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PubMed2001

Conjugated linoleic acid isomers have differential effects on triglyceride secretion in Hep G2 cells.

The effect of different conjugated linoleic acid (CLA) isomers (trans-10,cis-12 (t10,c12)-CLA and cis-9,trans-11 (c9,t11)-CLA), compared with oleic acid (OA) and linoleic acid (LA), on hepatic lipid synthesis and secretion were investigated in Hep G2 cells. The cells were incubated in a medium containing 1 mmol/l fatty acid-bovine serum albumin (BSA) complex for 5 h, with BSA alone as control. [(3)H]Glycerol and [(14)C]acetate were used to monitor lipid synthesis and secretion. The results show that cellular uptake rates of these fatty acids were similar. Incubation with OA, t10,c12-CLA, c9,t11-CLA and LA resulted in 6-, 4-, 2- and 1.8-fold increases in intracellular [(3)H]triglyceride ([(3)H]TG) compared with incubation with BSA alone. OA, LA and c9,t11-CLA increased [(3)H]TG secretion 3.6-, 2.5- and 1.2-fold above the control, whereas t10,c12-CLA markedly suppressed the secretion of [(3)H]TG. Hepatic secretion of TG mass increased 3.5-, 3.3-, 2.7- and 1.5-fold in the cells incubated with OA, LA, c9,t11-CLA and t10,c12-CLA, respectively. Since the secreted TG is mainly contained in very low density lipoproteins (VLDL), the decreased ([(3)H])TG secretion by t10,c12-CLA reflects a diminished secretion of VLDL. With respect to cholesterol synthesis OA was more effective in stimulating the incorporation of [(14)C]acetate into cellular total cholesterol followed in descending order by LA, c9,t11-CLA and t10,c12-CLA. In conclusion, the biological properties of 18-carbon fatty acids are clearly influenced by both the number and (geometric) positions of their double bonds. Furthermore t10,c12-CLA is more effective than c9,t11-CLA on suppressing hepatic TG secretion in vitro.

Acetic Acid↗
PubMed1980

[Linoleic acid in nutritional balance: experimental studies].

In the male rat a diet rich in beef fat facilitates the occurrence of hyperinsulinemia after a glucose load whereas fats rich in linoleic acid produce no such effect. The combination of saturated fat and saccharose facilitates the occurrence of hypertriglyceridemia in the male rat, no such effect is produced by the combination of fats rich in linoleic acid and saccharose. Linoleic acid prevents natrium chloride from provoking hypertriglyceridemia in male and in female rats subjected to a diet enriched in saccharose and fat. Estrogen-induced hypertriglyceridemia in castrated animals is strongly inhibited if the diet is rich in linoleic acid. Physical effort can prevent saccharose combined with saturated fats from inducing hypertriglyceridemia.

Animals↗
PubMed1976

The mechanism of immunoinhibition by arachidonic and linoleic acid: effects on the lymphoid and reticulo-endothelial systems.

Subcutaneous injection with certain polyunsaturated fatty acids (PUFA), in particular linoleic acid (C18:2), has recently been shown to prolong the survival of skin allografts in mice and to reduce both primary and secondary cytotoxic responses by isolated spleen cells. In this study we have examined changes in the lymphoid and reticulo-endothelial systems of both grafted and ungrafted mice treated according to the schedules shown to prolong allograft survival. Many of the changes in the lymphoid and reticulo-endothelial systems which can be produced by allografting could also be produced in ungrafted animals by PUFA treatment. These changes included: increased 125IudR uptake by spleen, lymph nodes, and bone marrow, increased spleen and lymph node weight, increased proportion of red pulp and granulocyte precursors in the spleen, and reticulo-endothelial activation as shown by an increased rate of carbon clearance. The combined effects of allografting and C18:2 on peripheral lymph node weight were greater than the effect of either treatment alone, but fell short of the sum of both treatments. Allografting increased 125IudR uptake/unit organ weight, not only in the peripheral lymph nodes, but also in bone marrow, thymus and spleen. When allografted animals were C18:2 treated, this increase was considerably reduced, uptake being little different from that in C18:2 treated ungrafted controls. The number of theta-positive cells in the spleen was markedly increased by a tumor allograft, but such an increase could not be seen in allografted animals when treated with C18:2. Whilst prolonged C18:2 treatment led to destructive changes in the spleen, immunoinhibition could still be demonstrated after shorter treatments with C18:2 when no gross histological evidence for tissue destruction was apparent. Partial reversibility of inhibition of cytotoxic activity of isolated spleen cells could be domonstrated when treatment was discontinued.

