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Results for “Erucic Acids”

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At least 19 recordsLinked to original sources
PubMed1983

Induction of a reversible cardiac lipidosis by a dietary long-chain fatty acid (erucic acid). Relationship to lipid accumulation in border zones of myocardial infarcts.

Previous studies have demonstrated that cardiac myocytes in the border zone of acute myocardial infarction become markedly overloaded with neutral lipid during the transition from reversible to irreversible injury. To examine directly the role of these changes in neutral lipid metabolism in the development of irreversible cellular injury and associated increases in tissue Ca2+ content, the authors fed rats large amounts of a fatty acid (erucic acid) that is poorly oxidized by the heart and that subsequently accumulates as neutral lipid. Rats fed a high erucic acid (C22:1) diet in the form of 20% rapeseed oil for 3-5 days had a fourfold increase in triglyceride (49.5 +/- 3.8 SEM mg/g wet wt versus 13.6 +/- 13, n = 4) and a 60% increase in long-chain acyl CoA content (166.0 +/- 21.9 versus 91.5 +/- 9.0 nM/g wet wt, n = 4), compared with controls. However, there was no change in long-chain acyl carnitine or total phospholipid content. Histochemical studies showed accumulation of numerous lipid droplets in the myocytes, and electron microscopy revealed localization of lipid vesicles in direct contact with mitochondria, thus mimicking the lipid-laden cells in the border zone regions of acute myocardial infarcts. The acute lipidosis was reversible with either continued feeding of erucic acid for several weeks or conversion to a normal diet. It was not associated with an increased tissue Ca2+ content, nor with cell necrosis. However, continued erucic acid intake for 3 months was associated with focal myocardial degeneration and loss of myocytes. These results suggest that acute increases in neutral lipids, as found in the border zone of acute myocardial infarction, may not be the cause of progression to irreversible damage during acute myocardial injury, but that the persistent presence of similar lipid material over months may result in focal myocardial degeneration.

Animals↗
PubMed1997

Erucic acid and erucic acid anilide-induced oxidative burst in human polymorphonuclear leukocytes.

Human polymorphonuclear leukocytes (PMNL) were exposed to erucic acid or erucic acid anilide to explore their effects on the production of reactive oxygen species (ROS) and the levels of free intracellular calcium. The compounds did not change the levels of intracellular calcium, but both dose-dependently induced respiratory burst in PMNL. Maximal production of ROS by erucic acid exceeded that induced by its anilide 13-fold. A protein kinase C inhibitor, Ro 31-8220, completely inhibited erucic acid and erucic acid anilide-induced production of ROS. Neither erucic acid nor erucic acid anilide modified FMLP-induced production of ROS. However, erucic acid (500 microM) amplified 5 nM PMA-induced ROS production 1.8-fold, but did not have this effect at a lower PMA concentration. On the contrary, erucic acid anilide inhibited PMA-induced oxidative burst, and shifted the peak ROS production induced by PMA to a later time-point. The present results show that aniline moiety modifies the effects of erucic acid on the activation of PMNL, and suggest that both erucic acid and erucic acid anilide may activate PMNL through a protein kinase C-dependent mechanism.

Anilides↗
PubMed1979

[Effects of conjugates of linolenic acid and erucic acid on rat cardiac and liver lipids].

Cardiac and liver lipids (triglycerides and phospholipids) were analyzed in weanling rats fed for 8 days diets containing 15% by weight of four different lipid mixtures: trierucin and peanut oil (1/1), trierucin and linseed oil (1/1), triolein and peanut oil (1/1), triolein and linseed oil (1/1). Linolenic acid (8 cal% of the diet) does not influence the steatogenic effect of erucic acid (15 cal% of the diet) on the myocardium but seems to increase the hepatic conversion of erucic acid into shorter monoenes (C 18:1 mainly). The (n-6), (n-3) fatty acid spectra in heart and liver phospholipids are strongly affected when linolenic acid is added to the diet whereas erucic acid has little effect.

