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PubMed1998

Effect of modified dairy fat on postprandial and fasting plasma lipids and lipoproteins in healthy young men.

Fatty acid profile of milk fat can be modified by cow feeding strategies. Our aim was postprandially and after 4 wk to compare the effect of a modified milk fat (M diet) [with 16% of the cholesterolemic saturated fatty acid (C12-16) replaced by mainly oleic and stearic acids] with the effect of D diet, including a conventional Danish milk fat on plasma lipids and lipoproteins. A side effect of the cow feeding regime was a 5% (w/w) increase in trans fatty acid in M diet. Eighteen subjects were fed for two periods of 4 wk strictly controlled isoenergetic test diets with 40% of energy from total fat and the same content of dietary cholesterol in a randomized study with cross-over design. Contrary to expectations, fasting low density lipoprotein (LDL) cholesterol concentration did not differ after the experimental periods. However, M diet resulted in a higher fasting total triacylglycerol concentration compared to D diet (P = 0.009). Postprandial samples were taken at two different occasions (i) at day 21, after breakfast and lunch and (ii) on the last day of the study 2, 4, 6, and 8 h after a fat load. Postprandial plasma triacylglycerol and chylomicron triacylglycerol showed higher peak values after D diet than M diet (interaction effect, diet x times P < 0.05). In conclusion, M diet did not lower LDL cholesterol compared to D diet. Thus any cholesterol-lowering effect of oleic and stearic acids may have been obscured by the high content of cholesterol-raising saturated fatty acids in milk fat. A higher content of the trans fatty acids in M diet might have counteracted the cholesterol neutral/decreasing effect and increased plasma triacylglycerol.

Adult↗
PubMed1994

The selective use of stearoyl-polyunsaturated molecular species of phosphatidylcholine and phosphatidylethanolamine for the synthesis of phosphatidylserine.

In rat liver microsomes, [3H]serine was incorporated primarily into the two most abundant molecular species of microsomal phosphatidylserine (PS), 18:0/20:4 and 18:0/22:6, by Ca(2+)-dependent base exchange. The pattern of PS molecular species synthesized was very similar to the species composition of PS and markedly different from the species composition of either microsomal precursor, phosphatidylcholine (PC) or phosphatidylethanolamine (PE). The data indicated that the enrichment of rat liver PS in mainly three fatty acids--stearic, arachidonic, and docosahexaenoic acids, occurred by (1) the preference by PS synthases for the stearoyl-polyunsaturated molecular species, 18:0/20:4 and 18:0/22:6, of PC and PE and (2) a discrimination against the use of the palmitoyl-polyunsaturated species, 16:0/20:4 and 16:0/22:6, and the stearoyl-diunsaturated species, 18:0/18:2. The preferential use of the two species of PC and PE, based on their acyl chain content and not on their relative abundance, demonstrates that an individual molecular species can be selected out of the total pool for a defined function.

Animals↗
PubMed1991

Binding of spin-labeled fatty acids and lysophospholipids to hydrophobic region of calmodulin.

In the presence of bovine brain calmodulin activated by calcium, the sharp triplet electron spin resonance (ESR) lines of free doxyl stearic acids decreased, and the broad resonance lines increased concomitantly, suggesting that the doxyl stearic acids bound to calmodulin calcium-dependently. The bound molecules were displaced by a calmodulin inhibitor, W-7, whereas their nitroxide radicals were hardly reduced by ascorbic acid, suggesting that the spin-labeled fatty acids bind to hydrophobic regions of calmodulin, and consequently inhibit calmodulin-dependent phosphodiesterase activity. These binding characteristics to calmodulin were different from those to bovine serum albumin. Moreover, the ESR spectra of two spin-labeled derivatives of lysophospholipid having a spin-labeled acyl group or a spin-labeled polar head group showed that it is the acyl chain of lysophospholipid that interacts with the hydrophobic region of calmodulin. The interactions of fatty acids and lysophospholipids with calmodulin seem to be quite different from those of acidic phospholipids, described previously [Suzuki, T., Katoh, H., & Uchida, M.K. (1986) Biochim. Biophys. Acta, 873, 379-386]. Thus, from the results of ESR study, we can obtain information on the function of fatty acids and lysophospholipids on calmodulin. Instead of enzyme assay, ESR spectroscopy is a useful means to examine lipid-protein interaction.

Animals↗
PubMed1998

A drug-lipid interaction model: atropine induces interdigitated bilayer structure.

