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PubMed2006

Effect of ionic surfactants on bauxite residues suspensions viscosity.

Measurement of the rheological property of bauxite residue sample received from an Australian alumina refinery, treated with a number of cationic and anionic surfactant in laboratory has been carried out using a Brookfield viscometer for the assessment of the effect of surfactants on the residue viscosity. Sodium laurate, prepared with an excess of sodium hydroxide, was found to be effective while direct addition of anionic surfactants (lauric acid and sodium laureth sulphate) and cationic (cetyl trimethyl ammonium bromide) produce only moderate effect on the red mud suspension apparent viscosity at 65 degrees C. The experimental data appear to confirm the crucial role of the cation sodium in the process of adsorption of anionic surfactants on the flocculated red mud particles.

Journal Article↗
PubMed2006

Reverse micelle synthesis of rhodium nanoparticles.

Water-in-oil reverse micelles of butyl ammonium laurate in hexanes that contain sodium hexachlororhodate were reduced with sodium borohydride to yield rhodium nanoparticles. The size of the micelle, determined by dynamic light scattering, was from 3 to 20 nm and varied as the water to surfactant ratio (W) was changed. The rhodium nanoparticles exhibited a Gaussian size distribution (sigma=0.35 nm), with average diameters of 1.5, 2.2, and 2.9 nm. The products were characterized with TEM, HRTEM, and X-ray photoemission spectroscopy.

Journal Article↗
PubMed2005

The short-term effect of fatty acids on glucagon secretion is influenced by their chain length, spatial configuration, and degree of unsaturation: studies in vitro.

The influence of fatty acids on beta cell function has been well established whereas little is known about the role of fatty acids on alpha cell function. The aim of our study was to investigate the short-term effects of chain length, spatial configuration, and degree of unsaturation of fatty acids on glucagon secretion from isolated mouse islets and alpha tumor cell 1 clone 6 cells (alpha TC1-6 cells). Glucagon release was measured with different saturated and unsaturated fatty acids as well as cis and trans isomers of fatty acids at low and high glucose. Palmitate (0.1-0.5 mmol/L) immediately stimulated glucagon release in a dose-dependent manner from both isolated islets and alpha TC 1-6 cells. The longer chain length of saturated fatty acids, the higher glucagon responses were obtained. The average fold increase in glucagon to saturated fatty acids (0.3 mmol/L) compared to control was octanoate 1.5, laurate 2.0, myristate 2.9, palmitate 5.4, and stearate 6.2, respectively. Saturated fatty acids were more effective than unsaturated fatty acids in stimulating glucagon secretion. At an equimolar concentration, trans-fatty acids were more potent than their cis isomers. Fatty acids immediately stimulate glucagon secretion from isolated mouse islets pancreatic alpha cells. The chain length, spatial configuration, and degree of unsaturation of fatty acids influence the glucagonotropic effect.

Animals↗
PubMed2005

Safety assessment on polyethylene glycols (PEGs) and their derivatives as used in cosmetic products.

This assessment focusses on polyethylene glycols (PEGs) and on anionic or nonionic PEG derivatives, which are currently used in cosmetics in Europe. These compounds are used in a great variety of cosmetic applications because of their solubility and viscosity properties, and because of their low toxicity. The PEGs, their ethers, and their fatty acid esters produce little or no ocular or dermal irritation and have extremely low acute and chronic toxicities. They do not readily penetrate intact skin, and in view of the wide use of preparations containing PEG and PEG derivatives, only few case reports on sensitisation reactions have been published, mainly involving patients with exposure to PEGs in medicines or following exposure to injured or chronically inflamed skin. On healthy skin, the sensitising potential of these compounds appears to be negligible. For some representative substances of this class, information was available on reproductive and developmental toxicity, on genotoxicty and carcinogenic properties. Taking into consideration all available information from related compounds, as well as the mode and mechanism of action, no safety concern with regard to these endpoints could be identified. Based on the available data it is therefore concluded that PEGs of a wide molecular weight range (200 to over 10,000), their ethers (laureths. ceteths, ceteareths, steareths, and oleths), and fatty acid esters (laurates, dilaurates, stearates, distearates) are safe for use in cosmetics. Limited data were available for PEG sorbitan/sorbitol fatty acid esters, PEG sorbitan beeswax and PEG soy sterols. Taking into account all the information available for closely related compounds, it can be assumed that these compounds as presently used in cosmetic preparations will not present a risk for human health. PEG castor oils and PEG hydrogenated castor oils have caused anaphylactic reactions when used in intravenous medicinal products. Their topical use in cosmetics is, however, considered safe as they are not expected to be systemically available. As all PEGs and PEG derivatives, they must not be applied to damaged skin. Manufacturers of PEGs and PEG derivatives must continue their efforts to remove impurities and by-products such as ethylene oxide and 1,4-dioxane. Overall, it is concluded, that the PEGs covered in this review are safe for use in cosmetics under the present conditions of intended use.

