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PubMed1985

Dietary fats containing concentrates of cis or trans octadecenoates and the patterns of polyunsaturated fatty acids of liver phosphatidylcholine and phosphatidylethanolamine.

The effects of the mixed cis- 18:1 isomers and mixed trans- 18:1 isomers present in partially hydrogenated soybean oil (PHSO) upon the patterns of polyunsaturated fatty acids (PUFA) in liver phosphatidylcholine (PC) and phosphatidylethanolamine (PE) were studied in rats fed concentrates of cis- 18:1 or trans- 18:1 isomers isolated as triacylglycerides from PHSO. The cis- 18:1 and trans- 18:1 concentrates were fed at levels equal to those present in PHSO fed at 17.9% of the diet. All diets contained the required amounts of both linoleic and linolenic acids. The trans- 18:1 concentrate was found to suppress the levels of 20:4 omega 6 and 20:3 omega 9, and to increase the levels of 18:2 omega 6 and 20:5 omega 3 in PC and PE. The cis- 18:1 concentrate suppressed 20:4 omega 6 in PC, 20:5 omega 3 in PC and PE, and 18:2 omega 6 in PC, but increased the levels of 20:4 omega 6 in PE, and 20:3 omega 9 in PC and PE. The cis- 18:1 concentrate was more effective than the trans concentrate in suppressing 22:6 omega 3. The trans- 18:1 concentrate was more effective in suppressing 20:4 omega 6. The trans- 18:1 isomers appear to modify PUFA metabolism by inhibition of PUFA synthesis, whereas the cis- 18:1 isomers appear to complete with 2-position fatty acyl transfer and to inhibit omega 3 PUFA acylation.

Animals↗
PubMed1991

Concentrations of linoleic acid in adipose tissue differ with age in women but not men.

Samples of adipose tissue, taken post-mortem from the anterior abdominal wall near the umbilicus, were obtained from road-accident victims in the Aberdeen area; subjects were of either sex with a wide age distribution (7-88 years). Similar samples were obtained from elderly females (mean age 77) who had died in Aberdeen Royal Infirmary from a variety of causes. Fatty acid compositions of samples were determined by capillary gas chromatography of methyl esters, which were obtained by direct esterification of the adipose tissue. The mean linoleic acid content for all samples was low compared with published values for similar samples from Europe and North America. Cumulative frequency distribution curves for linoleic acid did not differ with age in males but significant differences (P less than 0.001) occurred in females, with decreased concentrations in those aged over 60 compared to younger groups. Concentrations of trans-unsaturated fatty acids ranged between 2 and 7 per cent but did not differ significantly between groups. Low adipose concentrations of linoleic acid are regarded as a reflection of its reduced long-term dietary intake and as a risk factor for the development of coronary heart disease.

Abdominal Muscles↗
PubMed2006

Comparison of fatty acid profiles of aorta and internal mammary arteries in patients with coronary artery disease.

BACKGROUND: Atherosclerosis represents the principal cause of death in the many societies. Since few data have been published about the composition of fatty acids in atherosclerotic arteries such as the aorta comparing to the non affected internal mammary artery which is used for aortocoronary bypass grafting, we compared the fatty acid profiles of atherosclerotic aorta and internal mammary arteries in human individuals. METHODS: Twenty-one angiographically documented coronary artery disease (CAD) patients who were admitted to the open heart surgery division enrolled in this study. They were operated electively for coronary artery bypass grafting surgery (CABG). Small segments of ascending aorta and internal mammary arteries were sampled during open heart surgery. The samples were subjected to lipid extraction and fatty acid analysis by high performance liquid chromatography. RESULTS: The results showed that different fatty acid profiles were seen in the aorta and internal mammary arteries. The atherosclerotic aorta contained lower amounts of unsaturated fatty acids (including trans isomer of oleic acid) and higher proportions of saturated fats comparing to the internal mammary. In the aorta also, the amounts of omega6 series of fatty acids were more and levels of omega3 fats were less than the internal mammary. CONCLUSION: This study suggests that modification of fatty acids may play a role during atherogenesis.

Adult↗
PubMed2004

Plasma cholesteryl esters provided by lecithin:cholesterol acyltransferase and acyl-coenzyme a:cholesterol acyltransferase 2 have opposite atherosclerotic potential.

