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PubMed1995

Activation of factors XII and VII induced in citrated plasma in the presence of contact surface.

Activated factor XII (XIIa), activated factor VII (VIIa) and factor VII coagulant activity (VIIc) were determined in non-treated and in treated (cold-incubated) citrated plasmas from women in late pregnancy and from norma volunteers. All three activities were higher in the non-treated plasmas from women in late pregnancy than from normal subjects. The incubation of citrated plasmas from women in late pregnancy, on ice for 24 hours, resulted in a many-fold increase of factor XIIa activity, factor VIIa levels and VIIc. The dilution of these plasmas resulted in a sharp decrease of all three activities in the post-incubation mixture, so that in the plasmas diluted 2:1 with buffer all three activities were similar to those in fresh plasmas. Similar incubations of diluted plasmas (1:1) from normal volunteers resulted in no increase of factor XIIa activity, factor VIIa levels and VIIc. However, the presence in the incubation mixture of micellar stearate resulted in a stearate concentration-dependent increase of all three activities in treated plasmas. Levels of factor XIIa activity and factor VIIa in the treated plasmas from both groups of subjects were highly correlated (r = 0.987; p < 0.001). There was also a highly significant correlation between VIIc and factor VIIa levels (0.989; p < 0.001). These results demonstrate that the in vitro increase in factor VIIa levels is due to the activation of the contact system of coagulation and is dependent on the potency of the contact surface. Moreover, VIIc over a wide range of values, observed in the present experiments, can provide an accurate measure of factor VIIa concentration.

Adult↗

PubMed1991

Estrogenic action of estriol fatty acid esters.

Recent studies suggest that, estriol, like estradiol, is biosynthetically esterified with fatty acids. We have synthesized the stearate estriol, at C-16 alpha, C-17 beta and the diester, C-16 alpha,17 beta and tested these D-ring esters for their estrogenic action both in vivo and in vitro, comparing them to estradiol, estriol and estradiol-17-stearate. None of the estriol esters bind to the estrogen receptor. They are only weakly estrogenic in a microtiter plate estrogen bioassay: stimulation of alkaline phosphatase in the Ishikawa endometrial cells. However, both estriol monoesters are extremely potent estrogens when injected subcutaneously (in aqueous alcohol) into ovariectomized mice. Compared to the free steroids, they produced a dramatically increased uterine weight with a greatly prolonged duration of stimulation. The 16 alpha,17 beta-diester also induced a protracted uterotrophic response, but the stimulation of uterine weight was comparatively low. Since the esters of estradiol and estriol do not bind to the estrogen receptor, their estrogenic signal must be generated through the action of esterase enzymes. These naturally occurring esters have the potential of being extremely useful pharmacological agents for long-lived estrogenic stimulation.

Alkaline Phosphatase↗

PubMed2005

Characterization of long-chain fatty-acid-degrading syntrophic associations from a biodegraded oil reservoir.

Molecular methods were used to characterize stearate- and heptadecanoate-degrading methanogenic consortia enriched from a low-temperature biodegraded oil field. Stearate- and heptadecanoate-degrading cultures formed acetate. Growth on heptadecanoate was also accompanied by the production of propionate. These fermentation products were transiently accumulated at the beginning of the exponential phase and were further consumed with the concomitant production of methane. Clone libraries of bacterial and archaeal 16S rRNA genes were generated for each stable enrichment. Our 16S rRNA gene-cloning analysis combined with fluorescence in situ hybridization revealed that the predominant microorganisms in the associations were affiliated with a clone cluster close to the genus Syntrophus in the class "Deltaproteobacteria" and with the methanogenic genera Methanocalculus and Methanosaeta. Confocal scanning laser microscopy showed that the bacterial and archaeal cells formed compact aggregates around the insoluble substrates. No layered structure was observed in the aggregate organization. This study reports the presence of new fatty-acid-degrading syntrophic consortia in oil fields and our results suggest that such associations may have an important ecological role in oil fields under methanogenic conditions.

Acetic Acid↗

PubMed2000

Unexpected skin barrier influence from nonionic emulsifiers.

