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PubMed1984

Permeation of long-chain fatty acid into adipocytes. Kinetics, specificity, and evidence for involvement of a membrane protein.

This study extends our earlier work (Abumrad, N. A., Perkins, R.C., Park, J.H., and Park, C.R. J. Biol. Chem. 256, 9183-9191) which showed that oleate permeates the plasma membrane of the rat adipocyte principally by a transport process with the characteristics of facilitated diffusion. In the present study, fatty acid (FA) transport is characterized with regard to its specificity and susceptibility to inhibition by protein modifiers. The kinetics of competitive inhibition for transport of oleate and stearate are shown under conditions where complications due to competition for binding of FAs to the albumin in the medium are minimized. Stearate inhibits influx of tracer oleate with a Ki that closely approximates its Km and, conversely, oleate inhibits similarly the influx of tracer stearate. Specificity of the FA transport system is shown in studies using a variety of natural FAs of different chain length, or FA analogues. Oleate (Km = 0.06 microM), stearate (Km = 0.16 microM), linoleate (Km = 0.22 microM), palmitate, (Km = 0.2 microM), and laurate (Km = 1.5 microM) are good substrates, but octanoate is not transported. An oxazolidine ring on C-5 but not on C-16 of stearate blocks binding to the transporter. Methylation of the carboxyl function but not alpha-bromination inhibits transport. These studies suggest that a FA must have a hydrocarbon chain of at least nine carbons and a free carboxyl function to be recognized by the transporter. FA transport does not require Na or ATP. Pronase but not trypsin treatment of intact cells reduces fatty acid influx. Transport is insensitive to maleimides. It is strongly and irreversibly blocked by pretreatment of the cells with the stilbene compounds, 4,4'-diisothiocyanostilbene-2,2'-disulfonate and 4-acetamido-4'-isothiocyanostilbene-2,2'-disulfonic acid, but only slightly inhibited by dipyridamole. Polyacrylamide gel electrophoresis of plasma membrane proteins from cells treated with [3H] 4,4'-diisothiocyanostilbene-2,2'-disulfonate shows a peak of radioactivity at about Mr = 85,000. When cells are incubated in various concentrations of this agent, the counts recovered in the peak reach a maximum coincident with maximum inhibition of transport. We conclude that permeation of the plasma membrane of the adipocyte by long-chain FAs at physiological concentrations is mediated by a protein transporter with distinct specificity requirements.

Adipose Tissue↗
PubMed1981

Purification and characterization of 2-enoyl-CoA reductase of Mycobacterium smegmatis.

2-Enoyl-CoA reductase was purified to homogeneity for the first time from the crude extract of Mycobacterium smegmatis. Its molecular weight was estimated to be 26,000 by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. NADH acted as an electron donor for the reduction of 2-enoyl-CoA, while NADPH did not. The Km value for NADH was 21.3 microM. On the other hand, NAD inhibited the reaction for competing against NADH, as the Ki value for NAD was 47 microM. Among the enoyl-CoAs used as substrates, those having C10-C16 were found to be most suitable substrates for the purified reductase in terms of both apparent Km and Vmax values. The enzyme was strongly inhibited, however, when the concentration of the C16-substrate was over 50 microM. The enzyme had almost no activity towards substrates having less than C8. When NAD3H was used as an electron donor to 2-dodecenoyl-CoA in the presence of the purified reductase, only laurate was tritiated as the product. Diacetyl and phenylglyoxal, agents that react specifically with arginine, inactivated the reductase in a time- and concentration-dependent manner during the preincubation. These results suggest that some arginine residues in the reductase protein are involved in the enzyme activity.

Diacetyl↗
PubMed1980

Acyl-CoA synthetase in rat liver peroxisomes. Computer-assisted analysis of cell fractionation experiments.