Animals↗
PubMed1975

[Short term comparative study of effects of n-9 trans-docosenoic (brassidic) acid and n-9, cis-docosenoic (erucic) acid on the cardiac lipids of weanling rats].

Cardiac lipids (triglycerides and phospholipids) of weanling rats fed diets containing 15% by weight of rapeseed oil (RSO), hydrogenated rapeseed oil (HRSO), trierucin (TE) or tribassidin (TB) were analyzed after 3 and 7 days of feeding. The amount of C22:1 was made equal in the 4 diets. Trans-isomers of erucic acid found in HRSO and TB do not cause as high an accumulation of lipids and docosenoic acids in the heart as erucic acid. Digestibility of brassidic acid (46%) is lower than that or erucic acid (83%) but even then, the amount of brassidic acid found in cardiac lipids (calculated per gram of absorbed fatty acid) after 7 days of feeding is 10 times less than that of erucic acid. Brassidic acid, like erucic acid, can be converted into shorter monoenes (C20:1 and C18:1) since transC18:1 has been found in cardiac phospholipids of rats fed trans-docosenoic acid as the only source of trans-acid in the diet.

Animals↗
PubMed1995

Lysophosphatidic acid acyltransferase from meadowfoam mediates insertion of erucic acid at the sn-2 position of triacylglycerol in transgenic rapeseed oil.

Lysophosphatidic acid acyltransferase acylates the sn-2 hydroxyl group of lysophosphatidic acid to form phosphatidic acid, a precursor to triacylglycerol. A cDNA encoding lysophosphatidic acid acyltransferase was isolated from developing seeds of meadowfoam (Limnanthes alba alba). The cDNA encodes a 281-amino acid protein with a molecular mass of 32 kD. The cDNA was expressed in developing seeds of transgenic high-erucic-acid rapeseed (Brassica napus) using a napin expression cassette. Erucic acid was present at the sn-2 position of triacylglycerols from transgenic plants but was absent from that position of seed oil extracted from control plants. Trierucin was present in the transgenic oil. Alteration of the sn-2 erucic acid composition did not affect the total erucic acid content. These experiments demonstrate the feasibility of using acyltransferases to alter the stereochemical composition of transgenic seed oils and also represent a necessary step toward increasing the erucic acid content of rapeseed oil.

Acyltransferases↗
PubMed1995

Microsomal Lyso-Phosphatidic Acid Acyltransferase from a Brassica oleracea Cultivar Incorporates Erucic Acid into the sn-2 Position of Seed Triacylglycerols.

Developing seeds from Brassica oleracea (L.) var botrytis cv Sesam were examined for the ability to biosynthesize and incorporate erucic acid into triacylglycerols (TAGs). Seed embryos at mid-development contained a high concentration of erucic acid in diacylglycerols and TAGs, and substantial levels were also detected in free fatty acids, acyl-coenzyme A (CoA), phosphatidic acid, and phosphatidylcholine. Homogenates and microsomal fractions from seeds at mid-development produced [14C]eicosenoyl- and [14C]erucoyl-CoAs from [14C]oleoyl-CoA in the presence of malonyl-CoA and reducing equivalents in vitro. These fatty acids were incorporated into TAGs via the Kennedy pathway. However, unlike most Brassicaceae, the B. oleracea was able to insert significant erucic acid into the sn-2 position of TAGs. It was shown that the lyso-phosphatidic acid acyltransferase (LPAT) incorporated erucic acid into the sn-2 position of lyso-phosphatidic acid. The erucoyl-CoA:LPAT activity during seed development and the sn-2 erucic acid content of the TAG fraction in mature seed were compared to those in B. napus, Tropaeolum majus, and Limnanthes douglasii. There was a correlation between the in vitro erucoyl-CoA:LPAT activity and the sn-2 erucic acid content in seed TAGs. To our knowledge, this is the first member of the Brassicaceae reported to have an LPAT able to use erucoyl-CoA. This observation has important implications for efforts being made to increase the erucic acid content in B. napus, to supply strategic industrial feedstocks.

