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PubMed1979

Tissue-specific incorporation of positional isomers of dietary cis- and trans-octadecenoic acids in the rat.

The total lipids of liver, heart, blood serum, adipose tissue, testes and adrenals of rats fed a partially hydrogenated fat were found to contain each of the dietary delta 5- to delta 15- cis- and delta 3- to delta 16- trans-octadecenoic acids. The pattern of incorporation of individual isomeric octadecenoic acids was found to be specific for the different tissues. trans-Isomers were preferentially incorporated into liver and heart, whereas cis-isomers were enriched in the testes. The composition of positional isomers of both cis- and trans-octadecenoic acids in adipose tissue, testes and adrenals was similar to that of the dietary lipids, whereas the corresponding compositions in liver, heart and serum were distinctly different. Thus, within the series of cis-octadecenoic acids, less oleic acid (delta 9-isomer) and correspondingly higher proportions of vaccenic acid (delta 11-isomer) were found in liver and heart than in the dietary lipids. Within the series of trans-octadecenoic acids, the isomers ranging from delta 12 to delta 16, especially the delta 14-isomer, were preferentially incorporated into liver, heart and serum, whereas the delta 10- and delta 11-isomers, were distinctly excluded from these tissues.

Animals↗
PubMed2004

Accuracy of the double indicator method for measurement of extravascular lung water depends on the type of acute lung injury.

OBJECTIVE: The double indicator method is sensitive to alterations in the distribution of pulmonary blood flow. This distribution is influenced by the type of lung injury. The aim of this study was to compare measurements of lung water by the double indicator method with measurements obtained by gravimetry in a direct lung injury model induced by tracheal instillation of hydrochloric acid and in an indirect lung injury model induced by the intravenous injection of oleic acid. DESIGN: Prospective, randomized laboratory study. SETTING: Animal research laboratory. SUBJECTS: Forty-two female pigs (28+/-3 kg). INTERVENTIONS: Pigs were anesthetized and ventilated and were allocated into three groups: control (n = 6), hydrochloric acid (4 mL/kg intratracheally, n = 24), or oleic acid (0.1 mL/kg intravenously, n = 12). MEASUREMENTS AND MAIN RESULTS: Hydrochloric acid instillation or oleic acid injection resulted in a similar hypoxemia and induced a two- to three-fold increase in extravascular lung water (EVLW) by gravimetry (EVLWG) at 3 hrs compared with controls. In the oleic acid group, there was a significant correlation between EVLWG and EVLW by double indicator method (EVLWDI; r =.88, p <.0001). The bias for EVLWDI - EVLWG measurements was -5.2 mL/kg (95% confidence interval, -5.7 to -4.7 mL/kg) with 95% limits of agreement of -7 to -3.4 mL/kg. In the hydrochloric acid group, there was no significant correlation between EVLWDI and EVLWG values, and the double indicator method failed to detect pulmonary edema in 65% of the animals (EVLWDI <8 mL/kg). The bias was -7.9 mL/kg (95% confidence interval, -9.3 to -6.5 mL/kg) with 95% limits of agreement of -14.4 to -1.4 mL/kg. CONCLUSIONS: The double indicator method is useful for evaluation of pulmonary edema in indirect lung injury, as induced by oleic acid, but produces misleading values in direct lung injury, as produced by hydrochloric instillation.

Analysis of Variance↗
PubMed1970

Phosphatidic acid and phosphatidylinositol metabolism in Schizosaccharomyces pombe.

The phospholipid composition of Schizosaccharomyces pombe was not markedly affected by changes in the phosphate concentration of the medium or phase of growth. The major fatty acids in the total lipid extract and purified phosphatidylinositol were palmitic acid and oleic acid. Phosphatidic acid was synthesized by acylation of l-3-glycerophosphate in Schiz. pombe and phosphatidate phosphohydrolase was present. Phosphatidylinositol synthesis from inositol occurred in the absence of CDP-diglyceride. Even with dialysed cell-free preparations, the inositol lipid was synthesized by an apparently energy-independent route, at rates greater than would be required during cell growth. Phosphatidylinositol appeared to be broken down by a phospholipase D. All the enzymes examined were particulate; similar activities were found in Saccharomyces cerevisiae.

