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PubMed2000

Effects of two highly monounsaturated oils on lipid composition and enzyme activities in rat jejunum.

The effects of two monounsaturated fatty acid (MUFA) oils, olive oil (OO) and high-oleic sunflower oil (HOSO), with high content in oleic acid but differing in their non-fatty acid fraction, on brush-border membrane (BBM) lipid composition and fluidity and on mucosal enzyme activities of rat jejunum were studied. Animals were given semipurified diet with linoleic acid to prevent essential fatty acid deficiency (control group) or semipurified diet containing 10% of either OO or HOSO for 12 weeks. There was a significant decrease in the content of jejunal BBM phospholipids together with an increase in the level of free cholesterol in both oil-fed rats, when compared to control group. Although the increase in the BBM free cholesterol level was not statistically significant in HOSO-fed rats, a significant decrease in the phospholipid/free cholesterol ratio was found in both OO and HOSO-fed animals compared to control group. Rat jejunal BBM had a high level of free fatty acids which was increased in BBM isolated from OO and HOSO-fed animals. There was no statistical significant difference in the phospholipid distribution between the control and the OO group. However, HOSO-fed animals showed the lowest level of phosphatidylethanolamine together with the highest phosphatidylcholine content and the phosphatidylcholine/sphingomyelin ratio. The fatty acid pattern of jejunal BBM lipids was modified according to the major fatty acids in the oils. There was a decrease in both stearic acid (18:0) and linoleic acid (18:2 n-6), together with an increase in oleic acid (18:1 n-9) in jenunal BBM isolated from both oil experimental groups. All these results were accompanied by a significant increase in the BBM fluidity (as assessed by steady-state fluorescence polarization of diphenylhexatriene) isolated from oil-fed rat, when compared to control group. OO and HOSO-fed animals had the lowest activities of sucrase and maltase, while alkaline phosphatase activity only was decreased in HOSO-fed animals. The specific activity of maltase was not modified in any experimental rats. In summary, both MUFA oils induced similar effects on jejunal BBM lipid composition, fluidity, sucrase, maltase and lactase activities. Furthermore, HOSO intake resulted in a lowest alkaline phosphatase activity which was accompanied by changes in individual phospholipid composition. All these results suggest that effects of MUFA oils on jejunal BBM lipid composition and hydrolase activities are most likely due to the presence of high content of oleic acid rather than other components contained in the non-fatty acid of olive oil.

Alkaline Phosphatase↗
PubMed2001

Comparison of fatty acid profile in plasma phospholipids in women from Granada (southern Spain) and Malmö (southern Sweden).

We conducted a first pilot study on healthy women living in two countries with different dietary habits, Granada in the south of Spain and Malmö in the south of Sweden, in order to compare their levels of plasma phospholipid fatty acids, and to examine the relationship between the differences in food consumption. This study is part of a pilot study which is nested in the European Prospective Investigation into Cancer and Nutrition, a multi-centre prospective cohort study on diet, plasma concentrations of antioxidants and fatty acids, and markers of oxidative stress. Thirty-nine women in Granada and thirty-eight women in Malmö, aged 45-50 years (all pre-menopausal) were selected among the female participants in the cohorts from these two countries. Individual measurements of the women's habitual diet were obtained by a food frequency questionnaire. 24-hour diet recalls were used for the standardised measurement of diet at group level. Plasma phospholipid fatty acid composition was determined by capillary gas chromatography. We found a different fatty acid profile in plasma between the two populations, with higher mean levels of palmitic acid (16:0), palmitoleic acid (16:1) (n-7), oleic acid (18:1), alpha-linolenic acid (18:3) (n-3) and eicosapentaenoic acid (20:5) (n-3), and lower mean levels of stearic acid (18:0) in Malmö compared to Granada. Women in Malmö consumed more meat, alcoholic beverages and sugar, and less fish and shellfish than women in Granada. We conclude that the fatty acid composition in plasma phospholipids is different between women from the two European centres. For polyunsaturated fatty acids, differences were observed for (n-3) fatty acids. In relation to these differences, we observed that specific food intakes, particularly meat and fish, varied between the two centres.

