Phospholipid Composition of <Emphasis Type="Italic">Jatropha curcus</Emphasis> Seed Lipids

Jatropha curcus L. oil has emerged as one of the most important raw materials for biodiesel production. However, no detailed study has been reported on characterizing the lipid constituents of jatropha oil. The present study revealed that the total oil content of jatropha seeds was 32% with a composition of 97.6% neutral lipids, 0.95% glycolipids and 1.45% phospholipids. The fatty acid composition of total lipids, neutral lipids, phospholipids and glycolipids was also determined and found to contain oleic acid (18:1) and linoleic acids (18:2) as major fatty acids. The phospholipids fraction was further characterized and quantified and found to contain phosphatidyl choline (PC) 60.5%, phosphatidyl inositol (PI) 24% and phosphatidyl ethanolamine (PE) 15.5%. The fatty acid composition and the positional distribution of the fatty acids of individual phospholipids were also reported.     

Main constituents of rapeseed lecithin

Commercial rapeseed lecithin has been analyzed after separation by silicic acid column chromatography. Besides neutral oil (40%), four major constituents have been found, viz., phosphatidyl ethanolamine (18%), phosphatidyl inositol (8%), phosphatidyl choline (16%) and sterol glycosides (8%). Among the minor fractions lysophosphatidyl ethanolamine accounts for about 2%. The phosphatides are characterized by low erucic acid content and the major fatty acids are palmitic, oleic and linoleic acids.     

Effects of diets high in saturated fat and cholesterol on the lipid composition of canine platelets

The phospholipid composition of platelets from dogs on various experimental diets was determined. Thyroidectomized foxhounds were fed a control diet or the control diet supplemented with (1) beef tallow, (2) beef tallow and cholesterol, or (3) beef tallow, cholesterol, and safflower oil for 23 weeks prior to isolation of platelets. Platelets from animals fed the control diet contained 36.7% phosphatidylcholine (PC), 22.8% phosphatidylethanolamine (PE), 18.4% sphingomyelin (Sph), 11.8% phosphatidylserine (PS), 6.3% phosphatidylinositol (PI), and 2.2% lysophosphatidylcholine. The PE was 77.6% in the plasmalogen form. No highly significant changes in the phospholipid class composition resulted from the experimental diets. Cholesterol supplementation of the diets, however, caused consistent alterations in the fatty acid compositions of the platelet phospholipids including increases in the percentages of 18∶1ω9 (oleic acid), 18∶2ω6 (linoleic acid), and 20∶3ω6 (homo-gamma linolenic acid) and a decrease in the percentage of 20∶4ω6 (arachidonic acid). Addition of safflower oil to the tallow-cholesterol diet partially reversed these effects. These cholesterol-induced alterations in fatty acid composition could be due to exchange with plasma lipids, de novo synthesis, or altered platelet metabolism. The mechanism remains to be determined. Der. Nelson’s current affiliation is the Lipid Metabolism Branch, Division of Heart and Vascular Diseases, National Heart, Lung, and Blood Institute.     

Über trans-Lipoide: Die Lipoide des Hühnerei-Dotters

Trans Lipids: The Egg Yolk Lipids of the Hen The feeding of hens with a trans-containing edible fat resulted in an increase in the trans fatty acids of the egg yolk lipids to the extent of 10%, which completely disappeared within 14 days after stopping the trans-containing feed. The fatty acids in the triglyceride fractions contained in each case more trans unsaturated fatty acids than those in the corresponding phosphatide fractions. The gas chromatographic analysis of the fatty acid methyl esters showed that the triglycerides contained more oleic acid than the phosphatide fatty acids whereas stearic as well as polyunsaturated components were concentrated predominently in the phosphatides. The analysis of the fatty acid methyl esters from triglyceride and phosphatide fractions after feeding of trans-containing fat showed distinct changes in both the groups, thus for example a reduction of oleic acid in the neutral fat analogous to that in the total lipids as against its increase in phosphatides. The amount of linoleic acid in the phosphatide fatty acids increased while it remained constant in triglyceride fatty acids.     