Animals↗
PubMed1991

Kinetic analysis of delta-6-desaturation in liver microsomes: influence of gamma-linoleic acid dietary supplementation to young and old rats.

Previous experiments demonstrated the ability-of a gamma-linoleic acid (GLA) dietary supplementation (as evening primrose oil--EPO) to counteract the fall off in delta-6-desaturase (D6D) activity of linoleic acid and alpha-linoleic acid in aged rats. Kinetic parameters of the D6D were determined in order to test the possibility that there may be a significant influence of GLA administration to young and aged rats on the Vm and Km values for 6-desaturation of both the substrates. In young rats GLA supplementation did not affect the kinetic parameters, while in old rats it produced an increase of Vm values of 6-desaturation for both the substrates. Thus the administration of small doses of GLA to old rats might offer substantial protection against the loss of D6D affinity observed in aging, enhancing the capacity of the enzyme itself.

Aging↗
PubMed2000

Involvement of type I and type II mechanisms in the linoleic acid peroxidation photosensitized by tiaprofenic acid.

Analysis of the photomixtures resulting from irradiation of aqueous solutions of linoleic acid sensitized by tiaprofenic acid (TPA) or its major photoproduct (DTPA) by HPLC has shown the formation of all the four possible conjugated dienic hydroperoxides. According to laser flash photolysis experiments the rate constants for hydrogen abstraction from linoleic acid by the excited triplet states of TPA and DTPA are 2 x 10(5) and 3.2x 10(5) M(-1) s(-1), respectively. These data, together with the known rate constants for oxygen quenching of triplet (D)TPA and for the reaction of singlet oxygen with linoleic acid, show that the mechanism is mixed type I/type II. Finally, typical radical scavengers such as BHA and singlet oxygen quenchers such as DABCO and sodium azide are efficient quenchers of the triplet excited state of DTPA. This shows the risk of assigning mechanisms based on indirect 'evidences' using 'specific' additives.

Lasers↗
PubMed1982

Characterization of monohydroxylated lipoxygenase metabolites of arachidonic and linoleic acid in rabbit peritoneal tissue.

Rabbit peritoneal tissue contains a lipoxygenase which converts arachidonic acid preferentially into 15-hydroxy-5,8,11,13-eicosatetraenoic acid. Stereochemical analysis of the menthyloxycarbonyl derivative of this metabolite by means of a high-pressure liquid chromatography method, involving the use of a Ag+ -loaded cation-exchange column, indicated that it has mainly the 15-Ls-hydroxy configuration. The biosynthesis of 15-hydroxy-5,8,11,13-eicosatetraenoic acid could be confirmed during examination of the monohydroxy acids obtained without addition of fatty acids, thus formed from endogenously released substrate. However, the 9-and 13-hydroxy derivatives of linoleic acid were also formed and in quantities exceeding those of 15-hydroxy-5,8,11,13-eicosatetraenoic acid.

Animals↗
PubMed2001

Modulation of prostaglandin H synthase activity by conjugated linoleic acid (CLA) and specific CLA isomers.

Conjugated linoleic acid (CLA) has been shown to inhibit tumorigenesis in animal models and is cytostatic to numerous cell lines in vitro. However, the mechanism of action is unknown. In the current study, we determined the effects of CLA and specific isomers of CLA on the rate of oxygenation of arachidonic acid by prostaglandin H synthase (PGHS) in ram seminal vesicle microsomes. The enzyme was incubated with 0.1 to 100 microM CLA or specific isomers of CLA for 2 min prior to the addition of 44 to 176 microM arachidonate. The isomers tested were 9(E),11(E) CLA; 9(Z),11(E) CLA; 9(Z),11(Z) CLA, and 10(E),12(2) CLA. For a positive inhibitor control, flurbiprofen was used at 0.75 to 2.50 microM. Enzyme activity was assessed by measuring the rate of oxygen consumption. Inclusion of CLA or specific isomers of CLA in the incubation mixtures inhibits PGHS. The efficacy differs for each isomer, with the 9(Z),11 (E) CLA isomer being the most effective and the 9(Z),11 (Z) CLA isomer being the least effective inhibitor among the four CLA isomers tested. The Ki values obtained by Dixon replots range from 18.7 microM for the most effective isomer, 9(Z),11 (E) CLA, to 105.3 microM for the least effective isomer, 9(2),11(2) CLA. The Ki value for flurbiprofen with ram seminal vesicle microsomes was 0.33 microM. As the concentration of arachidonate was increased, the CLA-dependent inhibition of PGHS decreased, suggesting competitive inhibition. The results of this study demonstrate the potential of CLA and specific isomers of CLA to modulate prostaglandin biosynthesis.

