fecal bile acid output in the 18:0 group rather than transcriptional regulation of CYP7A1 by 18:0 or specific bile acids.

Animals↗