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Relative fatty acid composition of serum lecithin in the second half of the normal pregnancy.

Fasting vein blood samples from 21 apparently normal pregnant women were collected in 4-week intervals from the 24th week of gestation until delivery. The relative fatty acid composition of serum lecithin was analyzed by gas-liquid chromatography. Palmitic acid increased successively concomitant with a decrease in stearic acid which indicates that serum lecithin is predominantly synthesized along pathway I. Linoleic acid decreased successively parallel to an increased incorporation of longer polyunsaturated fatty acids and non-essential monoenoic (palmitoleic and oleic) acids. The increased incorporation of longer polyunsaturated fatty acids is suggested to be associated with the increased activity of the deacylation-reacylation cycle. The increase of nonessential monoenoic fatty acids is suggested to be associated with a reduced de novo incorporation of linoleic acid.

Adult↗

delta 9 Acyl-lipid desaturases of cyanobacteria. Molecular cloning and substrate specificities in terms of fatty acids, sn-positions, and polar head groups.

In cyanobacteria, the biosynthesis of unsaturated fatty acids is initiated by delta 9 acyl-lipid desaturase which introduces the first double bond at the delta 9 position of a saturated fatty acid that has been esterified to a glycerolipid. We have cloned genes, designated desC, for delta 9 acyl-lipid desaturases from two cyanobacteria, namely Anabaena variabilis and Synechocystis sp. PCC 6803. These desaturases, when expressed in Escherichia coli, desaturated stearic acid to yield oleic acid at the C-1 positions of phosphatidylethanolamine and phosphatidylglycerol, but did not desaturate palmitic acid, palmitoleic acid, and cis-vaccenic acid. These results indicate that the delta 9 acyl-lipid desaturases are specific to stearic acid esterified at the C-1 position of a glycerolipid and are nonspecific with respect to the polar head group of the glycerolipid. The deduced amino acid sequences of the delta 9 acyl-lipid desaturases are similar in part to those of stearoyl-CoA desaturases of the rat, the mouse, and Saccharomyces cerevisiae, but not to those of acyl-(acyl-carrier-protein) desaturases of higher plants.

Amino Acid Sequence↗

Structure and Biosynthesis of Cuticular Lipids: Hydroxylation of Palmitic Acid and Decarboxylation of C(28), C(30), and C(32) Acids in Vicia faba Flowers.

The structure and composition of the cutin monomers from the flower petals of Vicia faba were determined by hydrogenolysis (LiAlH(4)) or deuterolysis (LiAlD(4)) followed by thin layer chromatography and combined gas-liquid chromatography and mass spectrometry. The major components were 10, 16-dihydroxyhexadecanoic acid (79.8%), 9, 16-dihydroxyhexadecanoic acid (4.2%), 16-hydroxyhexadecanoic acid (4.2%), 18-hydroxyoctadecanoic acid (1.6%), and hexadecanoic acid (2.4%). These results show that flower petal cutin is very similar to leaf cutin of V. faba. Developing petals readily incorporated exogenous [1-(14)C]palmitic acid into cutin. Direct conversion of the exogeneous acid into 16-hydroxyhexadecanoic acid, 10, 16-dihydroxy-, and 9, 16-dihydroxyhexadecanoic acid was demonstrated by radio gas-liquid chromatography of their chemical degradation products. About 1% of the exogenous [1-(14)C]palmitic acid was incorporated into C(27), C(29), and C(31)n-alkanes, which were identified by combined gas-liquid chromatography and mass spectrometry as the major components of the hydrocarbons of V. faba flowers. The radioactivity distribution among these three alkanes (C(27), 15%; C(29), 48%; C(31), 38%) was similar to the per cent composition of the alkanes (C(27), 12%; C(29), 43%; C(31), 44%). [1-(14)C]Stearic acid was also incorporated into C(27), C(29), and C(31)n-alkanes in good yield (3%). Trichloroacetate, which has been postulated to be an inhibitor of fatty acid elongation, inhibited the conversion of [1-(14)C]stearic acid to alkanes, and the inhibition was greatest for the longer alkanes. Developing flower petals also incorporated exogenous C(28), C(30), and C(32) acids into alkanes in 0.5% to 5% yields. [G-(3)H]n-octacosanoic acid (C(28)) was incorporated into C(27), C(29), and C(31)n-alkanes. [G-(3)H]n-triacontanoic acid (C(30)) was incorporated mainly into C(29) and C(31) alkanes, whereas [9, 10, 11-(3)H]n-dotriacontanoic acid (C(32)) was converted mainly to C(31) alkane. Trichloroacetate inhibited the conversion of the exogenous acids into alkanes with carbon chains longer than the exogenous acid, and at the same time increased the amount of the direct decarboxylation product formed. These results clearly demonstrate direct decarboxylation as well as elongation and decarboxylation of exogenous fatty acids, and thus constitute the most direct evidence thus far obtained for an elongation-decarboxylation mechanism for the biosynthesis of alkanes.

