Embryonic fatty acid composition as a function of yolk fatty acid composition in eggs of the lesser spotted dogfish (Scyliorhinus canicula L.)

Yolk and embryonic total lipids were extracted from spotted dogfish eggs at two developmental stages. Total lipids were fractionated into neutral lipids (NL) and polar lipids (PL), and the fatty acid composition of each group was determined. Yolk lipid composition was found to be quantitatively different (NL/PL≊1) from embryo lipid composition (NL/PL≊0.5), for both stages of development. However, individual fatty acid composition did not differ from younger to older eggs for either yolk or embryo. There were significant differences (p<0.05) in major fatty acid groups from yolk and embryonic PL for saturated fatty acids, monounsaturated fatty acids (MUFA) and n−3 polyunsaturated fatty acids (PUFA) for younger eggs, and for MUFA and n−3 PUFA for older eggs. For NL, only MUFA composition from the oldest eggs showed differences between yolk and embryo. Results are discussed in terms of embryonic needs for highly unsaturated fatty acid (HUFA) biosynthesis, as well as to provide some explanations for the unusually high levels of 20∶4n−6 in both yolk and embryonic neutral lipids and polar lipids.     

Fertility and testicular fatty acid composition in the chicken as influenced by vitamin E and ethoxyquin

The fatty acid composition of testicular lipids has been determined and related to fertility data from groups of dubbed White Leghorn cockerels after a 50-week feeding period on rations containing 10% safflower oil or coconut oil. Supplements of ethoxyquin ord-α-tocopherol acetate maintained fertility in birds raised on rations containing safflower oils. This response was associated with higher proportions of 22∶4 ω6 and lower proportions of 18∶2 ω6 in testicular lipids. Testes size was quite variable in the unsupplemented group with changes in fatty acid composition being more pronounced in the smaller testes. A multiple regression was calculated using data from those birds on the safflower oil ration. With a correlation ratio of 0.90 fertility was expressed as a function of testes size, semen concentration and the proportions of 18∶2 ω6, 20∶4 ω6 and 22∶4 ω6 in testicular lipids. Despite the low intake of linoleate significant levels of polyunsaturated fatty acids were maintained in testicular lipids of birds fed the coconut oil rations. The major changes in fatty acid composition of testicular lipids produced by this variable was a decrease in the proportion of 18∶2 ω6 and an increase in the proportion of 18∶1. Paper No. 3050, Oregon Agricultural Experiment Station.     

Fatty acid composition of phospholipids and neutral lipids during embryonic and early larval development in Atlantic herring (Clupea harengus,L.)

The fatty acid compositions of total polar and total neutral lipids of Atlantic herring eggs and larvae were determined immediately before fertilization, after fertilization and at various times during subsequent embryonic and early larval development. Within 3 hr after fertilization the percentage of total PUFA in neutral lipid decreased from 33% to 20%, with a reciprocal increase in monoenes. Thereafter the percentage of PUFA in the neutral lipids increased progressively, attaining the original level in ripe eggs by the time of yolk sac absorption. During the larval stages the percentage of PUFA continued to increase in the neutral lipid, reaching almost 44% of the total by day 32 after fertilization, although it was reduced to 32% by day 36. The percentage of monoenes in the neutral lipid displayed a progressive decrease during the whole period of development from 3 hr after fertilization. Throughout all the developmental periods the fatty acid composition of total polar lipids remained essentially constant. The polar lipids of the yolk sac displayed virtually the same fatty acid composition as the larval bodies, but the neutral lipids of the yolk sac were low in PUFA compared to the larval bodies. The results are discussed with reference to changes in lipid class composition during development. The conservation of high levels of PUFA in lipids during embryogenesis and early larval development reflects the importance of these fatty acids during development.     

