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PubMed1998

Prevention of preeclampsia by linoleic acid and calcium supplementation: a randomized controlled trial.

OBJECTIVE: To determine the effect of low doses of linoleic acid and calcium on prostaglandin (PG) levels and the efficacy of this treatment in the prevention of preeclampsia. METHODS: In a randomized, double-blind, placebo-controlled study we treated 86 primigravidas with risk factors for preeclampsia (high biopsychosocial risk [above 3 points], positive roll-over test, and high mean blood pressure [above 85 mmHg)] with daily doses of either 450 mg linoleic acid and 600 mg calcium (n=43) or 450 mg starch and 600 mg lactose placebo (n=43) during the third trimester of pregnancy. RESULTS: Four women in the experimental group (9.3%) developed preeclampsia compared with 16 (37.2%) controls (relative risk 0.25, 95% confidence interval 0.09, 0.69, P < .001). The median serum levels of PGE2 after 4 weeks of treatment increased by 106% in the experimental group (P=.03) and decreased by 33% in the control group (P=.02). The median ratio between thromboxane B2 and PGE2 decreased by 40% in the experimental group (P=.02) and increased by 18% in the control group (P=.14). No significant differences were observed in the median ratio between thromboxane B2 and 6-keto PGF1alpha in either group. No serious maternal or neonatal side effects of treatment occurred in either group. CONCLUSION: The administration of low daily doses of linoleic acid and calcium during the third trimester of pregnancy reduced the incidence of preeclampsia significantly in women at high risk, possibly by correcting the PGE2 levels.

Calcium↗
PubMed1972

The enzymic conversion of linoleic acid into 9-(nona-1',3'-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers.

1. A major component of the lipids in aqueous (pH7.5) homogenates of tuber tissue from Solanum tuberosum was isolated and characterized as 9-(nona-1',3'-dienoxy)non-8-enoic acid. 2. This novel unsaturated ether fatty acid derivative, which contains a butadienylvinyl ether function, has the structure: [Formula: see text] and is formed from linoleic acid by a sequence of enzymic reactions. 3. A precursor of the unsaturated ether derivative is 9-d-hydroperoxyoctadeca-10,12-dienoic acid, formed by the action of S. tuberosum lipoxygenase on linoleic acid. 4. An enzyme that converts the fatty acid hydroperoxide into the unsaturated ether derivative was isolated from S. tuberosum. The pH optimum of this enzyme is approx. 9, although the overall conversion of linoleic acid into the ether derivative is maximal at pH7.5. 5. An unusual feature of this pathway is the insertion of an oxygen atom into the alkyl chain of a fatty acid. 6. This novel mechanism may play a role in the breakdown of polyunsaturated fatty acids to volatile products in plants.

Carbon Isotopes↗
PubMed2003

Conjugated linoleic acid (CLA) inhibits fatty acid synthetase activity in vitro.

This paper describes the in vitro effect of conjugated linoleic acid (CLA) on fatty acid biosynthesis. Among the rat liver enzymes involved in fatty acid biosynthesis, fatty acid synthetase (FAS) showed the largest activity fluctuation with the types of fatty acids. Of the fatty acids, CLA was the most potent inhibitor of FAS, and the 9c, 11t-rather than the 10t, 12c-isomer showed greater inhibition. CLA also significantly lowered the incorporation of [14C]-acetate into phospholipid in breast cancer cells, supporting the view that CLA inhibits fatty acid biosynthesis through the interaction with FAS.

Animals↗
PubMed1993

Continuous measurement of oxygen consumption by linoleic acid membranes exposed to free radicals generated by gamma-radiation.

Vesicles enclosed by membranes prepared from linoleic acid were exposed in the chamber of an oxygen electrode to free radicals generated by 60Co gamma-rays. Oxidation was observed by oxygen consumption, conjugated diene formation, and tri-iodide assay for hydroperoxides. There was a dose-dependent lag period before the onset of rapid peroxidation. The radiation chemical yields (G-values) ranged from 4.45 to 19.37 mu-mol J-1 for maximum rates of oxygen consumption and from 2.18 to 16.37 mumol J-1 for maximum rates of hydroperoxide production when the radiation dose-rate was varied between 5.39 and 0.14 Gy min-1. The magnitudes of these G-values and the linear relationship between yield of hydroperoxide and (dose-rate)1/2 were indicative of a chain mechanism for peroxidation operating in membranes. The lack of congruence between the amount of oxygen consumed and hydroperoxide formed suggested that the oxygen consumed in membrane oxidation led to the formation of oxidized derivatives of linoleic acid additional to the hydroperoxides.

