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PubMed1991

Omega-oxidation of fatty acids studied in isolated liver cells.

The omega- and beta-oxidation of medium- and long-chain fatty acids (C10-C18) were studied in hepatocytes from fasted, fed and clofibrate-fed rats. The omega-oxidation systems were most active with lauric acid (12:0) and decanoic acid (10:0) as substrates and there was decreasing activity with chain lengths from 14 to 18 carbon atoms. In fed rats no omega-oxidation of fatty acids was detected unless the mitochondrial beta-oxidation was inhibited. In fasted rats the omega-oxidation was less than 2% and preincubation with (+)-decanoylcarnitine increased the omega-oxidation to 15% of the total fatty acid oxidation. Clofibrate feeding did not increase the omega-oxidation in isolated hepatocytes. Inhibition of the alcohol dehydrogenase with 4-methylpyrazole inhibited both the oxidation of omega-hydroxylated fatty acid and the initial hydroxylation of lauric acid to dicarboxylic acid, suggesting the importance of the alcohol dehydrogenase in the omega-oxidation of fatty acids. 95% of the dicarboxylic acids and 80% of the hydroxy-fatty acids were excreted from the cells in the incubations with decanoic acid (10:0). No chain-shortened dicarboxylic acids were detected with [1-14C]decanoic- or [1-14C]lauric acid as substrate, while small amounts C10 and C12 dicarboxylic acids were observed in incubations with [1-14C]myristic acid (14:0).

Alcohol Dehydrogenase↗

PubMed1983

On the biologic origin of C6-C10-dicarboxylic and C6-C10-omega-1-hydroxy monocarboxylic acids in human and rat with acyl-CoA dehydrogenation deficiencies: in vitro studies on the omega- and omega-1-oxidation of medium-chain (C6-C12) fatty acids in human and rat liver.

C6-C10-dicarboxylic acid C6-C10-omega-1-hydroxy monocarboxylic acids were measured in postmitochondrial (10,000 g) fractions of rat liver after incubation with hexanoic, octanoic, and decanoic acids. In livers both from fed and starved rats, the proportion of decanoic acid converted to sebacic acid was high (approximately 25%) with only minor accumulation of the intermediate 10-hydroxy decanoic acid (1-2%). The conversion of octanoic and hexanoic acids to suberic and adipic acids, respectively, was low (less than 1%). The intermediate 8-hydroxy octanoic and 6-hydroxy hexanoic acids were also accumulated in very small amounts (less than 1%). It was concluded that cytochrome-P-450-mediated omega-hydroxylation was of decisive importance for the production rate of the dicarboxylic acids. Analysis of kinetic parameters of human and rat liver microsomal omega- and omega-1-hydroxylation of hexanoic, octanoic, decanoic, and dodecanoic acids gave the following results: in rats, the apparent Km values for the omega-hydroxylation for dodecanoic and decanoic acids are low, ie., 171 and 3.1 mumole/liter, respectively, whereas they are high for octanoic and hexanoic acids (8211 and 8822 mumole/liter, respectively). In two different humans, the corresponding Km values for dodecanoic, decanoic, octanoic, and hexanoic acids are 3.6-186, 522-247, 4861-3892, and 6825-10400 mumole/liter, respectively. Based on these results, it is argued that adipic and suberic acids found in urine from rats and humans with acyl-CoA dehydrogenation deficiencies are not biosynthesized by direct omega-oxidation of hexanoic and octanoic acids, but most probably by means of beta-oxidation of sebacic and dodecanedioic acids, produced by direct omega-oxidation.(ABSTRACT TRUNCATED AT 250 WORDS)

Adipates↗

PubMed1983

Medium chain fatty acids as specific substrates for diglyceride acyltransferase in cultured hepatocytes.

