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PubMed1985

An altered ratio of 18:2 (9,11) to 18:2 (9,12) linoleic acid in plasma phospholipids as a possible predictor of pre-eclampsia.

As a part of a larger study, 15 healthy primigravidas were studied from 28 weeks gestation until 3 days after deliver. In 6 of these women pre-eclampsia (PET) developed; the remaining 9 subjects, who were age matched had normal pregnancies. Plasma phospholipid-esterified 18:2(9,11):18:2(9,12)fatty acids were measured by high performance liquid chromatography (HPLC). The ratio of 18:2(9,11):18:2(9,12)linoleic acid was significantly higher in the PET group than in the normotensive group at 28 weeks' gestation--that is before the onset of symptoms and signs of PET. The ratio remained significantly higher in the PET group than in the normotensive group until deliver, except at 30 weeks when the difference between the ratios just failed to reach statistical significance. It is suggested that measurement of the ratio of 18:2(9,11) to 18:2(9,12)linoleic acid in plasma phospholipids may be useful as a predictor of the likely development of PET.

Chromatography, High Pressure Liquid↗
PubMed1983

Negative Ames tests of epoxide fatty methyl esters derived from hemolysis of linoleic acid hydroperoxides.

Five isomeric epoxyhydroxyene and epoxyoxoene fatty esters derived from hemolytic decomposition of linoleic acid hydroperoxide were tested for mutagenicity by the "Ames' top-agar incorporation method using S-9 mix derived from livers of male rats pretreated with Aroclor 1254. The epoxide fatty esters tested--methyl trans-12,13-epoxy-erythro-11-hydroxy-cis(trans)-9-octadecenoate and methyl trans-12,13-epoxy-threo-11-hydroxy-cis(trans)-9-octadecenoate (each composed of approximately 80% cis-9-ene and 20% trans-9-ene), methyl trans-12,13-epoxy-9-oxo-(trans-10-octadecenoate, methyl trans-12,13-epoxy-9-hydroxy-trans-10-octadecenoate and methyl cis-12,13-epoxy-9-oxo-trans-10-octadecenoate--had structural characteristics similar to certain potent mutagens. However, these esters were not mutagenic in Salmonella typhimurium strains TA100, TA98 or TA1537 at concentrations up to 2000 micrograms/test plate. Under the same test conditions, the methyl ester of hydroperoxy linoleic acid, from which these epoxides were derived, was weakly mutagenic in strain TA100 and possibly also in strain TA98.

Animals↗
PubMed2001

Dietary conjugated linoleic acid alters fatty acid composition of pig skeletal muscle and fat.

The dietary dose responsiveness of conjugated linoleic acid (CLA) addition relative to the fatty acid profile of edible lean tissue was examined in grower pigs treated with or without porcine somatotropin (pST). Gilts and barrows were fed CLA at 0, 0.25, 0.5, 1.0, or 2.0% of diet by weight from 20 to 55 kg BW. Additional pigs were administered (pST) at 0 or 100 microg x kg BW x d(-1) and fed either 0.5 or 2.0% CLA. Animals were fed diets containing 18% CP, 1.2% lysine, and 3.5 Mcal of DE/kg at 110% of ad libitum intake. The fatty acid profile in latissimus dorsi and dorsal s.c. adipose tissue samples was determined by gas chromatography. Dietary CLA replacement of corn oil increased the percentage of total fatty acids as stearic acid, whereas the percentages as oleic and linolenic acids were reduced in lattisimus muscle. Treatment with CLA + pST increased the percentages of linoleic and arachidonic acids while reducing the percentages of palmitic and oleic acids in lattisimus muscle. Dietary CLA increased the percentages of palmitic and stearic acids in s.c. adipose tissue while reducing the percentages of oleic, linoleic, linolenic, and arachidonic acids. The percentage of palmitic acid was reduced in s.c. adipose tissue, whereas linoleic acid was increased with CLA + pST. No synergistic effect was detected between CLA and pST for reducing carcass lipid content in grower pigs. However, pST increased the percentage of polyunsaturated fatty acids in lattisimus muscle and s.c. adipose tissue while reducing the percentages of saturated fatty acids in swine fed CLA.

Adipose Tissue↗
PubMed2000

Peroxynitrite mediated linoleic acid oxidation and tyrosine nitration in the presence of synthetic neuromelanins.