Fatty acids of bovine milk glycolipids and phospholipids and their specific distribution in the diacylglycerophospholipids

Milk lipids were fractionated by silicic acid column chromatography and preparative thinlayer chromatography (TLC). Ceramide monohexoside (CMH), ceramide dihexoside (CDH), phosphatidyl ethanolamine (PE), phosphatidyl choline (PC), phosphatidyl serine (PS), and sphingomyelin (Sph) were isolated, and the purity of each was checked by infrared spectroscopy and TLC. The diacylphospholipids were hydrolyzed with phospholipase A and the products separated by TLC. Fatty acid methyl esters were prepared from the various fractions and analyzed by gas chromatography. The glycolipids, CMH and CDH, and Sph contained large amounts of long-chain saturated fatty acids, especially C_22:0, C_23:0, and C_24:0, PE, PS, and PC contained C₁₀-C₂₂ normal and branched-chain saturated fatty acids, and C₁₅-C₂₀ unsaturated fatty acids (mainly monoenes). The distributions of saturated acids between the α′- and β-positions were respectively: PE, 46 and 11%; PS, 65 and 19%; and PC, 72 and 53%. PC was exceptional in that there was 10.8% myristic acid in the β-position and only 5.6% in the α′-position. PE and PS were similar in composition except that in PE oleic acid was evenly distributed, and in PS was largely in the β-position. In general, PC was much more saturated than PE or PS, and there was no overall pattern governing the specific distribution of the fatty acids in the three diacylphospholipids. Comparison with PC from other bovine tissues and from egg lecithin showed that fatty acids are located much less specifically in milk phospholipids than in PC from other sources. Presented at the AOCS Meeting, Houston, Texas, April, 1965.     

The composition of safflower seed

Safflower has some interesting variations in composition. Current commercial seed types have about 40% hull, 37% oil, and 23% meal. Varities also exist with from 59-18% hull and inversely varying oil and meal percentages. The fatty acid composition of the linoleic acid type oils is quite constant at about 78% linoleic, 11% oleic, 3% stearic, 6% palmitic. Experimental types have been described with about 45% oleic: 45% linoleic, 80% oleic: 10% linoleic, and with 10% stearic. Compositional data are reviewed with particular attention to major and minor constituents (especially linolenic acid) that influence safflower use. W. Utiliz. Res. Dev. Div., ARS, USDA.     

Lipid and fatty acid composition of testes of quaking mice

Testes of quaking mice (sterile mutants) and of controls were analyzed for major lipid classes and fatty acid composition. Of the main lipid classes, only cholesterol esters differed significantly in concentration between the two groups (1.01 for quakers vs 0.69 mg/g wet wt of tissue for controls). The concentration of triglycerides was 4.5–5.0, that of total phosphatides 18–19, and that of free cholesterol 1.9–2.0 mg/g for mutants and controls. The concentrations of phosphatidyl ethanolamine and of sphingomyelin were both lower in quaking than in normal mice, but only the change in the former was statistically significant. Phosphatidyl choline was the major phosphatide (43–45% of total phosphatides) followed by phosphatidyl ethanolamine (24–26%) and sphingomyelin, phosphatidyl serine, and phosphatidyl inositol (all ca. 7% of total phosphatides). Minor differences between the mutants and controls were observed in concentrations of fatty acids of major lipid classes. The mutants, sterile because of faulty spermatid differentiation, had normal quantities of 22∶6 w3 and 22∶5 w6. These data are consistent with the hypothesis that the 22-carbon polyenes are associated with the formation of spermatids, rather than with their final differentiation into spermatozoa.     

Effect of Irrigation Regimes on Oil Content and Composition of Safflower (Carthamus tinctorius L.) Cultivars

Safflower oil contains a large amount of unsaturated fatty acids, however, the composition of the oil may be affected by drought stress. This experiment determined the effect of three irrigation regimes (60, 75 and 90% soil moisture depletions of available water) on oil composition of safflower cultivars (Kuseh, PI and IL111). Amounts of oil and oil composition of the seeds were determined by gas chromatography (GC). The oil contents of IL111, PI and Kuseh cultivars were 30.73, 27.63 and 25.25%, respectively. The oil contents, palmitic, stearic, oleic and linoleic acid contents were reduced by about 13, 63, 60, 14 and 10% by drought, respectively. The stearic acid contents of PI, IL111 and Kuseh were reduced by 72, 61 and 37% and palmitic acid contents of the same cultivars were reduced by drought by 65, 53 and 51%, respectively. Whereas, the linoleic acid contents of Kuseh, PI and IL111 were reduced by only 10, 8 and 5% and oleic acid contents of the same cultivars were reduced by only 14, 13 and 14% under the drought stress, respectively. The results showed that although drought stress reduced the amount of oil and oil composition of safflower cultivars, the decrease was due to a dramatic reduction in saturated fatty acids contents. Thus, proper irrigation regimes may enhance safflower oil quality.     