The fatty acyl substrate specificity for de novo diglyceride, triglyceride, and phospholipid synthesis in cultured hepatocytes was evaluated. The fatty acyl availability for diglyceride and phospholipid synthesis is restricted to fatty acids longer than myristic acid with octanoic and decanoic acids being excluded. On the other hand, octanoic and decanoic acids may serve as substrates for the diglyceride acyltransferase. Dodecanoic acid appears to occupy an intermediate position between medium and long chain fatty acids with respect to its availability as substrate for the esterification sites concerned. The availability of octanoate as a specific substrate for the diglyceride acyltransferase reaction in cultured hepatocytes enables the measurement of this activity in situ under conditions of overall triglyceride synthesis.

Acyltransferases↗

PubMed1985

Purification and spectroscopic properties of pyrene fatty acids.

Pyrene fatty acids are routinely purified by silica based column chromatography and analyzed on thin-layer silica plates (H.-J. Galla et al., Chem. Phys. Lipids, 23 (1979) 239-251). Although pyrene decanoic acid runs as a single spot on thin-layer chromatography (TLC), gas-liquid chromatography (GC) of the methyl ester derivatives of a representative sample revealed four separate peaks with the major component only 92% of the total. High performance reverse phase liquid chromatography (HPLC) was used to purify pyrene decanoic acid and separate the contaminants. After two passes on a C18 reverse phase HPLC column, pyrene decanoic acid is 99.98% pure by GC analysis. Absorption, fluorescence, and NMR spectra were recorded for pyrene decanoic acid and the major impurities. The results indicate that one impurity is a C10 fatty acid with an altered aromatic moiety. Two other impurities are pyrene derivatives but their acyl chains probably are not decanoic acid.

Chromatography, Gas↗

PubMedDate not supplied

Chemical and physical characterization of four interfacial-active rhamnolipids from Pseudomonas spec. DSM 2874 grown on n-alkanes.

Four extracellular glycolipids produced under growth-limiting conditions were isolated from the culture broth of Pseudomonas spec. DSM 2874. After purification by column and thick-layer chromatography they were identified as anionic rhamnolipids. 1H and 13C-NMR studies showed that two of these, beta(beta(2-O-alpha-L-rhamnopyranosyloxy)decanoyl)decanoic acid and beta(beta(2-O-alpha-L-rhamnopyranosyl-alpha-L-rhamnopyranosylox y)decanoyloxy) decanoic acid, were identical with compounds described previously, while the other more hydrophilic compounds, beta(2-O-alpha-L-rhamnopyranosyloxy)decanoic acid and beta(2-O-alpha-L-rhamnopyranosyl-alpha-L-rhamnopyranosyloxy) decanoic acid, were new compounds. Surface and interfacial activity of the organic crude extract and of the purified components were determined in different aqueous solutions. The pH-dependence of surface and interfacial properties of the two previously described rhamnolipids (4, 20, 23) were examined in Teorell-Stenhagen-buffer (supplemented with 10% NaCl) at pH 3.0 and pH 9.0. All rhamnolipids reduced the surface-tension from 72 to about 30 mN/m and the interfacial-tension from 42 to about 1 mN/m. The critical micelle concentrations were of the order of 5 to 200 mg/l depending on the structure of the molecule.

Alkanes↗

PubMed2006

Study of the toxic effect of short- and medium-chain monocarboxylic acids on the growth of Saccharomyces cerevisiae using the CO2-auxo-accelerostat fermentation system.