Evidence suggests that ACAT2 is a proatherogenic enzyme that contributes cholesteryl esters (CEs) to apoB-containing lipoproteins, whereas LCAT is an antiatherogenic enzyme that facilitates reverse cholesterol transport by esterifying free cholesterol on HDL particles. We hypothesized that deletion of LCAT and ACAT2 would lead to absence of plasma CEs and reduced atherosclerosis. To test this hypothesis, ACAT2-/- LCAT-/- LDLr-/-, ACAT2-/- LDLr-/-, and LCAT-/- LDLr-/- mice were fed a 0.15% cholesterol diet for 20 weeks. In comparison to LDLr-/- mice, the total plasma cholesterol (TPC) of ACAT2-/- LCAT-/- LDLr-/- mice was 67% lower because of the complete absence of plasma CEs, leading to 94% less CE accumulation in the aorta. In the LCAT-/- LDLr-/- mice, TPC and atherosclerosis were significantly higher because of increased accumulations of ACAT2-derived CE. In ACAT2-/- LDLr-/- mice, again compared with LDLr-/- mice, TPC was 19% lower, whereas atherosclerosis was 88% lower. Therefore, the absence of ACAT2 led to a significant reduction in TPC although benefits in reduction of atherosclerosis were much more pronounced. Overall, the data suggest that ACAT2-derived CE is the predominant atherogenic lipid in blood, and that an important goal for prevention of atherosclerosis is to limit ACAT2-derived CE accumulation in lipoproteins.

Animals↗
PubMed1998

The effect of vitamin E supplementation of cow diets containing rapeseed and linseed on the prevention of milk fat oxidation.

Two experiments involving lactating Holstein cows were carried out to quantify the effect of a 550-g supplement of lipids from extruded rapeseed and linseed on milk fatty acid profiles and the susceptibility of milk fat to oxidation. The effect of a daily oral supplement containing 9616 IU of vitamin E (all-rac-alpha-tocopheryl acetate) on milk alpha-tocopherol and protection against oxidation was also evaluated. The intake of oilseeds decreased protein and fat contents in milk, and the proportion of all C18 fatty acids increased. The trans isomers were 2.7 and 10.76% of the milk fatty acids, respectively, for cows fed the control diet and the diet containing extruded rapeseed and linseed. The ratio of oleic to palmitic acid was doubled, and the resistance to oxidation was reduced by 30 to 40% in both experiments. The dietary vitamin E supplement increased the alpha-tocopherol concentration in milk by about 45% and was sufficient to prevent milk fat depression and oxidation. The diet containing oilseeds and supplemented with an adequate amount of vitamin E allowed cows to yield milk that could be used to manufacture butter with high oleic acid content, good spreadability, and resistance to oxidation.

Animal Feed↗
PubMed2004

Effect of lipid bilayer alteration on transdermal delivery of a high-molecular-weight and lipophilic drug: studies with paclitaxel.

Skin forms an excellent barrier against drug permeation, due to the rigid lamellar structure of the stratum corneum (SC) lipids. Poor permeability of drugs can be enhanced through alteration in partition and diffusion coefficients, or concentration gradient of drug with an appropriate choice of solvent system, along with penetration enhancers. The aim of the current investigation was to assess applicability of lipid bilayer alteration by fatty acids and terpenes toward the permeation enhancement of a high-molecular-weight, lipophilic drug, paclitaxel (PCL) through rat skin. From among the fatty acids studied using ethanol/isopropyl myristate (1:1) vehicle, no significant enhancement in flux of PCL was observed (p > 0.05). In the case of cis mono and polyunsaturated fatty acids lag time was found to be similar to control (p > 0.05). This suggests that the permeation of a high-molecular-weight, lipophilic drug may not be enhanced by the alteration of the lipid bilayer, or the main barrier to permeation could lie in lower hydrophilic layers of skin. A significant increase in lag time was observed with trans unsaturated fatty acids unlike the cis isomers, and this was explained on the basis of conformation and preferential partitioning of fatty acids into skin. From among the terpenes, flux of PCL with cineole was significantly different from other studied terpenes and controls, and after treatment with menthol and menthone permeability was found to be reduced. Menthol and menthone cause loosening of the SC lipid bilayer due to breaking of hydrogen bonding between ceramides, resulting in penetration of water into the lipids of the SC lipid bilayer that leads to creation of new aqueous channels and is responsible for increased hydrophilicity of SC. This increased hydrophilicity of the SC bilayer might have resulted in unfavorable conditions for ethanol/isopropyl myristate (1:1) along with PCL to penetrate into skin, therefore permeability was reduced. The findings of this study suggest that the permeation of a high-molecular-weight and lipophilic drug cannot be enhanced through bilayer alteration by penetration enhancers, and alteration in partitioning of drug into skin could be a feasible mode to enhance the permeation of drug.