Dose-Response Relationship, Radiation↗
PubMed1996

Dietary (n-9) eicosatrienoic acid from a cultured fungus inhibits leukotriene B4 synthesis in rats and the effect is modified by dietary linoleic acid.

Eicosatrienoic acid (ETrA) is the (n-9) homologue of (n-6) arachidonic acid (AA) and (n-3) eicosapentaenoic acid (EPA). ETrA can be synthesized endogeneously, but tissue levels are normally undetectable except in essential fatty acid (EFA) deficiency. An ETrA-rich oil extracted from a cultured fungus was used to prepare diets which had varying levels of ETrA (0-8 g/kg diet) in combination with one of two levels of linoleic acid (LA, 2.2 or 9.5 g/kg diet). All diets were sufficient in essential fatty acids. Groups of rats were fed these diets for 4 wk after which leucocyte fatty acid content and leukotriene B4 (LTB4) synthesis were measured. The influence of dietary LA on ETrA accumulation in cells was studied and correlations with LTB4 synthesis determined. ETrA was efficiently incorporated into peritoneal exudate cell (PEC) phospholipids with no evident saturation being observed with levels up to 10 mol/100 mol total fatty acids in peritoneal exudate cells. Cellular ETrA levels were lower (P < 0.001) in rats fed the higher level of LA. ETrA accumulation in peritoneal exudate cells correlated (r(2) = 0.63, P < 0.05) with reduced LTB4 synthesis which was attributable to LTA hydrolase inhibition. Thus, dietary ETrA from a biological source can accumulate in leucocytes and suppress inflammatory eicosanoid synthesis. The findings justify further studies into the biochemical and anti-inflammatory effects of dietary ETrA, which could be incorporated into palatable food additives.

8,11,14-Eicosatrienoic Acid↗
PubMed2001

Effect of conjugated linoleic acid on fungal delta6-desaturase activity in a transformed yeast system.

Conjugated linoleic acid (CLA; 18:2), a group of positional and geometric isomers of linoleic acid (LA; 18:2n-6), has been shown to modulate immune function through its effect on eicosanoid synthesis. This effect has been attributed to a reduced production of n-6 polyunsaturated fatty acid (PUFA), the precursor of eicosanoids. Since delta6-desaturase is the rate-limiting enzyme of the n-6 PUFA production, it is our hypothesis that CLA, which has similar chemical structure to LA, interacts directly with delta6-desaturase. A unique and simple model, i.e., baker's yeast (Saccharomyces cerevisiae) transformed with fungal delta6-desaturase gene, previously established, was used to investigate the direct effect of CLA on delta6-desaturase. This model allows LA to be converted to y-linolenic acid (GLA; 18:3n-6) but not GLA to its metabolite(s). No metabolites of CLA were found in the lipids of the yeast transformed with delta6-desaturase. The inability to convert CLA to conjugated GLA was not due to the failure of yeast cells to take up the CLA isomers. CLA mixture and individual isomers significantly inhibited the activity of delta6-desaturase of the transformed yeast in vivo. Even though its uptake by the yeast was low, CLA c9,t11 isomer was found to be the most potent inhibitor of the four isomers tested, owing to its high inhibitory effect on delta6-desaturase. Since CLA did not cause significant changes in the level of delta6-desaturase mRNA, the inhibition of GLA production could not be attributed to suppression of delta6-desaturase gene expression at the transcriptional level.

Fatty Acid Desaturases↗
PubMed1978

Steady-state kinetics of the anaerobic reaction of soybean lipoxygenase-1 with linoleic acid and 13-L-hydroperoxylinoleic acid.