The effect of aliphatic monocarboxylic acids (formic, acetic, propionic, valeric, octanoic and decanoic acids) on the growth and metabolic activity of Saccharomyces cerevisiae S288C was studied, using continuous cultivation method - CO(2)-auxo-accelerostat with smooth increase in the concentration of added monocarboxylic acids. Slow increase in the concentration of these acids resulted in the rapid decrease in the growth yield (Y(ATP)) and specific growth rate (micro), however, the specific ATP production rate (Q(ATP)) increased or stayed almost constant. On the other hand, Q(ATP) decreased if the concentration of formic, acetic or decanoic acids was increased rapidly. The toxic effect of aliphatic monocarboxylic acids on the growth of S. cerevisiae was characterized and quantified from the respective dose-effect curves as the IC(50) value (mM) using two different endpoints: a decrease of 50% in the specific growth rate (IC(50 micro)) and a decrease of 50% in the growth yield based on ATP production (IC(50YATP)). The concentrations of formic, acetic, propionic, valeric, octanoic and decanoic acids causing the 50% reduction in the specific growth rate (IC(50 micro)) were, respectively, 18.1, 47.1, 33.6, 2.3, 0.16 and 0.07 mM. The IC(50 micro) values were notably lower (up to 5-fold) in case of a more rapid increase in the concentration of acid in the medium. The results of the CO(2)-auxo-accelerostat experiments show that the toxic effect depends not only on the nature of the monocarboxylic acid (lipophilicity) but also on the rate at which its concentration changes in the growth environment.

Adaptation, Physiological↗

PubMed1977

Inhibitory action of a non-metabolizable fatty acid on the growth of Escherichia coli: role of metabolism and outer membrane integrity.

The inhibitory action of decanoic acid on both Escherichia coli K-12/154 (normal lipopolysaccharide) and E. coli RC59 (defective lipopolysaccharide) was studied. A correlation was found between the doubling time of E. coli 154 growing in different media and the lethal effect of 0.4% decanoic acid on this bacterium. Decanoic acid (0.4%) exerted a lytic action on glucose-starved and NaN3-inhibited cells of E. coli 154 and RC59. Exponentially growing cultures of both strains were not affected by the addition of 0.4% methyldecanoate, but cells of E. coli RC59 reaching the stationary phase were attacked by that compound. A bactericidal action of 0.4% methyldecanoate on exponential E. coli 154 and RC59 was observed when sodium azide was also present in the media. Concentrations lower than 0.01% methyldecanoate had a lytic effect on spheroplasts from E. coli 154 and RC59. These results indicate that the inhibitory action of a non-metabolizable fatty acid on E. coli depends on the cellular metabolic activity and the outer membrane integrity.

Azides↗

PubMed1984

Uptake of fatty acids by the yeasts, Saccharomyces uvarum and Saccharomycopsis lipolytica.

Yeast cells take up exogenous fatty acids with subsequent rapid incorporation into glycerolipids. beta-Oxidation does not occur in Saccharomyces uvarum and is observed in Saccharomycopsis lipolytica only 2-5 min after addition of radioactively labeled fatty acid. Rates of fatty acid uptake are linear up to 30 s with S. lipolytica and up to 2 min with S. uvarum. The uptake kinetics are consistent with a dual mode of transport, comprising a saturable component with KT values in the range 10(-5)-10(-6) M, and apparently simple diffusion that predominates at high substrate concentrations. Kinetics of fatty acid permeation are independent of metabolic energy and membrane potential. At least two fatty acid carrier systems exist in both S. lipolytica and S. uvarum, one being specific for fatty acids with 12 and 14 C atoms, respectively, the other for C16 and C18 saturated or unsaturated fatty acids. Octanoic acid and decanoic acid are not taken up by S. lipolytica. Internalization of lauric acid and oleic acid by S. lipolytica cells is preceded by a rapid (less than 5 s) initial uptake which most likely represents irreversible adsorption. This phenomenon was not observed with heat-inactivated S. lipolytica cells or with viable S. uvarum. In azide-poisoned cells of S. lipolytica an up to 20-fold accumulation of unesterified fatty acid was observed within 30 s after the addition of substrate.

Adsorption↗

PubMed2006

Treatment of oil spill by sorption technique using fatty acid grafted sawdust.

Treatment of oil spills remains a challenge to environmental scientists and technologists. Among all the existing techniques used for oil treatment, sorption is a popular technique because it is cheap, simple and effective. Among the various sorbents used, sawdust appears to be the most attractive material in terms of cost, versatility and abundance. In the present work, the efficacy of surface modification of sawdust by fatty acids (oleic acid, stearic acid and decanoic acid) and vegetable oils (castor oil or mustard oil) is demonstrated. Sorption of seawater contaminated with crude oil and also weathered oil was greatly enhanced by the surface modification. The results show that oleic acid grafted sawdust (OGSD) has the best sorption capacity for crude oil as well as weathered oil.