Peroxynitrite-mediated linoleic acid oxidation and tyrosine nitration were analysed in the presence of synthetic model neuromelanins: dopamine (DA) -melanin, cysteinyldopamine (CysDA) -melanin and various DA/CysDA copolymers. The presence of melanin significantly decreased the amount of 3-nitrotyrosine formed. This inhibitory effect depended on the type and concentration of melanin polymer. It was found that incorporation of CysDA-derived units into melanin attenuated its protective effect on tyrosine nitration induced by peroxynitrite. In the presence of bicarbonate, the melanins also inhibited 3-nitrotyrosine formation in a concentration dependent manner, although the extent of inhibition was lower than in the absence of bicarbonate. The tested melanins inhibited peroxynitrite-induced formation of linoleic acid hydroperoxides, both in the absence and in the presence of bicarbonate. In the presence of bicarbonate, among the oxidation products appeared 4-hydroxynonenal (HNE). CysDA-melanin inhibited the formation of HNE, while DA-melanin did not affect the aldehyde level. The results of the presented study suggest that neuromelanin can act as a natural scavenger of peroxynitrite.

Aldehydes↗
PubMed2001

Regulation of stearoyl-CoA desaturase activity by the trans-10,cis-12 isomer of conjugated linoleic acid in HepG2 cells.

Stearoyl-CoA desaturase (SCD) catalyzes the rate-limiting step in the cellular synthesis of monounsaturated fatty acids mainly oleate (C18:1) and palmitoleate (C16:1) which are the major monounsaturated fatty acids of membrane phospholipids, cholesterol esters, waxes, and triglycerides. Several SCD isoforms exist in the mouse whereas the human has one well-characterized SCD gene. The trans-10,cis-12 isomer of conjugated linoleic acid has been previously shown to repress the expression of the mouse SCD1 gene isomer by decreasing SCD gene expression as well as by direct inhibition of SCD enzyme activity. We studied the regulation of human stearoyl-CoA desaturase (SCD) expression by conjugated linoleic acid (CLA) in cultured human hepatoblastoma cell line, HepG2. Treatment of the cells with the trans-10,cis-12 CLA isomer did not cause changes in the SCD gene transcription, mRNA and protein levels. However, this isomer decreased both the SCD activity as well as the levels of monounsaturated fatty acids. The other major CLA isomer, cis-9,trans-11 CLA, had no effect on SCD gene expression and activity. These results suggest that in HepG2 cells the trans-10,cis-12 CLA isomer regulates human SCD activity mainly by a posttranslational mechanism.

Fatty Acids, Monounsaturated↗
PubMed2006

Brain elongation of linoleic acid is a negligible source of the arachidonate in brain phospholipids of adult rats.

The extent to which the adult brain can derive some of its arachidonic acid (AA) through internalized synthesis from linoleic acid (LA) is uncertain. Thus, we determined for plasma-derived LA in vivo rates for brain incorporation, beta-oxidation, and conversion to AA. Adult male unanesthetized rats, reared on a diet enriched in LA but low in AA, were infused intravenously for 5 min with [1-(14)C]LA. Timed arterial samples were collected until the animals were killed at 5 min and the brain was removed after microwaving. Within plasma lipids, >96% of radioactivity was in the form of unchanged [1-(14)C]LA, but [(14)C]AA was insignificant (<0.2%). Eighty-six percent of brain radioactivity at 5 min was present as beta-oxidation products, whereas the remainder was mainly in 'stable' phospholipid or triglyceride as LA or AA (11 and <1%, respectively). Unesterified unlabeled LA rapidly enters brain from plasma, but its incorporation into brain total phospholipid and triglyceride, in the form of synthesized AA, is <1% of the amount that enters the brain. Thus, in rats fed even a diet containing low amounts of AA, the LA that enters brain is largely beta-oxidized, and is not a major source of AA in brain.

Animals↗
PubMed2003

A Mucor rouxii mutant with high accumulation of an unusual trans-linoleic acid (9c,12t-C18:2).

Genetic and biochemical approaches reveal the existence of a gamma-linolenic acid biosynthetic pathway in Mucor rouxii. By treatment with ultraviolet light, combined with low temperature cultivation and filtration enrichment, a mutant defective in polyunsaturated fatty acid synthesis was isolated. Genetic analysis and fatty acid supplementation indicate that the defect occurred in the Delta(12)-desaturation resulting in the absence of cis-linoleic acid and gamma-linolenic acid and in the accumulation of monounsaturated fatty acids. In addition, an unusual fatty acid, trans-linoleic acid (9c,12t-C18:2), which has not been reported previously in this fungus, was found to increase in the mutant. The information gained from the mutant was used to develop the hypothetical pathway of fatty acid desaturation in M. rouxii.

Fatty Acid Desaturases↗
PubMedDate not supplied

Effects of dexamethasone and linoleic acid on hepatic secretion of biliary lipids and anionic polypeptide factor: In vivo and in vitro studies.