Skin disorders are often treated with creams containing various active substances. The creams also contain emulsifiers, which are surface-active ingredients used to stabilize the emulsion. Emulsifiers are potential irritants and in the present study the influence of stearic acid, glyceryl stearate, PEG-2, -9, -40, and -100 stearate, steareth-2, -10 and -21 on normal as well as on irritated skin have been evaluated with non-invasive measurements. Test emulsions were created by incorporating 5% emulsifiers in a water/mineral oil mixture (50:50). The emulsions and their vehicle were then applied to normal skin for 48 h and to sodium lauryl sulfate (SLS) damaged skin for 17 h in aluminum chambers. Twenty-four hours after removal of the chambers the test sites were evaluated for degree of irritation. In normal skin, the emulsifiers induced significant differences in TEWL but not in skin blood flow. Five of the emulsifiers increased TEWL. In SLS-damaged skin an aggravation of the irritation was expected. However, no differences regarding skin blood flow was noted from the emulsifiers. Furthermore, three emulsifiers unexpectedly decreased TEWL. These results highlight the possibility of absorption of these emulsifiers into the lipid bilayer, which increase TEWL in normal skin and decrease TEWL in damaged skin.

Administration, Topical↗

PubMed2000

Influence of neutron activation factors on matrix tablets for site specific delivery to the colon.

The impact of the neutron activation procedure, i.e. incorporation of samarium oxide (Sm(2)O(3)) and neutron irradiation, on the compression properties (including the crushing strength) and in vitro dissolution of potential colonic delivery systems based on matrix tablets of amidated pectin (Am.P) or two types of hydroxypropyl methylcellulose (HPMC) was investigated. The neutron activation factors did not influence the compression properties of the tablets. Replacement of magnesium stearate with samarium stearate in directly compressed Am.P tablets to achieve both radiolabelling and lubrication resulted in a greater extent of concentration-dependent reduction of the crushing strength. Dissolution tests demonstrated that irradiation increased the release of the model drug ropivacaine from the tablets. The extent of this increase was unexpectedly low considering the previously observed degradation of the polymer expressed as an irradiation-induced viscosity reduction in solutions prepared from the polymers. Delayed-release coating with Eudragit L 100 protected the HPMC tablets against the release-increasing effect of irradiation until the late phases of release. Sm(2)O(3) retarded the release to a varying extent depending on particle characteristics. Incorporation of Sm(2)O(3) in the coating layer did not influence the release. However, one-third of the radioactivity leached from the coating within 60 min in 0.1 M HCl.

Amides↗

PubMed2000

The influence of alkali fatty acids on the properties and the stability of parenteral O/W emulsions modified with solutol HS 15.

Arachis oil based parenteral O/W emulsions were prepared using soya bean phosphatidylcholine (SPC) and different combinations of co-emulsifiers containing polyethylene glycol fatty acid esters (Solutol HS 15) and alkali fatty acids (sodium laurate, sodium stearate). The parameters measured were droplet size (both by photon correlation spectroscopy and laser diffractometry), pH and zeta potential. All emulsions were subjected to autoclaving. The addition of polyethylene glycol 12-hydroxy stearate (Solutol HS 15) led to a significant decrease of mean oil droplet size. For long-term stability the amount added turned out to be the most important factor. With increased amounts of Solutol HS 15 the packing density of the emulsifier layer and the zeta potential decreased leading to instability. The optimum load of Solutol HS 15 was found to be 15 micromol/ml. Alkali fatty acids markedly improved the physical stability of the emulsions. Improved stability properties conferred to emulsions by alkali fatty acids could be attributed to the zeta potential increase even in the presence of Solutol HS 15. Consequently a mixed emulsifier film was established in which the ionized fatty acids determined the interface charge. In addition to this a strengthening of the molecular interactions occurring between phospholipid and Solutol HS 15 emulsifier in the presence of ionized fatty acids at the O/W interface can be assumed (L. Rydhag, The importance of the phase behaviour of phospholipids for emulsion stability, Fette Seifen Anstrichm. 81 (1979) 168-173). Different co-emulsifier mixtures were shown to have a pronounced impact on the plasma protein adsorption onto emulsion droplets.

Adsorption↗

PubMed1994

Structural studies on human muscle fatty acid binding protein at 1.4 A resolution: binding interactions with three C18 fatty acids.