Journal Article↗

An alternative explanation for the changes in erythrocyte fatty acids observed in diabetes mellitus.

Fatty acids in erythrocyte membranes and plasma were determined by capillary gas-liquid chromatography in 27 controls and 44 subjects with insulin-dependent diabetes mellitus. Significant decreases in stearic acid (P less than 0.00003) and arachidonic acid (P less than 0.001) and significant increases in palmitic acid (P less than 0.00003) were observed in erythrocytes from diabetic patients. The stearic:oleic acid ratios and arachidonic:linoleic acid ratios in erythrocytes were significantly lower in diabetic patients than in controls (P less than 0.0003 and less than 0.0007, respectively). The relative concentration of palmitic acid in plasma (as a percentage of the sum of the five major fatty acids) was increased in diabetic patients, as compared with controls (P less than 0.0125). We observed no other significant differences in fatty acids in plasma, making it unlikely that changes in fatty acids in erythrocyte membranes in diabetic patients can be accounted for simply by alterations in the fatty acids in plasma. We propose that impaired metabolic control associated with diabetes mellitus may interfere with the maintenance of fatty acid profiles in erythrocyte membranes against the concentration gradients in plasma.

Adolescent↗

Neonatal changes in fatty acid profile of phospholipids in rat heart muscle.

The fatty acid composition of rat heart phospholipids was examined during the neonatal and postnatal period. The rats were killed on days 1, 7, 14 and 21 after birth and at the ages of 2 and 6 months. The fatty acyl chain composition of the two major phospholipids, phosphatidylcholine (PC) and phosphatidylethanolamine (PE) changed significantly during the first 2 months. In PC there was a marked and immediate increase in stearic acid, a significant but transient increase in arachidonic acid and late increase in linoleic acid content. In PE there was an immediate increase in stearic acid and docosahexaenoic acid, followed by a late increase in linoleic acid content. The observed alterations in fatty acid composition of heart muscle phospholipids resemble changes induced by repeated administration of norepinephrine and subsequent recovery. Neonatal stress and increased cardiac function play an important role in the modification of the fatty acid composition of rat heart muscle phospholipids during early development.

Aging↗

The mobilization of free fatty acids in relation to adipose tissue triglyceride fatty acids in the rat.

Three diets, consisting respectively of formulations high in oleic and stearic acid, linolenic acid, and lauric acid, were fed to rats until the adipose tissue TGFA largely reflected the dietary pattern of fatty acids. The composition of the serum FFA under basal conditions and following noradrenaline-stimulated lipolysis, were examined in relation to the respective adipose tissue TGFA. It was found in both in vivo and in vitro studies that lauric acid appeared to be less easily mobilized than longer chain acids. The in vitro studies indicated that this could not be explained either by positional preference of the shorter chain acids for the alpha-position of esterification or by increased reesterification of the shorter chain acids. The possibility remains that the difference is due to some specificity of tissue lipases for certain ester linkages.

Adipose Tissue↗

[Postnatal development of the fatty acid composition of lipids of adipose and muscle tissue in rabbits on a low-fat diet].

