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PubMed1993

[The effect of palmitic, oleic and linoleic acids on thermogenesis in the model experiment in sows].

An animal model experiment was conducted with nine adult sows to study the effects of long-chain fatty acids on thermogenesis when different fatty acids were replaced for 30% of the energy of a basal diet based on cereals and soybean meal. The acids were fed as commercial products containing as main constituent either palmitic acid, oleic acid, or linoleic acid, according to a latin square design in experimental periods 2 to 4. In periods 1 and 5 the sows were submitted to basal diet alone. Digestibility of palmitic acid was only 36%, whereas the unsaturated fatty acids were highly absorbed (90%). Interaction effects of the undigested proportion of the long-chain fatty acids with the basal diet in hindgut fermentation could be ruled out since a supplementary experiment on three sows showed no influence of infusion of oleic or linoleic acid into the caecum on the energy utilization of the basal diet. There was no significant differences in thermogenesis among the fatty acids. Heat production in the treatment periods averaged -1.2% as compared to the basal diet periods. This result was in accordance with the value -1.0% calculated theoretically for the reduction in heat production in the treatment periods. Thus, the data did not indicate any stimulating effect of long-chain fatty acids on heat production, and utilization of energy of fatty acids occurred within the obligatory thermogenesis.

Absorption↗
PubMed2001

The metabolism of linoleic acid in healthy subjects after intake of a single dose of (13)C-linoleic acid.

OBJECTIVE: To investigate the in vivo oxidation of (13)C18:2n-6 and its conversion into longer-chain polyunsaturates (LCPs) in healthy subjects. DESIGN: Blood samples were collected from six subjects before (fasted) and 7, 11 (non-fasted), 24, 48, 72, 168 and 336 h (fasted) after ingestion of a single bolus of 45 mg uniformly labeled (13)C18:2n-6 dissolved in 8 g olive oil. In three subjects, breath was also sampled and CO(2) production measured every hour during the first 12 h. Subjects consumed their habitual diets. Plasma (13)C-enrichments were measured by GC-C-IRMS and fatty acid compositions by GC/FID. SETTING: Maastricht University, Department of Human Biology. SUBJECTS: Three men and three women, recruited by local advertisement. RESULTS: The tracer/tracee ratio (TTR) of C18:2n-6 in plasma total lipids was already increased 5 h after tracer intake. The mean peak amount (+/-s.e.m) of (13)C18:2n-6 (3.4+/-0.8 mg; 7.6% of dose) was found after about 17 h, (13)C18:3n-6 (0.018+/-0.008 mg; 0.04% of dose) after 7-48 h, and (13)C20:3n-6 (0.028+/-0.011 mg; 0.06% of dose) after 48-336 h. Time to peak TTRs of C20:4n-6 varied between subjects and were on average 0.022+/-0.006 mg (0.05% of dose). The proportion of (13)C18:2n-6 recovered in breath after 12 h ranged between 16.8 and 25.1%. CONCLUSIONS: These findings suggest that a single bolus of 45 mg U-(13)C18:2n-6 can be used to study the oxidation of (13)C18:2n-6. However, because of the low TTRs for C20:4n-6, a higher dose is recommended for studying the conversion of (13)C18:2n-6 into LCPs. In addition, since only about 35% of the tracer was found in plasma total lipids and as (13)CO(2) in breath, it might be necessary to study other accessible lipid fractions as well to study the overall conversion of linoleic acid.

Adult↗
PubMed2000

Gas chromatography-high resolution selected-ion mass spectrometric identification of trace 21:0 and 20:2 fatty acids eluting with conjugated linoleic acid isomers.

High-resolution selected-ion recording (SIR) of the exact molecular ion mass was used to confirm unambiguously the presence of conjugated linoleic acid (CLA) derivatives in biological matrices and standard mixtures and to differentiate non-CLA derivatives from CLA derivatives in the CLA region of the gas chromatogram. The success of this method was based on the selectivity of the SIR technique and its sensitivity, which was comparable to that of flame-ionization detection. A minor fatty acid methyl ester (FAME) was identified as methyl heneicosanoate (21:0), and six isomers of 20:2 FAME were found to elute in the CLA region. Isomerization of a standard CLA mixture resulted in a non-CLA flame-ionization response eluting in the CLA region of the gas chromatogram. It is therefore recommended that the identification of minor CLA isomers in natural products or biological matrices should include their direct confirmation by mass spectrometry.