Cell-Free System↗
PubMed2001

Influence of fatty alcohol and other fatty acid derivatives on fatty acid uptake into rat intestinal epithelial cells.

We investigated the influence of various substrates on the uptake of long-chain fatty acid into IEC-6, rat intestinal epithelial cell line. The uptake of [3H]oleic acid into IEC-6 cells was a saturable function of the oleic acid concentration. Long-chain fatty acids significantly inhibited the oleic acid uptake into IEC-6 cells and shorter-chain fatty acids had little or no effect. Various fatty acid esters suppressed the oleic acid uptake into IEC-6. Fatty alcohols also inhibited oleic acid uptake into IEC-6 and the length of the carbon chain played an important role. These results suggest that long-chain fatty acid uptake was inhibited by the substrates which had a structure similar to long-chain fatty acids, especially those with a long carbon chain. At least two molecules, fatty acid translocase and fatty acid transport protein type 4, which are considered to be involved in the long-chain fatty acid transport into the cell, were expressed on IEC-6 cells, supporting the existence of the carrier-mediated system of long-chain fatty acid transport on IEC-6 cells.

Animals↗
PubMedDate not supplied

The hypotensive drug 2-hydroxyoleic acid modifies the structural properties of model membranes.

We studied the interactions of the hypotensive drug, 2-hydroxyoleic acid (2OHOA), with model membranes using the techniques of DSC, 31P NMR and X-ray diffraction. We demonstrate that 2OHOA alters the thermotropic behaviour of 1,2-dielaidoyl-sn-glycero-3-phosphoethanolamine (DEPE), thereby promoting the formation of hexagonal phases (H(II)), despite stabilizing the lamellar phase (Lalpha). The lattice parameters of lamellar and non-lamellar structures were not altered by the presence of 2OHOA. The molecular bases underlying the alterations in membrane structure provoked by 2OHOA were analysed by comparing the effects produced by 2OHOA with the closely related fatty acids (FAs), oleic acid (OA) and elaidic acid (EA). The capacity of C-18 FAs to induce H(II)-phase formation followed the order OA > 2OHOA > EA. Furthermore, while 2OHOA stabilized the Lalpha phase, OA destabilized it. The net negative charge of 2OHOA at physiological pH (approximately 7.4) influenced its effect on membrane structure. By analysing the molecular architecture of 2OHOA in DEPE monolayers, interactions between the carboxylate groups of 2OHOA and the amine groups of DEPE were observed, as well as between the 2-hydroxyl group of the FA and the carbonyl oxygen of the phospholipid acyl chain. These structural characteristics provoked an increase in the P-to-N and P-to-P distances of neighbouring phospholipid headgroups in the presence of 2OHOA, with respect to those observed with OA and EA. The higher headgroup area at the lipid-water interface in presence of 2OHOA could account for the differential effect of this drug on the phase behaviour of DEPE membranes.

Calorimetry, Differential Scanning↗
PubMed2006

Mediterranean diet, olive oil and cancer.

Olive oil is an integral ingredient of the "Mediterranean diet" and accumulating evidence suggests that it may have a potential role in lowering the risk of several types of cancers. The mechanisms by which the cancer-preventing effects of olive oil can be performed, however, are not known. We recently hypothesized that a novel molecular explanation concerning the anti-cancer actions of olive oil may relate to the ability of its monounsaturated fatty acid (MUFA) oleic acid (OA; 18:1n-9) to specifically regulate cancer-related oncogenes. Supporting our hypothesis, exogenous supplementation of cultured breast cancer cells with physiological concentrations of OA was found to suppress the overexpression of HER2 (Her-2/neu, erbB-2), a well-characterized oncogene playing a key role in the etiology, progression and response to chemotherapy and endocrine therapy in approximately 20% of breast carcinomas. OA treatment was also found to synergistically enhance the efficacy of trastuzumab, a humanized monoclonal antibody binding with high affinity to the ectodomain (ECD) of the Her2-coded p185(HER2) oncoprotein. Moreover, OA exposure significantly diminished the proteolytic cleavage of the ECD of HER2 and, consequently, its activation status, a crucial molecular event that determines both the aggressive behavior and the response to trastuzumab of Her2-overexpressing breast carcinomas. Our most recent findings further reveal that OA exposure may suppresses HER2 at the transcriptional level by up-regulating the expression of the Ets protein PEA3 -a DNA-binding protein that specifically blocks HER2 promoter activity- in breast, ovarian and stomach cancer cell lines. This anti-HER2 property of OA offers a previously unrecognized molecular mechanism by which olive oil may regulate the malignant behavior of cancer cells. From a clinical perspective, it could provide an effective means of influencing the outcome of Her-2/neu-overexpressing human carcinomas with poor prognosis. Indeed, OA-induced transcriptional repression of HER2 oncogene may represent a novel genomic explanation linking "Mediterranean diet", olive oil and cancer as it seems to equally operate in various types of Her-2/neu-related carcinomas.