Phospholipid oxidation in emulsions

The autoxidation of purified phosphatidyl ethanolamine (PE) and phosphatidyl choline (PC), extracted from egg and soybean lipids, was followed by oxygen uptake measurements in emulsified systems. All emulsified phospholipid fractions had comparable activation energies. Measurement by various physico-chemical tests was made of specific changes in the phospholipid molecule during autoxidation. PE oxidized more rapidly and absorbed more oxygen than PC. Higher 2-thiobarbituric acid test and diene and triene conjugation absorbance values were observed for PE than for PC. Of the two major polyunsaturated fatty acids in egg phospholipids, arachidonic acid disappeared at a more rapid rate during oxidation while the concentration of linoleic acid decreased to a level that was relatively constant. Although typical unsaturated fatty acid oxidation appeared to occur in all phospholipid fractions, oxidation in aqueous emulsions was only partly a function of fatty acid composition. The nitrogen moieties, ethanolamine and choline influenced the induction period for the oxidation of PE and PC respectively. Michigan Agriculture Experiment Station Journal Article No. 4420. Presented in part at the AOCS Meeting, Chicago, October 1967.     

Composition and metabolism of fatty acids in phospholipids of density-separated red cells of rats

Fatty acid compositions of phosphatidylcholine (PC) and phosphatidylethanolamine (PE) and the rates of fatty acid esterification to these phospholipids (PL) were measured in intact rat red cell populations of different ages separated by density gradient centrifugation in order to clarify changes in membrane lipids of red blood cells during in vivo aging. Fatty acid compositions of PC and PE altered progressively as red cells became denser. Changes in unsaturated fatty acids occurred predominantly at the 2-position of PC and PE and those in saturated fatty acids at both positions. The esterification rates of 5 major fatty acids decreased as red cells became denser and those of oleic acid, linoleic acid and arachidonic acid to both PC and PE of fraction I cells (oldest cells) were 37–51% those of fraction IV cells (youngest cells). Reduction in the rates of fatty acid esterification appeared to occur in the course of red cell maturation because reticulocyte-enriched cell fractions showed 4.5–14.5 times higher rates of linoleic acid and arachidonic acid esterifications to PC and PE.     

Rapid separation of the major phospholipid classes on a single aminopropyl cartridge

A rapid method for the separation of the individual phospholipid classes phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylserine (PS) and phosphatidylinositol (PI) by a single solid-phase extraction was developed. PC, PE, PS and PI were sequentially eluted from aminopropyl bonded silica with acetonitrile/n-propanol (2∶1, vol/vol), methanol, isopropanol/methanolic HCl (4∶1, vol/vol) and methanol/methanolic HCl (9∶1, vol/vol). Standard recoveries were over 95% for PC and PE and over 85% for PS and PI with undistorted fatty acid composition. The separation of complex lipid mixtures on aminopropyl minicolumns can be refined to the level of individual phospholipid classes.     

Liver lipids during development

The fatty acid composition of the major liver microsomal phospholipids has been studied during pre- and postnatal development of the rabbit. The fatty acid composition of the total lipids, phosphatidyl choline, and phosphatidyl ethanolamine from animals −6, −3, 0, +3, +6, +9, +16, and +112 days of age was determined. Fatty acid composition is similar in phosphatidyl choline and phosphatidyl ethanolamine for oleic acid at +3, +6, +9, and +16 day old animals; palmitoleic acid at +9 day old animals and linoleic acid at −6, −3, and 0 day old animals. Palmitoleic acid demonstrated a uniform decrease during early development in the total lipids and in both phosphatidyl choline and phosphatidyl ethanolamine; however, in the 112 day animal, the amount was just slightly lower than that observed for the earliest prenatal animal studied. Oleic acid decreased considerably during early postnatal development in the total lipids, phosphatidyl choline and phosphatidyl ethanolamine, but an increase in the 112 day animal was observed. Linoleic acid fluctuated considerably throughout postnatal development in the total lipids as well as in the two major phosphatides. Lecithin biosynthesis has been studied by two pathways during development of rabbit liver from −6 days to +110 days. The two pathways of lecithin biosynthesis were evaluated by assaying the activities of the liver enzymes choline phosphotransferase and phosphatidylmethyltransferase at different time intervals during development. The greater enzymatic activity was observed in the cholinephosphotransferase during development.     

The plant geneticist’ contribution toward changing lipid and amino acid composition of safflower

Current research on the fatty acid composition of the seed oil of safflower (Carthamus tinctorius L.) has shown the following: (1) there is a possibility that the oleic acid content can be increased above 80%, though probably not above 85%, by use of modifying genes and the major geneol; (2) wild species do not look very promising as a source of genes for modifying fatty acid composition; (3) commercially grown high linoleic and high oleic types are temperature stable; (4) an experimental type with about equal amounts of oleic and linoleic acids is responsive to temperature, with high temperature increasing oleic acid and low temperature increasing linoleic acid; and (5) stearic acid in another experimental type with higher levels of stearic acid (5–10%) is reduced by low temperatures. One of seven papers presented at the Symposium, “The Plant Geneticist’s Contribution Toward Changing Lipid and Amino Acid Composition of Oilseeds,” AOCS Meeting, Houston, May 1971.     