Esters↗
PubMed1975

Enterotoxigenic intestinal bacteria in tropical sprue. IV. Effect of linoleic acid on growth interrelationships of Lactobacillus acidophilus and Klebsiella pneumoniae.

The factors responsible for colonization of the small intestine by enterotoxigenic coliform bacteria in Puerto Ricans with tropical sprue are unknown, but epidemiological observations have suggested that they may be related to an increased dietary intake of long-chain unsaturated fatty acids, particularly linoleic acid, which is known to exert an inhibitory effect on the growth of gram-positive organisms that normally comprise the flora of the small intestine. We have examined, by using a glucose-limited continuous-culture system, what effect this fatty acid exerts on the growth relationships of enteric gram-positive and coliform bacteria. In this system, colonization by an invading strain of Klebsiella pneumoniae was prevented by the presence of an established culture of Lactobacillus acidophilus, principally by virtue of a lowered pH of the medium that was incompatible with Klebsiella growth. However, when the population density of L. acidophilus was reduced by the presence of a sufficient concentration of linoleic acid, the invading K. pneumoniae successfully colonized the system and, once established, suppressed the growth of L. acidophilus. These observations indicate that, under the conditions of our chemostat, gram-positive enteric bacteria suppress coliform growth and that this effect is reversible by the presence of linoleic acid. It remains to be established, however, what pertinence these in vitro observations have to conditions within the intestinal tract of persons living in the tropics.

Enterotoxins↗
PubMed1999

Conjugated linoleic acid inhibits proliferation and induces apoptosis of normal rat mammary epithelial cells in primary culture.

The trace fatty acid conjugated linoleic acid (CLA) inhibits rat mammary carcinogenesis when fed prior to carcinogen during pubertal mammary gland development or during the promotion phase of carcinogenesis. The following studies were done to investigate possible mechanisms of these effects. Using a physiological model for growth and differentiation of normal rat mammary epithelial cell organoids (MEO) in primary culture, we found that CLA, but not linoleic acid (LA), inhibited growth of MEO and that this growth inhibition was mediated both by a reduction in DNA synthesis and a stimulation of apoptosis. The effects of CLA did not appear to be mediated by changes in epithelial protein kinase C (PKC) since neither total activity nor expression nor localization of PKC isoenzymes alpha, beta II, delta, epsilon, eta, or zeta were altered in the epithelium of CLA-fed rats. In contrast, PKCs delta, epsilon, and eta were specifically upregulated and associated with a lipid-like, but acetone-insoluble, fibrillar material found exclusively in adipocytes from CLA-fed rats. Taken together, these observations demonstrate that CLA can act directly to inhibit growth and induce apoptosis of normal MEO and may thus prevent breast cancer by its ability to reduce mammary epithelial density and to inhibit the outgrowth of initiated MEO. Moreover, the changes in mammary adipocyte PKC expression and lipid composition suggest that the adipose stroma may play an important in vivo role in mediating the ability of CLA to inhibit mammary carcinogenesis.

Adipocytes↗
PubMed2000

Trans-vaccenic acid is desaturated to conjugated linoleic acid in mice.