Animals↗
PubMed2002

Effects of cold exposure in vivo and uncouplers and recouplers in vitro on potato tuber mitochondria.

Effects of cold exposure in vivo and treatment with laurate, carboxyatractylate, atractylate, nucleotides, and BSA in vitro on potato tuber mitochondria have been studied. Cold exposure of tubers for 48-96 h resulted in some uncoupling that could be reversed completely by BSA and partially by ADP, ATP, UDP, carboxyatractylate, and atractylate. UDP was less effective than ADP and ATP, and atractylate was less effective than carboxyatractylate. The recoupling effects of nucleotides were absent when the nucleotides were added after carboxyatractylate. GDP, UDP, and CDP did not recouple mitochondria from either the control or the cold-exposed tubers. This indicates that the cold-induced fatty acid-mediated uncoupling in potato tuber mitochondria is partially due to the operation of the ATP/ADP antiporter. As to the plant uncoupling protein, its contribution to the uncoupling in tuber is negligible or, under the conditions used, somehow desensitized to nucleotides.

Adaptation, Physiological↗
PubMed1987

Saturated and trans-unsaturated fatty acids elicit high levels of superoxide generation in intact and cell-free preparations of neutrophils.

Saturated and trans-unsaturated fatty acids, such as laurate and elaidate, elicited O2- generation in intact porcine and human neutrophils and also in a cell-free preparation of porcine neutrophils. The activities thus induced were comparable to those induced by cis-unsaturated fatty acids. However, the activation by saturated or trans-unsaturated fatty acids was depressed almost completely in the presence of Ca2+ at around 1 mM, which is usually contained in the media for phagocytes. In contrast, the activation by cis-unsaturated fatty acids such as arachidonate was scarcely affected by Ca2+. These findings appear to demand reevaluation of the effects of long chain fatty acids on the respiratory burst system in phagocytes.

Animals↗
PubMed1998

Making vitamin C lipophilic enhances its protective effect against free radical induced peroxidation of low density lipoprotein.

The peroxidation of human low density lipoprotein (LDL) was initiated by water-soluble initiator 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) and copper and inhibited by vitamin C (VC) and its lipophillic derivatives ascorbyl-6-caprylate (VC-8), 6-laurate (VC-12) and 6-palmitate (VC-16), respectively. The peroxidation was monitored by oxygen uptake, by decay of alpha-tocopherol and by formation of lipid oxidation products. Kinetic analysis of the antioxidation process demonstrates that the VCs can work synergistically with endogenous antioxidants (vitamin E, ubiquinol-10, beta-carotene etc.) in LDL to suppress the peroxidation and that the synergistic effect of the lipophilic VCs is appreciably higher than that of their lipophobic parent molecule. It is also shown that VC and especially the lipophilic VCs, are much more effective in inhibition of copper-induced than AAPH-induced LDL peroxidation.

Amidines↗
PubMed2002

Efficient transesterification of sucrose catalysed by the metalloprotease thermolysin in dimethylsulfoxide.

Thermolysin catalyses the formation of sucrose esters from sucrose and vinyl laurate in dimethylsulfoxide, with a specific activity of 53 nmol/min/mg and 2-O-lauroyl-sucrose as the main product. Such transesterification reactions are normally observed only when the mechanism involves an acyl enzyme intermediate, as with lipases or serine proteases, and not with metalloproteases like thermolysin. A possible reason is the affinity of the active site of thermolysin for sugar moieties, as for the potent inhibitor phosphoramidon. The reaction is not catalysed by other proteins under the same conditions, and is inhibited by removal of the active site zinc.