The subcellular distribution of the acyl coenzyme A synthetases of rat liver was reinvestigated in order to determine whether part of this activity occurs in peroxisomes. Rat liver was fractionated by differential centrifugation and by equilibrium density centrifugation. Acyl-CoA synthetase was assayed using a new, simple extraction procedure on three substrates: palmitate, laurate, and octanoate. Comparison of the resulting synthetase distributions with the distributions of marker enzymes for peroxisomes, mitochondria, and endoplasmic reticulum demonstrated the presence of some synthetase activity in each of the three organelles. These trimodal synthetase distributions were evaluated quantitatively by means of a computer program that calculated optimal linear combinations of marker enzymes using a least squares criterion. Peroxisomes were found to contain 7% of the liver's palmitoyl-CoA synthetase activity and 6% of its lauroyl-CoA synthetase activity, but no demonstrable octanoyl-CoA synthetase activity. The remainder of these activities are divided between the mitochondria and endoplasmic reticulum, in a manner that agrees with previous studies. The chain length specificity of the synthetase(s) of each organelle appears to be unique. The absolute activity of the peroxisomal palmitoyl-CoA synthetase is sufficient to maintain maximal peroxisomal beta-oxidation. Clofibrate treatment of the rats caused a 2.6- to 3.1-fold increase in the liver's total acyl-CoA synthetase activities. The subcellular distribution was not greatly affected by this drug treatment.

Animals↗
PubMed1995

Mechanisms of absorption enhancement by medium chain fatty acids in intestinal epithelial Caco-2 cell monolayers.

Sodium salts of medium chain fatty acids (MCFAs) enhance the absorption of hydrophilic drugs across the intestinal mucosa, but the mechanism behind the effect is largely unknown. In this study, the dose-dependent effects of the sodium salts of four MCFAs, C6 (caproate), C8 (caprylate), C10 (caprate) and C12 (laurate), on the permeability of the hydrophilic marker molecule [14C]mannitol were studied in monolayers of the human intestinal epithelial cell line, Caco-2, grown on permeable supports. C8, C10 and C12, but not C6, enhanced the permeability of [14C]mannitol in a dose-dependent manner. Comparison of the cellular effects of the MCFAs at concentrations that gave comparable (8.1- to 8.5-fold) absorption enhancement showed that: 1) C8 was active as absorption enhancer only when the tonicity of the medium was increased; 2) absorption enhancement mediated by C10 was related to a redistribution of the cytoskeleton and structural dilatations in the tight junctions; and 3) C12 was without effect on the cytoskeleton and cellular morphology. Studies on C10 under anisotonic conditions showed that deviations from isotonicity enhanced its effect. These results suggest that structurally similar MCFAs display dramatic differences in their mechanism of action. In addition, the effects of osmolality provide an explanation for the previously reported variability in the efficacy of MCFAs as absorption enhancers.

Caco-2 Cells↗
PubMedDate not supplied

Biochemical properties of cultivated Mycobacterium lepraemurium.

1. Dehydrogenase activity of whole cell of cultivated M. lepraemurium is accelerated with sodium laurate, but not with the other substrates. 2. Dehydrogenase activity of cell free extract of cultivated M. lepraemurium is accelerated with citrate or malate. 3. There is no acceleration of oxygen consumption corresponding to added substrates in the respiration activity of whole cells of cultivated M. lepraemurium, but endogenous QO2 is 1.7 mul. 4. Cell free extract of cultivated M. lepraemurium shows slight acceleration of oxygen consumption with NADH, but does not with citrate or alpha-ketoglutarate. 5. NADH is not oxidized rapidly with the particle fraction of cultivated M. lepraemurium. 6. Type b1 cytochrome having an absorption peak at a wave length of 561 mmu and type a2 cytochrome having an absorption peak at 625 mmu are detected in an oxidoreductive difference spectrum or particle fraction of cultivated M. lepraemurium, but type c cytochrome having the absorption peak at 550 mmu is not seen. Since the other cultivable acid-fast bacilli always have type c cytochrome, nondetection of type c cytochrome is characteristic for M. lepraemurium. 7. These cytochromes are reduced with NADH. 8. M. lepraemurium produces a red pigment which emits a red fluorescence with ultraviolet light on its 1% Ogawa yolk medium. This phenomenon is a characteristic of M. lepraemurium, M. avium and M. intracellulare.

Cell-Free System↗
PubMed1994

Thermodynamics of binding water and solute to powdered long-chain salts of fatty acids.