Changes in liver lipid composition of male rats fed rapeseed oil diets

Studies are reported on the effect of feeding diets containing rapessed oils differing in their erucic acid content to male weanling rats for 16 weeks. Rapeseed oil high in erucic acid depressed growth. Total lipids, lipid phosphorous and cholesterol, in the livers were not significantly different between the experimental groups. The fatty acid composition of the total liver lipids, the neutral lipids, phosphatidylethanolamine and phosphatidylcholine are documented. Erucic and eicosenoic acids were found in all lipid classes at the same relative concentration; the amount being incorporated was proportional to that found in the dietary oil. The positional analysis of phosphatidylethanolamine and phosphatidylcholine are presented. Erucic acid was incorporated preferentially at position two of these phospholipids, whereas, twice the level of eicosenoic acid was found at position one, compared to that which occurred at the two position. This article represents part of an extensive experiment carried out by Agriculture Canada to investigate the nutritional value of rapeseed oils (see ref. 15). Contribution No. 497 from the Animal Research Institute.     

Egg yolk lipids and maternal diet in the nutrition of turkey embryo

Turkey hens were fed diets containing no added fat nor diets supplemented with soybean oil or neatsfoot oil. The composition of neutral and polar lipid fatty acids present in the unincubated turkey egg yolk was compared with that of those present in the yolk sac of the developing turkey embryo at different stages of development. Comparisons were made of the fatty acid fractions in the entire embryo homogenates, except liver and heart, which were analyzed separately. Changes in the relative amounts of the fatty acids are reported as affected by age of the embryo and by dietary lipids. The fatty acids from both the neutral and polar lipids which were utilized to the greatest extent for embryonic development were palmitoleic, oleic, linoleic, and linolenic, regardless of the dietary supplements. Arachidonic, tetracosenoic, and docosahexaenoic acids also were metabolized by the embryo. Saturated fatty acids, used by the embryo as development progressed, were palmitic, stearic, and arachidic acids. Analyses of the liver fatty acids showed that the C16∶0 C16∶1, C18∶0, C18∶1, and C20∶4 acids in the neutral and polar lipids decreased with embryonic development and varied with the type of diet. The heart contained low levels of myristic, palmitic, stearic, arachidic, and arachidonic acids in the neutral lipids and palmitoleic and oleic acids in the polar lipids.     

Lipids of cultured hepatoma cells: VIII. Utilization of D-[1-14C] glucose for lipid biosynthesis

Minimal deviation hepatoma 7288C cells (HTC) were incubated in serum-supplemented and serum-free Swim’s 77 medium in the presence of D-[1-¹⁴C] glucose for 1, 2, 4, 8, 12 and 24 hr. Glucose oxidation to CO₂, incorporation into total cell mass, and incorporation into cell and medium lipids were determined. The percentage distribution of total cell lipid radioactivity in individual neutral and polar lipid classes was followed as a function of time. Degradation studies of individual lipid classes were performed to ascertain the percentage of radioactivity in acyl and glycerol moieties. The percentage of D-[1-¹⁴C] glucose oxidized to¹⁴CO₂, incorporated into cell matter and cell lipids was elevated in cells incubated in serum-free medium as opposed to serum-supplemented medium. The percentage distribution of total cell lipid radioactivity into individual neutral lipid classes from both serum-free and serum-supplemented cultures was as follows: sterols > triglycerides > free fatty acids > sterol esters. The percentage distribution of total cell lipid radioactivity into individual polar lipid classes of serum-supplemented cultures was as follows: phosphatidylcholine > phosphatidylinositol > sphingomyelin > phosphatidylethanolamine > phosphatidylserine. The distribution of glucose radiolabel into individual polar lipid classes of serum-free HTC cells was different from their serum-supplemented counterparts: sphingomyelin > phosphatidylcholine > phosphatidylinositol > phosphatidylethanolamine > phosphatidylserine. Glycerol from glyceride classes contained a higher percentage of radioactivity than the acyl moieties, with this percentage significantly elevated in serum-free cultures. The data indicate that, although glucose is a substrate for HTC cell lipids, other precursors present in the culture system also contribute to the lipid constituency of this hepatoma cell line.     