Carboxypeptidases↗
PubMed2000

Characterisation of whiskeys using solid-phase microextraction with gas chromatography-mass spectrometry.

The application of solid-phase microextraction and gas chromatography-mass spectrometry to the detection of flavour volatiles present in Irish and Scottish whiskeys was investigated. A method was developed to characterise these volatiles which included the extraction, identification and quantification of 17 congeners which included fusel alcohols, acetates and esters. The method validation produced the optimum fibre [85 microm poly(acrylate)], extraction time (35 min), sample volume size (3 ml) and desorption time (5 min). The impact of salt on the absorption process was also studied. Characteristic profiles were determined for each whiskey and the flavour congeners were quantified using 4-methyl-2-pentanol as the internal standard. Calibration ranges were determined for each of the congeners with coefficients of linearity ranging from 0.993 (butan-1-ol) to 0.999 (ethyl laurate) and relative standard deviations ranging from 2.5% (2-methylbutan-1-ol) to 21% (furfural) at a concentration of 18.2 mg/l. Detection limits ranged from 0.1 mg/l (ethyl caprate) to 21 mg/l (butan-2-ol).

Alcoholic Beverages↗
PubMed2000

High-performance liquid chromatographic resolution of reverse isomers of 1,2-diacyl-rac-glycerols as 3,5-dinitrophenylurethanes.

The resolution of reverse isomers remains a major unsolved problem in glycerolipid chromatography. We have investigated the separation of the reverse isomers of 1,2-diacyl-rac-glycerols under a variety of high-performance liquid chromatography (HPLC) conditions. The reverse isomers of diacylglycerols having various pairs of acyl groups including short and highly unsaturated chains, which were prepared by partial Grignard degradation of the corresponding triacylglycerols, were chromatographed as 3,5-dinitrophenylurethanes. Excellent resolution was achieved for the reverse isomers of very different pairs of acyl groups, such as acetate-palmitate and docosahexaenoate-palmitate, by chiral-phase HPLC on columns containing (R)- and (S)-1-(1-naphthyl)ethylamine polymeric phases, reversed-phase HPLC on a highly efficient C18 column (4 microm particle size) and silver ion HPLC on a silver loaded cation-exchange column. The chiral-phase HPLC also permitted complete enantiomer resolution for all the reverse isomers examined. No satisfactory resolution by any of the HPLC methods, however, was obtained for the reverse isomers possessing minor differences in chain lengths and degree of unsaturation, such as laurate-palmitate and oleate-linoleate. The limitations of resolution and characteristics of elution are described.

Chromatography, High Pressure Liquid↗
PubMed1988

Separation of carotenol fatty acid esters by high-performance liquid chromatography.

Employing isocratic and gradient-elution high-performance liquid chromatography (HPLC) a number of straight-chain fatty acid esters (decanoate, laurate, myristate, palmitate) of violaxanthin, auroxanthin, lutein, zeaxanthin, isozeaxanthin, and beta-cryptoxanthin, prepared by partial synthesis, have been separated on a C18 reversed-phase column. Several chromatographic conditions were developed that separated a mixture of di-fatty acid esters (dimyristate, myristate palmitate mixed ester, dipalmitate) of violaxanthin, auroxanthin, lutein, and zeaxanthin in a single chromatographic run. Hydroxycarotenoids such as lutein, zeaxanthin, and isozeaxanthin that are not easily separated by HPLC on C18 reversed-phase columns, can be readily separated after derivatization with fatty acids and chromatography of their esters. Chromatographic conditions for optimum separation of carotenoids from various classes are discussed.

Carotenoids↗
PubMed2001

Analysis of steryl esters in cocoa butter by on-line liquid chromatography-gas chromatography.