Chromatography, Gas↗
PubMed2005

Mechanisms by which dietary fatty acids modulate plasma lipids.

Dietary fatty acids have a considerable effect on plasma LDL cholesterol (LDL-C) concentrations and therefore on the risk for coronary heart disease. Numerous studies have been conducted in animal models to elucidate the mechanisms by which different types of fatty acids modulate plasma cholesterol concentrations. In addition, multiple clinical trials and epidemiological data have demonstrated the effects of fatty acids in determining the concentrations of circulating LDL. SFAs and trans fatty acids have a detrimental effect on plasma lipids, whereas PUFAs of the (n-6) family and monounsaturated fatty acids decrease plasma LDL-C concentrations. Among the SFAs, stearic acid (18:0) appears to have a neutral effect on LDL-C, while lauric (12:0), myristic (14:0), and palmitic (16:0) acids are considered to be hypercholesterolemic. SFAs increase plasma LDL-C by increasing the formation of LDL in the plasma compartment and by decreasing LDL turnover. Although unsaturated fatty acids increase cholesterol synthesis, they also increase hepatic LDL receptor number and LDL turnover in vivo. Fatty acids are also ligands of important regulatory elements, which can play a role in determining plasma cholesterol. This article presents a summary of the major effects of various types of fatty acids on plasma lipid concentrations and the mechanisms involved.

Animals↗
PubMed1997

Fatty acids in serum cholesteryl esters as quantitative biomarkers of dietary intake in humans.

The fatty acid composition of serum cholesteryl esters is used as a qualitative biomarker of fatty acid intake, but quantitative data are scarce. Between 1987 and 1992, the authors fed various fatty acids in four controlled trials to 232 healthy Dutch volunteers and measured the proportion of fatty acids in participants' cholesteryl esters. Each 10% of energy fed as linoleic acid (18:2) raised the proportion of linoleic acid in cholesteryl esters by 9.3 g per 100 g of fatty acids (standard deviation (SD) 3.1). For oleic acid (cis-18:1), this figure was 6.5 g/100 g (SD 1.7); for trans fatty acids (trans-18:1), it was 1.1 (SD 0.5); for stearic acid (18:0), 1.0 (SD 0.4); for palmitic acid (16:0), 1.7 (SD 0.5); for myristic acid (14:0), 2.1 (SD 0.7); and for a mixture of saturated fatty acids (12:0, 14:0, and 16:0), it was 2.2 g/100 g (SD 1.0). The coefficient of variation of the responses was fairly constant, indicating that changes in intake for each of these fatty acids can be monitored with similar precision. These data can be used to estimate the degree of compliance in experimental studies involving exchanges of single dietary fatty acids. Most fatty acids in cholesteryl esters may also be used in observational studies to estimate differences in intake. However, because of multiple simultaneous differences in fatty acid intake between free-living individuals and between populations, such data cannot provide information on absolute intake of fatty acids.

Adult↗
PubMed1977

Studies on glycosphingolipids of fresh-water bivalves. III. Isolation and characterization of a novel globoside containing mannose from spermatozoa of the fresh-water bivalve, Hyriopsis schlegelii.

Three globosides were isolated from spermatozoa of the fresh-water bivalve, Hyriopsis schlegelii by mild alkaline hydrolysis, acetone precipitation, Unisil column chromatography and preparative thin-layer chromatography. These globosides are unique in their sugar chains, since they contain mannose instead of galactose found so far in all globosides of mammals and other animals examined. The main globoside in the spermatozoa was characterized as Glc-NAcbeta(1 leads to 2)Manbeta(1 leads to 3)Manbeta(1 leads to 4)Glcbeta(1 leads to 1)-ceramide by partial acid hydrolysis, analysis of its anomeric configuration with chromium trioxide, methylation analysis and enzymatic hydrolysis. The globoside contained normal saturated fatty acids ranging in length from C16 to C21, palmitic and stearic acids being predominant. Its main long-chain was octadeca-4-sphingenine.