Conjugated linoleic acid modulates hepatic lipid composition in mice

Conjugated linoleic acid (CLA) is a chemoprotective fatty acid that inhibits mammary, colon, forestomach, and skin carcinogenesis in experimental animals. We hypothesize that the ubiquitous chemoprotective actions of dietary CLA in extrahepatic tissues are dependent upon its role in modulating fatty acid composition and metabolism in liver, the major organ for lipid metabolism. This study begins to evaluate the role of CLA in lipid metabolism by determining the modulation of fatty acid composition by CLA. Female SENCAR mice were fed semipurified diets containing 0.0% (Diet A), 0.5% (Diet B), 1.0% (Diet C), or 1.5% (Diet D) CLA (by weight) for six weeks. Mice fed Diets B, C, and D exhibited lower body weights and elevated amounts of extractable total lipid in livers compared with mice fed diets without CLA (Diet A). Analyses of the fatty acid composition of liver by gas chromatography revealed that dietary CLA was incorporated into neutral and phospholipids at the expense of linoleate in Diets B, C, and D; oleate increased and arachidonate decreased in neutral lipids of CLA diet groups. In addition, increasing dietary CLA was associated with reduced linoleate in hepatic phospholipids. In an in vitro assay, CLA was desaturated to an unidentified 18:3 product to a similar extent as linoleate conversion to γ-linolenate (9.88, and 13.63%, respectively). These data suggest that CLA may affect metabolic interconversion of fatty acids in liver that may ultimately result in modified fatty acid composition and arachidonate-derived eicosanoid production in extrahepatic tissues. In addition to determining how dietary CLA modulates eicosanoid synthesis, further work is needed to identify enzymatic products that may result from desaturation of CLA.     

Effects of dietary saturated andTrans fatty acids on tissue lipid composition and serum LCAT activity in the rat

Groups of rats were fed from weaning with diets containing 5% by wt of hydrogenated coconut oil (HCO), safflower oil, or a concentrate of ethyl elaidate and linolelaidate (TRANS) as the sole source of dietary fat. Fatty acid composition of the lipid classes from serum, liver, heart, and kidney was determined, and the serum lecithin: cholesterol acyl transferase (LCAT) activities were assayed for each animal. Serum LCAT activity was increased by both the HCO and TRANS diets in the early stages of the development of an essential fatty acid (EFA) deficiency but was suppressed in the animals of the TRANS group as they became older. The HCO and TRANS groups exhibited changes in tissue lipid fatty acid composition, as well as reduced growth, characteristic of an EFA deficiency. Conversion of oleic acid to eicosatrienoic acid was impaired in the animals fed the TRANS diet, greatly increasing the octadecenoic acid content of the tissue lipids at the expense of eicosatrienoic acid. The TRANS diet also suppressed incorporation of eicosatrienoic acid into cholesteryl esters of tissue and serum, indicating that, when fed as the sole source of unsaturated fat,trans fatty acids influenced the metabolism of unsaturated fatty acids and cholesterol.     

Comparison of lipid composition ofCandida guilliermondii grown on glucose,ethanol and methanol as the sole carbon source

The carbon and energy source for aerobically grown cultures ofCandida guilliermondii profoundly influenced the neutral lipid content and the fatty acid composition of the individual lipid components. Methanol (0.80%, w/v) grown cells cultivated at 30 C in presence of 0.025% ammonium sulfate contained 12% total lipids, 67% of which was neutral lipids. Glucose (0.74%, w/v) or ethanol (0.53%, w/v) grown cells contained 21–22% total lipids, 80% of which was neutral lipids, under the same conditions. Methanol-grown cells contained a decreased 18∶1 acid (52–54% of total fatty acids) and an increased 18∶2 acid (23–25%), as compared with glucose- or ethanol-grown cells which contained 57–66% 18∶1 acid and 8–14% 18∶2 acid, in both neutral and polar lipid fractions. The relationship between methanol metabolism and desaturation of fatty acid in yeast was discussed.     