Animals↗
PubMed1994

Structure-activity relationship for potentiation of EGF-dependent mitogenesis by oxygenated metabolites of linoleic acid.

Epidermal growth factor induces the oxygenation of linoleic acid in Syrian hamster embryo fibroblasts, and the lipoxygenase-derived products potentiate the mitogenic signal. We have further characterized the linoleate metabolites of growth factor-activated cells by chiral phase HPLC analysis. The primary product was identified as the pure (S) enantiomer of 13-hydroxyoctadecadienoic acid (HODE). In comparison to 13(R)-HODE isomer, only the biologically derived 13(S)-HODE was active in augmenting DNA synthesis as assessed by [3H]thymidine incorporation. To extend these investigations, we defined the structural requirements of analogous lipid compounds necessary for stimulation of mitogenesis in these cells. Carbon-chain length, degree of unsaturation, type of oxidized functionality, position of oxygenated moiety, double-bond geometry, and chirality were all identified as factors that modulate the mitogenic activity of related compounds. The results demonstrate a high degree of specificity for (S)-isomer hydro(pero)xylinoleic acid metabolites in stimulating DNA synthesis and further define the relationship between linoleic acid metabolism and growth-factor-dependent cell growth.

Animals↗
PubMed1970

Effect of diet on linoleic acid desaturation and on some enzymes of carbohydrate metabolism.

The effect of diet on the desaturation of linoleic acid to gamma-linolenic acid by liver microsomal preparations, on blood glucose and insulin levels, and on activities of glucokinase, hexokinase, pyruvate kinase, and alpha-glycerophosphate dehydrogenase have been studied. The female rats used in these experiments were maintained on one of the following dietary regimes: (a) fasted, (b) fasted for 96 hr and refed glucose, (c) balanced diet, (d) carbohydrate-free diet, (e) lipid-free diet, or (f) protein-free diet. Fasting for 96 hr caused a decrease of both linoleic acid desaturation and glucokinase and pyruvate kinase activity together with a slight decrease of the blood insulin level. Alpha-glycerophosphate dehydrogenase activity was not modified. Refeeding of glucose for 50 hr increased the conversion of linoleic acid to linolenic acid as well as the activities of all the enzymes studied except alpha-glycerophosphate dehydrogenase. The increase in desaturation, however, was transient. The feeding of a lipid-free diet did not modify the tested parameters. Feeding a carbohydrate-free diet for 96 hr resulted in increased linoleic acid desaturation but decreased glucokinase and pyruvate kinase activity, thus apparently eliminating a putative correlation between the fatty acid desaturating activity and glycolytic activity or blood insulin levels under these experimental conditions. The findings suggest that dietary proteins may play an important role in determining the level of fatty acid desaturation.

Animals↗
PubMed1975

[Investigations of fat-quality of maize with special consideration of linoleic acid contents (author's transl)].

In the past years the cultivation of maize in the Federal Republic of Germany has been intensified, and with the processing of localy bred maize a production of maize germ oil from German varieties could be expected. In order to maintain certain essential points about the amplitude of variations in the specimen of fatty acids in the localy bred maize, a greater number of maize samples from cultural practice trials (varieties, locations and fertilizer) were taken for the year 1971 and 1972 and their fatty acid composition was analysed. The following results were obtained: 1. Comparared to maize of foreign origin, processed in the Federal Republic of Germany, in most cases the localy bred, has higher contents of linoleic acid and lower contents of oleic acid. Thus the linoleic acid contents of the Germany maize varies between 54.3 and 68.8% while the foreign maize varies between 39.5 and 58.7%. 2. Great differences in quality exist between the local genotypes (varieties). Also clear, but not so great differences are induced by ecological factors, as locations, weather and nutrient supply. The differences of local environment in the linoleic acid content in case of variety "Inrakorn" varies between 60.8 and 64.5%.

Europe, Eastern↗
PubMed1987

Reactions of linoleic acid peroxyl radicals with phenolic antioxidants: a pulse radiolysis study.