Journal Article↗
PubMed1997

Myocardial fatty acid pattern in rats fed on an erucic acid enriched diet.

Individual lipid classes and their fatty acid pattern in myocardium of rats fed on a diet containing 10% erucic acid ethyl ester (cis-13-docosenoic acid ethyl ester) were investigated and compared to rats fed on a normal diet. Two groups of rats were treated for 10 consecutive days with the erucic acid ethyl ester diet and the standard diet, respectively. After extracting total lipids from the myocardium of the rats, the individual lipid classes and the percentage of fatty acids in phospholipids, free fatty acids, diglycerides and triglycerides were measured. The data obtained demonstrate that the erucic acid ethyl ester diet induces a marked increase in free fatty acids and in triglycerides and marked differences in fatty acid pattern in triglycerides, free fatty acids and diglycerides, but only marginal differences in phospholipids, which seem to be carefully preserved as fundamental components of cell and mitochondria membranes.

Animals↗
PubMed1992

Fatty acid composition of blood lipids in Chinese children consuming high erucic acid rapeseed oil.

The fatty acid patterns of oils, blood plasma and erythrocyte lipids from 28 children in the Shaanxi province of the People's Republic of China were determined by capillary gas liquid chromatography. The main source of fat in this region is rapeseed oil. The analysis of locally available rapeseed oil shows a high erucic acid content (mean 43.83%, range 33.91-50.48%). According to protocol data, about 3% of the daily nutrient energy is provided by erucic acid. Despite a low fat intake in Chinese children, the composition of the fatty acids of the fractions analyzed showed normal patterns. However, erucic acid was found in all fractions analyzed. Data on erucic acid in human tissue are scarce. Although there are no indications of erucic acid toxicity in man, it is known to cause cardiac lipidosis and necrosis in rats. The question remains open if erucic acid aggravates selenium deficiency symptoms which are known to be associated with Keshan disease, an endemic cardiomyopathy.

Adolescent↗
PubMed2003

Formation of modified fatty acids and oxyphytosterols during refining of low erucic acid rapeseed oil.

Formation of trans fatty acids and cyclic fatty acid monomers was investigated during refining of low erucic acid rapeseed oil. The first steps of the refining process, that is, degumming, neutralization, and bleaching, hardly modified the fatty acid profile. In contrast, deodorization produced substantial quantities of trans fatty acids (>5% of total fatty acids) and small amounts of cyclic fatty acid monomers (650 mg of cyclic fatty acid monomers/kg of oil) when severe conditions (5-6 h at 250 degrees C) were used. Alpha-linolenic acid was the main precursor of cyclic fatty acid monomers. The influence of deodorization on the chemical composition of low erucic acid rapeseed oil was studied additionally. Whereas free fatty acids, peroxides, and tocopherols decreased, neither total polar compounds nor oxyphytosterols changed during deodorization. Oxyphytosterols were identified by GC-MS. Three oxyphytosterols not yet observed in oil were tentatively identified as 6beta-hydroxycampestanol, 6beta-hydroxysitostanol, and 6beta-hydroxybrassicastanol. Brassicasterol oxides were the most abundant oxyphytosterols.

Erucic Acids↗
PubMed1977

Erucic acid in edible fats and oils: a collaborative study on determination by open-tubular (capillary) gas-liquid chromatography.

An open-tubular (capillary) column gas-liquid chromatographic method for the determination of the specific isomer of docosenoic acid known as erucic acid (cis-docos-13-enoic) in the presence of other docosenoic acid isomers present in partially hydrogenated marine oils has been evaluated collaboratively. With wall-coated columns and the liquid phase SILAR-5CP, nine laboratories successfully analysed mixtures of partially hydrogenated marine oils, corn oil and rapeseed oil with a nominal content of 10% erucic acid, compatible with the regulations of the European Economic Community.

Chromatography, Gas↗