Mice were fed pure trans11 octadecenoic acid (trans-vaccenic acid; TVA) to determine whether it is desaturated to cis9, trans11 octadecadienoic acid, a predominant isomer of conjugated linoleic acid (CLA). In a preliminary trial, 12% of the TVA consumed during a 2-wk feeding period was recovered in the carcass as CLA. As a proportion of TVA in the tissues available for bioconversion, 48.8% was desaturated. We tested whether desaturation could be modified by supplementing no modifier, 0.5% clofibric acid to stimulate desaturation, or increasing the polyunsaturated fatty acids (PUFA) (10% corn oil vs. 4% corn oil) to inhibit desaturation in diets with or without 1% TVA. These diets were fed to six groups of mice in a 3x2 factorial arrangement of treatments. Feeding 1% TVA with 10% corn oil decreased feed intake (2.70 vs. 3.73 g/d, SEM 0.23; P<0.05). Bioconversion of dietary TVA was 12.0, 7.5 and 5.1% for mice fed no modifier of desaturation, clofibrate and increased PUFA, respectively. Conversion based on TVA available for desaturation was 52.6, 55.5 and 37.0%, respectively. Thus, clofibrate did not increase bioconversion, but increasing PUFA decreased conversion by 30%. To test whether TVA decreases food intake directly or after conversion to CLA, four groups of mice were fed diets containing 1% stearic, TVA, elaidic or conjugated linoleic acid. Dietary CLA decreased food intake and body fat, but did not change body protein. CLA was found in the carcass only when TVA or CLA was fed. CLA was found in both triacylglycerol and phospholipids when CLA was fed, but only in triacylglycerol when TVA was fed, suggesting that bioconversion occurred in the adipose tissue. In three trials, conversion of dietary TVA to CLA was 11.4+/-1.25%; conversion of stored TVA was 50.8+/-1.91%. Similar bioconversion of TVA in humans would increase current estimates of CLA available for the general population by 6- to 10-fold.

Administration, Oral↗
PubMed1975

Substitution reactions of linoleic acid hydroperoxide isomerase.

Linoleic acid hydroperoxide isomerase was extracted from corn germ and partially purified by differential centrifugation. This enzyme catalyzed the isomerization of linoleic acid hydroperoxide.(see article) Isomerase also catalyzed the substitution of various reagents at the carbon bearing the hydroperoxide group. These fatty acid products had the following functional groupings: (see article) where X is either oleoyloxy, ethylthio, or methoxy resulting from the presence of oleic acid, ethanethiol, or methanol, respectively. A crude wheat germ extract containing both lipoxygenase and isomerase enzymes reacted with linoleic acid to yield alpha-ketols, gamma-ketols, and a substitution product, the linoleoyloxy ester of alpha-ketol. Characterization of these products from wheat germ enzymes showed that the substitution reaction was not unique to corn germ. Because anions of the reagents tested are typical nucleophiles, the substitution reactions may proceed by a nucleophilic mechanism as mediated by the isomerase enzyme.

Isomerases↗
PubMed2003

Activity and mRNA levels of enzymes involved in hepatic fatty acid synthesis and oxidation in mice fed conjugated linoleic acid.

The effects of dietary conjugated linoleic acid (CLA) on the activity and mRNA levels of hepatic enzymes involved in fatty acid synthesis and oxidation were examined in mice. In the first experiment, male ICR and C57BL/6J mice were fed diets containing either a 1.5% fatty acid preparation rich in CLA or a preparation rich in linoleic acid. In the second experiment, male ICR mice were fed diets containing either 1.5% linoleic acid, palmitic acid or the CLA preparation. After 21 days, CLA relative to linoleic acid greatly decreased white adipose tissue mass but caused hepatomegaly accompanying an approximate 10-fold increase in the tissue triacylglycerol content irrespective of mouse strain. CLA compared to linoleic acid greatly increased the activity and mRNA levels of various lipogenic enzymes in both experiments. Moreover, CLA increased the mRNA expression of Delta6- and Delta5-desaturases, and sterol regulatory element binding protein-1 (SREBP-1). The mitochondrial and peroxisomal palmitoyl-CoA oxidation rate was about 2.5-fold higher in mice fed CLA than in those fed linoleic acid in both experiments. The increase was associated with the up-regulation of the activity and mRNA expression of various fatty acid oxidation enzymes. The palmitic acid diet compared to the linoleic acid diet was rather ineffective in modulating the hepatic lipid levels or activity and mRNA levels of enzymes in fatty acid metabolism. It is apparent that dietary CLA concomitantly increases the activity and mRNA levels of enzymes involved in fatty acid synthesis and oxidation, and desaturation of polyunsaturated fatty acid in the mouse liver. Both the activation of peroxisomal proliferator alpha and up-regulation of SREBP-1 may be responsible for this.

3-Hydroxyacyl CoA Dehydrogenases↗
PubMed1994

Can linoleic acid and gamma-linolenic acid be important in cancer treatment?