Lipid composition of 30 species of yeast

The detailed composition of cellular lipid of more than 23 species of yeast has been determined quantitatively by thinchrography on quartz rods, a method previously used for estimating cellular lipids of seven species of yeast. That data was fortified by neutral and phospholipid quantitations on 30 species of yeast cells. Most of the test organisms contained 7–15% total lipid and 3–6% total phospholipid per dry cell weight, except for the extremely high accumulation of triglycerides in two species ofLipomyces. Qualitatively, 30 species of yeast cells contained similar neutral lipid constituents (triglyceride, sterol ester, free fatty acid, and free sterol) and polar lipid components (phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl serine, phosphatidyl inositol, cardiolipin, and ceramide monohexoside) without minor constituents. Based on the quantitative composition of neutral lipids, the 30 species of yeast were divided into two groups, the triglyceride predominant group and the sterol derivative group. These groupings were fairly well overlapped from the standpoint of the distribution characteristics of fatty acid. The relative polar lipid compositions also grossly resembled each other. Only one exception of polar lipid composition in yeast cells was found inRhodotorula rubra species which contained phosphatidyl ethanolamine as the most abundant phospholipid. Fatty acid distribution patterns in yeast cells consistently coincided with other reports concerning fatty acid composition of yeast cells. Correlation of lipid composition and classification of yeasts are suggested and discussed. A part of this investigation has been reported at the 14th conference of the Japan Oil Chemists' Society, Nagoya, Japan, October 1975.     

Lipid analysis of Greek broad bean oil: Preparation of liposomes and physicochemical characterization

Liposomes were prepared from the isolated phospholipids of mature broad bean [Vicia faba L. (syn. Fabae calabaricae)] oil and their physical properties were studied. The method of preparation was the hydration of the thin lipid film, while the probe sonication methodology was used for reducing the size of the vesicles. The seeds of the broad bean were collected in two different periods of maturity and extracted by the Bligh‐Dyer method, and the lipid classes were studied by HPTLC/FID. The oils were found to be rich in polar lipids (63.1% and 60.2% of total lipids) and low in neutral lipids (36.9% and 39.8% of total lipids) for the immature and mature seed oils, respectively. The neutral lipid fraction consisted mainly of triacylglycerides (34.2% and 32.3%) whereas the polar lipids mainly consisted of phospholipids (60.2% and 54.2%) for the mature and immature seed oils, respectively. Sphingolipids (8.9%) were identified only in the immature seed oil. The overall goal of this study was the preparation of a new liposomal formulation with physicochemical properties such as unique lipid composition, size and ζ‐potential, which are important factors influencing drug delivery to the target tissues.     

Enantioselective Analysis of Chiral Anteiso Fatty Acids in the Polar and Neutral Lipids of Food

Anteiso fatty acids (aFA) are substituted with a methyl group on the antepenultimate carbon of the straight acyl chain. This feature leads to a stereogenic center. The 12-methyltetradecanoic acid (a15:0) and the 14-methylhexadecanoic acid (a17:0) are the most common aFA found in food, although they occur only in very small quantities. In this study we used gas chromatography in combination with a chiral stationary phase to determine the enantiomeric distribution of both a15:0 and a17:0 in the neutral and polar lipids of aquatic food samples and cheese. The best suited column was selected out of four custom-made combinations of heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin (β-TBDM) with different amount and polarity of an achiral polysiloxane. After separation of polar and neutral lipids of the food samples by solid phase extraction, fatty acid methyl esters were prepared and the fatty acid methyl esters were fractionated by reversed phase high performance liquid chromatography. Measurements of fractions high in aFA by enantioselective GC/MS in the selected ion monitoring mode verified the dominance of the (S)-enantiomers of a15:0 and a17:0 in both lipid fractions. However (R)-enantiomers were detectable in all samples. The relative proportion of the (R)-enantiomers was up to fivefold higher in the polar lipids than in the neutral lipids. The higher proportions in the polar lipids indicate that microorganisms might be involved in the formation of (R)-aFA.     

