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PubMed1994

Serum fatty acid profiles in type I and type II diabetes: metabolic alterations of fatty acids of the main serum lipids.

Fatty acid profiles of various lipid fractions were determined in carefully selected insulin-dependent and non-insulin-dependent diabetics to assess relationships between serum fatty acid composition and type of diabetes. Clear-cut hypertriglyceridemia with slight hypercholesterolemia was found in both diabetic types. The decrease of lignoceric acid in sphingomyelin is the only alteration found in both types of diabetes. In the insulin-dependent diabetics, there were increases in levels of oleic acid and of alpha-linolenic acid in esterified cholesterol, and in levels of alpha-linolenic acid in the triglyceride fraction. In the non-insulin-dependent diabetics, there were increases in levels of oleic acid and total monounsaturated fatty acids in the triglyceride fraction and there was an increase in levels of saturated fatty acids and a decrease in levels of polyunsaturated acids in phosphatidylcholine; in sphingomyelin, dihomogamma-linoleic acid levels were enhanced. Arachidonic acid levels were normal in our patient population.

Adult↗
PubMed1982

Effects of some hypolipidemic drugs and phthalic acid esters on fatty acid binding protein in rat liver.

Effects of clofibric acid, probucol, niceritrol, di-(2-ethylhexyl)phthalate (DEHP) and dibutyl phthalate (DBP) on the binding capacities of fatty acid binding protein (FABP) and ligandin fractions in rat liver were investigated. The binding capacity of FABP fraction in male rat liver to oleic acid was increased remarkably on clofibric acid-feeding for 7 d. The administration of either probucol or niceritrol had little influence on the binding capacity of FABP. Both DEHP and DBP increased the binding capacity of FABP in liver of male rats, but the extent of the increase was somewhat less significant in DEHP- or DBP-fed rats compared to that in clofibric acid-fed rats. Sex-related difference in the increase in the binding capacity of FABP fraction to oleic acid by either clofibric acid or DEHP was observed and the extent of the increase in female rats feeding clofibric acid or DEHP was about half of male rats. Effects of any drugs and agents tested here on the binding capacity of ligandin in liver to bromosulfophthalein (BSP) were little if any. The increase in the binding capacity of FABP fraction, but not ligandin in liver was confirmed in vivo by intravenous administration of BSP to rats which had been fed DEHP. In spite of marked increase in the binding capacity of FABP fraction in liver from clofibric acid-fed rats, no remarkable increase in the incorporation of radioactive oleic acid into esterified lipids was observed in vivo.

Animals↗
PubMed1997

Effects of dietary supplementation with alpha-linolenic acid on the phospholipid fatty acid composition and quality of spermatozoa in cockerel from 24 to 72 weeks of age.

The aim of this study was to investigate the effects of supplementing the diet of the male chicken with alpha-linolenic acid (18:3n-3) on the phospholipid fatty acid composition, motility and fertilizing ability of chicken spermatozoa. The birds in the control group received a diet supplemented with soybean oil rich in linoleic acid (18:2n-6) whereas those in the test group were supplemented with linseed oil rich in alpha-linolenic acid. A number of age-related changes in the lipid parameters of the spermatozoa were observed in control birds. Between 24 and 72 weeks of age the amount of total lipid in the spermatozoa of control birds increased by approximately 2.4 times and the proportions of cholesterol and free fatty acid also increased significantly, whereas the proportions of phospholipid and triacylglycerol decreased. In addition, the proportion of phosphatidylcholine in the total phospholipid increased, whereas the proportion of phosphatidylserine decreased during the same period. The proportion of docosatetraenoic acid (22:4n-6) in the phospholipid decreased significantly between 24 and 72 weeks of age. The concentration of spermatozoa in the semen of control birds increased to a maximum at week 39 and had decreased significantly by week 72. Supplementation with alpha-linolenic acid had little or no effect on the proportion of docosahexaenoic acid (22:6n-3) in the phospholipid profile of the spermatozoa. However, supplementation with alpha-linolenic acid did produce a significant but small increase in the proportion of docosapentaenoic acid (22:5n-3) recorded at 39 and 54 weeks. Thus, this study shows that the fatty acid composition of the sperm phospholipid demonstrates a marked resistance to dietary manipulation. Supplementation with alpha-linolenic acid significantly enhanced semen fertility at week 39. The results suggest that the small increase in the proportion of n-3 fatty acids in the sperm phospholipids induced by enriching the diet with alpha-linolenic acid is associated with a significant improvement in semen quality at 39 weeks of age.

