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PubMed1993

A Novel Delta5-Desaturase-Defective Mutant of Mortierella alpina 1S-4 and Its Dihomo-gamma-Linolenic Acid Productivity.

A novel Delta5-desaturase-defective mutant was derived from an arachidonic acid-producing fungus, Mortierella alpina 1S-4, after treating the parental spores with N-methyl-N'-nitro-N-nitrosoguanidine. The mutant produced only a trace (about 1%) amount of arachidonic acid, and the ratio of dihomo-gamma-linolenic acid (DGLA) to total fatty acids in each lipid class was markedly high, accounting for as much as 60% in phosphatidylcholine. Under submerged batch culture conditions, the mutant produced 2.4 g of DGLA per liter (43.3% of total fatty acids) when grown at 28 degrees C for 7 days in a 5-liter jar fermentor. The other major (more that 1%) fatty acids were palmitic acid (21.2%), stearic acid (9.6%), oleic acid (14.3%), linoleic acid (4.4%), and gamma-linolenic acid (5.8%). About 80 mol% of the DGLA produced was found in triacylglycerol.

Journal Article↗
PubMed1979

Alteration of the fatty acid composition of Escherichia coli by growth in the presence of normal alcohols.

The addition of normal alcohols in the series n-butanol to n-octanol to cultures of Escherichia coli ML308 grown on defined or lipid-free medium (at 17, 27, and 37 degrees C) caused an alteration in the fatty acid composition of this organism: the ratio of saturated to unsaturated fatty acids increased. Changes in the relative quantities of individual fatty acid species elicited by increasing concentrations of these alcohols were as follows: (i) myristic acid remained constant: (ii) palmitic acid increased; and (iii) the combined amount of palmitoleic plus cis-methylene hexadecanoic acids changed in a way which was reflected inversely by changes in the amount of cis-vaccenic acid. Comparable changes were not observed when cells were grown in the presence of n-nonanol and n-decanol in the concentration range tested. The changes observed upon addition of normal alcohols (n-butanol to n-octanol) paralleled, in part, the alterations in fatty acid composition observed when growth temperature was increased.

Alcohols↗
PubMed1962

EFFECT OF TEMPERATURE ON THE COMPOSITION OF FATTY ACIDS IN ESCHERICHIA COLI.

Marr, Allen G. (University of California, Davis) and John L. Ingraham. Effect of temperature on composition of fatty acids in Escherichia coli. J. Bacteriol. 84:1260-1267. 1962.-Variations in the temperature of growth and in the composition of the medium alter the proportions of individual fatty acids in the lipids of Escherichia coli. As the temperature of growth is lowered, the proportion of unsaturated fatty acids (hexadecenoic and octadecenoic acids) increases. The increase in content of unsaturated acids with a decrease in temperature of growth occurs in both minimal and complex media. Cells harvested in the stationary phase contained large amounts of cyclopropane fatty acids (methylenehexadecanoic and methylene octadecanoic acids) in comparison with cells harvested during exponential growth. Cells grown in a chemostat, limited by the concentration of ammonium salts, show a much higher content of saturated fatty acids (principally palmitic acid) than do cells harvested from an exponentially-growing batch culture in the same medium. Cells grown in a chemostat, limited by the concentration of glucose, show a slightly higher content of unsaturated fatty acids than cells from the corresponding batch culture. The results do not indicate a direct relation between fatty acid composition and minimal growth temperature.

Journal Article↗
PubMed1988

Adipose tissue glyceride synthesis in patients with hyperapobetalipoproteinemia.

Adipose tissue was obtained at thoracotomy in five control patients with valvular heart disease, all of whom were free of coronary artery disease and all of whom were normolipidemic with normal low density lipoprotein apolipoprotein B levels, and eight patients with coronary artery disease, all of whom had hyperapobetalipoproteinemia. In both groups, the rates at which linoleic acid and palmitic acid were incorporated into diglyceride and triglyceride were determined in vitro. The data indicate that fatty acid incorporation into adipose tissue glycerides was twice as rapid in controls as in patients with hyperapobetalipoproteinemia. By contrast there was no difference between the groups in the rate of net lipolysis of adipocyte glyceride. The data at hand do not establish the mechanism responsible for the difference in synthesis between normal subjects and patients with hyperapobetalipoproteinemia, but this may explain the delayed chylomicron triglyceride clearance previously observed in the disorder.

Adipose Tissue↗
PubMed2005

Potent block of inactivation-deficient Na+ channels by n-3 polyunsaturated fatty acids.

