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PubMed2004

Effects of odd-numbered medium-chain fatty acids on the accumulation of long-chain 3-hydroxy-fatty acids in long-chain L-3-hydroxyacyl CoA dehydrogenase and mitochondrial trifunctional protein deficient skin fibroblasts.

The treatment for patients with genetic disorders of mitochondrial long-chain fatty acid beta-oxidation is directed toward providing sufficient sources of energy for normal growth and development, and at the same time preventing the adverse effects that precipitate or result from metabolic decompensation. Standard of care treatment has focused on preventing the mobilization of lipids that result from fasting and providing medium-chain triglycerides (MCT) in the diet in order to bypass the long-chain metabolic block. MCTs that are currently available as commercial preparations are in the form of even-chain fatty acids that are predominately a mixture of octanoate and decanoate. Recently, the use of odd-chain fatty acids has been proposed as an alternative treatment. We have shown previously that the even-numbered medium-chain fatty acids (MCFAs) that are found in MCT preparations can reduce the accumulation of potentially toxic long-chain metabolites of fatty acid oxidation (FAO). In the current study, we undertook to determine if the same is true of odd-numbered MCFAs. We found that provision of odd-chain species does decrease the build-up of long-chain FAO intermediates in our in vitro skin fibroblast model, but to a lesser extent than even-numbered MCFAs.

3-Hydroxyacyl CoA Dehydrogenases↗
PubMed2006

Fatty acid metabolism in the freshwater fish Murray cod (Maccullochella peelii peelii) deduced by the whole-body fatty acid balance method.

The whole-body fatty acid balance method was used to investigate the fatty acid metabolism in Murray cod (Maccullochella peelii peelii) fed diets containing canola (CO) or linseed oil (LO). Murray cod were able to elongate and desaturate both 18:2n-6 and 18:3n-3. In fish fed the CO diet, 54.4% of the 18:2n-6 consumed was accumulated, 38.5% oxidized and 6.4% elongated and desaturated to higher homologs. Fish fed the LO diet accumulated 52.9%, oxidized 37% and elongated and desaturated 8.6% of the consumed 18:3n-3. The overall roles of n-6 fatty acids appeared more important in Murray cod compared to other freshwater species. Murray cod also showed a preferential order of utilization of C18 fatty acid for energy production (18:3n-3 > 18:2n-6 > 18:1n-9). Moreover, it is demonstrated that an increase in dietary 18:3n-3 is directly responsible of increased desaturase activity and augmented saturated fatty acid accumulation in the fish body. The present study also suggests that, in the context of the possible maximization of the natural ability of fish to produce long chain polyunsaturated fatty acids, the whole-body approach can be considered well suited and informative and Murray cod is a suited candidate to fish oil replacement for its diets.

Animals↗
PubMed1999

Selective retention of n-3 and n-6 fatty acids in human milk lipids in the face of increasing proportions of medium chain-length (C10-14) fatty acids.

This paper reports the results of our analysis of the impact high levels of de novo fatty acids have on the proportions of essential and non-essential fatty acids in human milk lipids. The data for seven fatty acids (linoleic, alpha-linolenic, arachidonic (AA), docosahexaenoic (DHA), palmitic, stearic and oleic) were derived from several studies conducted in Nigeria. The proportion by weight of each of these fatty acids was plotted versus the proportion of C10-14 fatty acids. As the proportion of C10-14 fatty acids increased from 15 to 65%, there was not a proportional decrease in the percentages of all seven fatty acids, but, instead, preferential incorporation of the essential fatty acids, AA and DHA into the triacylglycerol component of the milk. At the same time, the proportions of stearic and oleic acid declined by 69% and 86%, respectively. However, the proportions of linoleic acid, palmitic acid, DHA, AA and alpha-linolenic acid, in milk lipids decreased by only 44%, 40%, 39%, 28% and 2.3%, respectively. These observations indicate that as the contribution of C10-14 fatty acids increases, essential fatty acids are preferentially incorporated into milk triacylglycerols at the expense of oleic acid and stearic acid.

Adolescent↗
PubMed1999

Effect of fatty acid saturation in broiler diets on abdominal fat and breast muscle fatty acid composition and susceptibility to lipid oxidation.