Animals↗
PubMed1987

Mechanism of arachidonic acid liberation during ischemia in gerbil cerebral cortex.

Once brain ischemia was induced in the gerbil cerebral fronto-parietal cortex, serial changes occurred in energy metabolites and various lipids. The amounts of inositol-containing phospholipids began to decrease immediately after energy failure, followed by an increase in the amount of 1,2-diacylglycerol with a subsequent liberation of arachidonic acid and other free fatty acids. The fatty acid compositions of inositol-containing phospholipids, of 1,2-diacylglycerols produced by ischemia, and of free fatty acids liberated during ischemia were quite similar. The amount of stearic acid liberated was much larger than that of arachidonic acid between 30 s and 1 min of ischemia. On the other hand, there was no significant decrease in the amount of the other phospholipids except for phosphatidic acid. Furthermore, there was also no change in the fatty acid composition of phosphatidylcholine or phosphatidylethanolamine throughout 15 min of ischemia. The amount of cytidine-monophosphate reached a peak (36.7 nmol/g wet wt) at 2 min of ischemia. These results indicated that arachidonic acid was predominantly liberated from inositol-containing phospholipids by phospholipase C, and by the diglyceride lipase and monoglyceride lipase system rather than from phosphatidylcholine or phosphatidylethanolamine by phospholipase A2 or plasmalogenase or choline phosphotransferase during the early period of ischemia.

Animals↗
PubMed1979

Characteristics of lipid A-protein complex from endotoxin of Shigella dysenteriae type 1 (S and R strains).

Mild acetic acid hydrolysis of endotoxin (lipopolysaccharide-protein complex) of Shigella dysenteriae type 1 (S and R forms) yielded a lipid A-protein complex that consisted of amino acids, fatty acids, and sugar and, in terms of chemical composition, displayed no marked differences between the S and R forms. Its protein portion (53 to 56%) consisted of at least 16 amino acids. In the fatty acid portion (14 to 18%), myristic, 3-hydroxymyristic, palmitic, and stearic acids accounted for 50%. The sugar portion (10 to 12%) consisted solely of glucosamine. The remainder was unidentified substances, most of which contained phosphorus. Lipid A-protein complexes derived from both S and R forms were not toxic for mice in doses up to 1,000 microgram/mouse, but their Linulus test activity had increased considerably as compared with the starting lipopolysaccharide-protein complex material: from 10(-6) to 10(-10--10(-12) mg/ml. The lipid A-protein complexes were readily soluble in a water solution of triethylamine, in dimethyl sulfoxide, and in pyridine.

Amino Acids↗
PubMed1976

Biosynthesis of triacylglycerols by rat intestinal mucosa in vivo.

The structure of mucosal triacylglycerols was studied in rat intestinal mucosa in vivo during the absorption of a low molecular weight fraction of butter oil and of the corresponding free fatty acids of medium and long chain length. The mucosal lipids were isolated by solvent extraction and the acylglycerol structures were determined by combined AgNO3- thin-layer chromatography and gas-liquid chromatography techniques and stereospecific analysis. Evidence was obtained for a rapid biosynthesis of triacylglycerols from diacylglycerols arising from the operation of both the monoacylglycerol and the phosphatidic acid biosynthetic pathways. Both sn-1,2- and sn-2,3-diacylglycerols appeared to be converted to triacylglycerols at significant rates, but a preferential utilization of sn-1,2-diacylglycerols could not be excluded. Endogenous dilution varied from a miniumum of 5% during triacylglycerol biosynthesis from monoacylglycerols to 15% during their synthesis from free fatty acids, and was characterized by a preferential placement of the endogenous acids in the sn-3 and 2 positions of the triacylglycerol molecules. Exogenous myristic acid was preferentially associated with the sn-3 position, and stearic acid became preferentially bound to the sn-1 position. The complexity of the triacylglycerol end products prevented an exact estimate of the contribution of the phosphatidic acid pathway, but the acylglycerol structures were compatible with a minimum of 20% of total triacylglycerol yield at all times.