On-line liquid chromatography-gas chromatography (LC-GC) has been applied to the analysis of steryl esters in cocoa butter. Separation of the steryl esters was achieved after on-line transfer to capillary GC. HPLC removes the large amount of triglycerides and pre-separates the components of interest, thus avoiding time-consuming sample preparation prior to GC analysis. The identities of the compounds were confirmed by GC-MS investigation of the collected HPLC fraction and by comparison of the mass spectra (chemical ionization using ammonia as ionization gas) to those of synthesized reference compounds. Using cholesteryl laurate as internal standard, steryl esters were quantified in commercial cocoa butter samples, the detection limit being 3 mg/kg and the quantification limit 10 mg/kg, respectively. Only slight differences in percentage distributions of steryl esters depending on the geographical origin of the material were observed. The patterns were shown to remain unchanged after deodorization. The method described might be a valuable tool for authenticity assessment of cocoa butter.

Chromatography, Gas↗
PubMed2000

Study on the lifetime and attenuation properties of microbubbles coated with carboxylic acid salts.

Four kinds of surfactants, sodium laurate, sodium myristate, sodium palmitate and sodium oleate were used to study the effects of surfactant coatings on the lifetime and attenuation of microbubbles. The changes in the size distribution of microbubbles prepared with these surfactants in saline were measured with a Coulter Multisizer (Coulter Electronics Ltd., Luton, UK). Frequency characteristics of ultrasonic attenuation of the microbubble suspensions were measured between 400 kHz and 6 MHz. From the changes in attenuation in the microbubble suspensions over time, it was found that the lifetime of microbubbles in a suspension also depends on the frequency of the irradiating ultrasound. The effect of surfactants on the frequency characteristics of attenuation was also studied, and characteristics of the surfactant coating, including shell elasticity and shell friction parameters were calculated from the measurement results. Microbubbles produced with sodium palmitate had the longest lifetime and the smallest average size. The shell had very little effect on the ultrasonic properties of microbubbles produced with sodium palmitate, suggesting that the sodium palmitate microbubbles behaved ultrasonically as free microbubbles.

Air↗
PubMed1999

PCP in the freshwater and marine environment of the European Union.

This study collates monitoring data principally from 1991 to 1996, relating levels of pentachlorophenol (PCP) in the freshwater and marine environments of the European Union (EU) Member States of Belgium, France, Germany, the Netherlands and the UK. In general, PCP levels in the open freshwater and marine environments displayed a downward trend in these countries, and where increased PCP concentrations were observed, these were tentatively linked to specific point discharges. The monitoring data were compared against the relevant predicted no-effect concentration (PNEC) for PCP in a particular environmental medium. On this basis, the study suggests that PCP does not pose a risk to the coastal, estuarine, marine waters or marine sediments of the above countries, and that any risks posed by PCP to the freshwater environment can largely be attributed to sediments contaminated with PCP from historic usage, or due to the continued use of small quantities of sodium pentachlorophenyl laurate in northern France. Further analysis of the data was not possible owing to the lack of systematic reporting by Member States, the lack of information on usage quantities and patterns, and inconsistent environmental surveillance and reporting of environmental data. This is particularly relevant for south-west France, Portugal and north-east Spain, the region which accounts for almost 90% of the EU's consumption of NaPCP. These issues need to be addressed at a pan-European level to better inform the selection of risk management measures and to improve the effectiveness of such measures.

Animals↗
PubMed2000

Lysophosphatidylcholine synthesis with Candida antarctica lipase B (Novozym 435).

Immobilized lipase from Candida antarctica lipase B (Novozym 435) was effective in the synthesis of lysophosphatidylcholine (LPC). The transesterification of L-alpha-glycerophosphorylcholine (GPC) and vinyl laurate was carried out in a solvent free system or in the presence of 50% (v/v) t95%) were easily achieved. The lipase was selective for the sn10 times). High purity products could be produced by a decrease of the reaction temperature to induce precipitation of the product. The temperature needed depended on the fatty acid chain length. Thus, only lysophosphatidylcholine was produced with palmitic acid vinyl ester at 45 degrees C, whereas for the vinyl esters of lauric acid, capric acid, and caprylic acid, a lower reaction temperature (25 degrees C) was necessary to obtain solely the lysophospholipid products.