Adult↗
PubMed1988

Milk fat globules: fatty acid composition, size and in vivo regulation of fat liquidity.

Populations of large and small milk fat globules were isolated and analyzed to determine differences in fatty acid composition. Globule samples were obtained by centrifugation from milks of a herd and of individual animals produced under both pasture and barn feeding. Triacylglycerols of total globule lipids were prepared by thin layer chromatography and analyzed for fatty acid composition by gas chromatography. Using content of the acids in large globules as 100%, small globules contained fewer short-chain acids, -5.9%, less stearic acid, -22.7%, and more oleic acids, +4.6%, mean values for five trials. These differences are consistent with alternative use of short-chain acids or oleic acid converted from stearic acid to maintain liquidity at body temperature of milk fat globules and their precursors, intracellular lipid droplets. Stearyl-CoA desaturase (EC 1.14.99.5), which maintains fluidity of cellular endoplasmic reticulum membrane, is suggested to play a key role in regulating globule fat liquidity. Possible origins of differences between individual globules in fatty acid composition of their triacylglycerols are discussed.

Animals↗
PubMed1986

Effect of nutritional status on the fatty acid composition of rat liver and cultured hepatocytes.

The lipid concentration and fatty acid composition of the whole liver and of cultured hepatocytes isolated from the livers of rats fed ad libitum (fed), fasted for 24 hr (fasted), or fasted for 48 hr and then refed a fat-free, high carbohydrate diet for 48 hr (refed) was studied. Hepatocytes were maintained as monolayer cultures in serum-free, lipid-free media and their fatty acid composition was analyzed at 3, 24, 48, 72 and 96 hr. The livers of fed animals, as well as their hepatocytes, contained less total lipid than those from animals on either of the other dietary regimes. Livers of fasted animals had three times the amount of lipid found in the livers of fed animals, and the livers of refed animals contained five times the amount of lipid as the livers of fed animals (all based on mg lipid/g wet weight of liver). The fatty acid composition of hepatocytes after 3 hr of culturing was very similar to that of fresh liver when compared in each of the dietary regimes. However, while the fatty acid compositions of livers and hepatocytes from fed and fasted animals were similar, the pattern in liver of refed animals was quite distinct from that of the fed animals. In the fed and fasted animals palmitic acid (16:0), stearic acid (18:0), oleic acid (18:1[n-9]), linoleic acid (18:2[n-6]) and arachidonic acid (20:4[n-6]) were the major fatty acids of the liver; in refed animals 16:0, palmitoleic acid (16:1[n-7]), 18:0, 18:1(n-9) and cis-vaccenic acid (the n-7 isomer of oleic acid) were the major fatty acids.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1992

Preparation and properties of gem-dichlorocyclopropane derivatives of long-chain fatty esters.

Methyl oleate (18:1) and linoleate (18:2) were readily transformed to the corresponding gem-dichlorocyclopropane derivatives in high yield, using triethylbenzylammonium chloride as the phase-transfer catalyst in the presence of aqueous NaOH and CHCl3. Reaction of dichlorocarbene with methyl 12-hydroxystearate furnished methyl 12-chlorostearate (49%) and 12-O-formylstearate (19%). The hydroxy group in methyl ricinoleate was protected (O-tetrahydropyran-2'-yl) prior to dichlorocyclopropanation of the ethylenic bond. Removal of the protecting group allowed the hydroxy group to be converted to a chloride, O-acetyl, azido or O-formyl function. Treatment of methyl ricinoleate with thionyl chloride, followed by the reaction with dichlorocarbene gave the corresponding 12-chloro-dichlorocyclopropane derivative. The dichlorocyclopropane derivative of oleic acid was transformed to a C19 allenic fatty acid when treated with t-butyl lithium. However, the remaining dichlorocyclopropane derivatives containing an additional functional group in the alkyl chain, failed to yield the corresponding allenic derivatives. All derivatives were characterized by a combination of spectroscopic and chromatographic techniques, including infrared, 1H nuclear magnetic resonance (NMR), and 13C NMR spectroscopy.