A voltage-gated, small, persistent Na(+) current (I(Na)) has been shown in mammalian cardiomyocytes. Hypoxia potentiates the persistent I(Na) that may cause arrhythmias. In the present study, we investigated the effects of n-3 polyunsaturated fatty acids (PUFAs) on I(Na) in HEK-293t cells transfected with an inactivation-deficient mutant (L409C/A410W) of the alpha-subunit (hH1(alpha)) of human cardiac Na(+) channels (hNav1.5) plus beta(1)-subunits. Extracellular application of 5 microM eicosapentaenoic acid (EPA; C20:5n-3) significantly inhibited I(Na). The late portion of I(Na) (I(Na late), measured near the end of each pulse) was almost completely suppressed. I(Na) returned to the pretreated level after washout of EPA. The inhibitory effect of EPA on I(Na) was concentration dependent, with IC(50) values of 4.0 +/- 0.4 microM for I(Na) peak (I(Na peak)) and 0.9 +/- 0.1 microM for I(Na late). EPA shifted the steady-state inactivation of I(Na peak) by -19 mV in the hyperpolarizing direction. EPA accelerated the process of resting inactivation of the mutant channel and delayed the recovery of the mutated Na(+) channel from resting inactivation. Other polyunsaturated fatty acids, docosahexaenoic acid, linolenic acid, arachidonic acid, and linoleic acid, all at 5 microM concentration, also significantly inhibited I(Na). In contrast, the monounsaturated fatty acid oleic acid or the saturated fatty acids stearic acid and palmitic acid at 5 microM concentration had no effect on I(Na). Our data demonstrate that the double mutations at the 409 and 410 sites in the D1-S6 region of hH1(alpha) induce inactivation-deficient I(Na) and that n-3 PUFAs inhibit mutant I(Na).

Cell Line↗
PubMed1990

pH-sensitive liposomes composed of phosphatidylethanolamine and fatty acid.

pH-induced destabilization, aggregation and fusion of liposomes composed of phosphatidylethanolamine (PE) and various fatty acid were studied. Destabilization was examined as a fluorescent change caused by leakage of coencapsulated aminonaphthalene-3,6,8-trisulfonic acid (ANTS) and N,N-p-xylylenebispyridinium bromide (DPX). Fusion was monitored by two different methods, that is, intermixing assay of internal aqueous contents of liposomes, and lipid dilution assay of liposomes labeled with fluorescent phospholipids. Contents leakage from liposomes was observed by lowering the pH, and pH where the leakage began depended on fatty acid used. Fifty percent leakage of contents from PE liposomes containing alpha-hydroxypalmitic acid or alpha-hydroxy-stearic acid was observed at pH 5.5, that from liposomes containing stearic acid or palmitic acid was observed at pH 6.5-6.7, and that from ricinoleic acid at pH 7.2. Aggregation and fusion of the respective liposomes also occurred at a similar pH region. These results were interpreted by the notion that the protonation of the fatty acid triggers a series of pH-sensitive events. The liposomes developed in this study may be useful as a drug carrier which could release the contents in response to pH changes in their environment.

Chemical Phenomena↗
PubMed2001

Cyclooxygenase-2 inhibitory cerebrosides from phytolaccae radix.

A mixture of cerebrosides, called poke-weed cerebrosides, was purified from Phytolaccae Radix (Phytolaccaceae) and characterized as 1-O-beta-D-glucopyranosides of phytosphingosine type ceramides comprised of a common long chain base (2S,3S,4R,8Z)-2-amino-8-octadecene-1,3,4-triol and fatty acids. The fatty acyl chain of ceramide moieties was determined as (2R)-2-hydroxypentacosanoic acid, (2R)-2-hydroxylignoceric acid, (2R)-2-hydroxytricosanoic acid, (2R)-2-hydroxybehenic acid, (2R)-2-hydroxypalmitic acid, and palmitic acid. The pokeweed cerebroside inhibited the cyclooxygenase-2 dependent phase of prostaglandin D2 generation in bone marrow-derived mast cells in a concentration dependent manner with an IC50 of 6.2 microg/ml.

Animals↗
PubMed2003

Pentacyclic triterpenoids from the aerial parts of Lantana camara.