This hypothesis proposes that the essential fatty acids (EFAs), linoleic acid (LA) and gamma-linolenic acid (GLA), play important roles in cancer treatment. Oxidation of LA by lipoxidase especially increases tumour cell death, whilst GLA inhibits urokinase-type plasminogen activator (uPA) activity. Increased uPA activity is: firstly, responsible for cancer invasion and metastasis and secondly, responsible for proteolysis of lipoxidase which favours a decrease in cancer cell death. Addition of LA and GLA to available therapeutic regimens may be worth considering in cancer treatment.

Antineoplastic Agents, Phytogenic↗
PubMed1996

Production of hydroxy fatty acid (10-hydroxy-12(Z)-octadecenoic acid) by Lactobacillus plantarum from linoleic acid and its cardiac effects to guinea pig papillary muscles.

Lactobacillus plantarum produced 10-hydroxy-12(Z)-octadecenoic acid (10-OHODA) from linoleic acid. It was suspected that 10-OHODA might be closely related to leukotoxin (9,10-epoxy-12-octa-decenoic acid (LTx)) which was regarded as a toxic and/or defensive substance in living beings. The cardiac effect of 10-OHODA, which was biosynthesized by Lactobacillus plantarum, on an isolated guinea-pig papillary muscle was determined. Its effect on the contractile force of the tissue preparations was examined both in terms of its concentration and the time of exposure. A decrease in muscular tension was observed immediately after administration of 10-OHODA at concentrations of 30, 100, and 300 microM. We also compared the effect of 10-OHODA on muscle tension with that of LTx and its isomer 12,13-epoxy-9-octadecenoic acid (LTx'). Each inhibitory effect on the contractile force of the papillary muscle was statistically significant in the concentration of 300 microM 5 min after administration compared to the control in the absence of each fatty acid, suggesting that 10-OHODA is likely to exert some influence on the circulatory system together with LTx and LTx'.

Animals↗
PubMed1981

Investigation of [14C] linoleic acid conversion into [14C] arachidonic acid and placental transfer of linoleic and palmitic acids across the perfused human placenta.

In five separate experiments in which single placental lobes were perfused, [14C] antipyrine, [3H] dextran and a fatty acid mixture containing [14C] linoleic and [3H] palmitic acids were added to the maternal circuit. Samples of fetal and maternal perfusate, taken at intervals, were analysed for radioactivity and fatty acid content. The relative placental transport rates of antipyrine, linoleic and palmitic acids and the changes in maternal and fetal circuit content of linoleic, palmitic and arachidonic acids were measured. Mean transfer rates of 150, 0.023 and 0.034 mumol min-1 were obtained for [14C] antipyrine, [3H] palmitic and [14C] linoleic acids, respectively. The transfer of [3H] dextran was negligible. The transfer rates of linoleic and palmitic acids did not differ significantly from one another. The maternal circuit content of palmitic and arachidonic acids increased, whereas linoleic acid content decreased. The fetal content of all three acid increased but in the case of arachidonic and palmitic acids the increase was not as great as that seen in the maternal circuit. In no experiment was radioactivity detected in maternal or fetal perfusate arachidonic acid. It is concluded that linoleic and palmitic acids cross the placenta from the maternal to the fetal side. This transfer appears to be non-selective. The large amounts of arachidonic acid that are released into the perfusate probably originate from placental lipids other than free linoleic acid.

Antipyrine↗
PubMedDate not supplied

[Inhibitory effect of linoleyl-hydroxamic acid on the oxidation of linoleic acid by 12-lipoxygenase from porcine leukocytes].

Linoleic acid oxidation by 12-lipoxygenase from porcine leukocytes has been studied as affected by linoleyl-hydroxamic acid. Linoleyl-hydroxamic acid has been found to be an effective inhibitor of porcine leucocyte 12-lipoxygenase. Aerobic preincubation of 12-lipoxygenase with 0.1-6 microM of linoleyl-hydroxamic acid led to a time- and dose-dependent inhibition of the enzyme. The inhibitor's concentration able to induce a 50% loss of the enzyme activity with and without 15-min preincubation were 3.5 and 0.65 microM, respectively. Experimental results obeyed a kinetic scheme, which supposed 2 extra substrate molecules bounding with the enzyme-substrate complex in the presence of linoleyl-hydroxamic acid.