The steady-state kinetics of the anaerobic reaction of soybean lipoxygenase-1 with linoleic acid and 13-L-hydroperoxylinoleic acid were studied. Initial rates of the formation of oxodienoic acids**, absorbing at 285 nm, were measured at pH 10. About 50% of the consumed 13-L-hydroperoxylinoleic acid was converted into oxodienoic acids regardless of the initial ratio of the two substrates. A linear inhibition by both linoleic acid and 13-L-hydroperoxylinoleic acid was observed in the concentration range studied, which is on the upper side limited by the concentrations at which micelle- or acid-soap formation starts. A kinetic scheme is proposed based on one active site in lipoxygenase-1 which alternately binds the two substrates. Values for the kinetic constants were calculated by fitting simultaneously the complete set of data to the appropriate rate equation.

Keto Acids↗
PubMed2002

Oxidized products of linoleic acid stimulate adrenal steroidogenesis.

Adrenal steroidogenesis is under complex control, and clinical observations suggest that not all regulators have been identified. We postulated that fatty acid oxidation products found in the diet or formed in the body could affect steroidogenesis. Linoleic acid is a prominent constituent of animal fat and is readily oxidized. We found that several products of linoleic acid oxidation affect production of aldosterone and corticosterone by isolated cells from rat adrenals. We characterized one linoleic acid derivative by gas chromatography/mass spectrometry. It is 12,13-epoxy-9-oxo-10(trans)-octadecenoic acid ("EKODE"). At concentrations between 1 and 30 microM, EKODE stimulated production of aldosterone by zona glomerulosa cells, but at concentrations above 50 microM, it was inhibitory. In zona fasciculata cells, EKODE stimulated corticosterone production at concentrations of 5 microM or greater, and there was no evidence of inhibition at high concentrations. Stimulation of steroidogenesis was observed after 15 min of incubation and continued for at least 2 hrs. The potential relevance of our findings to the hypertension of obesity is discussed.

Aldosterone↗
PubMed2002

Effect of dietary linoleic acid on the progression of chronic renal failure in rats.

The role of linoleic acid in chronic renal failure (CRF) is controversial. In the present study 21 male Wistar rats submitted to 5/6 renal mass reduction (R) and 16 normal controls (C) were fed a supplement (S) or normal (N) linoleic acid diet for 60 days starting 10 days after CRF. As expected, serum creatinine, cholesterol and triglycerides (mean +/- SEM) were higher in the CRF groups compared to the C groups (P<0.05). The RS group presented lower cholesterol (84 +/- 4 vs 126 +/- 13 mg%) and triglyceride (88 +/- 9 vs 132 +/- 19 mg%) levels compared to the RN group. Proteinuria and kidney weight did not differ between CRF groups. Glomerular area increased 78% in RS and 100% in RN compared to control rats. Glomerular sclerosis index tended to be lower in RS (27%) compared to RN (38%), tubulointerstitial damage was similar between CRF groups (RS = 1.91 +/- 0.2 and RN = 2.14 +/- 0.3), and mesangial fractional volume increased to the same extent in both CRF groups. The data suggest that a linoleic acid-enriched diet did not protect against the progression of CRF after 60 days.

Animals↗
PubMed1998

A linoleic acid enriched diet increases serum cholesterol esterification by lecithin:cholesterol acyltransferase in meal-fed rats.

Dietary fats are known to influence the fatty acid profile of plasma lipids, including phospholipids which are substrates of lecithin:cholesterol acyltransferase (LCAT; EC 2.3.1.43), an important enzyme in lipoprotein metabolism. We tested whether the dietary fatty acid profile has an effect on LCAT activity in an animal model. Rats were conditioned to eat two meals per day, which were enriched in either palmitic, oleic or linoleic acids, for 10 weeks. Serum was isolated from blood samples taken prior to the meal. The LCAT activity was determined in two ways: (1) by measuring serum cholesterol esterification rates, which are an estimate of LCAT action on endogenous lipoproteins, and (2) by measuring serum LCAT activity levels with excess exogenous substrates, an estimate of LCAT mass. Animals receiving the linoleic acid diet had lower serum concentrations of unesterified cholesterol and triglycerides, if compared with animals fed oleic acid or palmitic acid diets (p < 0.05). Serum LCAT activity levels (measured with excess exogenous substrates) were not different, but both the absolute and fractional rates of cholesterol esterification were highest on the linoleic acid rich diet (p < 0.01), showing that LCAT action on endogenous lipoproteins is improved. No differences were found in serum apolipoprotein B and A-IV concentrations between the dietary groups. Apolipoprotein A-I levels were lowest in the palmitic acid group (oleic and linoleic > palmitic; p < 0.05), and apolipoprotein E levels were highest in the palmitic acid group (palmitic > oleic and linoleic; p < 0.05). It is concluded that a linoleic acid rich diet may cause increased metabolism of serum cholesterol by LCAT in rats. This effect is not due to elevated serum concentrations of LCAT or of its apolipoprotein activators, but most likely to changes in the chemical composition of endogenous lipoprotein substrates. It remains to be established whether the serum cholesterol esterification rates measured in vitro are related to in vivo rates of reverse cholesterol transport.