X-ray diffraction and fluorescence methods have been carried out to examine the effects of a drug, atropine, on the structure of model membranes: dipalmitoylphosphatidylglycerol(DPPG) multilamella vesicles(MLVs). A structural analysis by small angle x-ray diffraction shows that, with incorporation of atropine, the lamella repeating period of DPPG MLV is decreased from 5.89 nm to 4.52 nm. Using fluorescence probe 1,6-diphenyl-1,3,5-hexatriene(DPH) we find that the fluorescence intensity of DPH reduces largely at a narrow scope of atropine concentration. The experiments of fluorescence polarization of n-(9-anthroyloxyl)-stearic acid (nAS) and 16-(9-anthroyloxyl)-palmiticacid (16AP) discover that the normal polarization gradient almost disappears in DPPG/atropine system. By colligating the above results, we can draw a conclusion that atropine induces the transition from non-interdigitated to interdigitated stricture of DPPG vesicles in gel phase, which provides a sound model of drug-lipid interaction.

Atropine↗
PubMed1988

New trends in ganglioside chemistry.

New methods have been developed for the preparation of highly purified gangliosides, homogeneous in the saccharide, long chain base, and fatty acid moieties and gangliosides carrying different kinds of labelled probes. Gangliosides, homogeneous in the oligosaccharide portion, were prepared by preparative normal phase HPLC on a Lichrosorb-NH-2 column, using a gradient of acetonitrile-phosphate buffer, pH 5.6, as solvent system. Each class of ganglioside (from monosialo- to tetrasialogangliosides) was then submitted to reversed phase HPLC on a preparative RP-8 column, using acetonitrile-5 mM phosphate buffer, pH 7, as solvent system, to obtain gangliosides homogeneous in the long chain base moiety. Gangliosides containing C18 and C20 sphinganine were prepared by catalytic hydrogenation of the corresponding unsaturated gangliosides. GM1 with homogeneous acyl chain was prepared by alkaline hydrolysis in the presence of tetramethylammonium hydroxide (which forms a GM1 deacetylated at the level of sialic acid, and a GM1 deacetylated at the level of sialic acid and deacylated at the level ceramide), followed by re-N-acylation, carried out in the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, or of mixed anhydride of ethylchloroformate and 14C-stearic acid, and re-N-acetylation performed with acetic anhydride or labelled acetic anhydride. The GM1 derivative, de-acetylated at the level of sialic acid, also produced by alkaline treatment of GM1, was submitted to re-N-acetylation with 14C-acetic anhydride to produce specifically 14C-labelled GM1. Re-N-acylation was carried out a) in the presence of dimethylaminopropyl, ethylcarbodiimide and natural fatty acids, b) with mixed anhydride of ethylchloroformate and 14C-stearic acid. After re-N-acylations, re-N-acetylation was performed with acetic anhydride or labelled acetic anhydride. Gangliosides tritium labelled in the oligosaccharide moiety were prepared by the galactose oxidase/3H NaBH4 method, and gangliosides tritium labelled at carbon-3 of unsaturated long chain bases by the dicyano-dichlorobenzoquinone (DDQ)/3H NaBH4 method.

Animals↗
PubMed1978

The role of holotrichs in the metabolism of dietary linoleic acid in the rumen.

The uptake and metabolism of linoleic acid by rumen holotrichs (mainly Isotricha prostoma and I. intestinalis) has been examined in in vitro infusion experiments. Maximum absorption and metabolism of [1-14C]linoleate by 2 . 10(6) Isotricha suspended in 100 ml buffer was obtained using an infusion rate of 1.6 mg linoleate/h. After 90 min, 84% of the added substrate was recovered within the cells, mainly as free fatty acid or phospholipid. There was a rapid incorporation of radioactivity into phospholipid, mainly phosphatidylcholine, at the commencement of linoleate infusion but no further incorporation after about 40 min. The presence of bacteria during incubations, in approximately the same Isotricha/bacteria ratio as found in the rumen, reduced the uptake of linoleate and the accumulation of free fatty acid by holotrichs but the incorporation into phospholipid remained similar to that obtained in the absence of bacteria. Very little biohydrogenation of linoleic acid occurred in incubations with holotrichs alone. Bacterial suspensions converted linoleic acid to mainly trans monoene and a small amount of stearic acid, but in incubations containing both bacteria and holotrichs, both stearic acid and trans monoene were major products. Using the latter mixed culture, about 20% of the added [1-14C]linoleic acid was present in holotrich phospholipid of which 62% remained as octadecadienoic acid. The Isotricha population was 3 . 10(3)--2 . 10(4)/ml rumen fluid and it contributed about 23% of the linoleic acid in the rumen of a cow on a hay diet.

Animals↗
PubMed1981

Thermotropic behavior of bilayers formed from mixed-chain phosphatidylcholines.