Linoleic acid peroxyl radicals (LOO.) can be viewed as model intermediates occurring during lipid peroxidation processes. Formation and reactions of these species were investigated in aqueous alkaline solution using the technique of pulse radiolysis combined with kinetic spectroscopy. Irradiation of linoleic acid in N2O/O2-saturated solutions leads to a mixture of peroxyl radical isomers, whereas reaction of 13-hydroperoxylinoleic acid (13-LOOH) with azide radicals in N2O-saturated solution produces 13-LOO. radicals specifically. These peroxyl radicals cannot be observed directly, but their reactions with the two flavonols, kaempferol and quercetin, acting as radical-scavenging antioxidants, produced strongly absorbing aroxyl radicals (ArO.). The same aroxyl radicals were generated by .OH and N3. with rate constants exceeding 10(9) dm3 mol-1 s-1. Applying a reaction scheme that includes competing generation and decay reactions of both LOO. and ArO. radicals, we derived individual rate constants for LOO. reactions with the phenols (greater than 10(7) dm3 mol-1 s-1), with the aroxyl radicals to form covalent adducts (greater than 10(8) dm3 mol-1 s-1), as well as for their bimilecular decay (3.0 X 10(8) dm3 mol-1 s-1). These results demonstrate the high reactivity of both fatty acid peroxyl radicals and the flavone antioxidants in aqueous solution.

Antioxidants↗
PubMed1996

Attenuation of experimental hypertension by dietary linoleic acid is model dependent.

OBJECTIVE: The purpose of this study was to evaluate the interaction of a linoleic acid enriched diet with NaCl on the development of hypertension in Dahl salt sensitive (Dahl-S) rats and in two-kidney, one-clip Sprague Dawley rats. METHODS: In both experimental models, separate groups of animals were fed either linoleic acid enriched (provided as safflower oil) or control (containing coconut oil) diets for 5 weeks. Diets were further subdivided on the basis of either a low NaCl (0.3%) or a high NaCl (3.0%) content. Tail systolic blood pressure, direct mean intra-arterial pressure, and cardiac output were measured in chronically instrumented, conscious rats. RESULTS: In Dahl-S, on both NaCl intakes, and in two-kidney, one-clip rats on a high NaCl diet, safflower oil had no effect on arterial pressure. In contrast, in two-kidney, one-clip rats fed the low NaCl diet, both indirect tail systolic blood pressures and direct mean arterial pressure were lower (p<0.01) in animals on the linoleic acid enriched diet; total peripheral resistance was also decreased (p<0.01). CONCLUSION: Safflower oil has a hypotensive effect only in the two-kidney, one-clip rat on a low NaCl, but not on a high NaCl intake, and not in Dahl-S rats. Additional studies are required to identify the mechanism(s) for the hypotensive effect of safflower oil and to define the relationship of this animal study to human hypertension.

Animals↗
PubMed1989

The effect of dietary linoleic acid on blood pressure and erythrocyte sodium transport.

The influence of an increase in the polyunsaturated fat linoleic acid on blood pressure and erythrocyte membrane sodium transport was investigated in normotensive first degree relatives of hypertensive patients and controls by the double blind administration of safflower oil or paraffin oil (placebo) capsules for four weeks separated by a four week washout period. Systolic blood pressure fell in the controls with linoleic acid supplementation but there was no significant change in total sodium efflux rate constant. When the pattern of response was compared the changes in supine systolic blood pressure, plasma renin activity, total and ouabain-sensitive sodium efflux rate constant were significantly different in the controls compared to the relatives. These results show that dietary linoleic acid supplementation may have effects on ionic fluxes across cell membranes and cause a modest fall in blood pressure. In addition, since the response to the change in fat intake was different in the relatives and the controls, this provides further evidence of differences in the physicochemical structure of the plasma membrane in hypertensive subjects and their offspring.

Adult↗
PubMed2006

Effect of safflower oil, flaxseed oil, monensin, and vitamin E on concentration of conjugated linoleic acid in bovine milk fat.