Catalysis↗
PubMed1979

Triaglycerol metabolism in Saccharomyces cerevisiae. Relation to phospholipid synthesis.

The acylglycerol content of Saccharomyces cerevisiae has been examined during cellular growth. The cells maintained a constant amount of phospholipid and diacylglycerol throughout growth. Triacylglycerol content fell in the early exponential phase of growth and then increased sharply upon entry of the culture into the stationary growth phase. Pulse-chase experiments with [1-14C]oleic acid and [2-3H]- and [1-14C]glycerol indicated that the triacylglycerol molecule was utilized for phospholipid synthesis in early exponential phase probably through a diacylglycerol intermediate. A substantial turnover of phospholipid during growth was also apparent. No role for the triacylglycerol could be found in regulating the fatty acid species of the phospholipid nor in the storage of fatty acid for energy metabolism.

Diglycerides↗
PubMed2004

Calmodulin antagonist W-7 inhibits de novo synthesis of cholesterol and suppresses secretion of de novo synthesized and preformed lipids from cultured hepatocytes.

The effects of a calmodulin antagonist W-7 were studied on the synthesis and secretion of lipids in primary rat hepatocytes and McArdle-RH7777 cells. In time course experiments, W-7 (20 microM) inhibited secretion of newly synthesized triacyl[(3)H]glycerol by 35%. When the cells were pre-treated overnight with W-7 (20 microM), followed by incubation with [(3)H]oleate, a significant decrease in the secretion of triacylglycerol (TG) and cholesteryl ester (CE) was observed. De novo synthesis of cholesterol from acetate or mevalonolactone was inhibited by W-7, but not glycerolipid synthesis from glycerol and oleic acid precursors. Concentration-response curves for the effects of overnight pre-incubation with W-7 followed labeling with [(3)H]glycerol and [(14)C]mevalonolactone revealed that: (1). the inhibitory effect of W-7 was concentration-dependent and appeared even at the lowest concentration examined (1 microM). W-7 at a concentration of 20 microM suppressed secretion of TG by 60% (P<or=0.002), phosphatidylcholine (PC) by 31% (P<or=0.05), CE by 59% (P<or=0.002) and cholesterol by 64% (P<or=0.002). (2). The incorporation of [(14)C]mevalonolactone into cellular cholesterol and CE was decreased significantly, while W-7 did not have any significant effect upon incorporation of [(3)H]glycerol into glycerolipids, except at the highest concentration examined (50 microM), where synthesis of both TG and PC was significantly suppressed. (3). While the percentage of secreted de novo synthesized glycerolipids and CE decreased proportionally with increasing concentration of W-7, the percentage of secreted newly made cholesterol remained unaffected at any concentration of W-7. In the absence of W-7, about 19% of newly formed cholesterol became esterified into CE, whereas W-7 increased cholesterol esterification in a concentration-dependent manner. (4) W-7 (20 microM) also suppressed the secretion of preformed cholesterol by 24% and CE by 55% but did not affect the recruitment of preformed cholesterol for esterification. About 6.5% of pre-labeled cholesterol and 20% of CE were directed to secretion, which was suppressed in the presence of W-7 by 17% (P<or=0.09) and 48% (P<or=0.001), respectively. These results suggest that, W-7 in the range of 1-20 microM inhibited de novo synthesis of cholesterol and the secretion of both de novo synthesized and preformed lipids.

Animals↗
PubMed2006

Influence of Cultivar and Environmental Conditions on the Triacylglycerol Profile of Hazelnut (Corylus avellana L.).