Animals↗
PubMed1990

Alkylthioacetic acids (3-thia fatty acids) are metabolized and excreted as shortened dicarboxylic acids in vivo.

The metabolism of 1-14C-labeled long-chain alkylthioacetic acids (3-thia fatty acids) which are blocked for normal beta-oxidation by a sulfur atom in the beta-position has been investigated in vivo. Most of the injected radioactivity (greater than 50%) was excreted in the urine within the first 48 h. The recovered and identified metabolites were all short sulfoxydicarboxylic acids. The main metabolite from dodecylthioacetic acid was carboxypropylsulfoxy acetic acid. Some bis(carboxymethyl)sulfoxide (dithioglycolic acid sulfoxide) was also found. The main metabolite from nonylthioacetic acid was carboxyethylsulfoxyacetic acid. No sulfones were found. Less than 1% of the 1-14C from the dodecylthioacetic acid was recovered in respiratory CO2 and about 3% of the 1-14C from nonylthioacetic acid. [1-14C]Dodecyl-sulfonylacetic acid was recovered almost quantitatively as carboxypropylsulfonylacetic acid in the urine after 3 h. A significant fraction (10% of the dodecylthioacetic acid was recovered in the phospholipids and triacylglycerols from liver and epidymal fat pad 4 h after injection. These experiments show that the alkylthioacetic acids undergo an initial omega-oxidation followed by beta-oxidation to short dicarboxylic acids.

Animals↗
PubMed1991

Effects of perfluorodecanoic acid on de novo fatty acid and cholesterol synthesis in the rat.

Perfluorodecanoic acid (PFDA) is a peroxisome proliferator that causes a dose-dependent (20-80 mg/kg) increase in hepatic triacylglycerol and cholesteryl ester levels in the rat. We hypothesized that PFDA may cause an increase in the de novo synthesis of fatty acids and cholesterol in this species, which would explain observed effects. The incorporation of 3H2O into tissue lipids was examined 7 days after rats received vehicle or 20 or 80 mg/kg of PFDA. PFDA treatment decreased the rate of synthesis of cholesterol and fatty acids in the live and in epididymal fat pad. At a PFDA dose (20 mg/kg) that decreased de novo synthesis of fatty acids and cholesterol, there was no effect on the concentration of fatty acids and cholesterol in the liver, epididymal fat pads, and plasma. We conclude that PFDA induced fatty liver is due to either a decrease in the oxidation of fatty acids in the liver, or an impairment of triacylglycerol catabolism and/or export from the liver, and is not the result of an increase in de novo synthesis of fatty acids and cholesterol.

Adipose Tissue↗
PubMed1984

Analysis of fatty acids of the genus Rochalimaea by electron capture gas chromatography: detection of nonanoic acid.

The fatty acid compositions of Rochalimaea quintana, strains Fuller and Guadalupe, and R. vinsonii, the Canadian vole agent, were determined in an effort to further characterize these bacteria. The cells were saponified with 5% NaOH in 50% methanol and acidified to pH 2. The methanolysates were extracted with chloroform, derivatized with 2,2,2-trichloroethanol, and analyzed using a Hewlett-Packard gas chromatograph equipped with a frequency pulse-modulated electron capture detector and a 3% OV-101 packed-glass column. The fatty acid profiles of the three Rochalimaea strains were similar, with octadecenoic acid (C18:1) the most abundant, followed by octadecanoic (C18:0) and hexadecanoic (C16:0) acids. Moderate to trace amounts of other acids were also present. Unexpectedly, well-defined peaks of nonanoic acid (C9) were found consistently. A portion of this acid, but not all, was extractable with chloroform. Since C9 is not reported as a usual component of bacteria and most analyses do not include a search for this fatty acid, this study was extended to three strains of Legionella and one of Campylobacter. Comparable results were obtained. Since these bacteria were grown in complex media which contain some C9, it is possible that the medium is the source of bacterial C9. Whether this compound can be synthesized by the bacteria remains to be investigated.

Chloroform↗
PubMed1987

Influence of dietary lipids and linoleic acid amounts on fatty acid content and composition of pig serum lipoproteins.