Administration, Cutaneous↗
PubMed1987

Effect of phenolic acids and phenolics from plant cell walls on rumenlike fermentation in consecutive batch culture.

Information on the interaction between mixed populations in the rumen and plant phenolics is required to fully elucidate the limitations of phenolic compounds on forage digestibility. The objective of this study was to examine the degradation of Italian ryegrass (Lolium multiflorum L.) hay incubated with mixed ruminal populations in consecutive batch culture (CBC) with or without phenolic acids or phenolic compounds extracted from plant cell walls. Each CBC consisted of a series of 10 cultures (3 replicates per culture) inoculated (10%, vol/vol) in sequence at 48-h intervals with microbial suspension from the previous set of cultures. All cultures were grown on a semidefined medium containing Italian ryegrass hay, and each CBC was initiated with an inoculum from the rumen. Rumenlike fermentation characteristics were maintained in control CBCs by repeated inoculum transfer. Treatment CBCs were transferred as described above, but cultures 5, 6, and 7 were incubated in the presence of trans-p-coumaric, cis-p-coumaric, or trans-ferulic acid or phenolics extracted from the cell walls of maize stem or barley straw. Mean apparent dry matter disappearance in control CBC cultures was 495 mg per g of hay, whereas the presence of phenolics reduced the initial dry matter disappearance by 6.3 to 25.6%. trans-p-Coumaric acid and, to a lesser extent, the phenolics from cell walls of maize stem were the most inhibitory compounds for dry matter disappearance and for the production of volatile fatty acids; trans-p-coumaric acid altered the molar ratio of acetate/propionate/butyrate. The CBC further showed variations in the ability of the rumen microbial population to adapt to phenolic compounds.

Animals↗
PubMed1985

Chain-length specificities of mitochondrial and peroxisomal beta-oxidation of fatty acids in livers of rainbow trout (Salmo gairdneri).

Peroxisomes and mitochondria were prepared from livers of rainbow trout fed diets containing either 15% crude fish oil (CFO) or 11.5% partially hydrogenated fish oil (PHFO) plus 3.5% CFO. Peroxisomal preparations from the two dietary groups showed similar rates and substrate specificity patterns for acyl-CoA oxidation. The peroxisomal oxidation rate was highest with 12:0-CoA and decreased with increasing chain length, being negligible with 22-carbon acyl-CoA's. The trans isomer of 18:1(n-9) was oxidized at a higher rate than the cis isomer only by peroxisomes from the PHFO + CFO group. Mitochondria prepared from both groups of fish exhibited a broad chain-length specificity for the oxidation of acylcarnitines. Both polyunsaturated and trans monoenoic fatty acids were readily oxidized.

Acyl Coenzyme A↗
PubMed2002

Geometrical isomerism of monounsaturated fatty acids: thiyl radical catalysis and influence of antioxidant vitamins.

Thiyl radicals generated either from thiols or disulfides act as the catalyst for the cis-trans isomerization of a variety of monounsaturated fatty acid methyl esters in homogeneous solution. Similar results have also been obtained using alpha-lipoic acid and its reduced form. The effectiveness of the isomerization processes in the presence of the most common antioxidants has been addressed. The ability of thiyl radical scavenging was found to increase along the series alpha-tocopherol < ascorbic acid < all-trans retinol. The cis-trans isomerization of fatty acid residues in multilamellar vesicles of dioleoyl phosphatidyl choline by thiyl radical, in the absence and presence of the various antioxidants, has also been studied in detail. The influence of the isomerization process on the phospholipid bilayer has been tested by permeability measurements of vesicles and it is clearly shown that trans fatty acid-containing membranes have intermediate properties between those formed by all-cis and saturated components. This study contributes to the understanding of radical processes that can alter or protect the naturally occurring cis geometry of unsaturated lipids in cell membranes and demonstrates a new role of essential antioxidants.

