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PubMed1980

Desaturation of positional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver.

A range of cis- and trans-monoenoic fatty acids was tested as substrates for desaturation in microsomal preparations from rat liver. Trans-monoenoic acids were generally desaturated in the delta 9 position to the same extent as stearic acid. Acids with delta 7-trans- and delta 11-trans-olefinic unsaturation produced delta 7-trans, 9-cis- and delta 9-cis, 11-trans-conjugated dienoic acids, respectively, but the delta 8-trans-and delta 10-trans-monoenoic acids did not give delta 8,9- or delta 9,10-allenes. Of the cis-monoenoic acids examined, only those with double bonds at or beyond the delta 14 position gave any measurable delta 9 desaturation. When delta 9 desaturation of long chain saturated acids was inhibited by adding sterculic acid, these saturated acids were desaturated at the delta 5 and delta 6 positions. Many of the monoenoic acids tested were also desaturated at the delta 5 and/or delta 6 positions, although the percentage conversions were always low. delta 9-cis, 11-trans-, delta 9-cis, 12-trans- and delta 9-cis, 13-trans-dienoic acids, produced in situ by delta 9 desaturation of the corresponding monoenoic acids, were extensively desaturated in the delta 6 position. These results are discussed in terms of: (a) the various models proposed to explain the substrate specificities of the desaturases, and (b) the metabolism of unnatural fatty acids ingested from dietary sources.

Animals↗
PubMed2004

Regioselective cis-trans isomerization of arachidonic double bonds by thiyl radicals: the influence of phospholipid supramolecular organization.

Trans unsaturated fatty acids in humans may be originated by two different contributions. The exogenous track is due to dietary supplementation of trans fats and the endogenous path deals with free-radical-catalyzed cis-trans isomerization of fatty acids. Arachidonic acid residue (5c,8c,11c,14c-20:4), which has only two out of the four double bonds deriving from the diet, was used to differentiate the two paths and to assess the importance of a radical reaction. A detailed study on the formation of trans phospholipids catalyzed by the HOCH2CH2S* radical was carried out on L-alpha-phosphatidylcholine from egg lecithin and 1-stearoyl-2-arachidonoyl-L-alpha-phosphatidylcholine (SAPC) in homogeneous solution or in large unilamellar vesicles (LUVET). Thiyl radicals were generated from the corresponding thiol by either gamma-irradiation or UV photolysis, and the reaction course was followed by GC, Ag/TLC, and 13C NMR analyses. The isomerization was found to be independent of cis double bond location (random process) in i-PrOH solution. In the case of vesicles, the supramolecular organization of lipids produced a dramatic change of the isomerization outcome: (i) in egg lecithin, the reactivity of arachidonate moieties is higher than that of oleate and linoleate residues, (ii) in the linoleate residues of egg lecithin, the 9t,12c-18:2 isomer prevailed on the 9c,12t-18:2 isomer (3:1 ratio), and (iii) a regioselective isomerization of SAPC arachidonate residues occurred in the 5 and 8 positions. This effect of "positional preference" indicates that thiyl radicals entering the hydrophobic region of the membrane bilayer start to isomerize polyunsaturated fatty acid residues having the double bonds nearest to the membrane surfaces. We propose that arachidonic acid and its trans isomers can function as biomarkers in membranes for distinguishing the two trans fatty acid-forming pathways.

2-Propanol↗
PubMed2004

What are the health effects of fat?

In order to answer the question which health benefits are to be expected from dietary fat, we have to differentiate between different kinds of fat with varying fatty acid composition. Saturated fatty acids are commonly judged to have a negative health impact as they lead to increased serum cholesterol levels and a higher risk of coronary heart disease. Therefore, all recommendations stress the importance to limit the intake of saturated fatty acids. Monounsaturated fatty acids, on the other hand, have a positive impact on the serum lipid profile, lead to decreased LDL-oxidation and favorably influence the metabolism of diabetics. However, it is essential that monounsaturated fatty acids be mainly supplied by plant oils like rape seed or olive oil and not by foods that are simultaneously rich in saturated fatty acids. Concerning polyunsaturated fatty acids, it is important to increase the supply of n-3 fatty acids (ratio of n-6:n-3: about 5:1) as there is substantial evidence for their protective effects. If the fatty acid composition of the diet is optimized, even a total dietary fat content of 35% of total energy intake can be adequate as long as there is enough physical activity and the diet is rich in plant-derived foods like vegetables, fruits, cereals, potatoes, beans and legumes.