Animals↗
PubMed2003

A stearoyl-CoA-specific Delta 9 fatty acid desaturase from the basidiomycete Lentinula edodes.

A gene encoding a Delta 9 fatty acid desaturase (Delta 9-desaturase) was isolated from L. edodes. The open reading frame of this gene (named Le-FAD1) consisted of 1416 bp. The predicted protein of 471 amino acids shares 47-57% sequence identity with Delta 9-desaturases from other fungi. Expression of the Le-FAD1 ORF complemented genetic disruption of the Saccharomyces cerevisiae OLE1 gene (Sc-OLE1). Fatty acid analysis of the Le-FAD1-expressing S. cerevisiae ole1-disrupted strain showed that Le-FAD1 protein had slight activity with palmitic acid (16:0) as the substrate and high activity with stearic acid (18:0). Analysis of transcriptional expression showed that the levels of Le-FAD1 mRNA in the primordium and fruiting body of L. edodes were higher than in mycelia cultivated at 18 degrees C as well as 25 degrees C. These results correlated with the increase of unsaturated fatty acids (UFAs) in total lipids during fruiting-body formation.

Acyl Coenzyme A↗
PubMed2000

Novel approaches for designing 5'-O-ester prodrugs of 3'-azido-2', 3'-dideoxythymidine (AZT).

3'-Azido-2',3'-dideoxythymidine (AZT, 1, zidovudine, RetrovirTM) is used to treat patients with human immunodeficiency virus (HIV) infection. AZT, after conversion to AZT-5'-triphosphate (AZT-TP) by cellular enzymes, inhibits HIV-reverse transcriptase (HIV-RT). The major clinical limitations of AZT are due to clinical toxicities that include bone marrow suppression, hepatic abnormalities and myopathy, absolute dependence on host cell kinase-mediated activation which leads to low activity, limited brain uptake, a short half-life of about one hour in plasma that dictates frequent administration to maintain therapeutic drug levels, low potential for metabolic activation and/or high susceptibility to catabolism, and the rapid development of resistance by HIV-1. These limitations have prompted the development of strategies for designing prodrugs of AZT. A variety of 5'-O-substituted prodrugs of AZT constitute the subject of this review. The drug-design rationale on which these approaches are based is that the ester conjugate will be converted by hydrolysis and/or enzymatic cleavage to AZT or its 5′-monophosphate (AZT-MP). Most prodrug derivatives of AZT have been prepared by derivatization of AZT at its 5'-O position to provide two prominent classes of compounds that encompass: A) 5'-O-carboxylic esters derived from 1) cyclic 5'-O-carboxylic acids such as steroidal 17b-carboxylic acids, 1-adamantanecarboxylic acid, bicyclam carboxylic acid derivatives, O-acetylsalicylic acid, and carbohydrate derivatives, 2) amino acids, 3) 1, 4-dihydro-1-methyl-3-pyridinylcarboxylic acid, 4) aliphatic fatty acid analogs such as myristic acid containing a heteroatom, or without a heteroatom such as stearic acid, and 5) long chain polyunsaturated fatty acid analogs such as retinoic acid, and B) masked phosphates such as 1) phosphodiesters that include monoalkyl or monoaryl phosphate, carbohydrate, ether lipid, ester lipid, and foscarnet derivatives, 2) a variety of phosphotriesters that include dialkylphosphotriesters, diarylphosphotriesters, glycolate and lactate phosphotriesters, phosphotriester approaches using simultaneous enzymatic and chemical hydrolysis of bis(4-acyloxybenzyl) esters, bis(S-acyl-2-thioethyl) (SATE) esters, cyclosaligenyl prodrugs, glycosyl phosphotriesters, and steroidal phosphotriesters, 3) phosphoramidate derivatives, 4) dinucleoside phosphate derivatives that possess a second anti-HIV moiety such as AZT-P-ddA, AZT-P-ddI, AZTP2AZT, AZTP2ACV), and 5) 5'-hydrogen phosphonate and 5'-methylene phosphonate derivatives of AZT. In these prodrugs, the conjugating moiety is linked to AZT via a 5'-O-ester or 5'-O-phosphate group. 5'-O-Substituted AZT prodrugs have been designed with the objectives of improving anti-HIV activity, enhancing blood-brain barrier penetration, modifying pharmacokinetic properties to increase plasma half-life and improving drug delivery with respect to site-specific targeting or drug localization. Bypassing the first phosphorylation step, regulating transport and conferring sustained release of AZT prolong its duration of action, decrease toxicity and improve patient acceptability. The properties of these prodrugs and their anti-HIV activities are now reviewed.