Hydration of powdered fatty acids and their salts has been studied both in presence and absence of neutral salts, sucrose and urea using the isopiestic vapour pressure technique. Moles of water vapour adsorbed per mole or kg of soaps like sodium palmitate, sodium stearate, sodium myristate and sodium laurate have been measured in presence and absence of salts and compared with that of detergents (SDS, CTAB, DTAB and MTAB). For each case of positive excess adsorption of water vapour and negative excess adsorption of inorganic salts, urea and sucrose to different soaps, the standard free energy change (delta G degrees) per kg of substrate in bringing the bulk mole fraction from zero to unity have been calculated using an appropriate thermodynamic equation and the values so obtained have been compared critically.

Fatty Acids↗
PubMed1993

The effects of cyclosporin on renal microsomal cytochrome P-450 systems.

The effect of CsA on the renal microsomal cytochrome P-450 system was examined by using two animal models. Male Lewis rats and male white rabbits were treated with olive oil alone (Group A) or with CsA (30 mg/kg/day, Group B) by oral gavage for 7 and 14 days. Blood urea nitrogen and serum creatinine levels were determined at serial intervals after administration of CsA. In rats, BUN and S-Cr were increased, indicating the development of nephrotoxicity in group B by the 14th day after administration; BUN 78.8 mg/dl, S-Cr 3.2 mg/dl, but not in group A (BUN 29.3 mg/dl, S-Cr 0.7 mg/dl). In the rabbit experiments, BUN and S-Cr significantly increased in group B after 7 days of treatment but not in group A. P-450 content of the kidney microsomes prepared from rat and rabbit was examined. The renal specific P-450 content in group A was 68.8 pmol/mg protein in rats and 52.1 pmol/mg protein in rabbits, whereas those in group B showed 135.6 and 221.0 pmol/mg protein at day 14, respectively. SDS-PAGE also showed a significant increase in the content of P-450 after the CsA administration. Kidney microsomal aminopyrine N-demethylase activities were increased about 2.5 and 1.7 fold in rats and in rabbits, respectively. Monooxygenase activities for laurate and prostaglandin A1 were not significantly changed.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1995

Desulfuromonas palmitatis sp. nov., a marine dissimilatory Fe(III) reducer that can oxidize long-chain fatty acids.

Studies on the microorganisms living in hydrocarbon-contaminated sediments in San Diego Bay, California led to the isolation of a novel Fe(III)-reducing microorganism. This organism, designated strain SDBY1, was an obligately anaerobic, non-motile, non-flagellated, gram-negative rod. Strain SDBY1 conserves energy to support growth from the oxidation of acetate, lactate, succinate, fumarate, laurate, palmitate, or stearate. H2 was also oxidized with the reduction of Fe(III), but growth with H2 as the sole electron donor was not observed. In addition to various forms of soluble and insoluble Fe(III), strain SDBY1 also coupled growth to the reduction of fumarate, Mn(IV), or S0. Air-oxidized minus dithionite-reduced difference spectra exhibited peaks at 552.8, 523.6, and 422.8 nm, indicative of c-type cytochrome(s). Strain SDBY1 shares physiological characteristics with organisms in the genera Geobacter, Pelobacter, and Desulfuromonas. Detailed analysis of the 16S rRNA sequence indicated that strain SDBY1 should be placed in the genus Desulfuromonas. The new species name Desulfuromonas palmitatis is proposed. D. palmitatis is only the second marine organism found (after D. acetoxidans) to oxidize multicarbon organic compounds completely to carbon dioxide with Fe(III) as an electron acceptor and provides the first pure culture model for the oxidation of long-chain fatty acids coupled to Fe(III) reduction.

Electron Transport↗
PubMed1995

In vivo and in vitro binding of fatty acids to genetic variants of human serum albumin.