Three new pentacyclic triterpenoids, camaryolic acid (1), methylcamaralate (2) and camangeloyl acid (3) and six known compounds beta-sitosterol 3-O-beta-D-glucopyranoside (4), octadecanoic acid (5), docosanoic acid (6), palmitic acid (7), camaric acid (8) and lantanolic acid (9) were isolated from the aerial parts of Lantana camara. Structures of the new compounds were elucidated by spectroscopic and chemical methods.

Lantana↗
PubMed2006

Modulation of ATP-induced inward currents by docosahexaenoic acid and other fatty acids in rat nodose ganglion neurons.

The effects of docosahexaenoic acid (DHA) and other fatty acids on P2X-receptor-mediated inward currents in rat nodose ganglion neurons were studied using the nystatin perforated patch-clamp technique. DHA accelerated the desensitization rate of the ATP-induced current. DHA showed use-dependent inhibition of the peak ATP-induced current. Other polyunsaturated fatty acids, such as arachidonic acid and eicosapentaenoic acid, displayed a similar use-dependent inhibition. The inhibitory effects of saturated fatty acids including palmitic acid and arachidic acid were weaker than those of polyunsaturated fatty acids. The results suggest that fatty acids may modulate the P2X receptor-mediated response when the channel is in the open-state.

Adenosine Triphosphate↗
PubMed2006

Fatty acid composition of ruminal bacteria and protozoa, with emphasis on conjugated linoleic acid, vaccenic acid, and odd-chain and branched-chain fatty acids.

Knowledge of the fatty acid profile of microbial lipids is of great nutritional importance to the animals and, subsequently, their products. This study was conducted to examine the fatty acid profiles of mixed rumen bacteria and protozoa. Bacterial and protozoal cells were isolated by differential centrifugation of rumen contents. The main fatty acids were palmitic (16:0) and stearic (18:0) in both the bacterial and protozoal fractions. Palmitic acid was 74% greater in the protozoal fatty acids than in the bacterial fatty acids, whereas bacteria had 2.25-times greater stearic acid (18:0) proportions compared with protozoa. The total odd-chain plus branched-chain fatty acids were 16.5% of bacterial fatty acids and 11.0% of protozoal fatty acids. The anteiso-17:0 proportions in bacterial and protozoal fatty acids were 1.4 and 2.9%, respectively. The most abundant trans-18:1 isomer, vaccenic acid (18:1 trans-11), was 6.6% of total fatty acids in protozoa and 2.0% of total fatty acids in bacteria. The cis-9, trans-11 CLA was 8.6-times greater in the protozoal fraction (1.32% of total fatty acids) than in the bacterial fraction (0.15%). These results suggest that the presence of protozoa in the rumen may increase the supply of CLA and other unsaturated fatty acids for lower gut absorption by ruminants.

Animals↗
PubMed1995

Fatty acyl-CoA oxidase activity is induced before long-chain acyl-CoA hydrolase activity and acyl-CoA binding protein in liver of rat treated with peroxisome proliferating 3-thia fatty acids.

1. In this study we explored the relationship between specific acyl-CoA esters and induction of acyl-CoA binding protein (ACBP) and enzymes related to the proliferation of peroxisomes. Male Wistar rats were administered a single dose (150 mg/day/kg) of sulphur-substituted fatty acid analogues, and the effects of tetradecylthioacetic acid and 3-thiadicarboxylic acid, which both act as peroxisome proliferators, were compared with the effects of tetradecylthiopropionic acid and palmitic acid which do not induce peroxisome proliferation. 2. The hepatic level of total long-chain acyl-CoA was significantly increased within 12 h of feeding these fatty acids, except in rat fed tetradecylthioacetic acid. Hplc chromatograms of liver extracts prepared from rat fed tetradecylthioacetic acid showed that tetradecylthioacetyl-CoA ester accumulated in the liver 4 h after feeding and had disappeared after 24 h. In liver extracts of the tetradecylthiopropionic acid-treated rat tetradecylthiopropionyl-CoA was not observed, but the appearance of a new long-chain acyl-CoA ester, probably a metabolite of tetradecylthiopropionic acid, was detected. This new peak reached a maximum 4h after feeding. In rat fed tetradecylthioacetic acid and 3-thiadicarboxylic acid the hepatic level of fatty acyl-CoA oxidase mRNA increased 8 h after feeding, while the acyl-CoA oxidase activity had increased after 12 h. 3. The early accumulation of specific tetradecylthioacetyl-CoA suggests that this ester may be a possible mediator of the induction of fatty acyl-CoA oxidase. The level of hepatic acyl-CoA binding protein, long-chain acyl-CoA hydrolase activity and long-chain acyl-CoA synthetase activity did not change after a single dose of all four fatty acids. Prolonged administration of 3-thia fatty acids resulted, however, in a dose- and time-dependent increase in hepatic ACBP content and ACBP mRNA level. The amount of ACBP increased in parallel to the long-chain acyl-CoA hydrolase activity. The correlated induction of fatty acyl-CoA binding protein and long-chain acyl-CoA hydrolase seems to be dependent on a sustained accumulation of total long-chain acyl-CoA esters.