The six possible phosphatidylcholines containing two different chains derived from myristic, palmitic, and stearic acids were synthesized, and their bilayer structures were investigated by high-sensitivity differential scanning microcalorimetry. Chain migration during the syntheses caused each of the lipids to contain about 10% of the corresponding positional isomer. A phase diagram for each pair of isomers was constructed to permit estimation of the transition properties of the pure mixed-length phospholipids. The phase transitions of these lipids were found to be similar to those of saturated like-chain phosphatidylcholines. The main transition temperatures and enthalpies fall within the range of those for the like-chain lipids. In each pair of positional isomers, the isomer having the longer chain at position 2 on the glycerol backbone has the higher transition temperature and enthalpy. The transition curves of the pure mixed-chain lipids with myristic acid at position 2 and either palmitic or stearic acid at position 1 exhibited two partially separated peaks for the main transition. No satisfactory interpretation of this unexpected phenomenon has been developed.

Calorimetry, Differential Scanning↗
PubMed1975

Triglyceride lipase activity in bovine aorta.

The cell-free supernatant from homogenized bovine aorta hydrolyzed triglycerides, beta-naphthylesters of lauric and stearic acid and Tween 20, 40 and 60. The rate of hydrolysis decreases as the acyl chain length of the substrates increases. The activity against triglycerides of short-chain fatty acids and monoacylesters could be partially separated from that of glycerol-trioleate lipase by ammonium sulfate fractionation. The activity of glycerol-trioleate lipase remained unaffected by heating for 5 min at 60 degrees C or by addition of bile acids, whereas the activity causing hydrolysis of triglycerides with short-chain fatty acids and monoacylesters decreases up to 60% by analogous treatment.

Animals↗
PubMed1991

Effect of level of endophyte infection, nitrogen fertilization rate, grazing period, and paddock exchange on some chemical properties of four bovine tissues.

Three grazing experiments were conducted to determine the effect of level of endophyte infection, rate of N fertilization of tall fescue grass, grazing period, and paddock exchange on selected chemical properties of four bovine carcass tissues. Samples of semitendinosus and longissimus muscle and of subcutaneous and perinephric adipose tissue were excised from the left side of each carcass. In Exp. 1, percentage of stearic acid was higher (P less than .05) and percentages of palmitoleic and oleic acid were lower (P less than .05) in all tissues from steers grazed on LELN Au-Triumph fescue than in tissues from steers grazed on LELN KY-31 fescue. Grazing periods of 175 or 245 d or paddock exchange (Exp. 2) had no significant effect on proximate composition of semitendinosus and longissimus muscles; however, moisture content was higher (P less than .05) in the semitendinosus muscle from steers grazed on 100% (100E) endophyte-infected KY-31 fescue. Forage treatment, grazing period, and paddock exchange (Exp. 2 and 3) had no significant effect on percentage of saturated fatty acids in the subcutaneous, semitendinosus, and longissimus tissue samples. In Exp. 2 and 3, percentages of saturated fatty acids were higher (P less than .05) in subcutaneous and perinephric adipose tissue samples from steers grazed on 100E than in samples from steers grazed on zero endophyte (OE) fescue.(ABSTRACT TRUNCATED AT 250 WORDS)

Adipose Tissue↗
PubMed1990

[Chemical constituents in the stem of Premna crassa Hand. -Mazz].

In this paper four compounds isolated from the stem of Premna crassa are described. Their structures have been identified as friedelin, epifriedelanol, stearic acid and beta-sitosterol respectively by comparing their chemical and spectroscopic data with those of the authentic samples.

Drugs, Chinese Herbal↗
PubMed1989

[Percent composition of fatty acids in Tigriopus fulvus from rocky pools on the Ligurian coast (Copepoda harpacticoida)].

The study concerns the Tigriopus fulvus specimens fatty acid composition, sampled in Ligurian coast rockpools from September 1980 to June 1981. By the study of frequency distribution it was observed that the fatty acid found in greater quantity was the palmitic one, followed by the palmitoleic, the oleic and stearic acids. Short and long chain fatty acids are less frequent. Investigation about each fatty acid concentration shows that the seasonal trends between males and females are different and the trend of some fatty acids (e.g. linolenic and stearic acid) is characteristic.

Animals↗
PubMed2004

Effect of lubricant type and concentration on the punch tip adherence of model ibuprofen formulations.