The effect of genetic variation on the fatty-acid binding properties of human serum albumin was studied by two methods involving the use of sequenced albumin variants isolated from bisalbuminaemic persons. First, the amount of total fatty acid and of several individuals fatty acids bound to eighteen different variants and to their normal counterpart (Alb A) were determined by a gas-chromatographic micromethod. Pronounced effects on total fatty acid binding were found for the glycosylated variants Alb Redhill (modified in domain II) and Alb Casebrook (domain III) in which cases a 1.7- and 8.6-fold increment, respectively, was found. By contrast, Alb Malm0 (glycosylated in domain I) carried the same amount of fatty acid as Alb A. The fatty acid loads on three chain-termination variants were normal. Finally, eight albumins with single amino-acid substitutions bound normal amounts of fatty acid, whereas one bound increased (1.7-fold) and three albumins bound diminished amounts (0.5-0.6-fold). Information on nineteen individual fatty acids was also obtained. It was possible, based on the type of changes in their relative amounts, to group the fatty acids as follows: (a) = C6:0 - C14:0, (b) = C15:0 - C18:0, (c) = C16:1 - C18:1, and (d) a group composed of essential and conditionally essential fatty acids. For nine variants, in most cases modified in domain III, large changes in one or more of these groups were observed. The changes were not related to any changes in total fatty acid load. Second, the binding of laurate, as a representative of the group (a) fatty acids, to delipidated albumin preparations was studied at pH 7.4 by a kinetic dialysis technique. The first stoichiometric association constant for binding to Alb Redhill (0.7-fold) and Alb Casebrook (0.6-fold) was diminished as compared with binding to their corresponding Alb A, whereas binding to one chain-termination variant and three single amino-acid substitutions were all unaffected by the mutation.

Chromatography, Gas↗
PubMed1996

Mechanism of stereoselective serum binding of ketoprofen after hemodialysis.

In vitro studies of serum protein binding were conducted to examine the influence of hemodialysis therapy on the stereoselectivity for ketoprofen (KP) in patients with renal dysfunction. In normal volunteers, only small differences in binding to undiluted serum were observed between the enantiomers of racemic KP (10 micrograms/mL). As compared with healthy volunteers, significantly impaired binding to undiluted serum was observed in uremic patients before they received dialysis. This reduced binding was not accompanied by alterations in stereoselectivity. At the end of dialysis, a similar extent of defective binding to undiluted serum was still observed, whereas interestingly, its stereoselectivity was significantly enhanced. These findings indicated that preferential inhibition for S-enantiomer serum binding was caused by changes that occurred during hemodialysis. Among various physiological parameters, only enantioselective inhibition of KP serum binding was correlated with heparin-induced increases in free fatty acids (FFA) levels and with unbound levels of uremic toxins with indole ring, indoxyl sulfate and indole acetate. To elucidate the effects of these accumulated endogenous substances in serum of patients, ultrafiltration was also used to study the binding of KP enantiomers to isolated human serum albumin under various conditions. After dialysis, mean albumin level and pH value in patients were slightly but significantly altered, but in vitro binding data indicated that these factors could clearly be ruled out as an explanation for the origin of the induced stereoselectivity. In contrast to palmitate, oleate and laurate markedly induced the stereoselective inhibition, which indicated that these fatty acids preferentially inhibited the binding of S-KP via a competitive and allosteric mechanism. Among the four uremic toxins, only indoxyl sulfate and indole acetate predominantly displaced the S-enantiomer rather than its antipode through competitive interaction. In addition, serum unbound levels of indole uremic toxins were correlated with elevated FFA levels. FFA displaced those indole uremic toxins in a manner similar to KP, which suggests that FFA also indirectly inhibits the S-enantiomer binding by increasing the unbound levels of indole uremic toxins. Thus it is likely that combined direct and cascade effects of transiently increased FFA and unbound indole uremic toxins contributed to the preferential elevation of the pharmacologically active S-KP fraction in uremic patients at the end of hemodialysis.

Adult↗
PubMedDate not supplied

Enhancing effect of non-ionic surfactant on the inactivation of lipopolysaccharide by steam-heat treatment I.

Polyoxyethylene (20) sorbitan mono-fatty acid esters strongly enhanced the inactivation of lipopolysaccharide (LPS) by steam-heat treatment at 121 degrees C, as assayed by using the Limulus amebocyte lysate (LAL) and the pyrogen test. In an aqueous solution containing 0.1% surfactant, the decrease of LPS (1 microgram/ml) from E. coli 055:B5 at 121 degrees C followed first-order kinetics. Based on the LAL assay, 0.1% surfactant was essential to achieve 3-log cycle reduction of LPS with concomitant loss of pyrogenicity by steam-heat treatment for 20 min at 121 degrees C. Steam-heat treatment for 20 min at 121 degrees C in the absence of surfactant was insufficient to achieve depyrogenation. Polyoxyethylene (9) lauryl ether and decaglycerin mono-laurate similarly enhanced depyrogenation by steam-heat treatment. The effects of all the surfactants were concentration-dependent for all of the six kinds of LPS examined.