Anti-HIV Agents↗
PubMed1983

[Inhibition of the uterine binding of estrogens by unsaturated fatty acids in immature female rats].

We demonstrate that the interactions between the uterine cytosol proteins of 24 day old Rats and estradiol-17 beta (E2) are significantly influenced by physiological concentrations of non esterified fatty acids (2. 10(-4)M). We show that the specific binding of the hormone to the 8S uterine receptor, is markedly inhibited (50-80%) by the unsaturated fatty acids. The observed inhibition is a function both of acid dose and acid unsaturation degree. The polyunsaturated arachidonic and docosahexaenoic acids are the strongest inhibitors, whereas the saturated palmitic and stearic acids do not displace the E2 from the 8S receptor.

Animals↗
PubMed1980

[10 years - investigations of lipid-metabolism-parameters in the longitudinal study of Leipzig (author's transl)].

As part of the longitudinal gerontological study conducted in Leipzig, cholesterol and the fatty acid spectrum in the serum were determined (by gas chromatography) in 158 cases (46 men, 112 women) at intervals between 2 and 4 years over the period from 1968 to 1978. During the 10-year period the statistical values showed a definite increase in the percentage of cholesterol and linoleic acid. As a result of the significant decrease in the palmitic acid values, the saturated fatty acid percentages as a whole dropped despite an increase in stearic acid. The general trend was toward the elimination of differences between men and women and overweight persons and those with normal weights. There were definite correlations between a reduction in relative weight and a drop or reduced increase of cholesterol on the one hand an increase in linoleic acid on the other. This is most probably due to the fat-reduced and -modified diet to which especially the older test persons changes over during the 10-year period. This diet contained many polyene fatty acids. The changeover can therefore be suspected to lead to antiatherogenic fatty acid constellations in the serum.

Adult↗
PubMed1992

Altered platelet stearic to oleic acid ratio in malignancy.

Alteration of lipid metabolism associated with malignant disease is well-documented and some studies have suggested a reduced stearic to oleic acid ratio occurs in erythrocytes in cancer patients. In this study, the fatty acid composition was measured in platelets, which are capable of lipid synthesis and have a much shorter lifespan. While demonstrating any malignancy related change in the platelet stearic to oleic acid ratio the study aimed to assess whether it could be of value as a tumour marker. Patients with active malignancy (n = 46) had a lower ratio of stearic to oleic acid than those with malignant disease in clinical remission [mean (S.D.) 1.08 (0.22) vs. 1.26 (0.30), P less than 0.01], and 22 healthy controls [1.29 (0.24), P less than 0.001]. However in a group of 17 patients with chronic, non-malignant diseases the ratio was also lower than in normal controls and similar to that seen in the active malignancy group [0.97 (0.29)]. Thus while a reduction in platelet stearic to oleic acid ratio was found in active malignancy, it is not specific to neoplastic disease.

Adolescent↗
PubMed1991

Effects of dietary fatty acids on the early stages of neoplastic induction in the rat pancreas. Changes in fatty acid composition and development of atypical acinar cell nodules.