The effects of hyperlipidic polyunsaturated fat diets (PF) and saturated fat diets (SF) versus control diet (CO) on total lipid, phospholipid (PL) and cholesteryl ester (CE) content and composition of pig serum lipoproteins were studied in Large White pigs who first underwent a PF period for 14 days followed by a CO period and third a SF feeding during a fortnight. PF and SF diets induced an increase of linoleic acid in serum total lipids, especially in HDL fraction; this increase in CE and PL involved a reverse change of oleic acid. The modifications induced by the amounts of dietary linoleic acid could be explained by an alteration of LCAT activity. The fatty acid pattern of PL which constitute the LCAT substrate lead to an enrichment of cholesterol linoleate.

Animals↗
PubMed1994

Glycosphingolipid receptor function is modified by fatty acid content. Verotoxin 1 and verotoxin 2c preferentially recognize different globotriaosyl ceramide fatty acid homologues.

Verotoxins (VT) are a family of Escherichia coli-derived toxins which have been associated with hemolytic uremic syndrome, the leading cause of acute pediatric renal failure, and hemorrhagic colitis. Verotoxins (VT1 and VT2c) both show terminal gal alpha 1-4gal-dependent binding to globotriaosylceramide (Gal alpha 1-4Gal beta 1-4Glc-Cer; Gb3), yet VT2c shows a thousandfold lower specific cytotoxic activity in vitro. Our previous studies have shown this discrepancy is a function of the receptor binding B subunit and that VT1/Gb3 binding in a lipid matrix is affected by heterogeneity in the ceramide fatty acid chain length. The influence of the fatty acid composition of Gb3 on the binding of VT1 and VT2c has now been compared using 14 homogeneous semisynthetic Gb3 molecular species of differing fatty acid chain length and degree of saturation from C12 to C24. The binding of verotoxin was quantitated by Scatchard analysis using a solid-phase binding assay in the presence of auxiliary lipids, which may in some respects approximate to receptor function within the plasma membrane of sensitive cells. Differential binding was observed for several of these species in the lipid matrix, indicating that the fatty acid moiety of Gb3 is important for VT binding under such conditions. The short chain fatty acid containing Gb3 (C12 and C14) showed minimal binding. Middle and long chain fatty acid Gb3 homologues (C16, C18, C20, C22, and C24) were effectively recognized by VTs. The presence of an unsaturated fatty acid in Gb3 significantly increased VT binding in all cases. C20:0 and C22:1 containing Gb3 had the greatest capacity to bind VT1. In contrast, C18:0 and C18:1 homologues showed the greatest capacity for VT2c binding (higher than VT1). These results were, in general, reflected in cell cytotoxicity in that receptor-deficient cells reconstituted with C22:1Gb3 were maximally sensitive to VT1 in vitro whereas cells reconstituted with C18:1Gb3 were maximally sensitive to VT2c. VT2c was an ineffective inhibitor of 125I-VT1 binding to C22:1 Gb3 but in contrast, more effective than VT1 to compete binding to C18:1 Gb3. Similarly, VT1 was less effective than VT2c to compete binding of 125I-VT2c to C18:1 but more effective than VT2c to compete for C22:1 Gb3 binding. These results suggest that VT1 and VT2c bind selectively to different but overlapping carbohydrate epitopes on the Gb3 molecule which are differentially available in these Gb3 fatty acid homologues in a lipid environment.(ABSTRACT TRUNCATED AT 400 WORDS)

Bacterial Toxins↗
PubMed2002

Intake of conjugated linoleic acid, fat, and other fatty acids in relation to postmenopausal breast cancer: the Netherlands Cohort Study on Diet and Cancer.

BACKGROUND: Conjugated linoleic acid (CLA), which is present in milk products and meat from ruminants, appears to have anticarcinogenic activity against breast cancer in animal and in vitro experiments. To date, few epidemiologic data are available in humans. OBJECTIVE: This study evaluated the relation between intakes of CLA and other fatty acids and breast cancer incidence in the Netherlands Cohort Study. DESIGN: Intake data derived from a validated 150-item food-frequency questionnaire were linked to an existing database with analytic data on specific fatty acids in European foods (the TRANSFAIR study). With 6.3 y of follow-up and 941 incident cases of breast cancer, multivariate rate ratios and 95% CIs were calculated for energy-adjusted intakes of fatty acids and CLA-containing food groups (eg, butter, cheese, milk, other milk products, and meat). RESULTS: CLA intake showed a weak, positive relation with breast cancer incidence (rate ratio for highest compared with lowest quintile: 1.24, 95% CI: 0.91, 1.69; P for trend = 0.02). Statistically significant positive associations were found with total trans fatty acids and (borderline) with saturated fatty acids. Significant inverse associations were found with monounsaturated and cis unsaturated fatty acids, whereas total fat and energy intake of CLA-containing food groups were not related to breast cancer incidence. CONCLUSION: The suggested anticarcinogenic property of CLA in animal and tissue culture models could not be confirmed in this epidemiologic study in humans.