Cholesterol↗
PubMed1986

Atherogenesis. An epidemiological model based on the presence of unnatural trans and cis isomers of unsaturated fatty acids in the maternal diet and in mothers milk.

The hypothesis that the presence of unnatural trans and cis isomers of unsaturated fatty acids in the maternal diet and in human mothers milk could be responsible for initiating atherosclerosis in utero or in infants is proposed. It is suggested that the key etiological factor involved in the formation of atherosclerotic plaques could be uncontrolled division of smooth muscle cells of the intima resulting from the intracellular excess of linoleic acid and deficiency of its metabolites gamma-linolenic acid and dihomogamma-linolenic acid. This imbalance is brought about by competitive inhibition of the enzyme delta-6-desaturase by unnatural trans and cis unsaturated fatty acids. Delta-6-desaturase is the enzyme responsible for converting linoleic acid to dihomogamma-linolenic acid. The cellular presence of unnatural trans and cis isomers of unsaturated fatty acids would therefore enhance increased levels of linoleic acid and deficiency of its metabolites gamma-linolenic acid and dihomogamma-linolenic acid. It is proposed that prophylaxis against the effects of delta-6-desaturase inhibition could be achieved by the adoption of an Eskimo-like diet containing the essential fatty acid metabolites gamma-linolenic acid and/or dihomogamma-linolenic acid and eicosapentaenoic acid per se in high concentrations.

Arteriosclerosis↗
PubMed1990

Inhibition of nuclear T3 binding by fatty acids: dependence on chain length, unsaturated bonds, cis-trans configuration and esterification.

1. Fatty acids have the capacity for inhibition of nuclear T3 binding (INB). The present studies were undertaken to describe the INB-activity of fatty acids as a function of chain length, unsaturated bonds, cis-trans configuration, and esterification. 2. Isolated rat liver nuclei were incubated with [125I]T3 in the absence or presence of fatty acids in concentrations of 0.011, 0.033, 0.1 and 0.3 mM respectively. 3. INB-activity depended on the chain length, being greatest at 14 carbon atoms. 4. INB by unsaturated fatty acids was greater than that of saturated fatty acids, and increased with increasing number of double bonds. 5. Fatty acids in the cis configuration had greater INB-activity than those in trans configuration. 6. Esterification of fatty acids decreased INB-activity: monoglycerides still had some effect, but di- and triglycerides had no effect.

Animals↗
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↗
PubMed2003

Effects of dietary cis 9, trans 11-18:2, trans 10, cis 12-18:2, or vaccenic acid (trans 11-18:1) during lactation on body composition, tissue fatty acid profiles, and litter growth in mice.