Acyl Coenzyme A↗
PubMedDate not supplied

Degumming of crude palm oil by membrane filtration.

The application of membrane separation in palm oil refining process has potential for energy and cost savings. The conventional refining of crude palm oil results in loss of oil and a contaminated effluent. Degumming of crude palm oil by membrane technology is conducted in this study. The objective of this research is to study the feasibility of membrane filtration for the removal of phospholipids in the degumming of crude palm oil, including analyses of phosphorus content, carotene content free fatty acids (as palmitic acid), colour and volatile matter. A PCI membrane module was used which was equipped with polyethersulfone membranes having a molecular weight cut off of 9,000 (type ES209). In this study, phosphorus content was the most important parameter monitored. The membrane effectively removed phospholipids resulting in a permeate with a phosphorus content of less than 0.3 ppm The percentage removal of phosphorus was 96.4% and was considered as a good removal. Lovibond colour was reduced from 27R 50Y to 20R 30Y. The percentage removal of carotene was 15.8%. The removal of colour was considered good but the removal of carotene was considered insignificant by the membrane. Free fatty acids and volatile matter were not removed. Typical of membrane operations, the permeate flux decreased with time and must be improved in order to be adopted on an industrial scale. Membrane technology was found to have good potential in crude palm oil degumming. However, an appropriate method has to be developed to clean the membranes for reuse.

Carotenoids↗
PubMed1992

Effects of adrenoceptor blockade on cardiac hypertrophy and myocardial phospholipids.

Catecholamines have been proposed as a stimulus for the hypertrophic response to pressure overload of the heart and could also mediate the membrane lipid changes associated with cardiac hypertrophy. To address both of these possibilities, cardiac hypertrophy was induced by aortic constriction in the presence or absence of chronic alpha- or beta-adrenoceptor blockade. Heart weights and heart weight to body weight ratios in aortic-constricted rats of the adrenoceptor-blocked and vehicle-treated groups were elevated to the same extent when compared with values in sham-operated rats of each group. Analysis of the fatty acyl composition of the major phospholipid classes revealed that similar changes occurred in vehicle-treated, alpha-blocked, and beta-blocked aortic-constricted rats when compared with respective groups of sham-operated rats. Specifically, linoleic acid was reduced in the phosphatidylcholine, phosphatidylethanolamine (PE), and cardiolipin (CL) fractions in all groups of aortic-constricted rats. This reduction was accompanied by increased docosahexaenoic acid, arachidonic acid, or palmitic acid in phosphatidylcholine; docosahexaenoic acid in phosphatidylethanolamine; and oleic acid in cardiolipin fractions. Adrenoceptor blockade did not prevent or attenuate the major changes in the fatty acyl composition of phospholipids or the increase in heart weight associated with aortic constriction. This suggests that a change in the level of adrenoceptor stimulation is not the stimulus for cardiac hypertrophy or the observed alterations in phospholipid composition in the pressure-overloaded rat heart.

Adrenergic alpha-Antagonists↗
PubMed2006

[Analysis of constituents in urushi wax, a natural food additive].

Urushi wax is a natural gum base used as a food additive. In order to evaluate the quality of urushi wax as a food additive and to obtain information useful for setting official standards, we investigated the constituents and their concentrations in urushi wax, using the same sample as scheduled for toxicity testing. After methanolysis of urushi wax, the composition of fatty acids was analyzed by GC/MS. The results indicated that the main fatty acids were palmitic acid, oleic acid and stearic acid. LC/MS analysis of urushi wax provided molecular-related ions of the main constituents. The main constituents were identified as triglycerides, namely glyceryl tripalmitate (30.7%), glyceryl dipalmitate monooleate (21.2%), glyceryl dioleate monopalmitate (2.1%), glyceryl monooleate monopalmitate monostearate (2.6%), glyceryl dipalmitate monostearate (5.6%), glyceryl distearate monopalmitate (1.4%). Glyceryl dipalmitate monooleate isomers differing in the binding sites of each constituent fatty acid could be separately determined by LC/MS/MS.