The oil of several hazelnut (Corylus avellana L.) samples was extracted and evaluated for their triacylglycerol (TAG) composition. Trials were conducted in two Portuguese localities (Vila Real and Felgueiras) during three consecutive years and involved a total of 19 cultivars. The samples were analyzed by reversed-phase high-performance liquid chromatography with evaporative light-scattering detection. Sample preparation was fast and simple, consisting only of the dissolution of the oil in acetone, homogenization, and filtration, allowing this technique to be suitable for routine analyses. All samples presented a similar qualitative profile composed of eleven compounds: LLL, OLL, PLL, OOL, POL, PPL, OOO, POO, PPO, SOO and PSO (P, palmitoyl; S, stearoyl; O, oleoyl; and L, linoleoyl). The main components were OOO, LOO, and POO, reflecting the high content of oleic acid in hazelnut oils. A total of 79 different samples were studied, and the obtained data were statistically analyzed. Significant differences were verified in canonical variate plots when cultivars were grouped by country of origin. In general, the American cultivars were richer in TAGs with saturated fatty acids moieties, and the group of French, German, and English cultivars was richer in TAGs containing linoleic acid moieties. Differences were also significant when cultivars were grouped by year of production, showing that besides genetic factors, the TAG composition can be influenced by environmental factors.

Chromatography, High Pressure Liquid↗
PubMed2004

An alternative pathway of oleate beta-oxidation in Escherichia coli involving the hydrolysis of a dead end intermediate by a thioesterase.

The degradation of 2-trans,5-cis-tetradecadienoyl-CoA, a metabolite of oleic acid, by the purified complex of fatty acid oxidation from Escherichia coli was studied to determine how much of the metabolite is converted to 3,5-cis-tetradecadienoyl-CoA and thereby diverted from the classical, isomerase-dependent pathway of oleate beta-oxidation. Approximately 10% of the 2,5-intermediate was converted to the 3,5-isomer. When the latter compound was allowed to accumulate, it strongly inhibited the flux through the main pathway. Since Delta(3,5),Delta(2,4)-dienoyl-CoA isomerase was not detected in E. coli cells grown on oleate, the 3,5-intermediate cannot be metabolized via the reductase-dependent pathway. However, it was hydrolyzed by a thioesterase, which was most active with 3,5-cis-tetradecadienoyl-CoA as substrate and which was induced by growth of E. coli on oleate. An analysis of fatty acids present in the medium after growth of E. coli on oleate revealed the presence of 3,5-tetradecadienoate, which was not detected after cells were grown on palmitate or glucose. Altogether, these data prompt the conclusion that oleate is mostly degraded via the classical, isomerase-dependent pathway in E. coli but that a small amount of 2-trans,5-cis-tetradecadienoyl-CoA is diverted from the pathway via conversion to 3,5-cis-tetradecadienoyl-CoA by Delta(3),Delta(2)-enoyl-CoA isomerase. The 3,5-intermediate, which would strongly inhibit beta-oxidation if allowed to accumulate, is hydrolyzed, and the resultant 3,5-tetradecadienoate is excreted into the growth medium. This study provides evidence for the novel function of a thioesterase in beta-oxidation.

Carbon-Carbon Double Bond Isomerases↗
PubMed1988

Cardiovascular effects of leukotoxin (9, 10-epoxy-12-octadecenoate) and free fatty acids in dogs.

Leukotoxin (9,10-epoxy-12-octadecenoate) biosynthesised from linoleate by neutrophils is highly toxic to cellular function. Its cardiovascular effects were studied in dogs together with the effects of various fatty acids. Aortic flow, left ventricular peak dP.dt-1, and aortic pressure were measured in 60 anaesthetised dogs, which were divided into 10 groups of six animals each--namely, control group (10 ml of physiological saline), three leukotoxin groups (5, 10, and 50 mg.kg-1), two linoleic acid groups (10 and 50 mg.kg-1), two oleic acid groups (10 and 50 mg.kg-1), and two stearic acid groups (10 and 50 mg.kg-1). Leukotoxin injected intravenously depressed cardiac function in a dose dependent manner. Administration of leukotoxin 5 mg.kg-1 showed no significant cardiotoxic effect. However, 10 mg.kg-1 of leukotoxin significantly decreased aortic flow from 0.74(0.04) to 0.40(0.07) litre.min-1 (mean(SEM], left ventricular peak dP.dt-1 from 2040(205) to 1140(217) mmHg.s-1, and aortic pressure from 106(7.1)/67(6.3) to 75(9.2)/48(6.5) mmHg 5 min after injection. Dogs given leukotoxin 50 mg.kg-1 showed more pronounced cardiodepressive effects; aortic flow was decreased to 0.19(0.06), left ventricular dP.dt-1 to 560(134), and aortic pressure to 72(15.1)/41(10.6) 5 min after injection. All dogs in this group were dead within 45 min. Administration of 10 mg.kg-1 of linoleic acid, oleic acid, or stearic acid caused no significant haemodynamic changes. Administration of linoleic acid 50 mg.kg-1 had cardiotoxic effects, but the effect was less than that of leukotoxin. Since leukotoxin appears to be a potent cardiodepressive agent it may be an important factor in the development of heart failure observed in patients with severe burns.