The relative fatty acid profiles of perirenal adipose tissue and muscle tissue of the hind legs were studied in New Zealand rabbits 21 to 140 days old. The rabbits were fed a low-fat diet covering the essential fatty acid requirements and distributed either ad libitum or in rationed amounts. The whole of the fatty acids were established earlier in hind leg muscle tissue than in perirenal adipose tissue. In the latter, the growth allometry of fatty acids in relation to the carcass was already higher between 21 and 74 days (a = 1.39) and distinctly higher between 74 and 140 days (a = 2.68). In the muscle tissue, an isometric phase (a = 0.96) preceded a major allometric phase (a = 1.76). In young suckling rabbits, the fatty acid profile of perirenal lipids was influenced by that of the milk lipids. In the muscle tissue, the presence of a large proportion of phospholipids resulted in a higher percentage of stearic acid and polyunsaturated fatty acids of the (n-6) family (linoleic, dihomo-gamma-linolenic and arachidonic acids). After weaning, the proportion of saturated fatty acids (C greater than or equal to 14) in the perirenal adipose tissue remained constant. The endogenous production of monounsaturated fatty acids (higher allometry) caused a progressive dilution of polyunsaturated fatty acids (lower allometry). This dilution was slowed down when the diet was rationed. Changes in the fatty acid composition of muscle tissue were, in general, comparable to those of perirenal adipose tissue. The differences observed could be attributed to the more active participation of phospholipids in the total lipids of the muscle tissue. Stearic acid, abundant in the phospholipids, showed a lower allometry compared to total fatty acids. Its dilution was an expression of triglyceride dilution of the phospholipids during growth. The same was true of polyunsaturated fatty acids. Rationing had the reverse effect.

Adipose Tissue↗

Effects of arachidonic acid and the other long-chain fatty acids on the membrane currents in the squid giant axon.

The effects of arachidonic acid and some other long-chain fatty acids on the ionic currents of the voltage-clamped squid giant axon were investigated using intracellular application of the test substances. The effects of these acids, which are usually insoluble in solution, were examined by using alpha-cyclodextrin as a solvent, alpha-cyclodextrin itself had no effect on the excitable membrane. Arachidonic acid mainly suppresses the Na current but has little effect on the K current. These effects are completely reversed after washing with control solution. The concentration required to suppress the peak inward current by 50% (ED50) was 0.18 mM, which was 10 times larger than that of medium-chain fatty acids like 2-decenoic acid. The Hill number was 1.5 for arachidonic acid, which is almost the same value as for medium-chain fatty acids. This means that the mechanisms of the inhibition are similar in both long- and medium-chain fatty acids. When the long-chain fatty acids were compared, the efficacy of suppression of Na current was about the same value for arachidonic acid, docosatetraenoic acid and docosahexaenoic acid. The suppression effects of linoleic acid and linolenic acid on Na currents were one-third of that of arachidonic acid. Oleic acid had a small suppression effect and stearic acid had almost no effect on the Na current. The currents were fitted to equations similar to those proposed by Hodgkin and Huxley (Hodgkin, A.L., Huxley, A.F. (1952) J. Physiol (London) 117:500-544) and the change in the parameters of these equations in the presence of fatty acids were calculated.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗

Is there a blood-brain relationship for saturated fatty acids during development?

Transport of subcutaneously injected [1-14C]-stearic acid through the blood-brain barrier is compared with endogenous biosynthesis (within the brain) during postnatal brain development in mice. The uptake is very important during glial cell multiplication and myelination; endogenous microsomal synthesis is most active during myelination, soluble de novo mechanism is prominent during cell multiplication (mitochondrial systems are not directly related to these events). A parallel is drawn between myelin fatty acids, microsomal synthesis and uptake from the blood.

Animals↗

Lipid and fatty acid analysis of fresh and frozen-thawed immature and in vitro matured bovine oocytes.