Animal Feed↗
PubMed1998

Dietary oxidized cholesterol modulates cholesterol metabolism and linoleic acid desaturation in rats fed high-cholesterol diets.

The interactive effect of high dietary levels of oxidized cholesterol on exogenous cholesterol and linoleic acid metabolism was examined in male 4-wk-old Sprague-Dawley rats given high-cholesterol diets. The rats were pair-fed purified diets free of or containing either 0.5% cholesterol alone or both 0.5% cholesterol and 0.5% oxidized cholesterol mixture (containing 93% oxidized cholesterol) for 3 wk. Hepatic 3-hydroxy-3-methylglutaryl CoA reductase activity was reduced in rats given cholesterol alone or both cholesterol and oxidized cholesterol. However, hepatic cholesterol 7alpha-hydroxylase activity was lowered only when rats were given both cholesterol and oxidized cholesterol, although dietary cholesterol increased this activity. Reflecting this effect, acidic steroid excretion was lowest among the groups of rats given cholesterol and oxidized cholesterol. On the other hand, the activity of hepatic delta6 desaturase, a key enzyme in the metabolism of linoleic acid to arachidonic acid, was increased in rats given both cholesterol and oxidized cholesterol, although dietary cholesterol alone lowered its activity. As a result, the delta6 desaturation index, 20:3n-6 + 20:4n-6/18:2n-6, in liver and serum phospholipids tended to be higher in the group fed both cholesterol and oxidized cholesterol than in the one fed cholesterol alone. Thus, dietary oxidized cholesterol significantly modulated exogenous cholesterol metabolism and promoted linoleic acid desaturation even when it was given at high levels together with a high cholesterol diet.

Animals↗
PubMed1991

Insect tissues, not microorganisms, produce linoleic acid in the house cricket and the American cockroach.

Biosynthesis of linoleic acid, 18:2 (n-6), was unambiguously demonstrated to occur in the cockroach, Periplaneta americana, and the cricket, Acheta domesticus. Axenic tissue from both of these insect species was demonstrated by radio-gas-liquid chromatography (radio-GLC) and radio-high-performance liquid chromatography (radio-HPLC) to incorporate [1-14C]acetate and [1-14C]oleate into this essential fatty acid.

Animals↗
PubMed1989

Utero-placental transfer of octanoic, palmitic and linoleic acids during late gestation in gilts.

The transfer across the swine uterus and placenta of [1-14C]octanoic acid, [9,10(n)-3H]palmitic acid and [1-14C]linoleic acid was studied in five gilts and their fetuses during late gestation following a single bolus injection. Only trace amounts of labeled fatty acids were found in fetal plasma lipid. The highest fetal plasma lipid values were less than 1.2% of the peak maternal values. The concentration of plasma free fatty acids (FFA) and fatty acid profiles in the umbilical artery (FA) and vein (FV) and uterine artery (UA) and vein (UV) were compared. There were no measurable umbilical arterio-venous differences. Concentrations of FFA in FA and FV were about 40% of the UA and UV values (187, 194, 73, 82 microEq/liter for UA, UV, FA and FV, respectively). Fetal plasma contained larger amounts of 14:0, 16:1, 18:1 and 20:4, whereas maternal plasma contained larger amounts of 18:0 and 18:2. There was difference between fetal and maternal plasma for 16:0 and 18:3; the latter was present only in minute amounts. In conclusion, only trace amounts of FFA cross the swine placental tissues during late gestation; therefore, their contribution to fetal energy supply or lipid storage appears limited.