Conjugated linoleic acid (CLA) refers to a mixture of conjugated octadecadienoic acids of predominantly ruminant origin. The main isomer in bovine milk fat is the cis-9, trans-11 CLA. Interest in CLA increased after the discovery of its health-promoting properties, including potent anticarcinogenic activity. Two experiments were conducted to evaluate dietary strategies aimed at increasing the concentration of CLA in bovine milk fat. Both experiments were organized as a randomized complete block design with a repeated measures treatment structure. In Experiment 1, 28 Holstein cows received either a control diet or one of 3 treatments for a period of 2 wk. The control diet consisted of 60% forage (barley silage, alfalfa silage, and alfalfa hay) and 40% concentrate on a dry matter (DM) basis, fed as a total mixed ration (TMR). The concentrate was partially replaced in the treatment groups with 24 ppm of monensin (MON), 6% of DM safflower oil (SAFF), or 6% of DM safflower oil plus 24 ppm of monensin (SAFF/M). Average cis-9, trans-11 CLA levels in milk fat after 2 wk of feeding were 0.45, 0.52, 3.36, and 5.15% of total fatty acids for control, MON, SAFF, and SAFF/M, respectively. In Experiment 2, 62 Holstein cows received either a control diet or one of 5 treatment diets for a period of 9 wk. The control diet consisted of 60% forage (barley silage, alfalfa silage, and alfalfa hay) and 40% concentrate on a DM basis, fed as a TMR. The concentrate was partially replaced in the treatment groups with 6% of DM safflower oil (SAFF), 6% of DM safflower oil plus 150 IU of vitamin E/kg of DM (SAFF/E), 6% of DM safflower oil plus 24 ppm of monensin (SAFF/M), 6% of DM safflower oil plus 24 ppm of monensin plus 150 IU of vitamin E/kg of DM (SAFF/ME), or 6% of DM flaxseed oil plus 150 IU of vitamin E/kg of DM (FLAX/E). Average cis-9, trans-11 CLA levels during the treatment period were 0.68, 4.12, 3.48, 4.55, 4.75, and 2.80% of total fatty acids for control, SAFF, SAFF/E, SAFF/M, SAFF/ME, and FLAX/E, respectively. The combination of safflower oil with monensin was particularly effective at increasing milk fat CLA. The addition of vitamin E to the diet partially prevented the depression in milk fat associated with oilseed feeding, but had no significant effect on the concentration of CLA in milk.

Animal Feed↗
PubMed1986

High content of dietary linoleic acid does not reduce platelet reactivity in patients with hyperlipoproteinaemia.

Seventeen patients with hypertriglyceridaemia were given a lipid-lowering diet with a high P/S-ratio 2.1 during a 3-week period. The very low density lipoprotein triglycerides decreased by 43%, low density lipoprotein cholesterol by 19% and high density lipoprotein cholesterol by 12%. There was a marked increase of linoleic acid (18:2 n-6) in all plasma lipid esters with a concomitant decrease of the saturated and monounsaturated fatty acids. There was a slight increase of the linoleic acid metabolites 18:3 n-6, 20:3 n-6 and 20:4 n-6 in serum triglycerides whereas the fatty acids of the n-3 series decreased in all plasma lipid esters. In the platelets a similar pattern was found with an increase of linoleic acid and its metabolite 22:4 n-6 and a decrease of 18:1 n-9 as well as of the n-3 fatty acids. No significant differences in platelet reactivity was found. However, in a few patients there was an increased platelet aggregation after the diet period. Our results suggest that this diet based on a very high content of linoleic acid may not affect platelet reactivity in a beneficial way. The reason may be an increased turnover of arachidonic acid in the platelets or an imbalance between the n-6 and n-3 series of fatty acids.

Adult↗
PubMed1999

Hydrogenated fat high in trans monoenes with an adequate level of linoleic acid has no effect on prostaglandin synthesis in rats.

Our study was designed to determine whether hydrogenated fat high in trans monoenes concentration affected prostaglandin synthesis. Corn oil (CO), butter (B), hydrogenated vegetable oil (HF) and coating fat (CF) were used in this study. These fats were fed to rats for 10 wk at 10 g/100 g diet. The phospholipid (PL) fatty acid content of platelets, aorta and heart was determined by gas liquid chromatography, and the in vitro aorta production of prostacyclin (PGI2) from exogenous or endogenous arachidonic acid (AA) was measured using the radioimmuno-assay (RIA) method. Serum thromboxane B2 (TXB2) released by platelets as thromboxane A2 (TXA2) during incubation of whole blood was also measured by this method. In the group fed CF, AA was significantly lower in the PL of aorta, platelet and heart, and the ratio 20:3(n-9)/20:4(n-6) was greater than in the groups fed CO, B or HF, indicating that the group fed CF was essential fatty acid (EFA) deficient. Although AA was significantly lower in the aorta and platelet PL of the group fed HF compared to the group fed CO, that difference did not affect the amounts of PGI2 or TXB2 produced in these groups. The group fed CF had significantly less PGI2 and TXB2 released by aorta and platelets than the other groups. This was the result of the reduced level of AA and the presence of higher amounts of 20:3(n-9) acid in the PL, which might act as a competitive inhibitor for cyclooxygenase. The aortic production of PGI2 from exogenous AA did not differ among the groups indicating that prostaglandin synthetase was not affected by the dietary fat. We conclude that the consumption of hydrogenated fats high in trans 18:1 acids with adequate amount of linoleic acid had no effect on the amount of thromboxane or prostacyclin produced by platelet or aorta in vitro.

Animals↗