BACKGROUND: Muscle fatty acid binding protein (M-FABP) is one of a family of cytosolic lipid-binding proteins involved in fatty acid processing. In order to investigate the precise interactions between M-FABP and its ligands and to understand the structural basis of differential binding affinity, we have compared the structures of M-FABP in complex with three C18 fatty acids. RESULTS: We describe the crystal structures of M-FABP in complex with n-octadecanoate (stearate), trans-delta 9-octadecenoate (elaidate) and cis-delta 9-octadecenoate (oleate). These structures were refined using least-squares positional and anisotropic temperature factor refinement to final R-factors of 11.4%, 12.1% and 13.2% respectively for all the data between 8.0 A and 1.4 A resolution. CONCLUSIONS: Stearate, elaidate and oleate each adopt highly similar U-shaped conformations when they bind to M-FABP within a large interior binding cavity, which also contains 13 ordered water molecules. The atomic structure of the protein is virtually identical, regardless of the nature of the bound ligand. The fatty acid is thought to enter the interior cavity of the protein via a portal in its surface while interior solvent is released through a secondary opening. The ligand affinity can be correlated with the conformational energy and the solubility of the bound ligand.

Carrier Proteins↗

PubMed2003

Amounts and types of fatty acids in meals affect the pattern of retinoids secreted in human chylomicrons after a high-dose preformed vitamin A intake.

High doses of preformed vitamin A are commonly used to correct vitamin A deficiency. Newly absorbed vitamin A is secreted mainly as retinyl esters in chylomicrons. The effect of changing types and amounts of fatty acids on fatty acid composition of chylomicron retinoid esters when a high dose of vitamin A is ingested have not been studied previously. In the present study, 10 healthy young men ingested, in a random order, mixed meals containing 15,000 retinol equivalents (RE) of vitamin A (as retinyl palmitate) and either no fat or 40 g of fat provided as butter, olive oil, or sunflower oil. Fasting and postprandial blood samples were obtained for 7 hours after meals. Free retinol and the main retinyl esters (retinyl palmitate/oleate, stearate, and linoleate) were measured in chylomicrons by high-performance liquid chromatography (HPLC). Chylomicron retinyl palmitate/oleate and retinyl stearate concentrations significantly increased after intake of the 4 test meals. Conversely, chylomicron retinyl linoleate and chylomicron free retinol significantly increased only after the sunflower and the fat-free meals, respectively. The main retinoid secreted in chylomicrons after the intake of the fat-rich meals was retinyl palmitate/oleate, accounting for 63% to 79% of total RE, but it was free retinol after the fat-free meal (51% of total RE). Thus, the retinoid pattern secreted in chylomicrons after the intake of a high dose of preformed vitamin A depends on type and amounts of fatty acids ingested. To explain this result we suggest that the esterification process of retinol in the enterocyte by lecithin:retinol acyltransferase can be overwhelmed by a high load of vitamin A. Consequently, a significant proportion of the retinol is esterified by acyl coenzyme A:retinol acyltransferase (ARAT) with ingested fatty acids, explaining the appearance of retinyl linoleate in chylomicrons after the sunflower oil meal. If a high dose of preformed vitamin A is ingested with a fat-free meal, a significant proportion of retinol is not esterified, owing to the lack of fatty acids for ARAT, which explains the appearance of free retinol in chylomicrons.

1-Acylglycerophosphocholine O-Acyltransferase↗

PubMed1992

Modification of Brassica seed oil by antisense expression of a stearoyl-acyl carrier protein desaturase gene.

Molecular gene transfer techniques have been used to engineer the fatty acid composition of Brassica rapa and Brassica napus (canola) oil. Stearoyl-acyl carrier protein (stearoyl-ACP) desaturase (EC 1.14.99.6) catalyzes the first desaturation step in seed oil biosynthesis, converting stearoyl-ACP to oleoyl-ACP. Seed-specific antisense gene constructs of B. rapa stearoyl-ACP desaturase were used to reduce the protein concentration and enzyme activity of stearoyl-ACP desaturase in developing rapeseed embryos during storage lipid biosynthesis. The resulting transgenic plants showed dramatically increased stearate levels in the seeds. A continuous distribution of stearate levels from 2% to 40% was observed in seeds of a transgenic B. napus plant, illustrating the potential to engineer specialized seed oil compositions.

Base Sequence↗

PubMedDate not supplied

The curvature and cholesterol content of phospholipid bilayers alter the transbilayer distribution of specific molecular species of phosphatidylethanolamine.