Animals↗
PubMed1994

Dietary alpha-linolenic and linoleic acids competitively affect metabolism of polyunsaturated fatty acids in Arctic charr (Salvelinus alpinus).

We investigated the effects of various levels of dietary 18:2(n-6) (linoleic acid) and 18: 3(n-3) (alpha-linolenic acid) on the growth, feeding, body composition and metabolism of polyunsaturated fatty acids in liver and muscle of Arctic charr. Fish were fed 8 or 12 casein-based semipurified diets in two separate experiments for 12 or 14 wk, respectively. Low levels of dietary 18:2(n-6) and 18:3(n-3) supplemented with pure methyl esters or linseed (flax) oil had an additive effect on fish growth. For each 100 g of diet, the addition of 1.6-1.7 g of 18:3(n-3) and 2.6 g of 18:2(n-6) led to significantly lower fish growth compared with the treatment diets with lower amounts of 18:2(n-6). Whereas 18:2(n-6) was converted to 20:4(n-6) and 22: 5(n-6) in the absence or presence of dietary 18: 3(n-3), the dominant product of 18:3(n-3) conversion was consistently 22:6(n-3). High levels of dietary 18: 3(n-3) markedly inhibited the conversion of 18:2(n-6), whereas the inhibition of dietary 18:2(n-6) on 18: 3(n-3) conversion was noted only when the ratio of dietary 18:2(n-6) to 18:3(n-3) changed from 1.0 to 1.5. Feeding diets rich in 18:3(n-3) led to a marked accumulation of 18:3(n-3) and 18:4(n-3) in fish muscle but a negligible change in 20:5(n-3) and 22:6(n-3), regardless of the level of 18:3(n-3) in the diets.

Animals↗
PubMed2002

Conjugated linoleic acid in combination with supplemental dietary fat alters pork fat quality.

Interest in fortification of human foods, including pork, with conjugated linoleic acid (CLA) is growing and may provide benefits as a neutraceutical based on research evaluating CLA as an anticarcinogen, immune modulator, antiatherogenic agent and a body composition modulator. This study evaluated the combined effects of dietary CLA and supplemental fat source on growth, fatty acid composition and belly quality of lean genotype gilts (n = 144). Pigs (49.3 kg) were randomly assigned to six diets (3 x 2 factorial) varying in supplemental fat (none, 4 g/100 g yellow grease or 4 g/100 g tallow) and linoleic acid [1 g/100 g corn oil (CO) or 1 g/100 g CLA (CLA-60)] for 47 d. Both the cis-9, trans-11 and the trans-10, cis-12 isomers of CLA were increased in belly and longissimus fat depots from pigs fed CLA, and that increase was up to 92% greater when CLA was fed with 4 g/100 g supplemental fat (fat source x linoleic acid interaction, P < 0.05). Pigs fed CLA had a greater concentration of 18:0 and less 18:1 cis-9 (P < 0.01) in various fat depots, suggesting a reduction in Delta(9) desaturase activity. The iodine value of belly fat from pigs consuming tallow and CLA combined was reduced to 62.0 from an initial value of 70.4. CLA supplementation also increased belly weights (P < 0.05). CLA did not affect longissimus muscle area, backfat depth and the percentage of fat-free lean (P > 0.10), but it increased the subjective intramuscular fat score by 18.8% (P < 0.01). In conclusion, CLA enrichment of pork products may be enhanced when combined with additional supplemental dietary fat, and together with tallow can be used to increase the saturated fatty acid content of pork.

Adipose Tissue↗
PubMed2004

Oxidation rate of conjugated linoleic acid and conjugated linolenic acid is slowed by triacylglycerol esterification and alpha-tocopherol.

We have recently shown that alpha-eleostearic acid (alpha-ESA), a conjugated linolenic acid, has a stronger antitumor effect than conjugated linoleic acid (CLA), both in vitro and in vivo. In this study, the oxidative stability of alpha-ESA was examined compared with linoleic acid (LA), alpha-linolenic acid (LnA), and CLA. Thin layers of the FA (LA, 9Z,11 E-CLA, 10E,12Z-CLA, LnA, and alpha-ESA) were auto-oxidized at 37 degrees C, and the FA remaining, the absorbed oxygen volume, the lipid hydroperoxide content, and the TBARS content were determined. The oxidation rate of alpha-ESA was faster than that of the unconjugated FA and CLA (9Z, 11 E-CLA and 10E, 12Z-CLA). However, the lipid hydroperoxide and TBARS contents following alpha-ESA oxidation were low, suggesting production of only small amounts of rapid-reacting secondary oxidation products. Furthermore, the oxidative stability of conjugated FA (CLA and CLnA) in which the carboxylic acid group was esterified with triacylglycerol was greater than that of the FFA. Addition of an antioxidant (alpha-tocopherol) also increased the stability of the conjugated FA to a level similar to that of the unconjugated FA.