Cis 9, trans 11 (c 9, t11)-18:2 and trans 10, cis 12 (t10, c12)-18:2 are the major conjugated linoleic acid (CLA) isomers in dietary supplements which reduce milk fat content in nursing women. The present study evaluated the effects of each CLA isomer or vaccenic acid on body composition and tissue fatty acids during lactation in mice. Dams were fed 30 g rapeseed oil (control)/kg diet or 20 g control plus 10 g 18:0, trans 11-18:1 (t11-18:1), c 9, t11-18:2, or t10, c12-18:2. Dietary t10, c12-18:2 reduced food intake by 18 % and carcass fat weight of the dams by 49 % compared with the other treatments. Milk fat percentage ranked by treatment was 18:0>t11-18:1=c 9, t11-18:2>t10, c12-18:2. The sum of saturated 12:0 to 16:0 in milk fat was lower when c 9, t11-18:2 was fed compared with the control, 18:0, or t11-18:1 treatments. Dietary t10, c12-18:2 caused further reductions in milk fat 12:0 to 16:0. The proportion of CLA isomers was 3-fold greater in milk fat than in the carcasses of the dams. The pups nursing from the dams fed t10, c12-18:2 had the lowest body weights and carcass fat, protein, and ash contents. Nursing from the dams fed c 9, t11-18:2 also resulted in lower carcass fat compared with the 18:0 or t11-18:1 treatments. The ratios of cis 9-16:1:16:0 or cis 9-18:1:18:0, proxies for Delta(9)-desaturase activity, were markedly lower in the carcasses of the dams and pups fed t10, c12-18:2. The ratio of 20:4n-6:18 : 2n-6, a proxy for Delta(6)- and Delta(5)-desaturase and elongase activity, in the liver of the dams and pups fed t10, c12-18:2 also was lower. Dietary t11-18:1 enhanced the content of c 9, t11-18:2 in milk fat and carcasses. As in previous studies, the reduction in food intake by t10, c12-18:2 could not entirely account for the marked decrease in carcass fat content and milk fat concentration. T10, c12-18:2 probably had a negative effect on Delta(9)-desaturase and mammary de novo fatty acid synthesis. Although these effects need to be confirmed in lactating women, the results suggest that the consumption of supplements containing t10, c12-18:2 should be avoided during the nursing period.

Animals↗
PubMed1994

Adaptation of Pseudomonas putida S12 to ethanol and toluene at the level of fatty acid composition of membranes.

Pseudomonas putida S12 was more tolerant to ethanol when preadapted to supersaturating concentrations of toluene. Cellular reactions at the membrane level to the toxicities of both compounds were different. In growing cells of P. putida S12, sublethal concentrations of toluene resulted in an increase in the degree of saturation of the membrane fatty acids, whereas toxically equivalent concentrations of ethanol led to a decrease in this value. Contrary to this, cells also reacted to both substances with a strong increase of the trans unsaturated fatty acids and a corresponding decrease of the cis unsaturated fatty acids under conditions where growth and other cellular membrane reactions were totally inhibited. While the isomerization of cis to trans unsaturated fatty acids compensates for the fluidizing effect caused by ethanol, a decrease in the degree of saturation is antagonistic with respect to the chemo-physical properties of the membrane. Consequently, the results support the hypothesis that the decrease in the degree of saturation induced by ethanol is not an adaptation mechanism but is caused by an inhibitory effect of the compound on the biosynthesis of saturated fatty acids.

3-Oxoacyl-(Acyl-Carrier-Protein) Synthase↗
PubMed1982

Evidence for a modified pathway of linoleate degradation. Metabolism of 2,4-decadienoyl coenzyme A.

The enzymatic degradation of 2,4-decadienoyl-CoA, an assumed metabolite of linoleic acid, was studied in vitro. 2-trans,4-trans-Decadienoyl-CoA, a metabolite of unsaturated fatty acids with trans double bonds, was readily degraded by a beta-oxidation system reconstituted from purified enzymes, as well as by rat heart mitochondria. In contrast, a mixture of 2-cis,4-cis-decadienoyl-CoA and 2-trans,4-cis-decadienoyl-CoA, the latter of which is assumed to be a metabolite of linoleic acid, was acted upon neither by the reconstituted beta-oxidation system nor by the beta-oxidation system present in rat heart mitochondria. However, all three 2,4-decadienoyl-CoA isomers were rapidly reduced by the NADPH-dependent 2,4-dienoyl-CoA reductase of rat heart mitochondria. Based on these observations, we conclude that 2-trans,4-cis-decadienoyl-CoA, a metabolite of linoleic acid, is not directly degraded via the beta-oxidation cycle, but instead is reduced by the NADPH-dependent 2,4-dienoyl-CoA reductase to 3-decenoyl-CoA which is further degraded via the beta-oxidation pathway.

3-Hydroxyacyl CoA Dehydrogenases↗
PubMed1987

Summation: which fat/how much fat--animals.