The lipid content and fatty acid composition of fresh immature and in vitro matured bovine oocytes cultured in media with or without serum, and also those of frozen-thawed immature oocytes were analysed. All oocytes were ranked (A or B) on the basis of their cytoplasmic quality. Fatty acid composition (mol %; w/w) in the total lipid fraction was analysed by gas chromatography. Triglyceride, total cholesterol, phospholipid (phosphocholine-containing phospholipid) and non-esterified fatty acid contents of immature and in vitro matured oocytes were determined using lipid analysis kits. Phosphocholine-containing phospholipid and non-esterified fatty acid contents were determined in frozen-thawed immature bovine oocytes. Palmitic acid was the most abundant fatty acid in immature oocytes (A: 35%, B: 36%), and in in vitro matured oocytes cultured in the medium containing serum (A: 36%, B: 35%) or polyvinyl alcohol (A: 33%, B: 36%). Oleic acid was the second most abundant fatty acid in all A ranked oocytes, whereas stearic acid was the second most abundant fatty acid in all B ranked oocytes. There were significant differences (P < 0.05) in linoleic and arachidonic acid fractions between A and B ranked immature oocytes. In vitro matured oocytes had significantly (P < 0.05) lower proportions of linoleic and arachidonic acids, and significantly (P < 0.01) lower contents of triglyceride and total cholesterol compared with those of immature oocytes. The fatty acid composition of in vitro matured oocytes cultured in medium containing fetal calf serum or polyvinyl alcohol was similar, but significant differences (P < 0.01) in triglyceride and the total cholesterol content were observed. There was a significant decrease (P < 0.05) in the arachidonic acid proportion in frozen-thawed immature oocytes compared with that in fresh immature oocytes. In addition, significant (P < 0.05) decreases in both phospholipid (15.8--10.6 pmol) and non-esterified fatty acid (11.0--4.1 pmol) were found in frozen--thawed immature oocytes. The results indicate that lipids are available for use as an energy source for maturation and that serum lipids are incorporated into the oocyte cytoplasm during in vitro maturation. The changes in the lipid content (mainly phospholipid) and fatty acid composition were also observed in frozen--thawed immature oocytes. The study indicates that the alteration of fatty acid composition in bovine oocytes might improve maturation and cryopreservation.

Animals↗

Interaction of alpha-tocopherol with fatty acids in membranes and ethanol.

The techniques of fluorescence polarization, ultraviolet light absorbance and fluorescence quenching by acrylamide are used to probe the structural role of alpha-tocopherol in phospholipid bilayers. Using 1,6-diphenyl-1,3,5-hexatriene (DPH) and a series of (anthroyloxy)stearic acid (AS) fluorescence probes, alpha-tocopherol is shown to increase fluidity and decrease order of gel state bilayers, and to decrease fluidity and increase order of bilayers in the liquid crystalline state. More complex behavior is noted for bilayers made from mixed acyl chain phosphatidylcholines (PCs) where the sn-1 position is saturated and the sn-2 position unsaturated compared to bilayers composed of PCs where both acyl chains are either saturated or unsaturated. Complexation between alpha-tocopherol and either free fatty acids or fatty acids esterified to the sn-2 position of PCs is indicated by ultraviolet light absorbance in both organic solution and in lipid bilayers. The strength of the complexes, expressed as interaction constants, are dependent upon the number of acyl chain unsaturations from 0 (stearic acid), to 6 (docosahexaenoic acid). Relation of the strength of these complexes to the degree of acyl chain unsaturation is confirmed by monitoring the fatty acid protection from acrylamide bleaching of alpha-tocopherol. These experiments suggest that the extent of acrylamide bleaching is related to the extent of association with the fatty acids.

Acrylamide↗

Differences in the interconversion between 20- and 22-carbon (n - 3) and (n - 6) polyunsaturated fatty acids in rat liver.

When male weanling rats were fed diets containing either 5% corn oil or a diet in which half of the corn oil was replaced by fish oil, the 20:5(n - 3) in liver choline and ethanolamine phosphoglycerides, not only partially replaced arachidonate but also paired with palmitic and stearic acids in the same molar ratio as did arachidonate. The 22:5(n - 3)/22:6(n - 3) ratio in the liver phospholipids of corn oil fed rats was similar to that found when the esterified levels of these two acids were increased 5-fold by feeding fish oil. Moreover, the pairing of both 22:5(n - 3) and 22:6(n - 3) with palmitic and stearic acids, on a molar ratio basis, was relatively independent of the total amount of esterified 22:5(n - 3) and 22:6(n - 3). When (3-14C)-labeled 22:4(n - 6) was injected into rats raised on a chow diet or incubated with hepatocytes from these animals, its primary metabolic fate was retroconversion to arachidonate followed by esterification. Conversely, [3-14C]22:5(n - 3) was a poorer substrate for retroconversion with a larger amount being esterified directly into phospholipids and, in addition, this acid served as a precursor for 22:6(n - 3). The enhanced metabolism of both [3-14C]22:4(n - 6) to 22:5(n - 6) and of [3-14C]22:5(n - 3) to 22:6(n - 3) in animals raised on a diet devoid of fat or in their hepatocytes may possibly be due to elevated 6-desaturase activity and/or the level of this enzyme or enzymes. This hypothesis is based on studies showing that the synthesis of 22:6(n - 3) proceeds via a pathway independent of a 4-desaturase but requires the use of a 6-desaturase at two steps (Voss, A., Reinhart, M., Sankarappa, S. and Sprecher, H. (1991) J. Biol. Chem. 266, 19995-20000).