Fat-Soluble Bioactives,Fatty Acid Profile and Radical Scavenging Activity of <Emphasis Type="Italic">Semecarpus anacardium</Emphasis> Seed Oil

Semecarpus anacardium (family Anacardiaceae) has many applications in the Ayurvedic and Siddha systems of medicine in India. Detailed knowledge on the composition of S. anacardium oil, in consideration of potential utilization, is of major importance. In this investigation, column chromatography, gas chromatography, thin layer chromatography and liquid chromatography techniques were performed to analyze lipid classes, fatty acids and fat-soluble bioactives of S. anacardium crude seed oil. The amount of neutral lipids in the crude seed oil was the highest, followed by glycolipids and phospholipids, respectively. Linoleic followed by palmitic and oleic were the major fatty acids. The ratio of unsaturated fatty acids to saturated fatty acids was higher in neutral lipid classes than in the polar lipids. The main sterol compounds were β-sitosterol, campesterol and stigmasterol. δ-Tocopherol followed by β-tocopherol were the main tocopherols. When S. anacardium seed oil and extra virgin olive oil were compared for their radical scavenging activity toward 1,1-diphenyl-2-picrylhydrazyl radical and galvinoxyl radical (by electron spin resonance spectrometry), S. anacardium seed oil exhibited a stronger RSA.     

Sterol lipids in finger millet(Eleusine coracana)

Neutral lipids, glycolipids, and phospholipids (1.3%, 0.25%, and 0.10% of seed weight) were isolated from the total lipids (chloroform-methanol) of finger millet seeds(Eleusine coracana), and four sterol-containing lipids further isolated from neutral and glycolipids by preparative column and thin layer chromatography. On seed weight, these comprised: free sterols (S) 0.091%, sterol esters (SE) 0.013%, sterol glycosides (SG) 0.025%, acyl sterol glycosides (ASG) 0.020%, and total 0.149%. The major fatty acids, totaling 85-90%, were the same in both esterified sterols, but the proportions varied: 16:0, 18:1, and 18:2 comprising 24, 49, and 17% in SE (calculated iodine value 75) and 43, 36, and 7% in ASG (calculated iodine value 46). All four sterol lipids contained 80-84% of β-sitosterol, the remainder being stigmasterol. The only sugar in SG and ASG was D-glucose. It is deduced that the major representative species are: SE, β-sitosterol oleate/palmitate; SG, β-D-glucopyranosyl-(l → 3)-β-sitosterol; and ASG, 6-0-palmitoyl-β-D-glucopyranosyl-(l → 3)-β-sitosterol.     

Polar lipids ofMacrophomina phaseolina

Macrophomina phaseolina was grown on a defined medium at three different carbon/nitrogen ratios. The lipids of the mycelia and the sclerotia were extracted; fractionated into polarity groups; and separated by thin layer, column, and gas liquid chromatographies. Sclerotia contained higher levels of neutral lipids and lower amounts of polar lipids than mycelia. The neutral lipid content of sclerotia increased, up to 77% of total lipids, and phospholipids decreased as carbon/nitrogen ratio increased from 10 to 320. The glycolipid content was not altered significantly by changes in carbon/nitrogen ratios. Although cardiolipin could not be detected in sclerotial polar lipids, both sclerotia and mycelia contained similar phospholipid profiles with major quantitative differences. Phosphatidic acid and phosphatidyl glycerol were major components of sclerotia, whereas phosphatidyl ethanolamine and phosphatidyl inositol were the major phosphatides of mycelia. Phosphatidyl choline was present in both mycelia and sclerotia. The fatty acid distribution did not show any particular pattern of saturation or unsaturation due to differences in carbon/nitrogen ratio. However, mycelial lipids tended to contain C24∶1, C18∶3, and C22∶1 as major fatty acids, whereas the major fatty acids in sclerotial lipids were C18∶2, C18∶1, C22∶1, C20∶0, and C16∶1. Saturated fatty acids were present in lesser concentrations.     