Diets enriched with fat, especially unsaturated fat, promote experimental pancreatic carcinogenesis, but little is known of the effects of individual fatty acids. The effect of stearic and oleic acid on pancreatic fatty acids and atypical acinar cell nodules (preneoplastic lesions) was studied in 14-day-old weanling male Leeds strain rats (n = 60) given the carcinogen azaserine. Rats were allocated to one of six groups: untreated controls (n = 10), 20% stearic acid diet (n = 10), 20% oleic acid diet (n = 10), carcinogen alone (n = 10), carcinogen plus 20% stearic acid diet (n = 10) or carcinogen plus 20% oleic acid diet (n = 10). Azaserine was administered by intraperitoneal injection in a dose of 30 mg/kg at 2, 3 and 4 weeks of age. When total lipid extracts of pancreas were examined, there was an increase in stearic acid in the stearic acid fed group and an increase in oleic acid in the oleic acid fed group, irrespective of carcinogen treatment. The relative content of all other pancreatic fatty acids was suppressed by feeding oleic acid. At 26 weeks, the number and volumetric indices of pancreatic atypical acinar cell nodules was increased only in rats given azaserine and oleic acid. The enhancing effect of oleic acid on pancreatic carcinogenesis may be associated with pancreatic fatty acid changes.

Animals↗
PubMed1990

Time-course of utilization of [stearic or lignoceric acid]sphingomyelin from high-density lipoprotein by rat tissues.

Utilization of stearic and lignoceric acids supplied by high-density lipoprotein (HDL) sphingomyelin to different tissues was followed for 24 h after rats were injected with HDL containing [[1-14C]stearic (18:0) or [1-14C]lignoceric (24:0) acid [Me-3H]choline]sphingomyelin. Both isotopes reached a maximum in tissue lipids 3-12 h after injection and were recovered mainly in the liver (30%) and small intestine (3%), whereas the other tissues contained approx. 1% or less of the injected dose. All the tissues were able to take up some intact sphingomyelin from HDL and hydrolyze it. In the lung and erythrocytes, the 3H:14C ratio of sphingomyelin remained unchanged throughout the studied period, while an increase in the isotopic ratio was observed in the kidney due to the 3H choline moiety re-used for synthesis of new sphingomyelin. Conversely, the isotopic ratio of sphingomyelin decreased in the liver, indicating a saving of the 14C-labelled fatty acids, especially 24:0. Furthermore, [24:0]ceramide in the liver remained at a high level (6% of the injected dose), whereas [18:0]ceramide decreased to 1%. When the tissues were examined 24 h after injection, the proportion of the 14C linked to sphingomyelin in the total 14C was always higher for both kinds of sphingomyelin than the molar proportion of sphingomyelin in the whole of lipid classes. However, in the majority of the extra-hepatic tissues, more [14C]18:0 than [14C]24:0 was recovered in sphingomyelin, and more 14C radioactivity from 18:0 than from 24:0 was redistributed in the other lipids. The choline moiety from both kinds of sphingomyelin was re-used to synthesize phosphatidylcholine, especially in the liver (up to 20% of the injected dose). All these results show that utilization of sphingomyelin from HDL by tissues normally occurs in vivo and that this phenomenon should be taken into account in the study of the phospholipid turnover of cell membranes. They also show that metabolism of sphingomyelin from HDL in the liver and other tissues is dependent on the sphingomyelin acyl moiety.

Animals↗
PubMed1996

Sympathoadrenergic overactivity and lipid metabolism.