Antioxidants↗
PubMed2000

A fluorescence study of the interaction and location of (+)-totarol, a diterpenoid bioactive molecule, in model membranes.

(+)-Totarol, a diterpene extracted from Podocarpus totara, has been reported as a potent antioxidant and antibacterial agent. Although the molecular mechanism of action of this hydrophobic molecule remains unknown, recent work made in our laboratory strongly suggests that it could be lipid-mediated. Since (+)-totarol contains a phenolic ring, we have studied the intrinsic fluorescent properties of this molecule, i.e., quantum yield, lifetime, steady-state anisotropy and emission spectra, both in aqueous and in phospholipid phases, in order to obtain information on the interaction and location of (+)-totarol in biomembrane model systems. The phospholipid/water partition coefficient of (+)-totarol was found to be very high (K(p)=1.8x10(4)), suggesting that it incorporates very efficiently into membranes. In order to estimate the transverse location (degree of penetration) of the molecule in the fluid phase of DMPC model membranes, the spin labelled fatty acids 5-NS and 16-NS were used in differential quenching experiments. The results obtained show that (+)-totarol is located in the inner region of the membrane, far away from the phospholipid/water interface. Since (+)-totarol protects against oxidative stress, its interaction with an unsaturated fatty acid, trans-parinaric acid, was studied using fluorescence resonance energy transfer. No significant interactions were observed, molecules of trans-parinaric acid distributing themselves randomly amongst those of (+)-totarol in the phospholipid membrane.

Abietanes↗
PubMed2004

Dietary fats and oils: technologies for improving cardiovascular health.

The role of dietary lipids in the etiology of coronary heart disease (CHD) continues to evolve as we gain a better understanding of the metabolic effects of individual fatty acids and their impact on surrogate markers of risk. A recent meta-analysis of 60 human studies suggests that for each 1% energy replacement of carbohydrates in the diet with saturated fat or trans fat, serum low-density lipoprotein cholesterol concentrations increase by 0.032 (1.23 mg/dL) and 0.04 mmol/L (1.54 mg/dL), respectively. Current dietary recommendations to keep saturated fat and trans fat intake as low as possible, and to increase the intake of cis mono-unsaturated and polyunsaturated fatty acids, as well as growing recognition of these recommendations by consumers and food regulatory agencies in the United States, have been major driving forces for the edible oil industry and food manufacturers to develop alternative fats and oils with nutritionally improved fatty acid compositions. As solutions for use of trans fatty acids are being sought, oilseeds with modified fatty acid compositions are being viewed as a means to provide such solutions. Additionally, oilseeds with modified fatty acid composition, such as enhanced content of long-chain omega-3 fatty acids or conjugated linoleic acid, have been developed as a way to increase delivery of these fatty acids directly into the food supply or indirectly as use for feed ingredients for livestock. New processing technologies are being utilized around the world to create dietary fats and oils with specific physiologic functions relevant to risk factors for cardiovascular disease.

Cardiovascular Diseases↗
PubMed1999

Ligand selectivity of the peroxisome proliferator-activated receptor alpha.

Peroxisome proliferator-activated receptors (PPAR alpha, beta, and gamma) are nuclear hormone receptors that play critical roles in regulating lipid metabolism. It is well established that PPARs are the targets for the hypolipidemic synthetic compounds known as peroxisome proliferators, and it has been proposed that various long-chain fatty acids and metabolites of arachidonic acid serve as the physiological ligands that activate these receptors in vivo. However, a persistent problem is that reported values of the equilibrium dissociation constants (Kds) of complexes of PPARs with these ligands are in the micromolar range, at least an order of magnitude higher than the physiological concentrations of the ligands. Thus, the identity of the endogenous ligands for PPAR remains unclear. Here we report on a fluorescence-based method for investigating the interactions of PPAR with ligands. It is shown that the synthetic fluorescent long-chain fatty acid trans-parinaric acid binds to PPARalpha with high affinity and can be used as a probe to monitor protein-ligand interactions by the receptor. Measurements of Kds characterizing the interactions of PPARalpha with various ligands revealed that PPARalpha interacts with unsaturated C:18 fatty acids, with arachidonic acid, and with the leukotriene LTB4 with affinities in the nanomolar range. These data demonstrate the utility of the optical method in examining the ligand-selectivity of PPARs, and resolve a long-standing uncertainty in understanding how the activities of these receptors are regulated in vivo.