Effects of dietary marine oils and olive oil on fatty acid composition, platelet membrane fluidity, platelet responses, and serum lipids in healthy humans

The influence of various dietary marine oils and olive oil on fatty acid composition of serum and platelets and effects on platelets and serum lipids were investigated as part of an extensive study of the effects of these oils on parameters associated with cardiovascular/thrombotic diseases. Healthy volunteers (266) consumed 15 mL/d of cod liver oil (CLO); whale blubber oil (refined or unrefined); mixtures of seal blubber oil and CLO; or olive oil/CLO for 12 wk. In the CLO, seal oil/CLO, and whale oil groups, serum levels of eicosapentaenoic acid (EPA) were increased. In platelets, EPA was increased in the CLO, seal/CLO, and olive oil/CLO groups. The localization of n-3 polyunsaturated fatty acids in the triacylglycerols did not seem to influence their absorption. Intake of oleic acid is poorly reflected in serum and platelets. No significant differences in triacylglycerols (IG), total cholesterol, or high density lipoprotein cholesterol were observed, even though TG were reduced in the CLO, CLO/seal oil, and whale oil groups. Mean platelet volume increased significantly in both whale oil groups and the CLO/olive oil group. Platelet count was significantly reduced in the refined whale oil group only. Lipopolysaccharide-stimulated blood tended to generate less thromboxane B₂ in CLO, CLO/seal, and CLO/olive groups. The whale oils tended to reduce in vivo release of β-thromboglobulin. In conclusion, intake of various marine oils causes changes in platelet membranes that are favorably antithrombotic. The combination of CLO and olive oil may produce better effects than these oils given separately. The changes in platelet function are directly associated with alterations of fatty acid composition in platelet membranes.     

Fungi pathogenic to insects: III. Neutral and polar lipids ofEntomophthora coronata

The neutral and polar lipid composition ofEntomophthora coronata was determined qualitatively. The fungus was grown on a chemically nondefined medium (Sabouraud dextrose yeast extract) and a chemically defined medium for a period up to 26 days. The lipids were characterized by thin-layer, column, gas chromatography, and selective sprays,³²P-labeling, and mass spectrometry. The neutral lipids consist of monoglycerides, diglycerides, cholesterol, free fatty acids, triglycerides, and cholesteryl esters. The polar lipids consist of phospholipids (phosphatidyl ethanolamine, phosphatidyl choline, lysophosphatidyl ethanolamine, lysophosphatidyl choline, and spingomyelin), a number of glycolipids including cerebrosides, and many unrecognizable lipids, most of which are present in trace amounts. The cerebrosides and spingomyelin are present in significant amounts, and their concentration increased with age of the culture. The major fatty acids (>10%) of the total, neutral, and polar lipids of the mycelia are 14∶0, 16∶0, 18∶1, 18∶3(γ), and 24∶1. The polar lipids of total culture (unsaturation index 0.88) and of the conidia (unsaturation index 1.48) are considerably more unsaturated than the corresponding neutral lipids (unsaturated index 0.50 and 0.49). The mycelial polar lipids, compared to the neutral lipids, possess less 14∶0 and 18∶1 but contain a greater percentage of 16∶0, 18∶2, 18∶3(γ), 24∶0, and 24∶1. The major fatty acid of the conidia (>10%) are 13∶0, 14∶0, 18∶1, 18∶2, 18∶3(γ), and 20∶4. Their polar lipids have a higher proportion of 18∶2, 18∶3(γ), and 20∶4. The cerebrosides possess 24.1 in high relative proportion (30.1%). Presented at the AOCS Meeting, Atlantic City, October 1971.     