The curvature, cholesterol content, and transbilayer distribution of phospholipids significantly influence the functional properties of cellular membranes, yet little is known of how these parameters interact. In this study, the transbilayer distribution of phosphatidylethanolamine (PE) is determined in vesicles with large (98 nm) and small (19 nm) radii of curvature and with different proportions of PE, phosphatidylcholine, and cholesterol. It was found that the mean diameters of both types of vesicles were not influenced by their lipid composition, and that the amino-reactive compound 2,4,6-trinitrobenzenesulphonic acid (TNBS) was unable to cross the bilayer of either type of vesicle. When large vesicles were treated with TNBS, approximately 40% of the total membrane PE was derivatized; in the small vesicles 55% reacted. These values are interpreted as representing the percentage of total membrane PE residing in the outer leaflet of the vesicle bilayer. The large vesicles likely contained approximately 20% of the total membrane lipid as internal membranes. Therefore, in both types of vesicles, PE as a phospholipid class was randomly distributed between the inner and outer leaflets of the bilayer. The proportion of total PE residing in the outer leaflet was unaffected by changes in either the cholesterol or PE content of the vesicles. However, the transbilayer distributions of individual molecular species of PE were not random, and were significantly influenced by radius of curvature, membrane cholesterol content, or both. For example, palmitate- and docosahexaenoate-containing species of PE were preferentially located in the outer leaflet of the bilayer. Membrane cholesterol content affected the transbilayer distributions of stearate-, oleate-, and linoleate-containing species. The transbilayer distributions of palmitate-, docosahexaenoate-, and stearate-containing species were significantly influenced by membrane curvature, but only in the presence of high levels of cholesterol. Thus, differences in membrane curvature and cholesterol content alter the array of PE molecules present on the surfaces of phospholipid bilayers. In cells and organelles, these differences could have profound effects on a number of critical membrane functions and processes.

Animals↗

PubMed1960

Interactions of veratrum alkaloids, procaine, and calcium with monolayers of stearic acid and their implications for pharmacological action.

The interactions of veratridine, cevadine, veracevine, and veratramine with monolayers of stearic acid show marked differences. Veratridine and cevadine, at concentrations that are known from potential, ionic flux, and other measurements to affect living membranes, react strongly with the film and appear to cause an "interfacial dissolution" whereby both the alkaloid and the stearate leave the surface. Veracevine at the same concentration does not interact with the film. The veratramine reaction is weak, much like that of the local anesthetic procaine. The veratridine and cevadine effects are antagonized by 10(-3)M Ca(++), low pH, and 3.7 and 7.4 x 10(-3)M procaine. These differences among the veratrum alkaloids and the antagonisms parallel effects observed in living systems. Such parallelism suggests that similar physical interactions are involved in the stearate film and in natural membranes.

Anesthetics, Local↗

PubMed1975

Dietary effects of the esters of butyric, caproic, caprylic, capric, lauric, myristic, palmitic, and stearic acids on food intake, weight gain, plasma glucose, and tissue lipid in the male white rat.

Eight saturated fatty acid esters were fed to male white rats for 30 days in a 1/81 fractional factorial experiment in which diets contained 12-38% of their total energy as lipid. Marked increases in food intake, feed efficiency, and weight gain were achieved when lipid provided 36% of diet energy, and when that lipid was more than half caproate, caprate, myristate, and/or stearate. Caproate was the only saturated fatty acid to increase plasma glucose levels. The feeding of stearate or caprylate decreased plasma and liver cholesterol. Caprate increased liver fat. The short-chain fatty acids (butyrate to myristate) increased the concentration of fat in the carcass.

Animal Nutritional Physiological Phenomena↗

PubMed2006

Two aerobic pathways for the formation of unsaturated fatty acids in Pseudomonas aeruginosa.