A total of 600 1-d-old Hybro N broiler chicks were randomly distributed into 24 litter pens and fed from 21 to 52 d of age isocaloric and isonitrogenous diets containing 8% of three different fat sources (tallow, lard or sunflower oil). Dietary treatment produced a significant effect (P < 0.05) in fatty acid composition of the intramuscular neutral lipids among all dietary treatments and for all lipid classes. A similar range of variation was obtained for abdominal fat fatty acid composition. In the intramuscular polar lipid fraction, dietary fat led to a narrow range in the variation of poly- and monounsaturated fatty acid composition, while the concentration of saturated fatty acids was maintained constant in all groups. A wide range in the melting point temperature of abdominal fat was observed (mean values of dietary treatments from 8.49 to 30.91 C), which indicates a major effect of dietary fatty acids on fat consistency. The variation of breast meat oxidation was small (mean values from 7.68 to 9.76 nmol malonaldehyde/mg protein). A dietary fat source rich in linoleic acid produces a marked effect on fat consistency, but only a moderately higher susceptibility to lipid oxidation of meat compared to tallow or lard.

Animal Feed↗
PubMed1975

Actions of ricinoleic acid and structurally related fatty acids on the gastrointestinal tract. II. Effects on water and electrolyte absorption in vitro.

Ricinoleic acid, the active component of castor oil, and related fatty acids were studied to determine their relative inhibitory effects on water and electrolyte absorption using everted hamster jejunal and ileal segments. Differences were found between hydroxylated and nonhydroxylated congeners as well as between cis and trans geometric isomers. At a mucosal concentration of 2.0 mM, the unsaturated fatty acids had the following rank order of potency on inhibition of water absorption: ricionoleate greater than or equal to ricinelaidate- greater than equal to linoleate greater than oleate greater than linelaidate greater than elaidate. Ricinoleyl alcohol was effective at 2.0 mM but the methyl ester of ricinoleic acid was ineffective at this concentration. Among a series of saturated fatty acids including palmitate, stearate, a mixture of 9- and 10-hydroxystearate, and 12-hydroxystearate, only the last compound had any inhibitory effect on water absorption. The results define those portions of the ricinoleic acid molecule required for its effect on water and electrolyte absorption and suggest that classification of this cathartic as an "irritant" or "stimulant" should be re-evlauated.

Animals↗
PubMed1965

Folic acid involvement in cyclopropane fatty acid synthesis in lactobacilli.

Henderson, Thomas O. (North Carolina State University, Raleigh), John J. McNeill, and S. B. Tove. Folic acid involvement in cyclopropane fatty acid synthesis in lactobacilli. J. Bacteriol. 90:1283-1287. 1965.-Evidence for the involvement of folic acid in the synthesis of lactobacillic acid (11,12-methyleneoctadecanoic acid) was obtained with Lactobacillus plantarum and L. casei. L. plantarum, in the presence of aminopterin, incorporated 25% less radioactivity from methionine-methyl-C(14) into long-chain fatty acids than did control cultures, whereas the incorporation of acetate-1-C(14), representing overall fatty acid synthesis, was the same in both conditions. Control cultures of L. plantarum contained 3 to 4.5 times more lactobacillic acid than did aminopterin-grown cultures. Similarly, L. casei, in the presence of folic acid, synthesized six times more lactobacillic acid than did folic-deficient cultures. The results of this study indicate that coenzymes of the folic acid group are involved in the synthesis of lactobacillic acid in these organisms.

Acetates↗
PubMed1984

[Rumen fermentation with special reference to volatile fatty acid production during reproduction. 1. Methods and results of volatile fatty acid levels and production rates in vitro].

The target of the investigations was to register part of the synthesis performance in the rumen of ewes during the complete reproduction cycle. With the help of in-vitro experiments with artificial rumen the concentration and production rates of volatile fatty acids in the rumen fluid were measured. From the experiments the measured data of fertility-accentuated crossbreeding (experiment 1) and crossbreeding (experiment 2) ewes were contrasted. The average concentrations of volatile fatty acids in ewes are 95.4 m mol/l in experiment 1 and 109.2 m mol/l in experiment 2 during the early stage gestation, 121.4 m mol/l in experiment 1 and 99.8 m mol/l in experiment 2 in the last stage stage of gestation, 129.6 m mol/l in experiment 1 and 112.8 m mol/l in experiment 2 during lactation and 106.6 m mol/l in experiment 1 and 112.9 m mol/l in experiment 2 during the dry period. The production rates of volatile fatty acids calculated form their concentration amount to 4.8 m mol/l X h in experiment 1 and 2.6 m mol/l X h in experiment 2 in the early stage of gestation, 3.5 m mol/l X h in experiment 1 and 3.1 m mol/l X h in experiment 2 in the last stage of gestation, 3.2 m mol/l X h in experiment 1 and 2.7 m mol/l X h in experiment 2 during lactation and 3.7 m mol/l X h in experiment 1 and 2.9 m mol/l X h in experiment 2 in the dry period. The correlation between the concentration and the production rate of volatile fatty acids is not significantly negative in either of the ewe experiments. The scattering of the individual values is wide so that the individual influence of the test animals as well as the influence of the in-vitro method used permit the conclusion that a significant statement on the influence of the genotype and the stage of reproduction on the production rates cannot be made.