Epidemiological studies have identified high heart rates as a risk factor for coronary heart disease mortality, and heart rate was found to correlate with the severity of coronary atherosclerosis. Heart rate was positively correlated with serum concentrations of total cholesterol, triglycerides, and non-HDL cholesterol. Since heart rate responds sensitively to sympathoadrenergic activity, it was hypothesized that catecholamines play a crucial role in the unfavorable lipid alterations. In addition to influences on circulating lipids, the question arose whether catecholamines have more specific effects on molecular species of structural lipids. Of particular importance is the question of the involvement of catecholamines in the recently suggested correlation between arachidonic acid and stroke mortality. It is therefore attempted to delineate the possible effects of catecholamines on the fatty acid composition of the phospholipids of heart muscle and vasculature. This was achieved in rats by either catecholamine injection or by swimming, a condition known to be associated with marked sympatho-adrenergic stimulation. In swimming rats, linoleic acid was decreased by up to 40% in heart phospholipids, whereas stearic acid and arachidonic acid were increased. Similarly, chronic norepinephrine treatment in rats resulted in a net decrease in linoleic acid and an increase in arachidonic acid and docosahexaenoic acid, which was particularly pronounced when rats were fed an n-3 polyunsaturated fatty acid (PUFA)-rich oil diet. Thus, catecholamines do affect the PUFA composition of heart membranes, mainly through an increase in arachidonic acid content. To further define the action of catecholamines on structural lipids, isolated rat ventricular myocytes in culture were subjected four times to 30 minutes of isoproterenol (10(-6) M) stimulation over 48 hours. No changes in membrane lipid parameters were observed, although the beating rate was increased by 30% during the stimulation. When the cell membranes were enriched in n-3 PUFAs (in association with a decrease in arachidonic acid), the positive chronotropic effect elicited by isoproterenol was raised to + 50%, indicating the modulation of adrenergic function by membrane PUFAs. However, isoproterenol treatment again had no effect on the phospholipid fatty acid composition. Thus, the effect of catecholamines on membrane lipids observed in intact organism appears to be indirect and to involve most probably organs such as the liver and adipose tissue. Catecholamines are expected to induce a lipolysis-linked quantitative and qualitative alteration in circulating fatty acids, which in turn alter the heart membrane composition, similar to the composition changes elicited by diet lipid alterations. Since there is increasing evidence that such fatty acid changes affect the activity of membrane proteins, the possibility emerges that this mechanism may contribute to the catecholamine-linked cardiovascular mortality.

Animals↗
PubMed1996

Fatty acid double bond orientation alters interaction with L-cell fibroblasts.

Relatively little is known of fatty acid specificity in cellular fatty acid uptake. In this study L-cells, a fibroblastic cell line with very low levels of endogenous cytosolic fatty acid binding protein, were used to examine the role of cis and trans unsaturation on fatty acid uptake. The fluorescent fatty acids, trans-parinaric acid and cis-parinaric acid, were used as analogs of straight-chain saturated, and kinked-chain unsaturated fatty acids, respectively, in order to evaluate the fatty acid specificity of the uptake system. Parinaric acid is poorly metabolizable; greater than 97% was unesterified while 3H-oleic acid was almost totally metabolized after 30 min uptake. Cis- and trans-parinaric acid uptake was saturable and dependent on the concentration of fatty acid. However, the initial rate and maximal amount of trans-parinaric acid taken up by the L-cells was greater than for cis-parinaric acid under the same conditions. The affinity of L-cell uptake for trans-parinaric acid (Km = 0.12 uM) was 35-fold higher than that for cis-parinaric acid (Km = 4.17 uM). Based on competition studies with oleic and stearic acids, it was concluded that the cis- and trans-parinaric acid were taken up by the same L-cell fatty acid uptake system. The results suggest that the L-cell fatty acid uptake system has selectivity for straight chain rather than kinked chain unsaturated fatty acids.

Animals↗
PubMed2000

Selective acylation of plasma membrane proteins of Mycoplasma agalactiae: the causal agent of agalactia.

Revealed by in vivo labeling with (14)C-palmitic acid, about 15 acylated proteins were identified in the plasma membrane of Mycoplasma agalactiae (type strain PG2), including the major component p40. Triton X-114 phase partitioning and Western blotting demonstrated the amphiphilic properties of the acyl proteins and showed that they were also antigenic components. Chemical analyses of fatty acids bound to proteins revealed the following selectivity order within acylation: stearic acid (18:0) > linoleic acid (18:2c) approximately palmitic acid (16:0) > oleic acid (18:1c) > myristic acid (14:0), with 16:0 and 18:1c preferred for the O-acylation and 18:0 for the N-acylation. The ratio [O-ester- + amide-bound acyl chains]/O-ester-linked chains being close to 1.4 as well as the presence of S-glycerylcysteine suggest that acyl proteins in M. agalactiae are true lipoproteins containing N-acyl diacyl glycerylcysteine, probably processed by a mechanism analogous to that described for Gram-negative eubacteria.

Acylation↗

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