Feasibility Studies↗
PubMed1997

Ascorbic acid deficiency decreases the expression of CYP4A1 in liver microsomes of guinea pigs.

The cytochrome P-450 monooxygenase system plays a central role in the oxidation of a wide variety of structurally unrelated compounds. Its contribution is affected by nutritional and several other factors. Ascorbic acid (AA) deficiency decreases the content of cytochrome P-450 in liver microsomes of guinea pigs (GPs). Included in the group of cytochromes P-450 are the phenobarbital and 3-methylcholanthrene inducible moieties. In the present study the effect of AA status on another specific cytochrome P-450, CYP4A1, laurate omega-hydroxylase was investigated. Ascorbic acid may selectively increase or decrease certain forms of cytochromes. For four weeks adult male Hartley GPs were fed a diet containing 2.5 (Group I), 0.1 (Group II) and 0% (Group III) AA. The liver microsomes were isolated at this stage and cytochrome P-450 content was determined. Group III showed a significant decrease in cytochrome P-450 compared to groups I and II. They also showed a marked decrease in aminopyrine N-demethylase activity. The expression of CYP4A1 was evaluated using Western blot and anti-CYP4A1 antibody. Group III GPs showed a marked decrease in CYP4A1 expression. Groups I and II showed similar expression. This study demonstrates that CYP4A1, a specific cytochrome induced by hypolipidemic agents, is decreased by AA deficiency.

Animals↗
PubMed1997

Cytochrome c potentiates fatty acid-induced cyclosporin A-sensitive permeability transition in liver mitochondria.

Addition of 0.5-5 microM cytochrome c and 30 microM lauric acid to rat liver mitochondria stimulated the respiration rate. Stimulation of respiration by cytochrome c was prevented by cyclosporin A and was not observed in the absence of lauric acid. High amplitude swelling of mitochondria in the presence of lauric acid was also potentiated by cytochrome c; this effect was prevented by cyclosporin A or by EGTA. Polylysine (0.35 microM) induced cyclosporin A-insensitive high amplitude swelling of mitochondria. Polylysine-induced swelling was stimulated by lauric acid and cytochrome c; the effect was prevented by cyclosporin A. Incubation of mitochondria with 30 microM lauric acid resulted in an increase in cytochrome c concentration in the incubation medium. Added cytochrome c is supposed to potentiate the laurate-induced cyclosporin A-sensitive permeability transition in cytochrome c-depleted mitochondria.

Animals↗
PubMed1976

Hepatic 7alpha-hydroxylation of cholesterol in ascorbate-deficient and ascorbate-supplemented guinea pigs.

Cholesterol 7alpha-hydroxylase activity was assayed in liver microsomes from guinea pigs supplemented with ascorbate and from guinea pigs in a state of ascorbate deficiency. A mass fragmentographic method was used by which the 7alpha-hydroxylation of endogenous cholesterol could be measured. The 7alpha-hydroxylation was markedly reduced in the ascorbate-deficient animals as compared to animals treated with ascorbate. Addition of ascorbate to the incubations did not increase this activity. 11- and 12-Hydroxylation of laurate as well as 25- and 26-hydroxylation of 5beta-cholestane-3alpha, 7alpha-diol were not significantly affected by the ascorbate status of animals. In the presence of excess NADPH-cytochrome P-450 reductase and a phospholipid, partially purified cytochrome P-450 from the microsomal fraction of liver of an ascorbate-deficient guinea pig had a much lower capacity to 7alpha-hydroxylate [4-14C]cholesterol than a corresponding system containing cytochrome P-450 from liver of an ascorbate-supplemented guinea pig. It is suggested that ascorbate affects the synthesis or breakdown of the 7alpha-hydroxylating system, in particular the cytochrome P-450 component.

Animals↗
PubMed1998

Involvement of aspartate/glutamate antiporter in uncoupling effect of fatty acids in heart mitochondria.