Journal Article↗
PubMedDate not supplied

The phthalate diesters DEHP and DBP do not induce lauric acid hydroxylase activity in rainbow trout.

Aquatic organisms are extensively exposed to phthalate esters. We have investigated in trout the effects of diethylhexylphthalate (DEHP) and dibutylphthalate (DBP) on xenobiotic metabolizing enzymes which have been suggested as possible environmental biomarkers. Rainbow trout (Oncorhynchus mykiss) were waterborne exposed to DEHP (1 mg/l) or DBP (0.1 or 1 mg/l) for 72 h. Another group of rainbow trout received daily for 3 days an intraperitoneal injection of 50 mg/kg of DEHP or DBP. Laurate hydroxylation, ethoxyresorufin-o-deethylation, UDP-glucuronyltransferase activity and glutathione-S-transferase activity were measured in liver and extrahepatic tissues. The phthalate esters have been found not to induce these enzymes; in particular, the results do not support the previously described induction of lauric acid hydroxylase in sea bass treated with DEHP [Comp. Biochem. Physiol. B122 (1999) 253.].

Animals↗
PubMed2001

Fatty acid remodeling of glycosyl phosphatidylinositol anchors in Trypanosoma brucei: incorporation of fatty acids other than myristate.

Trypanosoma brucei is the protozoan parasite that causes African sleeping sickness. Its surface is packed with 10(7) copies of the glycosyl phosphatidylinositol (GPI)-anchored variant surface glycoprotein (VSG). This GPI anchor is unusual in that it contains two myristates (14:0) in its lipid moiety. This fatty acid specificity is achieved through myristoylation of the GPI precursor, and the acyltransferases involved in the GPI remodeling were presumed to be specific for myristate. However, their specificity had never been fully evaluated. Here we found as expected that the remodeling acyltransferases completely excluded palmitate (16:0) and stearate (18:0) in a cell-free fatty acid remodeling system. In contrast, we found surprisingly that one of these enzymes was permissive to shorter fatty acids such as laurate (12:0) and octanoate (8:0). However, the rates of incorporation of shorter fatty acids were lower than that of myristate at low substrate concentration. Since shorter fatty acids are virtually absent in the parasite and in the host bloodstream, it is unlikely that shorter fatty acids compete effectively with myristate as remodeling substrates under physiological conditions. Even if they were present in small quantities, a recently identified specialized fatty acid synthetase efficiently elongates shorter fatty acids to myristate prior to incorporation into GPIs (Morita et al., Science 288 (2000) 140-3.). Therefore, even though a remodeling acyltransferase is permissive with regard to substrate chain length, the myristate specificity in GPI anchors is very high.

Acyltransferases↗
PubMed2004

A bacterial gene homologous to ABC transporters protect Oenococcus oeni from ethanol and other stress factors in wine.

The wine lactic acid bacteria Oenococcus oeni has to cope with harsh environmental conditions including an acidic pH, a high alcoholic content, non-optimal growth temperatures, and growth inhibitory compounds such as fatty acids, phenolic acids and tannins. We here describe characterisation and cloning of the O. oeni omrA gene encoding a protein belonging to the ATP-binding cassette superfamily of transporters. The OmrA protein displays the highest sequence similarity with the subfamily of ATP-dependent multidrug resistance (MDR) proteins, most notably the bacterial Lactococcus lactis LmrA homologue of the human MDR1 P-glycoprotein. The omrA gene proved to be a stress-responsive gene since its expression was increased at high temperature or under osmotic shock. The OmrA protein function was tested in Escherichia coli, and consistent with the omrA gene expression pattern, OmrA conferred protection to bacteria grown on a high salt medium. OmrA also triggered bacterial resistance to sodium laurate, wine and ethanol toxicity. The homologous LmrA protein featured the same stress-protective pattern than OmrA when expressed in E. coli, and the contribution to resistance of both OmrA and LmrA transporters was decreased by verapamil, a well-known inhibitor of the human MDR1 protein. Genes homologous to omrA were detected in other wine lactic acid bacteria, suggesting that this type of genes might constitute a well-conserved stress-protective molecular device.

ATP-Binding Cassette Transporters↗