The double bond in anaerobic unsaturated fatty acid (UFA) biosynthesis is introduced by the FabA dehydratase/isomerase of the bacterial type II fatty acid biosynthetic pathway. A DeltafabA mutant of Pseudomonas aeruginosa grew aerobically, but required a UFA supplement for anaerobic growth. Wild-type cells produced 18:1Delta11 as the principal UFA, whereas the DeltafabA strain produced only 16:1Delta9. The double bond in the 16:1Delta9 was introduced after phospholipid formation and was localized in the sn-2 position. Two predicted membrane proteins, DesA and DesB, possessed the conserved histidine clusters characteristic of fatty acid desaturases. The DeltafabADeltadesA double mutant required exogenous fatty acids for growth but the DeltafabAdesB double mutant did not. Exogenous stearate was converted to 18:1Delta9 and supported the growth of DeltafabADeltadesA double mutant. A DeltafabADeltadesAdesB triple mutant was unable to desaturate exogenous stearate and was an UFA auxotroph. We detected a 2.5-fold increase in desA expression in DeltafabA mutants, whereas desB expression was derepressed by the deletion of the gene encoding a transcriptional repressor DesT. These data add two aerobic desaturases to the enzymes used for fatty acid metabolism in proteobacteria: DesA, a 2-position phospholipid Delta9-desaturase that supplements the anaerobic FabA pathway, and DesB, an inducible acyl-CoA Delta9-desaturase whose expression is repressed by DesT.

Aerobiosis↗

PubMedDate not supplied

Lipid composition of hepatic and adipose tissues from normal cats and from cats with idiopathic hepatic lipidosis.

The purpose of this study was to characterize the lipid classes in hepatic and adipose tissues from cats with idiopathic hepatic lipidosis (IHL). Concentrations of triglyceride, phospholipid phosphorus, and free and total cholesterol were determined in lipid extracts of liver homogenates from 5 cats with IHL and 5 healthy control cats. Total fatty acid composition of liver and adipose tissue was also compared. Triglyceride accounted for 34% of liver by weight in cats with IHL (338 +/- 38 mg/g wet liver) versus 1% in control cats (9.9 +/- 1.0 mg/g wet liver, P < .001). The mass of cholesterol ester was significantly higher in triglyceride-free (TG-free) liver from cats with IHL (741 +/- 340 micrograms/g TG-free wet liver) compared to healthy cats (31 +/- 11 micrograms/g TG-free wet liver, P < .05). Total fatty acid composition of hepatic tissue in the 2 groups differed; palmitate was higher (19.5 +/- 1.1% of total fatty acids in cats with IHL versus 9.2 +/- 2.7% in controls, P < .05), stearate was lower (8.5 +/- 0.8% versus 16.8 +/- 1.1%, P < .05), oleate was higher (41.2 +/- 1.6% versus 31.1 +/- 1.8%, P < .05), and arachidonate was lower (1.2 +/- 0.2% versus 6.0 +/- 0.9%, P < .05). The total fatty acid composition of adipose tissue also differed between the 2 groups; palmitate was higher (26.2 +/- 1.2% in cats with IHL versus 21.3 +/- 0.6% in controls, P < .05), total monounsaturated fatty acids were higher (48.4 +/- 1.0% versus 45.0 +/- 0.8%, P < .05), linolenate was lower (13.3 +/- 1.6% versus 17.5 +/- 0.9%, P < .05), total (n-6) fatty acids were lower (13.8 +/- 1.38% versus 18.4 +/- 0.83%, P < .05), linolenate was lower (0.2 +/- 0.04% versus 0.7 +/- 0.06%, P < .06), and total (n-3) fatty acids were lower (0.3 +/- 0.02% versus 1.3 +/- 0.32%, P < .05). The fatty acid composition of both liver and adipose tissue was similar for stearate, oleate, linoleate, and linolenate in cats with IHL. These results support the hypothesis that the origin of hepatic triglyceride in cats with IHL is the mobilization of fatty acids from adipose tissue.

Adipose Tissue↗

PubMed2000

Loss of regulation of lipogenesis in the Zucker diabetic (ZDF) rat.

We present here a study on the role of leptin in the regulation of lipogenesis by examining the effect of dietary macronutrient composition on lipogenesis in the leptin receptor-defective Zucker diabetic fatty rat (ZDF) and its lean litter mate (ZL). Animals were pair fed two isocaloric diets differing in their fat-to-carbohydrate ratio providing 10 and 30% energy as fat. Lipogenesis was measured in the rats using deuterated water and isotopomer analysis. From the deuterium incorporation into plasma palmitate, stearate, and oleate, we determined de novo synthesis of palmitate and synthesis of stearate by chain elongation and of oleate by desaturation. Because the macronutrient composition and the caloric density were controlled, changes in de novo lipogenesis under these dietary conditions represent adaptation to changes in the fat-to-carbohydrate ratio of the diet. De novo lipogenesis was normally suppressed in response to the high-fat diet in the ZL rat to maintain a relatively constant amount of lipids transported. The ZDF rat had a higher rate of lipogenesis, which was not suppressed by the high-fat diet. The results suggest an important hormonal role of leptin in the feedback regulation of lipogenesis.