Promotion of carcinogenesis in rats by dietary fat depends on the amount and type of fatty acids ingested, mainly as triglycerides. A certain amount of essential fatty acid of the linoleate type (n-6) is required for promotion of mammary cancer and pancreatic cancer and probably also for colon cancer. Promotion is also enhanced by a high level of dietary fat, and this additional effect seems to be relatively independent of the type of fat. Saturated fatty acids, either medium or long chain, and cis and trans monoenoic fatty acids appear to have no specific promoting effects. Fish oils containing long-chain polyunsaturated fatty acids of the linolenate type (n-3) are inhibitory, and this may also be true for rapeseed oil high in erucic acid, a long-chain monoenoic fatty acid. The promoting action of dietary fat can be modified by other components of the diet, such as starch, sugar, and fiber. Promotion is also dependent on the length of time animals are exposed to the high-fat diet. The overall tumor yield can be decreased by reducing the level and degree of unsaturation of the dietary fat after a period of feeding a high polyunsaturated-fat diet.

Animals↗
PubMed1994

Incorporation of trans long-chain n-3 polyunsaturated fatty acids in rat brain structures and retina.

During heat treatment, polyunsaturated fatty acids and specifically 18:3n-3 can undergo geometrical isomerization. In rat tissues, 18:3 delta 9c,12c,15t, one of the trans isomers of linolenic acid, can be desaturated and elongated to give trans isomers of eicosapentaenoic and docosahexaenoic acids. The present study was undertaken to determine whether such compounds are incorporated into brain structures that are rich in n-3 long-chain polyunsaturated fatty acids. Two fractions enriched in trans isomers of alpha-linolenic acid were prepared and fed to female adult rats during gestation and lactation. The pups were killed at weaning. Synaptosomes, brain microvessels and retina were shown to contain the highest levels (about 0.5% of total fatty acids) of the trans isomer of docosahexaenoic acid (22:6 delta 4c,7c,10c,13c,16c,19t). This compound was also observed in myelin and sciatic nerve, but to a lesser extent (0.1% of total fatty acids). However, the ratios of 22:6 trans to 22:6 cis were similar in all the tissues studied. When the diet was deficient in alpha-linolenic acid, the incorporation of trans isomers was apparently doubled. However, comparison of the ratios of trans 18:3n-3 to cis 18:3n-3 in the diet revealed that the cis n-3 fatty acids were more easily desaturated and elongated to 22:6n-3 than the corresponding trans n-3 fatty acids. An increase in 22:5n-6 was thus observed, as has previously been described in n-3 fatty acid deficiency. These results encourage further studies to determine whether or not incorporations of such trans isomers into tissues may have physiological implications.

Animals↗
PubMed1988

Distribution of trans and cis 18:1 fatty acid isomers in chicks fed different fats.

The effects of dietary trans isomers of 18:1 (t-18:1) were studied in chicks by feeding purified diets containing soybean oil (SBO) as the control lipid source, saturated fat (SF), hydrogenated soybean oil (HSBO), or spent restaurant grease (SRG) for three weeks. Argentation thin-layer chromatography and gas-liquid chromatography were used to separate trans and cis (c) isomers of 18:1 and to determine the fatty acid composition in chick tissues. Chicks fed HSBO (34% t-18:1 of total 18:1) had weight gains similar to those of chicks fed SF but significantly (P less than .05) lower gains than those of chicks fed SBO or SRG. No differences were observed in feed conversion ratios (total feed:total gain) across treatments. Trans-18:1 was incorporated into liver, heart, lung, and abdominal fat pad of chicks fed HSBO. Chicks fed HSBO had higher levels of c-16:1 omega 7 and 18:1 and lower levels of linoleate and arachidonate in tissue lipids. Similar changes were observed in liver microsomal fatty acids of chicks fed SRG that was adequate in linoleate, but which contained low levels of t-18:1 (4% of total 18:1). Positional and geometrical isomers of 18:1 appear to impair essential fatty acid metabolism in the chick.

Adipose Tissue↗
PubMed1976

Motion of spin-labeled fatty acids in murine macrophages. Relation to cellular phagocytic activity.