Animals↗
PubMed2002

Nutritional regulation of porcine bacterial-induced colitis by conjugated linoleic acid.

Excessive intake of saturated fatty acids and/or linoleic acid favors the induction of an array of lipid mediators and cytokines enhancing inflammatory responses. Conversely, dietary supplementation with (n-3) fatty acids or vitamin D ameliorates inflammation and autoimmune diseases. Although it was well accepted that conjugated linoleic acid (CLA) prevented diseases with a common inflammatory pathogenesis (i.e., cancer and atherosclerosis), no studies were available on the roles of CLA in mucosal inflammation. The present study was designed to investigate the anti-inflammatory actions and molecular mechanisms underlying the regulation of colonic health by CLA. We hypothesized that colonic inflammation can be ameliorated by dietary CLA supplementation. To test this hypothesis, inflammation of the colonic mucosa was triggered by challenging pigs fed either soybean oil-supplemented or CLA-supplemented diets with an enteric bacterial pathogen (i.e., Brachyspira hyodysenteriae). Immunoregulatory cytokines and peroxisome proliferator-activated receptor-gamma (PPAR-gamma) mRNA expression were assayed in colonic lymph nodes and colon of pigs. Colonic mucosal lesions and lymphocyte subset distribution were evaluated by histology and immunohistochemistry. Supplementation of CLA in the diet before the induction of colitis decreased mucosal damage; maintained cytokine profiles (i.e., interferon-gamma and interleukin-10) and lymphocyte subset distributions (i.e., CD4+ and CD8+), resembling those of noninfected pigs; enhanced colonic expression of PPAR-gamma; and attenuated growth failure. Therefore, CLA fed preventively before the onset of enteric disease attenuated inflammatory lesion development and growth failure.

Animal Nutritional Physiological Phenomena↗
PubMed1993

Effect of dietary alpha-linolenic acid and its ratio to linoleic acid on platelet and plasma fatty acids and thrombogenesis.

The effect of dietary alpha-linolenic acid (18:3n-3) and its ratio to linoleic acid (18:2n-6) on platelet and plasma phospholipid (PL) fatty acid patterns and prostanoid production were studied in normolipidemic men. The study consisted of two 42-d phases. Each was divided into a 6-d pre-experimental period, during which a mixed fat diet was fed, and two-18 d experimental periods, during which a mixture of sunflower and olive oil [low 18:3n-3 content, high 18:2/18:3 ratio (LO-HI diet)], soybean oil (intermediate 18:3n-3 content, intermediate 18:2/18:3 ratio), canola oil (intermediate 18:3n-3 content, low 18:2/18:3 ratio) and a mixture of sunflower, olive and flax oil [high 18:3n-3 content, low 18:2/18:3 ratio (HI-LO diet)] provided 77% of the fat (26% of the energy) in the diet. The 18:3n-3 content and the 18:2/18:3 ratio of the experimental diets were: 0.8%, 27.4; 6.5%, 6.9; 6.6%, 3.0; and 13.4%, 2.7, respectively. There were appreciable differences in the fatty acid composition of platelet and plasma PLs. Nevertheless, 18:1n-9, 18:2n-6 and 18:3n-3 levels in PL reflected the fatty acid composition of the diets, although very little 18:3n-3 was incorporated into PL. Both the level of 18:3n-3 in the diet and the 18:2/18:3 ratio were important in influencing the levels of longer chain n-3 fatty acid, especially 20:5n-3, in platelet and plasma PL. Production of 6-keto-PGF1 alpha was significantly (P < 0.05) higher following the HI-LO diet than the LO-HI diet although dietary fat source had no effect on bleeding time or thromboxane B2 production.(ABSTRACT TRUNCATED AT 250 WORDS)

Adult↗
PubMed1989

Lack of effects of trans fatty acids on eicosanoid biosynthesis with adequate intakes of linoleic acid.