Animals↗
PubMed1998

Effects of three trans isomers of eicosapentaenoic acid on rat platelet aggregation and arachidonic acid metabolism.

Three trans isomers of eicosapentaenoic acid (EPA) were added to rat platelets stimulated with arachidonic acid (AA) in order to compare their effects on platelet aggregation and on AA oxygenation with those of EPA. The production of metabolites from radiolabelled 20:5delta 17trans was studied also. EPA induced an inhibition of platelet aggregation of 26.7 +/- 6.6% for a 20:5/20:4 ratio equal to 1. The 20:5delta 11trans and the 20:5delta 11trans,17trans were twice as antiaggregant. In contrast, the 20:5delta 17trans induced similar antiaggregant effect as its cis homologue. Each fatty acid showed a dose-dependent effect. In opposition to EPA, 20:5delta 17trans was also able to induce platelet aggregation (12 +/- 4.9% at 5 microM). With regards to the metabolism of AA, 20:5delta 11trans, 20:5delta 17trans and 20:5delta 11trans,17trans (20:5/20:4 = 1) reduced the formation of the cyclooxygenase metabolites (-63%, -37% and -68%, respectively) and enhanced that of 12-HETE (+67%, +38% and +74%, respectively) as compared to EPA. The analysis showed that radiolabelled 20:5delta 17trans was metabolized into five compounds which remained to be identified. The Rf of three of these compounds (X1, X2 and X4) were those of the metabolites of EPA. Experiments using baicalein induced an inhibition of the production of X2. This suggested that this compound was formed through the 12-lipoxygenase pathway. In the same way, using indomethacin as inhibitor, we observed that X1 and X4 were produced by the cyclooxygenase pathway. Our results suggest that the trans double bond in the delta 11 position may be responsible of the different physiological effects of the trans polyunsaturated fatty acids as compared to their cis homologue (EPA). Furthermore, 20:5delta 17trans seems to be recognised by the enzymatic system as 20:4 n-6.

Animals↗
PubMed1996

Triacylglycerol and cholesterol transport during absorption of glycerol trioleate vs. glycerol trielaidate.

We used conscious, chronic lymph-fistula rats to compare intestinal lymphatic transport of glycerol trioleate (TO) vs. glycerol trielaidate (TE) and to determine the effect of TO vs. TE on absorption and transport of cholesterol. Rats were implanted with intestinal lymph fistulas and duodenal cannulas and then given intraduodenal infusions of lipid emulsions containing purified TO or TE (40 mumol/h) and cholesterol (7.8 mumol/h + 2 microCi [14C]cholesterol). Lymph samples were collected at 0, 2, 4, 5, 6, 7, and 8 h after the start of lipid infusion. Lymphatic output and luminal and gut wall recovery of radioactive lipid at 8 h were quantified. Triacylglycerol (TG) fatty acid isomers did not affect lymphatic output of TG; lymph TG fatty acid composition and output reflected infusate composition. Lymphatic output of cholesterol (mass and radioactivity) did not differ between groups; luminal and gut wall recovery of [14C]cholesterol was also similar between groups. Similar lymphatic transport of TG and cholesterol between triolein- and trielaidin-infused rats was maintained for up to 16 h after the cessation of an infused lipid load. These results indicate that TO and TE are transported into lymph similarly, and that cholesterol absorption and transport are similar irrespective of whether TO or TE is the TG source. The data suggest that trans fatty acid-induced hypercholesterolemia is not due to altered intestinal absorption and transport of cholesterol.

Animals↗
PubMed2000

No effect of dietary trans isomers of alpha-linolenic acid on platelet aggregation and haemostatic factors in european healthy men. The TRANSLinE study.