Aged↗
PubMed2005

Omega-3 fatty acids in health and disease: part 2--health effects of omega-3 fatty acids in autoimmune diseases, mental health, and gene expression.

Omega-3 fatty acids from marine and plant sources provide a wide range of benefits in several human health conditions. In vivo studies indicate that omega-3 fatty acids influence the course of several human diseases, including those that involve abnormal immune function, mental disorders, and genetic abnormalities in lipid metabolism. Omega-3 fatty acids are taken up by virtually all body cells and affect membrane composition, eicosanoid biosynthesis, cell signaling cascades, and gene expression. These fatty acids are especially important during human brain development; maternal deficiency of omega-3 fatty acids may lead to several neurological disorders. The review highlights recent findings on omega-3 fatty acids' influence on autoimmune diseases, mental health, and gene expression.

Autoimmune Diseases↗
PubMed1998

Protonophoric activity of fatty acid analogs and derivatives in the inner mitochondrial membrane: a further argument for the fatty acid cycling model.

The protonophoric (uncoupling) action of various long-chain fatty acids and their derivatives in mitochondria was investigated as related to their ability for rapid transbilayer movement in the inner mitochondrial membrane (flip-flop) and interaction with the ADP/ATP carrier (AAC). Flip-flop was assessed from a rapid decrease of internal mitochondrial pH. It was found that long-chain unsubstituted fatty acids (with the exception of very-long-chain unbranched homologs) and their thia and oxa analogs performed a rapid flip-flop, inhibited AAC activity and increased proton permeability of the inner mitochondrial membrane, resulting in dissipation of mitochondrial membrane potential and increased resting state respiration. Bipolar fatty acid analogs, i.e., those containing a second carboxylic group or OH group(s) at the hydrocarbon tail, phenyl-substituted fatty acid derivatives, and fatty acid analogs containing strongly ionized sulfonyl or sulfate groups instead of the carboxylic group, did not flip-flop and were not uncoupling, although some of them were weak inhibitors of AAC. These results provide further confirmation of the fatty acid cycling model (V. P. Skulachev, FEBS Lett. 294, 158-162, 1991) in which the protonophoric function of fatty acids is a result of the spontaneous transbilayer passage of undissociated (protonated) molecules of the fatty acid from the external side of the inner mitochondrial membrane to the matrix side and the AAC-mediated transport of the fatty acid anion in the opposite direction.

Adenosine Diphosphate↗
PubMed1999

Essentiality of fatty acids.

All fatty acids have important functions, but the term "essential" is applied only to those polyunsaturated fatty acids (PUFA) that are necessary for good health and cannot be completely synthesized in the body. The need for arachidonic acid, which is utilized for eicosanoid synthesis and is a constituent of membrane phospholipids involved in signal transduction, is the main reason why the n-6 class of PUFA are essential. Physiological data indicate that n-3 PUFA also are essential. Although eicosapentaenoic acid also is a substrate for eicosanoid synthesis, docosahexaenoic acid (DHA) is more likely to be the essential n-3 constituent because it is necessary for optimal visual acuity and neural development. DHA is present in large amounts in the ethanolamine and serine phospholipids, suggesting that its function involves membrane structure. Because the metabolism of n-6 PUFA is geared primarily to produce arachidonic acid, only small amounts of 22-carbon n-6 PUFA are ordinarily formed. Thus, the essentiality of n-3 PUFA may be due to their ability to supply enough 22-carbon PUFA for optimal membrane function rather than to a unique biochemical property of DHA.

Animals↗
PubMed1989

Progestin increases gene transcription and messenger ribonucleic acid stability of fatty acid synthetase in breast cancer cells.