A model formulation, comprising ibuprofen and direct compression lactose (Tablettose 80) was used to assess the influence of two lubricants, magnesium stearate and stearic acid, on punch tip adherence. Lubricant concentrations were varied from 0.25% to 2% w/w. Formulations in the presence and absence of 0.5% w/w colloidal silica (Aerosil 200) were examined, to assess the influence of the glidant on the anti-adherent effects of the lubricants. Differential scanning calorimetry (DSC) was used to examine the effect of the lubricants on the melting temperature of ibuprofen. Tablets were compacted using a single punch tablet press at 10 kN using hard chrome-plated punches or at 40 kN using uncoated steel punches, tooling was 12.5-mm diameter in each case. The upper punch faces were characterized by obtaining Taylor Hobson Talysurf surface profiles. Following compaction, ibuprofen attached to the face was quantified by spectroscopy. At low concentrations of each lubricant, the levels of sticking observed were similar. Whilst sticking increased at magnesium stearate concentrations above 1%, sticking with stearic acid remained relatively constant at all concentrations. DSC revealed that the melting temperature of ibuprofen was lowered by the formation of eutectic mixtures with both lubricants. However, the onset temperature of melting and melting point were lowered to a greater extent with magnesium stearate compared with stearic acid. When using uncoated tooling at 40 kN, the deleterious effects of magnesium stearate on the tensile strength of the tablets also contributed to sticking. When using chrome-plated punches at 10 kN, the tensile strength reduction by the presence of magnesium stearate was less pronounced, as was the level of sticking.

Adhesiveness↗
PubMedDate not supplied

Effects of ethanol on the incorporation of free fatty acids into cerebral membrane phospholipids.

Chronic ethanol exposure is known to affect deacylation-reacylation of membrane phospholipids (PL). In our earlier studies we have demonstrated that chronic exposure to ethanol (EtOH) leads to a progressive increase in membrane phospholipase A2 (PLA2) activity. In the current study, we investigated the effects of chronic EtOH exposure on the incorporation of different free fatty acids (FFAs) into membrane PL. The results suggest that the incorporation of fatty acids into four major PL varied from 9.6 fmol/min/mg protein for docosahexaenoic acid (DHA) into phosphatidylinositol (PI) to 795.8 fmol/min/mg protein for linoleic acid (LA) into phosphatidylcholine (PC). These results also suggest a preferential incorporation of DHA into PC; arachidonic acid (AA) into PI; oleic acid into phosphatidylethanolamine (PE) and PC;LA into PC and stearic acid into PE. Chronic EtOH exposure affected the incorporation of unsaturated fatty acid into PI, phosphatidylserine (PS) and PC. However, EtOH did not affect significantly the incorporation of any of the fatty acids (FA) studied into PE. No significant differences were observed with the stearic acid. It is suggested that acyltransferases may play an important role in the membrane adaptation to the injurious effects of EtOH.

Animals↗
PubMed1999

Significance of fatty acids in pregnancy-induced immunosuppression.

Pregnancy can exert suppressive effects on chronic inflammatory conditions. We have previously demonstrated a depression in polymorphonuclear leukocyte (PMN) respiratory burst during pregnancy which could explain this amelioration. To elucidate the biochemical mechanism, we have examined PMN phospholipase A2 (PLA2) activity and its relationship to cellular and circulating fatty acids in pregnant women (30 to 34 weeks) and nonpregnant controls. PMN PLA2 activity was determined by arachidonic acid (AA) and leukotriene B4 (LTB4) release, respiratory burst activity was determined by lucigenin-enhanced chemiluminescence, and total serum and PMN fatty acid levels were determined by gas-liquid chromatography. AA release was significantly reduced for pregnancy PMNs in response to N-formyl-met-leu-phe (fMLP) under unprimed and tumor necrosis factor alpha (TNF-alpha)- or interleukin 8-primed conditions. Similarly, LTB4 liberation was significantly reduced in response to fMLP and phorbol myristate acetate in unprimed and TNF-alpha-primed pregnancy PMNs. All major fatty acid classes were altered in the pregnant state. Of these differences in PMNs, oleic acid and alpha-linolenic acid showed a significant increase (13 and 26%, respectively) and stearic acid and AA showed a significant decrease (8 and 30%, respectively). The stearic acid, oleic acid, and AA compositions of all cells analyzed correlated with their corresponding changes in serum fatty acid levels. Crossover serum incubations modified both fatty acid profiles and the PMN respiratory burst accordingly, while individual fatty acid incorporation studies highlighted the importance of polyunsaturated fatty acids for NADPH oxidase efficiency. These findings indicate that the attenuation of PMN function in pregnancy may originate from a reduction in the available pool of cellular fatty acids. Furthermore, this reduction arises as a direct result of a pregnancy-induced shift in circulating fatty acids from polyunsaturated to monounsaturated forms.