Acetate and mevalonate labeling studies with developingCuphea lutea seeds

Cuphea seeds contain large amounts of medium chain (C₈ to C₁₄) fatty acids, mainly as triacylglycerols. The biosynthesis of these lipids was studied in vivo by incubating developingCuphea lutea seeds with labeled acetate. Incorporation of label into triacylglycerols and into medium chain fatty acids occurred principally during the period of endogenous lipid deposition, but some label was encountered in these products even during seed dehydration. At this later stage palmitate and oleate were the dominant labeled fatty acids. During the period of rapid endogenous lipid deposition acyl lipids other than triacylglycerols were minor labeled components. The labeling patterns were consistent with the Kennedy pathway for triacylglycerol biosynthesis. The fatty acid composition of the acyl-CoA pool was similar to the total lipid fatty acid composition, but the acyl-ACP pool contained relatively more short chain acyl groups. Squalene was labeled from acetate throughout the period of seed development, but labeled sterols were not detected. Using [2-¹⁴C]mevalonic acid lactone as substrate, squalene was the principal labeled product. Small amounts of label were found in free sterols. However, in terms of mass, free sterol dominated over squalene. The possibility of two independent sites of isoprenoid biosynthesis in the developing embryo is discussed.     

Myogenic differentiation of the muscle clonal cell line BC3H-1 is accompanied by changes in its lipid composition

Phospholipid and neutral lipid composition was studied in the course of myogenic differentiation of the clonal cell line BC3H-1. Total phospholipid content increased during differentiation, predominantly in the major classes of choline and ethanolamine glycerophospholipids. The contents of other lipids, such as triacylglycerols, diminished more than 50% during this period. The content and distribution of fatty acids also underwent marked differentiation-dependent changes. The polyunsaturated (tetrapenta- and hexaenoic) fatty acid species of several phospholipid classes diminished during differentiation, especially those in choline, serine and inositol glycerophospholipids. Most noticeable were the changes in phosphatidylserine; long-chain fatty acids having 20 to 22 carbon atoms and 4 to 6 double bonds decreased from about 30 to about 10 mol%. Although increased levels of saturation in other phospholipid fatty acyl chains appear to accompany the myogenic changes of BC3H-1 cells, some unsaturated fatty acids, such as oleic acid (18∶1), increased by as much as 80% during the same period, suggesting the activation of a Δ9 desaturase. Sphingomyelin contained only saturated and monoenoic fatty acids and exhibited a four- to five-fold decrease in its content of monoenoic acyl groups. Diacylglycerols became enriched in arachidonate and docosahexaenoate. The amount of cholesterol and its esters increased slightly during differentiation of BC3H-1 cells. The data show that several metabolic pathways change during myogenic differentiation of the BC3H-1 clonal cell line, particularlyde novo biosynthetic pathways, elongation/desaturation reactions, and acyl chain turnover. As a consequence of this, the lipid composition of the myoblast form of the BC3H-1 cell, in which the nicotinic acetylcholine receptor and other cell surface receptors are expressed, is thus different from that of the nondifferentiated cell.     

Synthesis of spin-labeled neutral lipids: Nitroxyl derivatives of triglycerides and sterol esters

Methods for the preparation of useful spin-labeled neutral lipids are described. A spin-labeled triglyceride has been prepared by acylation of 1,3-distearoylglycerol with stearic acid anhydride bearing the 4′,4′-dimethyloxazolidine-N-oxyl ring at carbon-12. The same fatty acid anhydride has been used to acylate the 3-hydroxy group of cholesterol to obtain a cholesteryl ester with the nitroxyl function in the fatty acyl chain. The 4′,4′-dimethyloxazolidinyl-1-oxyl derivative of 5α-an drostan-3-one-17β-ol has been esterified with stearic acid anhydride to obtain a steroid ester with the paramagnetic center in the steroid nucleus.