Synthetic glucocorticoids, such as dexamethasone, and diets enriched with unsaturated fatty acids have been shown to stimulate hepatic bile salt synthesis. This fact led us to investigate the effects of dexamethasone and linoleic acid supplementation on bile secretion. Cholesterol (Ch) and phospholipid secretions are bile acid dependent. Ch and phospholipid in bile are also highly bound to a small apoprotein, the anionic polypeptide factor (APF). In bile, APF may play a physiological role in stabilizing cholesterol:phospholipid vesicles and might also be important in the regulatory process of bile lipid secretion. In order to study the factors influencing bile secretion, the biliary secretion rates of bile lipids and APF were experimentally modulated in perfused rat liver (PRL) and HepG2 cells. As expected, dexamethasone induced an increase in the biliary secretion rate of bile salts (BS) in the two models (PRL: 34 up to 67 nmol/l/min/g liver; HepG2 cells: 234% vs. 100% in controls). The bile secretion rates for phospholipids (PRL: from 5 down to 1.5 nmol/l/min/g liver; HepG2 cells: 93 vs. 100% in controls) and APF (PRL: from 0.34 down to 0.12 microg/l/min/g liver; cells: 86 vs. 100% in controls) rapidly decreased independently from those of BS. The data from experimental cell models supplemented with linoleic acid indicated a correlation between the BS and APF levels (APF: 71 and 63%; BS: 161 and 197% vs. 100% in controls). The phospholipid level was regulated independently from that of APF and BS and increased (106 and 111% vs. 100% in controls), while Ch remained nevertheless unchanged. Our data showed that dexamethasone induced changes in bile and that linoleic acid clearly impaired the regulation exerted by the dexamethasone on bile lipids.

Animals↗
PubMed2000

The effect of nonstructural carbohydrate and addition of full fat extruded soybeans on the concentration of conjugated linoleic acid in the milk fat of dairy cows.

Conjugated linoleic acid (CLA), a naturally occurring anticarcinogen found in dairy products, is a byproduct of incomplete ruminal biohydrogenation of unsaturated fatty acids. Our objective was to determine the effect of nonstructural carbohydrate sources, addition of full fat extruded soybeans as a source of unsaturated fatty acids, and possible interactions on the milk fat content of CLA. Cows (n = 20) were assigned to a 4 x 4 Latin square involving two sources of nonstructural carbohydrate, high starch (corn) or high pectin (citrus pulp), with or without addition of extruded soybeans. Milk yield was not affected by nonstructural carbohydrate source, but milk production was increased by 7.8 to 10.5% with dietary additions of extruded soybeans. Milk fat content did not differ between treatments, but fatty acid composition was affected. Cows fed extruded soybean diets had reduced concentrations of C8 to C16 fatty acids and increased concentrations of octadecenoic acids. Diets with extruded soybeans also resulted in more than a doubling in milk fat concentration and yield of CLA. Nonstructural carbohydrate source had only minor effects on CLA, and there was no interaction with extruded soybeans. Milk fat content of trans-C18:1 and CLA were closely related (r2 = 0.77). However, variation among cows was about threefold for each of the diets and rank order of individual cows differed among diets. Overall, we demonstrated that diet modification can be used to alter CLA content of milk fat, but there was substantial individual cow variation for all diets.

Animal Feed↗
PubMed2001

The growth inhibitory effect of conjugated linoleic acid on a human hepatoma cell line, HepG2, is induced by a change in fatty acid metabolism, but not the facilitation of lipid peroxidation in the cells.

We investigated the growth inhibitory effect of conjugated linoleic acid (CLA) on HepG2 (human hepatoma cell line), exploring whether the inhibitory action occurs via lipid peroxidation in the cells. When the cells were incubated up to 72 h with 5-40 microM of CLA (a mixture of 9c,11t-18:2 and 10t,12c-18:2), cell proliferation was clearly inhibited in a dose and time dependent manner but such an inhibition was not confirmed with linoleic acid (LA). In order to evaluate the possible contribution of lipid peroxidation exerted by CLA to cell growth inhibition, alpha-tocopherol (5-20 microM) and BHT (1-10 microM) as potent antioxidants were added to the medium with CLA (20 microM), which did not restore cell growth at all. Furthermore, after 72 h incubation, the membranous phospholipid hydroperoxide formation in the CLA-supplemented cells was suppressed respectively to 25% and 50% of that in LA-supplemented cells and control cells. No difference was observed by a conventional lipid peroxide assay, the TBA test, between CLA-supplemented cells and LA-supplemented cells. Although the cellular lipid peroxidation was not stimulated, lipid contents (triacylglycerol, total cholesterol and free cholesterol) and fatty acid contents (palmitic acid, palmitoleic acid and stearic acid) markedly increased in CLA-supplemented cells compared with LA-supplemented and control cells. Moreover, supplementation with 20 microM LA and 20 microM arachidonic acid profoundly interfered with the inhibitory effect of CLA in HepG2. These results suggest that the growth inhibitory effect of CLA on HepG2 is due to changes in fatty acid metabolism but not to lipid peroxidation.