Adsorption↗

PubMed2000

Chemistry, ontogeny, and role of pygidial gland secretions of the vinegaroon Mastigoproctus giganteus (Arachnida: Uropygi).

Pygidial gland secretions of the vinegaroon, Mastigoproctus giganteus, consist of 26% water and 74% short-chained fatty acids, with acetic acid and octanoic acids the dominant acids. The organic composition of the secretion consists of 83% acetic acid, 15% octanoic acid, 1% (Z)-5-octenoic acid, 0.0002% of the corresponding (E)-isomer, 0.11% heptanoic acid, 0.02% hexanoic acid, 0.007% decanoic acid, and in some individuals a trace of 2-nonanone. Formic acid is absent from the secretion. Glandular composition, especially in the concentrations of the minor components, varies dramatically among individuals and shows no age pattern differences among the four free-living subadult instars, or sex differences between adult males and females. Each individual exhibits its own specific blend of components which is identical in the two separate and different sized glands. The secretions act solely as allomones against potential predators, and do not act as pheromones, or elicit a communicative or behavioral response. Behavioral tests using live animals or a synthetic blend of vinegaroon secretion revealed that the secretion is maximally effective on sensitive respiratory, visual, or sensory systems of potential predators and is ineffective, or nearly so, when contact is restricted to inside the predator's mouth. Thus, the effectiveness of the secretion apparently results from its delivery as a spray of fine droplets, rather than as an exudate or vapor.

Journal Article↗

PubMed1965

Incorporation of 14C-labelled fatty acids into the mammary-gland lipids of the lactating rabbit.

1. [1-(14)C]Stearic acid, [9-(14)C]stearic acid, [9-(14)C]palmitic acid and [9-(14)C]decanoic acid were fed to lactating rabbits, and the fatty acids of the mammary gland were separated and partially degraded. 2. Most of the (14)C recovered was located in the acids fed. Stearic acid was least efficiently absorbed; decanoic acid was the most extensively metabolized. 3. Resynthesis after degradation to C(2) units led to uniform alternate labelling in the C(2)-C(10) acids, whereas C(12)-C(18) acids had excess of (14)C at the carboxyl end. 4. Acids formed by beta-oxidation down to C(12), but not below, were also present in the mammary-gland lipids. Desaturation of the administered acids was a very minor reaction.

Animals↗

PubMed1994

Characterization of the lipopolysaccharide of Moraxella catarrhalis. Structural analysis of the lipid A from M. catarrhalis serotype A lipopolysaccharide.

The lipopolysaccharide of Moraxella catarrhalis serotype A (ATCC 25238) was found to consist of a short-chain oligosaccharide attached to a lipid A moiety. Composition and NMR analyses showed the oligosaccharide component in O-deacylated LPS to be composed of D-glucose, D-galactose, 2-acetamido-2-deoxy-D-glucose and 3-deoxy-D-manno-octulosonic acid in the molar ratio of 5:2:1:2. In addition, the lipid A region contained phosphate, D-glucosamine, 3-hydroxydodecanoic acid, dodecanoic acid and decanoic acid. The lipid A was examined in detail by high-field NMR spectroscopy and mass spectrometry. It was found to consist of a beta-1,6-D-glucosamine disaccharide backbone esterified at C4' by a phosphomonoester and glycosidically at C1 by diphosphoethanolamine or phosphomonoester. The amide group of the reducing and nonreducing glucosamine residues were acylated by 3-dodecanoyloxydodecanoic acid and 3-decanoyl-oxydodecanoic acid, respectively. The hydroxyl group at C3 and C3' were acylated by 3-decanoyl-oxydodecanoic acid and 3-hydroxydodecanoic acid respectively, while the hydroxyl groups at C4 and C6' were unsubstituted.