Animals↗

PubMed1979

Clinical and pharmacological evaluation of different preparations of oral erythromycin.

The activity of erythromycin stearate in respiratory tract infections was evaluated. This study involved 269 out-patients. Of these, 76 satisfied the strict criteria for detailed bacteriological study with positive cultures of a known pathogen before treatment and bacteriological follow-up after treatment. The results of erythromycin stearate were good against the haemolytic streptococcal infections. The activity of this antibiotic was shown to be insufficient against Haemophilus influenzae. A second clinical trial with 20 patients with acute exacerbations of chronic bronchitis demonstrated quite good activity from erythromycin ethylsuccinate and no intolerance when administered in a dose of 1 g q.i.d. The administration of 1 g of the ethylsuccinate immediately after a meal gave a peak serum concentration after 60 min of 3.36 micrograms/ml. Blood levels on the fourth day of this treatment showed some accumulation, concentrations of greater than 4 micrograms/ml being found at 30, 60 and 90 min after the dose. With its good absorption, its lack of toxicity and its reputation for good diffusion into bronchial secretions, we consider that erythromycin ethylsuccinate should have a major place in the treatment of respiratory tract infections.

Administration, Oral↗

PubMed1977

Treatment of acute bacterial infections of the upper respiratory tract.

An open comparative study was carried out to assess the effectiveness of 4 antibiotic regimens in eradicating acute bacterial infections of the upper respiratory tract. Patients in each treatment group had similar physical parameters, severity of disease and bacterial pathogens, and were treated for 10 days with either erythromycin estolate, erythromycin stearate, ampicillin or oxytetracycline in the recommended dosage. Each patient was reviewed daily by physical examination and the bacteriological findings from throat swab and salivary washings. The results showed that erythromycin stearate produced more rapid bacterial eradication and clinical resolution of symptoms and fever than with the other antibiotic preparations, and was well tolerated by most patients.

Acute Disease↗

PubMed2002

Acute effects of fatty acids on insulin secretion from rat and human islets of Langerhans.

Fatty acids have both stimulatory and inhibitory effects on insulin secretion. Long-term exposure to fatty acids results in impaired insulin secretion whilst acute exposure has generally been found to enhance insulin release. However, there are conflicting data in the literature as to the relative efficacy of various fatty acids and on the glucose dependency of the stimulatory effect. Moreover, there is little information on the responses of human islets in vitro to fatty acids. We have therefore studied the acute effects of a range of fatty acids on insulin secretion from rat and human islets of Langerhans at different glucose concentrations. Fatty acids (0.5 mM) acutely stimulated insulin release from rat islets of Langerhans in static incubations in a glucose-dependent manner. The greatest effect was seen at high glucose concentration (16.7 mM) and little or no response was elicited at 3.3 or 8.7 mM glucose. Long-chain fatty acids (palmitate and stearate) were more effective than medium-chain (octanoate). Saturated fatty acids (palmitate, stearate) were more effective than unsaturated (palmitoleate, linoleate, elaidate). Stimulation of insulin secretion by fatty acids was also studied in perifused rat islets. No effects were observed at 3.3 mM glucose but fatty acids markedly potentiated the effect of 16.7 mM glucose. The combination of fatty acid plus glucose was less effective when islets had been first challenged with glucose alone. The insulin secretory responses to fatty acids of human islets in static incubations were similar to those of rat islets. In order to examine whether the responses to glucose and to fatty acids could be varied independently we used an animal model in which lactating rats are fed a low-protein diet during early lactation. Islets from rats whose mothers had been malnourished during lactation were still able to respond effectively to fatty acids despite a lowered secretory response to glucose. These data emphasise the complex interrelationships between nutrients in the control of insulin release and support the view that fatty acids play an important role in glucose homeostasis during undernutrition.

Animals↗