The cDNA clone (Pg8) corresponding to the 3'-end of fatty acid synthetase (FAS) mRNA is one of the few probes to study in cell lines the mechanism by which an endogenous gene is regulated by progestins. The steady-state level of FAS mRNA is known to be increased by the synthetic progestin R5020 in the human breast cancer cell line MCF7. We show here that it is also increased in another progesterone-receptor-positive cell line T47D but not in progesterone-receptor-negative cell lines BT20, MDA-MB231, and HBL100. In R5020-treated MCF7 cells, the FAS mRNA concentration increased with cell density. Protein synthesis inhibitors did not abolish progestin induction of FAS suggesting a primary effect of the hormone. In vitro nuclear run-on transcription assays showed that the FAS gene transcription rate was increased about 4-fold by progestin. This stimulation of transcription was detectable 30 min after addition of R5020 and was maximal after 4 h, but could not totally account for the total increase in the mRNA steady state level. Chase experiments in the presence of Actinomycin D or Cordycepin showed that progestin also increased the half-life of FAS mRNA from 6-9 h to 24-33 h. We conclude that progestin stimulates the FAS concentration both by increasing the transcription rate of the gene and by stabilizing the mRNA.

Blotting, Northern↗
PubMed1980

Elevated thromboxane levels in the rat during endotoxic shock: protective effects of imidazole, 13-azaprostanoic acid, or essential fatty acid deficiency.

The potential deleterious role of the proaggregatory vasoconstrictor, thromboxane A(2), in endotoxic shock was investigated in rats. Plasma thromboxane A(2) was determined by radioimmunoassay of its stable metabolite thromboxane B(2). After intravenous administration of Salmonella enteritidis endotoxin (20 mg/kg), plasma thromboxane B(2) levels increased from nondetectable levels (<375 pg/ml) in normal control rats to 2,054+/-524 pg/ml (n = 8), within 30 min to 2,071+/-429 at 60 min, and decreased to 1,119+/-319 pg/ml, at 120 min. Plasma levels of prostaglandin E also increased from 146+/-33 pg/ml in normal controls (n = 5) to 2,161+/-606 pg/ml 30 min after endotoxin (n = 5). In contrast to shocked controls, rats pretreated with imidazole, a thromboxane synthetase inhibitor, or essential fatty acid-deficient rats, which are deficient in arachidonate and its metabolites, did not exhibit significant elevations in plasma levels of thromboxane B(2). Imidazole did not however inhibit endotoxin-induced elevations in plasma prostaglandin E. Essential fatty acid deficiency significantly reduced mortality to lethal endotoxic shock. This refractoriness could be duplicated in normal rats pretreated with the fatty acid cyclo-oxygenase inhibitor, indomethacin (10 mg/kg), intravenously 30 min before endotoxin injection. Imidazole (30 mg/kg) administered intraperitoneally 1 h before or intravenously 30 min before endotoxin, also significantly (P < 0.01) reduced mortality from lethal endotoxin shock to 40% compared to a control mortality of 95% at 24 h. Likewise pretreatment with 13-azaprostanoic acid (30 mg/kg), a thromboxane antagonist, reduced mortality from endotoxic shock at 24 h from 100% in control rats to only 50% (P < 0.01). The results suggest that endotoxin induces increased synthesis of thromboxane A(2) that may contribute to the pathogenesis of endotoxic shock.

Animals↗
PubMed2006

Effect of dietary conjugated linoleic acid and monounsaturated fatty acid content on pig muscle and adipose tissue lipase and esterase activity.

Three levels (0%, 1%, and 2%) of conjugated linoleic acid (CLA) were combined with two levels (low and high) of monounsaturated fatty acids (MUFA) for pig feeding. The activity of neutral lipase (NL), acid lipase (AL), phospholipase (PL), neutral esterase (NE), and acid esterase (AE) was measured in extracts from muscle and subcutaneous adipose tissues. The addition of CLA in the diet only affected the lipolytic activity in muscle, whereas differences in MUFA content of pig diets were mainly responsible for the lipolytic enzyme modifications observed in adipose tissue. Nevertheless, a significant effect of the interaction CLA x MUFA on the activity of several lipolytic enzymes was observed in both tissues. The effect of either linoleic acid (LA) or CLA on the activity of muscle and adipose lipolytic enzymes was determined by in vitro assays. Remarkable inhibitory or activation effects were detected depending on the enzyme and kind of tissue.

Adipose Tissue↗