Animals↗
PubMed1993

Peroxisomal beta-oxidation of polyunsaturated long chain fatty acids in human fibroblasts. The polyunsaturated and the saturated long chain fatty acids are retroconverted by the same acyl-CoA oxidase.

The metabolism of the C22 unsaturated fatty acids erucic acid (22:1(n-9)), adrenic acid (22:4(n-6)), docosapentaenoic acid (22:5(n-3)) and docosahexaenoic acid (22:6(n-3)) was studied in cultured fibroblasts from patients with acyl-CoA oxidase deficiency, the Zellweger syndrome, X-linked adrenoleukodystrophy (X-ALD) and normal controls. [3-14C] 22:4 (n-6) and [3-14C] 22:5 (n-3) were shortened (retroconverted) to [1-14C] 20:4 (n-6) and [1-14C] 20:5 (n-3), respectively, in normal and X-ALD fibroblasts. In Zellweger and acyl-CoA oxidase deficient fibroblasts these reactions were deficient. Since the retroconversion is normal in X-ALD fibroblasts peroxisomal very long chain (lignoceryl) CoA ligase is probably not required for the activation of C22 unsaturated fatty acids. The present work with fibroblasts from patients with a specific acyl-CoA oxidase deficiency, previously shown to have a deficient peroxisomal clofibrate-inducible acyl-CoA oxidase, and which accumulate 24:0 and 26:0 fatty acids, supports the view that this enzyme is responsible for the chain-shortening of docosahexaenoic acid (22:6(n-3)), erucic acid (22:1(n-9)), docosapentaenoic acid (22:5(n-3)), and adrenic acid (22:4(n-6)) as well.

Acyl-CoA Oxidase↗
PubMed1984

The effects of dietary cholesterol on blood and liver polyunsaturated fatty acids and on plasma cholesterol in rats fed various types of fatty acid diet.

Male rats were fed on a fat-free diet for 8 weeks and then switched to diets containing 10% hydrogenated coconut oil (HCO), safflower oil (SFO) or evening primrose oil (EPO). Half of each group was also given 1% of cholesterol in the diet. After 5 further weeks, plasma, red cell and liver fatty acids were measured in the various lipid fractions. Plasma and liver cholesterol also were estimated. In almost all fractions and on all three diets, feeding cholesterol led to accumulation of the substrates of desaturation reactions and to deficits of the products of these reactions. The results were consistent with inhibition of delta-6, delta-5 and delta-4 desaturation of n-6 essential fatty acids. Since the diets were deficient in n-3 fatty acids, levels were very low but were also consistent with inhibition of desaturation. In contrast, cholesterol had relatively less consistent effects on 20:3n-9, suggesting that desaturation of n-9 fatty acids was less inhibited. Plasma cholesterol levels rose sharply in the HCO and SFO groups but not at all in the EPO group. EPO contains the product of delta-6-desaturation, 18:3n-6, suggesting that conversion of linoleic acid to 18:3n-6 and possibly to further metabolites may be important for the cholesterol-lowering effect of polyunsaturates.

Animals↗
PubMed1988

[Early modification of the fatty acid composition of cardiolipins and other phospholipids in rat liver mitochondria during dietary deficiency of essential fatty acids followed by repletion].