Animals↗

[The effect of fatty acids in the feed on xanthine dehydrogenase activity in the Japanese quail].

The aim of the present study is to determine the effect of different fatty acids on the amino acid catabolism judged on the level of xanthine dehydrogenase (XDH). The model system of protein depletion with subsequent repletion was used in the trial consisted of Japanese quails 71 days old. In the period of protein repletion, the fatty acid (stearic, palmitic, oleic, linolenic, linoleic and lauric, respectively) was used instead of common fatty compound in the diet. Specific activities of XDH in liver, kidneys and pancreas of quails were tested dynamically from the first to the eighth day of feeding. It was demonstrated that neither lauric, palmitic nor oleic acid, respectively, had an effect on the development of the specific activity of XDH (Fig. 3). Stearic acid as a sole fatty compound in the diet however evoked reactibility of XDH in liver or in pancreas in different way as in kidneys (Fig. 4). The dynamics of the XDH development in kidneys was practically identical than that in the control. However, XDH in liver and pancreas raised statistically already from the first day of feeding. The effects of linoleic and linolenic acids on the development of specific activity of XDH were organ selective, too (Fig. 5). XDH in kidneys was shown in the same manner as in the control group. In liver and pancreas, however, the specific activity of XDH was diminished markedly just from the first day of feeding.

Animal Feed↗

Effect of trans fatty acids on calcium influx into human arterial endothelial cells.

BACKGROUND: A recent task force of The American Society for Clinical Nutrition and American Society for Nutritional Sciences recommended in a position paper on trans fatty acids that models be developed to assess the effects of changes in fat intake on disease risk. OBJECTIVE: The objective was to investigate, using human arterial endothelial cells as a model, the influence of trans fatty acids and magnesium on cell membrane composition and on calcium influx into arterial cells, a hallmark of atherosclerosis. DESIGN: Endothelial cells were cultured for 3 d in media with high (adequate) or low (inadequate) amounts of magnesium plus various concentrations of trans,trans linoelaidic; cis,cis linoleic; trans elaidic; oleic; or stearic acids. The cells were then harvested and the fatty acid composition and the amount of (45)Ca(2+) incorporated into the cell was determined. RESULTS: The percentage of fatty acids incorporated into the endothelial cells was proportional to the amount added to the culture medium. Adequate magnesium was crucial in preventing calcium influx into endothelial cells. Without an adequate amount of magnesium in the culture medium, linoelaidic and elaidic acids, even at low concentrations, increased the incorporation of (45)Ca(2+) into the cells, whereas stearic acid and oleic acid did not (P < 0.05). CONCLUSION: Our model indicated that a diet inadequate in magnesium combined with trans fat may increase the risk of calcification of endothelial cells.

Calcium↗

Characterization of a hemocyte intracellular fatty acid-binding protein from crayfish (Pacifastacus leniusculus) and shrimp (Penaeus monodon).