Earlier it was shown that fatty acid-induced uncoupling in liver mitochondria is suppressed by the substrates of the aspartate/glutamate antiporter (V. N. Samartsev, A. V. Smirnov, I. P. Zeldi, O. V. Markova, E. N. Mokhova, and V. P. Skulachev (1997) Biochim. Biophys. Acta, 1319, 251-257). In this study it is shown that in heart mitochondria aspartate, glutamate, and diethyl pyrocarbonate do not affect oxygen consumption and membrane potential in the presence of laurate at pH 7.4. These compounds have a weak (versus carboxyatractylate) coupling effect at pH 7.0. This effect is manifested only in the presence of carboxyatractylate, magnesium, and phosphate in the incubation medium. It is suggested that these tissue-specific effects are due not only to the specific characteristics of aspartate/glutamate antiporter, but also to the differences in the content of endogenous metabolites in heart mitochondria.

Animals↗
PubMed1998

Abortifacient effects of lodgepole pine (Pinus contorta) and common juniper (Juniperus communis) on cattle.

Lodgepole pine (Pinus contorta) and common juniper (Juniperus communis) contain high levels of isocupressic acid that has been identified as the abortifacient component of ponderosa pine needles in cattle. Therefore, the abortifacient potential of P contorta and J communis needles was tested in feeding trials with pregnant cattle. Cows (2 groups of 2 each) were fed by gavage 4.5-5.5 kg/d ground dry needles from either P contorta or J communis starting on gestation day 250. Isocupressic acid (ICA) levels in P contorta needles and J communis plant material were 0.8 and 2.0% (dry weight) respectively. Cows fed P contorta received a daily dose of 62-78 mg ICA/kg body weight and aborted after 8 and 10 d. The 2 cows fed J communis received a daily dose of 190 and 245 mg ICA/kg body weight and aborted after 3 and 4 days respectively. All cows retained fetal membranes and had classical clinical signs of pine needle-induced abortion. Pinus ponderosa, P contorta, J communis, and Cupressus macrocarpa samples were also analyzed for the presence of myristate and laurate esters of 1,14-tetradecanediol and 1,12-dodecanediol. These lipid like compounds of P ponderosa have potent vasoconstrictive activity in a placentome perfusion assay and are proposed as possible abortifacients in cattle. Concentration of the vasoactive lipids were 0.028% (P ponderosa), 0.023% (P contorta), 0.001% (J communis), and none detected (C macrocarpa). It was concluded that these compounds are not required for the plant material to be abortifacient in cattle.

Abortifacient Agents↗
PubMed1999

In vivo involvement of cytochrome P450 4A family in the oxidative metabolism of the lipid peroxidation product trans-4-hydroxy-2-nonenal, using PPARalpha-deficient mice.

Trans-4-hydroxy-2-nonenal (HNE) is a potent cytotoxic and genotoxic compound originating from the peroxidation of n-6 polyunsaturated fatty acids. Its metabolism has been previously studied in the rat (Alary et al. 1995. Chem. Res. Toxicol., 8: 35-39). In addition to major urinary mercapturic derivatives, some polar urinary metabolites were isolated and could correspond to hydroxylated compounds. 4-Hydroxynonenoic acid (HNA), resulting from the oxidation of the HNE carbonyl group, is a medium chain fatty acid and its omega-hydroxylation might be hypothesized. Therefore, the involvement of the CYP 4A family isoenzymes in the metabolism of [3H]HNE has been investigated in vivo using inducer treatments (fibrates) in wild-type or in peroxisome proliferator-activated receptor alpha (PPARalpha)-deficient mice. In wild-type mice, but not in PPARalpha (-/-) mice, fibrate treatments resulted in an increase of two urinary metabolites characterized, after HPLC purifications and mass spectrometry analyses, as the omega-hydroxylated metabolite of HNA, i.e., 4,9-dihydroxy-2-nonenoic acid, and its oxidized form, 4-hydroxy-2-nonene-1,9-dicarboxylic acid. The formation of the latter is correlated accurately to laurate hydroxylase activity studied concurrently in microsomes prepared from the liver of these animals. Basal levels of these two metabolites were measured in urine of normal and PPARalpha-deficient mice. These results are in accord with an implication of the P450 4A family in the extended oxidative metabolism of 4-HNE.

Aldehydes↗