Macrophage membrane fluidity was investigated with respect to cellular phagocytic activity through the use of fatty acid spin labels. Spin-labeled fatty acid derivatives were incorporated into intact mouse peritoneal macrophages by exchange from bovine serum albumin. The electron spin resonance (ESR) spectra of the spin-labeled fatty acids in the macrophages showed a pronounced temperature dependence and a decrease in the hyperfine splittings (2 T11) of the spectra as the nitroxide radical was moved away from the polar head group of the fatty acid derivatives. Spin-labeled macrophages underwent a time- and temperature-dependent decay, which was inhibited by preincubating the cells with mercuric chloride, heating at 56 degrees C, or by fixing them with 0.25% glutaraldehyde. No correlation between the phagocytic activity of macrophages and membrane freedom of motion could be demonstrated. Treatment of macrophages with anti-macrophage serum or extended in vitro cultivation inhibited cellular phagocytic activity but exerted no effect on the motional freedom of the macrophage membrane. Enrichment of the fatty acid composition of the macrophage membrane with cis- or trans-unsaturated fatty acids had striking effects on cellular phagocytic activity, while no significant changes could be detected in the freedom of motion of incorporated fatty acid spin labels at the degree of specific enrichment achieved here. Thus no correlation between cellular phagocytic activity and lipid motion could be detected.

Animals↗
PubMed1990

Trans n-3 eicosapentaenoic and docosahexaenoic acid isomers exhibit different inhibitory effects on arachidonic acid metabolism in human platelets compared to the respective cis fatty acids.

N-3 trans geometrical isomers of 20:5 n-3 and 22:6 n-3 were isolated from rats fed heated linseed oil. The ability of these acids to inhibit 20:4 n-6 metabolism by human platelets was examined. The concentrations required to inhibit 50% of platelet aggregation (IC50) induced by 2.5 microM 20:4 n-6 were higher for the 20:5 delta 17t isomer compared to all cis 20:5 n-3; means 29.2 and 7.6 microM, respectively (P less than 0.05). There were no significant differences in IC50 between 22:6 delta 19t and all cis 22:6 n-3; means 4.3 and 5.6 microM, respectively (P greater than 0.05). Inhibition of action of cyclooxygenase on 20:4 n-6 was similar for 20:5 delta 17t and 20:5 n-3 when examined at their IC50s, but comparison at equal concentrations indicated that 20:5 n-3 was a significantly better inhibitor (P less than 0.05). The ability to inhibit platelet aggregation was paralleled by cyclooxygenase inhibition as determined by thromboxane B2 and 12-hydroxyheptadecatrienoic acid formation. 22:6 delta 19t appeared to inhibit cyclooxygenase more completely than 22:6 n-3, examined at their IC50s or at similar concentrations (P less than 0.05). Isomers of 20:5 n-3 and 22:6 n-3 having an n-3 cis or trans bond appear to have similar modes of action, although levels required for effectiveness are different for the C20 acids.

Arachidonic Acids↗
PubMed2003

Serum fatty acids and breast cancer incidence.

Fatty acid composition of the diet may be essential to the development of breast cancer. We studied the ability of several fatty acids of serum total lipids to predict breast cancer incidence in a case-control study nested within a longitudinal population study. The proportions of fatty acids in serum total lipids were determined from stored serum samples collected at baseline for 127 incident breast cancer cases and 242 matched controls. Women with a higher proportion of total polyunsaturated fatty acids (PUFAs) in serum had a reduced risk of breast cancer. The odds ratio (OR) between the highest and lowest tertiles of serum PUFA was 0.31 (95% confidence interval, CI = 0.12-0.77). This association was mainly due to n-6 PUFAs and especially to linoleic acid. The ORs were 0.35 (CI = 0.14-0.84) and 0.29 (CI = 0.12-0.73), respectively. Of the monounsaturated fatty acids (MUFAs), higher trans-11-18:1 levels were related to an increased breast cancer risk (OR = 3.69, CI = 1.35-10.06). The association was stronger in postmenopausal than in premenopausal women. The present study suggests that higher serum proportions of the n-6 PUFA linoleic acid and lower proportions of the MUFA trans-11-18:1 fatty acid predict a reduced incidence of breast cancer.

Adult↗