The aim of this study was to investigate the effect of trans alpha-linolenic acid on platelet aggregation and blood haemostasis. A randomized, double blind dietary intervention trial was carried out with healthy male volunteers (n=88) in three European centers. After a 6-week washout period where subjects avoided foods containing all trans fats, subjects either continued for 6 weeks with a low trans diet or a diet where trans alpha-linolenic acid provided 0.6% of energy (supplied as oil, margarine, cheese, muffins, and biscuits). At the end of the washout period the intake of trans polyunsaturated fats was 58+/-115 mg/day; this increased in patients on the high trans diet by +1344+/-328 mg/day, compared with +10+/-67 mg/day in patients on the low trans diet (p<0.01). The change in trans alpha-linolenic acid in plasma cholesteryl esters was 0.26+/-0. 20 on the high trans and 0.00+/-0.07% of fatty acids on the low trans diet (p<0.001). No effect of the high trans diet was observed on platelet aggregation: collagen EC(50) high trans 157+/-100, low trans 152+/-90 ng/mL (NS); U44619 EC(50) high trans 81+/-61, low trans 59+/-27 nM (NS). The high trans diet did not affect platelet thromboxane production, fibrinogen levels, factor VII, activated factor VIIa, or plasminogen activator inhibitor activity. There were no center-specific differences in response to the high trans diet. A relatively high amount of trans alpha-linolenic acid for 6 weeks does not increase the risk of coronary heart disease by promoting platelet aggregation and blood coagulation.

15-Hydroxy-11 alpha,9 alpha-(epoxymethano)prosta-5↗
PubMed2005

Geometrical trans lipid isomers: a new target for lipidomics.

Evidence that lipids play different roles in the biological environment, particularly in dealing with metabolic regulation and cell signaling, has led to a growing interest in these molecules, and nowadays the research field of lipid structures and functions is called lipidomics. The term describes diverse research areas, from mapping the entire spectrum of lipids in organisms to describing the function and metabolism of individual lipids. Recent investigations on geometrical trans isomers of fatty acid derivatives, which have the double bonds in the same position as the natural compounds but with the trans instead of the naturally occurring cis geometry, highlighted these compounds as a new target for lipidomics. In addition to the identification of their structures and functions, research in a multidisciplinary context aims at understanding the biochemical significance of cis and trans lipid geometry, and a chemical biology approach can be envisaged to explore the role of the geometry change as either an alteration or a signal that can perturb a biological system and induce a cellular response.

Animals↗
PubMed1979

[Comparison of mean-term physiological effects of cis and trans docosenoic acids in the rat. II. Effects on the lipids and fatty acids of plasma, adipose tissue, liver and heart].

The mean term effects (16 weeks) of brassidic acid (n-9 trans docosenoic acid) and erucic acid (n-9, cis docosenoic acid) on the lipids and fatty acids of different organs in the rat (plasma, adipose tissue, liver, heart) and compared to those of their C 18 homologues, elaidic and oleic acid, in a 2(3) factorial experiment; the three tested factors are: 1) the chain length of the dietary monoenes (C 22:1 vs. C 18:1), 2) the geometrical configuration of their double bond (trans vs. cis) and 3) the dietary levels (30% vs. 1,7% of dietary fatty acids). Experimental details have been reported previously [Astorg and Levillain, 1979]. With a low supply of linoleic acid, brassidic acid, brassidic acid induces a large increase of plasma triacylglycerols (TG), but this can be caused by a slow fat absorption. However, the plasma contents of cis and trans docosenoic acids do not differ greatly. Both docosenoic acids incorporate more into the lipids of heart and adipose tissue than into liver lipids, and, for each organ, more into TG than into phospholipids (PL). In heart and adipose tissue lipids, the percentage of brassidic acid is lower than that of erucic acid. In these 2 organs and in the liver, linoleic acid subdeficiency decreases the incorporation of both C 22:1 isomers into the lipids. Dietary brassidic acid is readily converted to other trans monoenes, mainly elaidic acid, which incorporates into organ lipids. The extent of this chain-shortening may be greater than that of erucic acid (to oleic acid), and this would explain the lower level of brassidic acid found in organ lipids. Last, dietary trans monoenes (brassidic and elaidic acids) induce, as compared to their cis isomers, slight but visible changes in the profile of (n-9) polyunsaturated fatty acids in organ lipids. These results are discussed and related to the fact that brassidic acid does not seem to have the heart pathogenic potency of erucic acid [see part 1 of this paper, Astorg and Levillain, 1979].

Adipose Tissue↗