Antioxidants↗
PubMed2006

Effects of conjugated linoleic acid (CLA) isomers on oxygen diffusion-concentration products in liposomes and phospholipid solutions.

Conjugated linoleic acids (CLAs) are a group of octadecadienoic acids (18:2) that are naturally present in food products and may have beneficial health effects. Liposomes and ethanol solutions were prepared by mixing synthetic phosphatidylcholines (PCs) with c9,t11-CLA, t10,c12-CLA, and linoleic acid (LA) in the sn-2 position into natural PCs from soybean, egg yolk, rat brain, and rat heart at 5 mol %. The oxygen diffusion-concentration products were measured using electron spin resonance spin-label oximetry methods. Individual synthetic PCs, the phospholipid matrix, and the tested lipid systems all exhibited influence on oxygen diffusion-concentration products during lipid peroxidation. Incorporating 5 mol % PC(c9,t11-CLA) into soy and egg yolk PC increased oxygen consumption in liposome suspensions while it was decreased in rat heart and brain PCs. On the other hand, PC(t10,c12-CLA) increased oxygen consumption in mixtures with egg yolk and rat heart PC but decreased it in soybean and rat brain PC. By comparison, PC(LA) decreased oxygen consumption in every case. In ethanol solutions, all of the synthetic PCs suppressed the capacity to generate peroxide radicals in the order of LA > c9,t11-CLA > t10,c12-CLA. In addition, PCs containing individual CLA isomers and LA differed in their capacities to react with and quench DPPH radicals in both ethanol solution and liposome, suggesting differences between CLA isomers and LA in DPPH radical-fatty acid interactions. Incorporation of CLA isomers and LA into dimyristyl-PC reduced the phase transition temperature from 23.6 to 23.1 and 23.3 degrees C, respectively. The results of this study provide evidence that the behavior of CLA isomers differs in the microenvironment of membranes possibly due to structural differences that affect the permeability of membranes to oxygen and lipid peroxidation.

Cell Membrane Permeability↗
PubMed2001

Linoleic acid both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.

Linoleic acid (LA) had two effects on human Kv1.5 and Kv2.1 channels expressed in Chinese hamster ovary cells: an increase in the speed of current activation process (EC(50) = 2.4 and 2.7 microM for Kv1.5 and Kv2.1, respectively) and current inhibition (IC(50) = 6.6 and 7.4 for Kv1.5 and Kv2.1, respectively). LA affected the activation kinetics via two processes: a leftward shift in the instantaneous activation curves and an increase in the rate of current rise. Current inhibition by LA was time dependent but voltage independent. Hill slopes for plots of current inhibition (3.5 and 3.9 for Kv1.5 and Kv2.1, respectively) vs. dose of LA suggested that cooperativity was involved in the mechanism of current inhibition. A similar analysis of the effects of LA on current activation did not reveal cooperative interactions. The effects of LA were mediated from the external side of the channels, since addition of 10 microM LA to the patch pipette solution was without effect. Additionally, the methyl ester of LA was effective at enhancing peak current and promoting channel activation for Kv1.5 and Kv2.1 without inducing significant current inhibition.

Animals↗
PubMed1988

Metabolism of chylomicron arachidonic and linoleic acid in the rat.

Chyle and chylomicrons, obtained after feeding thoracic duct cannulated rats [3H]arachidonic (20:4) and [14C]linoleic acid (18:2) in cream, were injected i.v. into recipient animals. 7.5-15 min after injection, the 14C/3H ratio of the triacylglycerols remaining in plasma was about half of that in the injected chylomicrons, indicating that the chylomicron remnants formed retained relatively more [3H]20:4 than [14C]18:2. The 14C/3H ratio of plasma diacylglycerols was about 6-fold lower than that of plasma free fatty acids. The proportion of [3H]20:4 found in plasma cholesteryl esters was several-fold higher than that of [14C]18:2. Inhibition of hepatic lipase by a specific antiserum did not significantly influence the clearance of triacylglycerols, but increased the amount of 3H in plasma diacylglycerols. It also prevented the rapid clearance of phosphatidylethanolamine from plasma. The liver uptake of [3H]20:4 exceeded that of [14C]18:2. Antiserum against hepatic lipase diminished the difference. In contrast, the 14C/3H ratio of adipose tissue was higher than that of the injected chyle lipoproteins.