The minimum requirement of linoleic acid to prevent effects of dietary C18 trans fatty acids on eicosanoid biosynthesis in rats was assessed. In a first experiment, six groups of animals were fed diets with a high content of trans fatty acids [20% of energy (en%)], and increasing amounts of linoleic acid (0.4 to 7.1 en%). In a second experiment, four groups of rats were fed diets designed to compare trans fatty acids with saturated and cis-monounsaturated fatty acids of the same chain length at the 2 en% linoleic acid level. After 9-14 weeks the biosynthesis of prostacyclin by pieces of aorta and the biosynthesis of hydroxy-heptadecatrienoic acid and 12-hydroxy-eicosatetraenoic acid by platelets were measured. The fatty acid compositions of aorta phospholipid and platelet lipid were also determined. Both the prostacyclin-production by aorta pieces and the production of hydroxy-heptadecatrienoic acid and 12-hydroxy-eicosatetraenoic acid by platelets appeared to be a linear function of the arachidonic acid level in aorta phospholipid and platelet lipid, irrespective of the trans fatty acid content in the diet. This indicates that trans fatty acids do not directly influence enzymes involved in eicosanoid biosynthesis. In a direct comparison with cis-monounsaturated or saturated fatty acids with 2 en% linoleic acid in the diet, only a moderate reduction in arachidonic acid level in aorta phospholipids in the group fed trans fatty acids was observed. The geometry of the double bond did not influence the arachidonic acid level in platelet lipid, although the diet rich in saturated fatty acids increased arachidonic acid levels significantly compared with all other diets.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1980

Platelet fatty acids and prostaglandin turnover during defined linoleic acid intake with formula diets.

Platelet fatty acids, platelet aggregation and excretion of main urinary metabolites of prostaglandins were investigated in six healthy females under the influence of liquid formula diets providing a linoleic acid supply of 0 g or 50 g per day for three weeks each. With high intake we found an increase of linoleic acid in platelet lipids from 4.5 to 8.3% on average, while dihomogamma-linolenic acid (20:3 w 6) decreased, and arachidonic acid content of platelet lipids was not changed. ADP induced platelet aggregations decreased under high linoleic acid intake to 84 +/- 6 (mean +/- S.D.) percent of control values. This occurred despite enhanced prostaglandin turnover, measured by determination of main urinary prostaglandin metabolites. It seems, therefore, that the influence of high linoleic acid intake on arachidonic acid metabolism is different in platelets and other body tissue.

Adult↗
PubMed1999

Milk yield and composition during abomasal infusion of conjugated linoleic acids in dairy cows.

Conjugated linoleic acids refer to a mixture of positional and geometric isomers of linoleic acid with conjugated double bounds. Three supplements of conjugated linoleic acids which differed in isomer enrichment were infused into the abomasum of lactating dairy cows to determine postruminal effect on milk yield and composition. Four Holstein cows were used in a 4 x 4 Latin square design. Treatments were 3-d abomasal infusion of 1) control, 5 kg of skim milk (carrier for conjugated linoleic acid supplements), 2) conjugated linoleic acid supplement 1 (28.8 g/d; 6.9 g of cis/trans 9,11; 6.4 g of cis/trans 8,10), 3) conjugated linoleic acid supplement 2 (48.5 g/d; 7.1 g of cis/trans 9,11; 4.1 g of cis/trans 8,10; 8.3 g of cis/trans 10,12; 5.5 g of cis/trans 11,13), and 4) conjugated linoleic acid supplement 3 (16.3 g/d; 7.1 g of cis/trans 9,11; 7.2 g of cis/trans 10,12). Infusions increased the conjugated linoleic acids content of milk fat from 0.43 g/100 g of fat for the control treatment to 1.02, 1.52, and 0.95 g/100 g of fat for conjugated linoleic acid supplements 1, 2, and 3, respectively. Apparent efficiency of transfer in milk fat was 25.2, 33.5, 21.0, and 28.4% for cis/trans 8,10, cis/trans 9,11, cis/trans 10,12, and cis/trans 11,13, respectively. Infusion of conjugated linoleic acids had no effect on dry matter intake, milk yield, and milk protein content. However, conjugated linoleic acid supplements reduced the content and yield of milk fat by 28 and 25%, respectively. The similarity of response for the different conjugated linoleic acid supplements did not allow us to identify the specific role of different isomers, but the changes in milk fatty acid composition indicated that effects were primarily on de novo fatty acid synthesis and the desaturation process.

Abomasum↗