Weaned rats (21-day old, 44 +/- 2 g) were distributed into 3 groups. The first group was raised on a laboratory diet for 7 or 20 days (control group). The second was fed a diet containing 0.07% fat for 1, 2, 3, 7 or 66 days. The third one was fed the low-fat diet for 7 days and then switched to a laboratory chow diet for 1, 2, 5 or 9 days. Cardiolipin (CL) on the one hand and other mitochondrial phospholipids taken as a whole (PLm) on the other hand were prepared from liver mitochondria and their fatty acids analysed. Polyunsaturated fatty acids in PLm (18:2 (n-6), 20:4 (n-6), 22:6 (n-3) acids) decreased abruptly during the first 3 days of fat deficiency and then remained rather stable till day 7. CL behaved in a quite different way. 18:2 (n-6) acid, the major polyunsaturated fatty acid of CL, decreased continuously between day 1 and day 7 from 79% to 33%. A value of 19.6% was reached on day 66. When deficient rats were transferred to an equilibrated diet, the fatty acid profile of PLm was rapidly restored. Major effects were already achieved during the first 24 h and a fatty acid composition identical to that of control rats was reached within 2 days. A considerably longer period (about 9 days) was necessary for CL to reach a level analogous to that of control rats. The diminution of linoleic acid in CL was brought about by increases in the levels of monoenoic acids: palmitoleic (16:1 (n-7)), oleic (18:1 (n-9)) and cis-vaccenic (18:1 (n-7)) acids which accounted for 18.0%, 17.7% and 17.9% respectively on day 7. Increases in the (n-7) monoenes remained comparatively low in PLm, which showed a sharp rise in their oleic acid content (from 3.9% to 12.7% in 3 days). The proportion of cis-vaccenic acid relative to total octadecenoic acids was decreased from 75% to 50% in CL. A similar trend, but of smaller magnitude, was also noticed in PLm.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed1994

Essential fatty acid metabolism in the feline: relationship between liver and brain production of long-chain polyunsaturated fatty acids.

A comparison was made between the liver and brain conversion of linoleic acid, 18:2n-6, and linolenic acid, 18:3n-3, to long chain polyunsaturated fatty acids in domestic felines. This report demonstrates that 6-desaturase activity does exist in the feline. The liver produced deuterium-labeled polyunsaturated fatty acids up to 22:4n-6 and 22:5n-3. The brain was found to accumulate the deuterium-labeled polyunsaturated fatty acids, 22:5n-6, 22:6n-3, 24:4n-6, 24:5n-6, 24:5n-3, and 24:6n-3. Adult felines were provided a diet consisting of either 10% fat (hydrogenated coconut oil-corn oil 9:1) containing no 20- or 22-carbon n-6 or n-3 fatty acids or a chow diet with meat and meat by-products that contained these long chain polyunsaturated fatty acids for a 6-month period. During this time, the in vivo production of long chain polyunsaturated fatty acids was evaluated in these animals. The cats were given oral doses of both [17,17,18,18,18,2H]18:3n-3 and [9,10,12,13-2H]18:2n-6 and the deuterium-labeled fatty acid metabolites were measured in the blood, liver, and brain using a highly sensitive and specific gas chromatography-mass spectrometry technique. Contrary to previous claims, 6-desaturase activity was shown to exist in the feline. The evidence for this was the detection of [9,10,12,13-2H] 18:3n-6 which was converted from [9,10,12,13-2H]18:2n-6 and observed in the plasma.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1987

Modification of fatty acid composition of membrane phospholipid in hepatocyte monolayer with n-3, n-6 and n-9 fatty acids and its relationship to triacylglycerol production.

The objective of these studies with rat hepatocytes in primary culture was to establish that: (a) membrane phospholipids would become enriched with the specific fatty acid supplemented to the media and (b) hepatocyte monolayer triacylglycerol synthetic rates were dependent on the type of fatty acid enrichment of the membrane phospholipids. Hepatocytes cultured in the absence of media lipid developed a phospholipid fatty acid composition which is indicative of an essential fatty acid deficiency. The extensive rise in 18:1(n - 9) content indicated that delta 9-desaturase was active. The fatty acid composition of phosphatidylcholine, phosphatidylethanolamine and phosphatidylinositol in the microsomal- and mitochondrial-enriched fractions was highly dependent upon the type of fatty acid supplemented to the medium. Incorporation of fatty acids into phospholipids was rapid, and a new steady-state in fatty acid composition was achieved within approx. 36 h. Changes in the fatty acid composition of these hepatocyte phospholipid subclasses resulting from media supplementation with 18:2/20:4(n-6) or 20:5(n-3) were similar, but not identical, to changes which occurred in vivo as a result of consuming diets rich in 18:2(n-6) or 20:5(n-3). Hepatocyte lipogenesis was highly dependent upon the type of fatty acid supplemented to the medium. Prior conditioning with 16:0 increased triacylglycerol synthesis and secretion. Secretion of triacylglycerol was reduced by polyenoic fatty acid enrichment with 20:5(n-3) greater than 20:4/18:2(n-6). The suppression of triacylglycerol synthesis by 20:5(n-3) was due to an increased (P less than 0.05) diacylglycerol specific activity, which indicates that 20:5(n-3) suppression of hepatic triacylglycerol production may be caused in part by the inhibition of diacylglycerol acyltransferase.

Animals↗