Adipose Tissue↗
PubMed2004

Incorporation of cis-9,trans-11 or trans-10,cis-12 conjugated linoleic acid into plasma and cellular lipids in healthy men.

This study investigated the incorporation of cis-9,trans-11 conjugated linoleic acid (c9,t11 CLA) and trans-10,cis-12-CLA (t10,c12 CLA) into plasma and peripheral blood mononuclear cell (PBMC) lipids when consumed as supplements highly enriched in these isomers. Healthy men (n = 49, age 31 +/- 8 years) consumed one, two, and four capsules containing approximately 600 mg of either c9,t11 CLA or t10,c12 CLA per capsule for sequential 8 week periods followed by a 6 week washout before consuming the alternative isomer. Both isomers were incorporated in a dose-dependent manner into plasma phosphatidylcholine (PC) (c9,t11 CLA r = 0.779, t10,c12 CLA r = 0.738; P < 0.0001) and cholesteryl ester (CE) (c9,t11 CLA r = 0.706, t10,c12 CLA r = 0.788; P < 0.0001). Only t10,c12 CLA was enriched in plasma nonesterified fatty acids. Both c9,t11 CLA and t10,c12 CLA were incorporated linearly into PBMC total lipids (r = 0.285 and r = 0.273, respectively; P < 0.0005). The highest concentrations of c9,t11 CLA and t10,c12 CLA in PBMC lipids were 3- to 4-fold lower than those in plasma PC and CE. These data suggest that the level of intake is a major determinant of plasma and PBMC CLA content, although PBMCs appear to incorporate both CLA isomers less readily.

Adult↗
PubMed1994

Inhibition of lipoperoxidation of linoleic acid by five antioxidants of different lipophilicity.

The efficacy of oxidation inhibition of five natural and synthetic antioxidants (BHT, BHA, nordihydroguaiaretic acid (NDGA), quercetin and rutin) was studied in O/W emulsions. Linoleic acid was used as a reference molecule; the reaction was initiated by an azo-compound. The kAH characterizing the reaction of the antioxidant with the peroxyl radical decreases in the following order: kAH(BHA) > kAH(BHT) > kAH(NDGA) > kAH(quercetin) > kAH(rutin).

Antioxidants↗
PubMed1968

Placental transport of free palmitic and linoleic acids in the guinea pig.

Radioisotopic tracers were used to measure the unidirectional transfer rates of free fatty acids across the placenta of fed and fasted pregnant guinea pigs. Free (14)C-labeled palmitic and linoleic acids (in serum) were injected simultaneously into a jugular vein of an anesthetized pregnant guinea pig. Serial samples of maternal blood were collected from a carotid artery; fetal blood was collected from the umbilical vein of an exposed fetus. Analysis of maternal and fetal plasma revealed that: (a) the half-lives of free palmitic and linoleic acid in maternal plasma are approximately 1.3 min and 0.7 min, both in fed animals with low plasma concentrations of these acids and in fasted animals with high concentrations; (b) free linoleic and palmitic acids cross the placenta from maternal to fetal plasma in a ratio of approximately 2.0, a value which appears not to change as the transfer rates of these acids from maternal to fetal plasma are increased by fasting the mother. It is suggested that the ratio in which free linoleic and palmitic acids cross the placenta from maternal to fetal plasma is determined by the ratio of the unbound free linoleic and palmitic acid concentrations in maternal plasma. A comparison of several species indicates that a much greater proportion of fetal fatty acids comes from the mother in the guinea pig and rabbit than in the rat, the sheep, or man.

Adipose Tissue↗
PubMed1985

Measurement of the diene conjugated form of linoleic acid in plasma by high performance liquid chromatography: a questionable non-invasive assay of free radical activity?

It has been previously reported that the main diene-conjugated fatty acid in human plasma is a non-oxygen containing linoleic acid isomer (PL-9, 11-LA'). It has also been proposed that this isomer can be used as a specific marker of free radical-mediated lipid peroxidation in humans. Here we report that the in vitro induction of lipid peroxidation in human and rat blood with either UV irradiation or phenylhydrazine failed to increase the plasma levels of this isomer. The induction of lipid peroxidation in vivo in rats pretreated with either phenylhydrazine or bromotrichloromethane also failed to increase the plasma levels of this isomer. These findings demonstrate that PL-9, 11-LA' cannot be used as an in vivo marker of free radical-mediated lipid peroxidation in rats and casts doubts on its validity as a specific marker in humans.

Animals↗