Animals↗
PubMed1998

Synergistic hemodynamic effects of low-dose endotoxin and acute lung injury.

We evaluated the effects of low-dose endotoxin (15 microg/kg) on the pulmonary and systemic responses to oleic acid (OA)-induced acute lung injury in dogs. Animals given endotoxin alone (n = 5) showed a modest decrease in arterial blood pressure, but no effects on pulmonary hemodynamics, blood gases, cardiac output, or lung water accumulation. Animals (n = 6) given only OA (0.08 ml/kg) showed the expected development of mild-moderate pulmonary hypertension, a comparable reduction in arterial blood pressure, hypoxemia, increased lung water concentration, and an altered intrapulmonary perfusion pattern, as assessed by positron emission tomography. Animals (n = 7) given the same dose of endotoxin, followed 30 min later by the same dose of OA, developed a similar increase in lung water concentration as the group given OA alone, but failed to develop pulmonary hypertension or to redistribute pulmonary blood flow away from the edematous lung regions. In addition, arterial blood pressure fell significantly more than in the other groups. These responses were associated with a 30-fold increase in circulating prostacyclin (assayed as 6-keto prostaglandin F1 alpha [PGF1alpha]). The effects on systemic blood pressure, intrapulmonary blood flow redistribution, and eicosanoid production were eliminated by pretreating (n = 5) animals with meclofenamate (2 mg/kg). The results are consistent with a "priming" effect of low-dose endotoxin on the pulmonary endothelium, with exaggerated prostacyclin production in response to a subsequent lung injury. This interaction leads to altered intrapulmonary hemodynamics that exacerbate the development of hypoxemia, and to significant decreases in systemic blood pressure. To the extent that the lung is the most likely source of the increased prostacyclin production, the synergistic effects of low-dose endotoxin and lung injury may produce a kind of "lung shock."

6-Ketoprostaglandin F1 alpha↗
PubMed2000

[Studies on chemical constituents of fat oil of Polygala tenuifolia].

OBJECTIVE: To study the chemical constituents of fat oil from root of Polygala tenuifolia Willd. METHOD: The components were separated and identified by gas chromatograpy-mass spectrometry and elucidated on the standard mass spectral data and the percentages were determined by gas chromatographic area normalization method. RESULT: Eighteen constituents were separated and sixteen of them were identified. CONCLUSION: The major components of the fat oil were established first time as oleic acid, linoleic acid, palmitic acid, eicosenoic acid and stearic acid, which make up 87.0%, 7.31%, 3.27%, 1.07%, 0.91% of fat oil respectively.

Fatty Acids↗
PubMed2000

[Studies on the supercritical CO2 fluid extraction and separation of psoralen, isopsoralen and fatty oils from Psoralea corylifolia].

Opimum extraction conditions were studied by supercritical carbon dioxide fluid extraction technology and orthogonal tests. Crystal of psoralen can be achieved directly from the extractives. Magnified experiments were carried out. The chemical constituents of fatty oils were analyzed by GC-MS. The result shows that the optimum conditions are: extraction pressure 27 MPa, extraction temperature 70 degrees C; seperation pressure 9 MPa, seperation temperature 60 degrees C. Six components such as oleic acid, linoleic acid etc. were identified in the fatty oils.

Carbon Dioxide↗

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