Carbohydrate Sequence↗

PubMed1997

Nonanoic Acid, a Fungal Self-Inhibitor, Prevents Germination of Rhizopus oligosporus Sporangiospores by Dissipation of the pH Gradient.

Germination of Rhizopus oligosporus sporangiospores is characterized by swelling of the spores and subsequent emergence of germ tubes. Changes in spore morphology and alterations in intracellular pH (pH(infin)) of the sporangiospores were assessed during the germination process by flow cytometry. Sporangiospores were stained with carboxyfluorescein by incubation with carboxyfluorescein diacetate. The nonfluorescent carboxyfluorescein diacetate is passively transported into intact cells and subsequently cleaved by esterases, which results in intracellular accumulation of the fluorescent carboxyfluorescein. Given that the fluorescence of carboxyfluorescein is pH dependent, the pH(infin) of the individual spores could be assessed simultaneously with spore size. For R. oligosporus, swelling of the sporangiospores was accompanied by an increase of pH(infin). In the presence of nonanoic acid, a self-inhibitor produced by various fungi, increase of the pH(infin) was prevented and swelling was inhibited at concentrations of less than 1 mM. Octanoic acid and decanoic acid were equally effective. Acetic acid also inhibited germination but at much higher concentrations (>8 mM). The mechanism of action of these fatty acids is most likely dissipation of the pH gradient. A model is proposed in which the pH(infin) plays a crucial role in the germination of R. oligosporus sporangiospores.

Journal Article↗

PubMed2003

Plasma fatty acids and [13C]linoleic acid metabolism in preterm infants fed a formula with medium-chain triglycerides.

Most preterm infant formulas contain medium-chain triacylglycerols (MCT), but the effects of MCT on polyunsaturated fatty acid status and metabolism are controversial. Thus, we studied the effects of MCT on linoleic acid metabolism using stable isotopes. Enterally fed preterm infants were randomized to receive for 7 days 40% of fat as MCT (n = 10) or a formula without MCT (n = 9). At study day 5, infants received orally 2 mg/kg body weight of (13)C-labeled linoleic acid. Fatty acids in plasma lipid classes and (13)C enrichment of phospholipid fatty acids were measured and tracer oxidation was monitored. Compared with the control group, the MCT group showed lower breath (13)CO(2) and higher plasma triacylglycerol contents of octanoic acid, of decanoic acid, and of total long-chain polyunsaturated fatty acids (57.1 +/- 4.4 micro mol/l vs. 37.9 +/- 4.8 micro mol/l, P < 0.01). Concentrations of several polyunsaturated fatty acids in plasma phospholipids and non esterified fatty acids were higher in the MCT group. (13)C concentrations in phospholipid n-6 fatty acids indicated no difference in the relative conversion of linoleic to arachidonic acid. We conclude that oral MCT effectively reduce polyunsaturated fatty acid and long chain polyunsaturated fatty acid oxidation in preterm infants without compromising endogenous n-6 long chain polyunsaturated fatty acid synthesis.

Carbon Dioxide↗

PubMed1997

Resin glycosides. XXV. Multifidins I and II, new jalapins, from the seed of Quamoclit x multifida.

Alkaline hydrolysis of the ether-soluble resin glycoside fraction of seeds of Quamoclit (Q.) x multifida, a hybrid between Q. pinnata and Q. coccinea, gave new glycosidic acids, multifidinic acids A and B, along with two known glycosidic acids, quamoclinic acid A and operculinic acid A, and three organic acids, (2S)-2-methylbutyric acid, n-decanoic acid and n-dodecanoic acid. Further, as major ether-soluble resin glycosides, new jalapins named multifidins I and II, were isolated accompanied by quamoclins I-IV, which were previously obtained from seeds of Q. pinnata. The structures of multifidins I and II, and multifidinic acids A and B have been determined on the basis of chemical and spectral data.