Adolescent↗
PubMed1984

Fatty acid-induced modifications of mouse mammary alveolar lesions in organ culture.

A newly developed adult RIII mouse mammary gland organ culture system was used to examine the effects of fatty acids and a prostaglandin synthase inhibitor on the survival and/or growth of lactogenic hormone-independent mammary alveolar lesions (MAL). The number of MAL per gland that persisted in the absence of lactogenic hormones was increased in cultures treated with arachidonic acid (24.0 +/- 3.4), and was decreased after treatment with stearic acid (4.0 +/- 3.4) or indomethacin (5.0 +/- 0.6). Arachidonic acid also induced higher incorporation of [3H]thymidine into the cellular DNA of MAL containing glands. A comparison of [3H]arachidonic acid uptake into intact (MAL containing) glands and parenchyma-free fat pads revealed a selectively higher incorporation of the labeled fatty acid in the intact glands. Arachidonic acid exposure produced higher cumulative amounts (4.02 ng) of prostaglandin E2 (PGE2) which was significantly inhibited (1.66 ng) by indomethacin (p less than 0.001). In contrast, exposure to stearic acid did not lower PGE2 levels below that of controls. A concomitant increase in MAL number and PGE2 production by arachidonic acid and a decrease in both caused by indomethacin suggest that arachidonic acid conversion to PGE2 may have a facilitative role in the survival of MAL.

Animals↗
PubMed2006

Thermodynamic modeling of activity coefficient and prediction of solubility: Part 2. Semipredictive or semiempirical models.

The solubility of stearic acid, ranitidine hydrochloride, and stavudine were predicted in selected organic solvents. The experimental solubility data of stearic acid and ranitidine hydrochloride were reported in previous work of the authors and stavudine's solubility was measured in this work. Equilibrium aqueous solubility of crystalline stauvudine was determined at controlled temperatures by stirring and filtration, with spectrophotometric quantification. The new model developed in Part 11 of this communication was modified as a semipredictive model with two adjustable parameters. Predicting the solubility data with the NRTL model using just one experimental point resulted in a big error while the modified new model and the UNIQUAC model showed much smaller errors. A new method was proposed in this work for predicting the solubility data of all polymorphs of a given compound using the experimental solubility data of one of the polymorphs of the same chemical compound. Although in general, the UNIQUAC model predictions were marginally superior, the new model is simpler and does not require the molecular parameters such as Van der Waals area and volume. The solubility prediction in a mixture of solvents using the NRTL and UNIQUAC models was also discussed.

2-Propanol↗
PubMed1992

Herman Award Lecture, 1992: lipid nutrition--a personal perspective.

In the 1950s excess dietary fat was thought to be a risk factor for development of atherosclerosis. Over the ensuing years we have examined and given advice concerning first, saturation and unsaturation, and later, specific fatty acids such as oleic and stearic acids. Current work is further refining the delineation of fatty acids that might be harmful. Eventually, we will probably again cite excess fat as the problem.

Awards and Prizes↗
PubMed1986

A 2H NMR study on alteration of the membrane organization of mouse B16 melanoma cells treated with 12-O-tetradecanoylphorbol-13-acetate.

In order to monitor the membrane fluidity of cells without perturbation by an introduced probe, we developed a method for large-scale preparation of 2H-labeled melanoma cells for a 2H NMR study by incubating melanoma cells with [18,18,18-2H3]stearic acid/phosphatidylcholine liposomes for 2 h at 37 degrees C. It turned out that this treatment did not significantly change the cell viability, lipid metabolism or membrane fluidity. The 2H from C-18 of stearic acid is dominantly located at the original position of the fatty acid in the 2H-labeled membrane vesicles, as studied by a tracer experiment with [1-14C]stearic acid. We found that three to four 2H-labeled species were present at 19 degrees C in 2H NMR spectra of the 2H-labeled membrane vesicles prepared from B16 melanoma cells. The extent of peak-splittings due to 2H-quadrupole interaction decreased as the temperature rose, and a definite point of phase transition was not observed. At elevated temperature, 2H-labeled lipids undergo fast exchange between the bilayer and an isotropic phase such as oil phase of triolein or inverted micelles in lipid polymorphs. We further analyzed the change of membrane organization in mouse B16 melanoma cells treated with 12-O-tetradecanoylphorbol-13-acetate (TPA), which strongly inhibited melanogenesis. The magnitude of the quadrupole splitting at 19 degrees C in membranes from TPA-treated cells was significantly less (40%) than in the untreated control. This is mainly explained by decreased molecular ordering (fluidity) due to the increased amount of unsaturated fatty acids in the membranes of TPA-treated cells.

Animals↗