Intracellular fatty acid-binding proteins (FABPs) are small members of the superfamily of lipid-binding proteins, which occur in invertebrates and vertebrates. Included in this superfamily are the cellular retinoic acid-binding proteins and retinol-binding proteins, which seem to be restricted to vertebrates. Here, we report the cDNA cloning and characterization of two FABPs from hemocytes of the freshwater crayfish Pacifastacus leniusculus and the shrimp Penaeus monodon. In both these proteins, the binding triad residues involved in interaction with ligand carboxylate groups are present. From the sequence and homology modeling, the proteins are probably FABPs and not retinoic acid-binding proteins. The crayfish transcript (plFABP) was detected at high level in hemocytes, hepatopancreas, intestine and ovary and at low level in hematopoietic tissue and testis. Its expression in hematopoietic cells varied depending on the state of the crayfish from which it was isolated. Expression was 10-15 times higher in cultures isolated from crayfish with red colored plasma, in which hemocyte synthesis was high, if retinoic acid was added to the culture medium. In normal colored crayfish, with normal levels of hemocytes, no increase in expression of p1FABP was detected. Two other putative plFABP ligands, stearic acid and oleic acid, did not have any effect on plFABP expression in hematopoietic cells. These results suggest that retinoic acid-dependent signaling may be present in crustaceans.

Amino Acid Sequence↗

[The effect of thyroliberin on the change in structure of various of lipid bilayer regions in biological membranes in vivo].

Thyroliberin (TRH) influence on microviscosity and thermoinduced structural transitions of biological membranes has been studied using spin probes and ESR technique. It was shown that TRH in three investigated concentrations (10(-6), 10(-10) and 10(-16) mol/l) in vivo resulted in increasing of the lipid microviscosity in the hydrophobic areas (20 A): the time of rotary correlation of 16-doxyl-stearic acid elevated by 17-50%. There were no statistically significant effects in the regions localized more close to the surface (8 A): the order parameter of 5-doxyl-stearic acid was not changed. The picture of thermoinduced structural transitions in described in this article. Under the action of TRH in vivo both the shift of structural transitions and the changes in their number have been observed. The results obtained indicated that the mechanism of the TRH effect has a non-receptor component.

Animals↗

Changes of polyphosphoinositides, lysophospholipid, and free fatty acids in transient cerebral ischemia of rat brain.

Phosphatidylinositol (PI), phosphatidylinositol 4-phosphate (PIP), phosphatidylinositol 4, 5-bisphosphate (PIP2), 1, 2-diglyceride (DG), lysophosphatidylcholine (LPC), and free fatty acids (FFA) contents, as well as their fatty acid composition, were measured in transient global cerebral ischemia. ATP and CTP were also studied. Male Wistar rats were subjected to 1, 5, and 30 min of ischemia and 10, 30, and 60 min of recirculation following 30 min of ischemia. In addition, for the quantification of PI, PIP, and PIP2, rats were also subjected to 30 and 60 min of recirculation following 5 min of ischemia. PIP2 and PIP decreased rapidly during 5 min of ischemia and recovered completely after recirculation. DG increased almost at the same rate during ischemia and returned to normal after recirculation. PI showed almost no changes throughout entire course. LPC increased during 5 min of ischemia and returned to normal after recirculation. Stearic acid and arachidonic acid contained in DG increased during 5 min of ischemia, whereas saturated fatty acids increased in LPC. Among the FFA accumulated during ischemia, stearic acid and arachidonic acid increased rapidly and were followed by increases of other FFA. From these results, the pathways for the increase of FFA during ischemia and the fate of FFA after recirculation are discussed. In addition, the importance of the changes of PIP, PIP2, and LPC is also discussed.

Adenosine Triphosphate↗

Lipid fluidity at different regions in LDL and HDL of beta-thalassemia/Hb E patients.

Atherosclerosis-related vascular complications in beta-thalassemia/hemoglobin E (beta-thal/Hb E) patients may result from iron induced oxidation of lipoproteins. To identify the specific site of oxidative damage, changes in lipid fluidity at different regions in LDL and HDL particle were investigated using two fluorescence probes and two ESR spin probes. The magnitude of increased lipid fluidity in thalassemic lipoproteins was dependent on the location of the probes. In hydrophobic region, the rotational correlation times for 16-doxyl stearic acid and DPH anisotropy were markedly changed in LDL and HDL of the patients. In the surface region, there was only a slight change in the order parameter (S) for 5-doxyl stearic acid and TMA-DPH anisotropy. Lipid fluidity at the core of LDL and HDL showed good correlation with oxidative stress markers, the ratio of CL/CO, and the level of alpha-tocopherol, suggesting that hydrophobic region of thalassemic lipoprotein was a target site for oxidative damage.

Adult↗