Butyrates↗

PubMed1977

Effect of premature weaning on the fatty acid composition of rat adipose tissue.

The authors described the effect of premature weaning on the fatty acid spectrum in the retroperintoneal fat of female rats during ontogenesis. Premature weaning reduced the lower fatty acid content [decanoic acid C 10:0, lauric acid C 12:0, myristic acid C 14:0] in 30- to 90-day-old rats, but in further development no differences between the amount of these fatty acids were observed in suckled and prematurely weaned animals. These changes concurred with the fatty acid composition of the relevant diet (rat milk and a standard laboratory diet). Changes induced in the amount of other acids by premature weaning were not permanent in character, with the exception of stearic acid C 18:0 and linoleic acid C 18:3, which were raised at 720 days in the retroperitoneal fat of prematurely weaned rats. The amount of lower saturated fatty acids fell with advancing age, whereas oleic C 18:1, linolic C 18:2 and linolenic C 18:3 acid rose.

Adipose Tissue↗

PubMed1990

Novel fatty acyl substrates for myristoyl-CoA:protein N-myristoyl-transferase.

Myristoyl-CoA:protein N-myristoyltransferase (NMT) catalyzes the covalent attachment of myristic acid to the NH2-terminal Gly residues of a number of viral and cellular proteins. The remarkable specificity of this enzyme for myristoyl CoA observed in vivo appears to arise in large part from a cooperativity between NMT's acylCoA and peptide binding sites: the length of the acylCoA bound to NMT influences the interactions of peptide substrates with NMT. We have previously synthesized analogs of myristic acid with single oxygen or sulfur for methylene substitutions. These heteroatom substitutions produce significant reductions in acyl chain hydrophobicity without accompanying alterations in chain length or stereochemical restrictions. In vitro studies have shown that the CoA thioesters of these analogs are substrates for S. cerevisiae NMT and that the efficiency of their transfer to octapeptide substrates is peptide sequence-dependent. In vivo studies with cultured mammalian cells have confirmed that these fatty acid analogs are selectively incorporated into a subset of cellular N-myristoylproteins, that only a subset of analog-substituted proteins undergo redistribution from membrane to cytosolic fractions, and that these analogs can inhibit the replication of human immunodeficiency virus I and Moloney murine leukemia viruses--two retroviruses that depend upon N-myristoylation of their gag polyprotein precursors for assembly. We have now extended our analysis of NMT-acylCoA interactions by synthesizing additional analogs of myristic acid and testing them in a coupled in vitro assay system. Myristic acid analogs with two oxygen or two sulfur substitutions have hydrophobicities comparable to that of hexanoic acid and decanoic acid, respectively.(ABSTRACT TRUNCATED AT 250 WORDS)

Acyl Coenzyme A↗

PubMed1980

[The neuroleptic efficiency of some butyrophenone and fluorinated phenothiazine derivatives (author's transl)].

The action of butaperazine was diminished and simultaneously prolonged by fluorination in the position 3 or 7 as evidenced by a number of tests (prolongation of the resting time, catalepsy, apomorphine and dexphenmetrazine antagonism, conditioned escape reflex, aggressivity, algesimetry) on the rat and the mouse. The same seems to apply, in principle, to promazine and prochlorperazine. In contrast, the action of 7-fluorperphenazine and its esters with adamantanic acid and decanoic acid was markedly increased, but not prolonged, as demonstrated by a test (conditioned escape reflex) on the rat. The potency of fluphenazine is reached, but not its duration of action. This finding still needs confirmation by other tests. The duration of action of the butyrylphenazine esters was scarcely longer than that of butyrylphenazine. Considerable irritation has been seen at the site of injection. The esters of long-chained fatty acids and fluperidol and trifluperidol seem to be more potent than the parent substances. There is obviously no prolongation of the duration of action. The activity of the haloperidol oxime ethers (and probably of the esters, too) is weak as compared to that of haloperidol. The duration of action is not prolonged.

Animals↗