Esterification↗
PubMed1987

Effect of maternal dietary linoleic acid and trans-octadecenoic acid on the fatty acid composition and prostaglandin content of rat milk.

The effects of seven levels of dietary linoleic acid (18:2), with and without trans-octadecenoic acid (18:1t), on the fatty acid composition and prostaglandin content of milk were investigated in lactating rat dams. At parturition, 14 groups of 4 rats each were fed diets containing 20% fat, with mixtures of coconut and safflower oils providing seven concentrations of 18:2 ranging from 3.6 +/- 0.5 to 44.5 + 2.3% of total fatty acids. Hydrogenated soybean oil was added such that 18:1t comprised 10.3 +/- 0.3% of total fatty acids. Milk samples were collected on day 12 postpartum for prostaglandin analyses and on day 16 for fatty acid analyses. The relationship of dietary 18:2 to milk 18:2 was linear (r = 0.98; P = 0.0001), with milk 18:2 ranging from 2.6 +/- 0.1% of total fatty acids at the lowest level of dietary 18:2 to 27.9 +/- 1.6% at the highest. Milk 18:1t was highly correlated (r = 0.99; P = 0.0001) with the amount of dietary 18:1t. In rats fed hydrogenated fat, milk 18:1t averaged 7.0 +/- 0.2% of total fatty acids. Transfer from diet to milk was 46.4 +/- 4.2% for 18:2 and 37.5 +/- 1.7% for 18:1t. Mean concentrations of prostaglandin F2 alpha and E in rat milk were 269 +/- 16 pg/mL and 477 +/- 24 pg/mL respectively. There were no significant differences in the concentrations of either prostaglandin relative to 18:1t consumption at any level of 18:2.

Animals↗
PubMed2002

Conjugated linoleic acid depresses the delta9 desaturase index and stearoyl coenzyme A desaturase enzyme activity in porcine subcutaneous adipose tissue.

Conjugated linoleic acid (CLA) has been shown to have an effect on subcutaneous fatty acid composition and has been reported to decrease stearoyl coenzyme A desaturase (SCD) activity by decreasing mRNA expression and(or) catalytic activity in rodents and rodent cell lines. This investigation was designed to study the effects of CLA, corn oil, or beef tallow supplementation on s.c. adipose tissue fatty acid composition, adiposity, SCD enzyme activity, and the delta9 desaturase index in piglets. Eighteen crossbred barrows 16 to 18 d of age were adapted to diet for 1 wk and then assigned randomly to one of three treatments: 1.5% added CLA, 1.5% added corn oil, or 1.5% added beef tallow. Barrows were penned individually and fed the supplemental oils for 35 d (to 25.6 +/- 0.6 kg BW). Subcutaneous adipose tissue samples were obtained after slaughter. Fatty acid composition of the s.c. adipose tissue differed for each fatty acid measured due to diet with the exception of 18:3. The concentrations of CLA trans-10, cis-12 and cis-9, trans-11 were elevated from nondetectable to 1.62 and 2.52 g/100 g lipid, respectively (P < 0.001 for both isomers). Conjugated linoleic acid decreased the delta9 desaturase index (P < 0.01) and SCD enzyme activity, expressed as nanomoles of palmitate converted to palmitoleate/(7 min x g of tissue) (P = 0.075) and nanomoles of palmitate converted to palmitoleate/(7 min 105 cells) (P= 0.056). Tallow-fed pigs had a greater proportion of large adipocytes (> 700 pL) and the greatest SCD activity. These data provide the first direct evidence that dietary CLA depresses SCD enzyme activity in porcine adipose tissue, which may in part be responsible for the depression of adiposity by CLA observed by others in market weight pigs.

Adipocytes↗