Chromatography, Liquid↗
PubMed2001

Cytosolic phospholipase A2 participates with TNF-alpha in the induction of apoptosis of human macrophages infected with Mycobacterium tuberculosis H37Ra.

Macrophage (MPhi) apoptosis, an important innate microbial defense mechanism induced by Mycobacterium tuberculosis (Mtb) H37Ra, depends on the induction of TNF-alpha synthesis. When protein synthesis is blocked, both infection with Mtb and addition of TNF-alpha are required to induce caspase 9 activation, caspase 3 activation and apoptosis. In this study, we show that the second protein synthesis-independent signal involves activation of group IV cytosolic phospholipase A2 (cPLA2). Apoptosis of Mtb-infected MPhi and concomitant arachidonic acid release are abrogated by group IV cPLA2 inhibitors (methyl arachidonyl fluorophosphate and methyl trifluoromethyl ketone), but not by inhibitors of group VI Ca2+-independent (iPLA2; bromoenol lactone) or of secretory low molecular mass PLA2. In MPhi homogenates, the predominant PLA2 activity showed the same inhibitor sensitivity pattern and preferred arachidonic acid over palmitic acid in substrates, also indicating the presence of one or more group IV cPLA2 enzymes. In concordance with these findings, MPhi lysates contained transcripts and protein for group IV cPLA2-alpha and cPLA2-gamma. Importantly, group IV cPLA2 inhibitors significantly reduced MPhi antimycobacterial activity and addition of arachidonic acid, the major product of group IV cPLA2, to infected MPhi treated with cPLA2 inhibitors completely restored the antimycobacterial activity. Importantly, addition of arachidonic acid alone to infected MPhi significantly reduced the mycobacterial burden. These findings indicate that Mtb induces MPhi apoptosis by independent signaling through at least two pathways, TNF-alpha and cPLA2, which are both also critical for antimycobacterial defense of the MPhi.

Adjuvants, Immunologic↗
PubMed1983

Isolation and partial characterization of a cerulenin-sensitive mutant of Pseudomonas aeruginosa.

Sensitivity of Pseudomonas aeruginosa to cerulenin was first tested. The result indicated that this bacterium is resistant to cerulenin. Cerulenin-sensitive mutants were isolated from P. aeruginosa PML 1552 by 1-methyl-3-nitro-1-nitrosoguanidine treatment and following carbenicillin plus D-cycloserine screening. Isolated mutants were designated CSM-1 to CSM-19, and some characters of CSM-19, which showed rapid growth almost as well as parent strain in the medium without cerulenin, were examined. The cell growth of CSM-19 was greatly inhibited by 50 micrograms/ml of cerulenin, but when the mixture of cellular fatty acids or both cis-vaccenic acid and palmitic acid were added to the medium, the growth was partially recovered. Incorporation of radioactivity into fatty acids from [1-14C]acetate was lowered by cerulenin. Those results mean that the fatty acid synthesis of CSM-19 was decreased by cerulenin. Although cellular fatty acid composition and amount were not notably different between CSM-19 and PML 1552, CSM-19 had less phosphatidylethanolamine, and more phosphatidylglycerol and cardiolipin than PML 1552. CSM-19 was also supersensitive to several other antibiotics, especially to carbenicillin and tetracycline, when compared with PML 1552, although both strains showed identical sensitivity to D-cycloserine, polymyxin B, and chloramphenicol.

Anti-Bacterial Agents↗
PubMed1997

[Chemical constituents of Strychnos nitida G. Don].

Six compounds were isolated from the root and stem of Strychnos nitida for the first time. On the basis of chemical properties and spectral data, the compounds were identified as beta-sitosterol, strychnine, brucine, cantieyine, lignoceric acid and palmitic acid.

Alkaloids↗
PubMed1997

[Chemical constituents of fructus Amomi].

Seven compounds have been isolated from Fructus Amomi. They were identified as bornyl acetate, camphor, borneol, beta-sitosterol, vanillic acid, stearic acid and palmitic acid. The vanillic acid was found in this medicine for the first time. Fifty-seven components were identified from the volatile oil of Fructus Amomi on the basis of GC-MS analysis. Eight components in the volatile oil over 1% in content are bornyl acetate, camphor, borneol, limonene, camphene, myrecene, carene-3 and alpha-terpeneol.

Drugs, Chinese Herbal↗