A conversion factor to determine phospholipid content in soybean and sunflower crude oils

The major phospholipids (PL) from soybeans and sunflowers were separated by 2-dimensional thin layer chromatography (TLC) and the fatty acid composition of each PL was determined by gas liquid chromatography (GLC). PL from soybeans and sunflowers contained high percentages of linoleic and palmitic acids. Only phosphatidylinositol (PI) from both oilseeds were similar in fatty acid composition and the principal acid was palmitic acid. Sunflower phospholipids, except for PI, contained twice as much oleic acid as did those from soybeans. Sunflower PI contained very low but measurable quantities of heptadecanoic acid. The molecular weights (MW) of individual PL were based on their fatty acid composition. The MW found for soybeans and sunflower PL were quite similar even though their fatty acid compositions were different. The average MW of PL in crude soybean and sunflower oils was determined based on the MW of individual PL and their composition in the PL fraction. From that MW, a factor for converting phosphorous content in oil to its PL content was calculated. For both oils, the factor was 25.     

The phosphatides of safflower seeds involved in color formation occurring in extracted and heated crude oils

Studies on crude safflower oils have established that three phosphatides extracted with the oil from the kernel of the seed are responsible for color formation. The phosphatides have been isolated and identified as phosphatidylethanolamine (PE), phosphatidylmyoinositol (PI) and phosphatidylcholine (PC). Phosphatidylethanolamine was the most potent contributor to color formation, followed by phosphatidylinositol and phosphatidylcholine. The color-forming compounds were separated from the crude oil by precipitation with water and obtained in pure form by column chromatography on DEAE cellulose. The components were identified by comparison of R_f values of intact and deacylated phosphatides with those of known reference compounds, by determination of molar ratios of ester, glycerol, choline, inositol, nitrogen and phosphorus, and by qualitative and quantitative gas chromatographic analysis of the fatty acid residues. Presented at the AOCS Spring Meeting, San Francisco, April 1969. W. Utiliz. Res. Dev. Div., ARS, USDA.     

Lipids ofKlebsiella pneumoniae: The presence of phosphatidyl choline in succinate-grown cells

The carbon and energy source for aerobically grown cultures ofKlebsiella penumoniae profoundly influenced the total lipid content and phosphatide composition. Glucose-grown cells contained 13% lipid, 56% of which was phospholipids. Succinate-grow cells contained 8% lipid, 66% of which was phospholipids. The predominant phosphatides of glucose-grown cells were phosphatidyl ethanolamine, 82%; phosphatidyl glycerol, 4.5%; phosphatidic acid, 5%; cardiolipin, 6.5%; phosphatidyl serine; and trace amounts of unidentified phosphatides. Phosphatides of succinate-grown cells were phosphatidyl ethanolamine, 38%; diphosphatidyl glycerol, 14%; phosphatidyl glycerol, 13%; phosphatidyl choline, 14.5%; phosphatidyl serine, 6%; phosphatidic acid, 4%; and 10% unknown lipids. No trace of phosphatidyl choline was found in glucose-grown cells. Paper 75-11-170 of the Kentucky Agricultural Experiment Station.     

Lipid class separation by HPLC combined with GC FA analysis: Comparison of seed lipid compositions from different <Emphasis Type="Italic">Brassica napus</Emphasis> L. varieties

A reliable HPLC method was established to evaluate the lipid composition of useful plants modified by breeding techniques. This study focused on the polar lipid distribution and polar lipid FA compositions of four rapeseed varieties. Structure and quantity of the distinct lipid classes were compared by HPLC using ELSD followed by a GC FA analysis. A baseline separation of 14 lipid classes could be achieved within one step by using an eluent gradient of hexane, tert-methylbutyl ether, isopropanol, acetonitrile, chloroform, triethylamine, acetic acid, and water supplemented with ammonium sulfate with a polyvinyl alcohol column. After automatic fractionation, the FA compositions of the distinct lipid classes were characterized by a subsequent complementary GC FA analysis through direct acetylchloride methylation. The rape varieties analyzed showed diversity in polar lipid content and distribution, dominated by PC, PE, PI, monoglycosyldiacylglycerols, and phytosterols. Extensive variations were detected in FA within the lipid classes of rape varieties with predominantly oleic acid, linoleic acid, and α-linolenic acid observed followed by palmitic acid and gondoic acid. Oleic acid was mainly connected to PC and linoleic acid to PE, whereas α-linolenic acid and γ-linolenic acid were predominantly linked to PI in all varieties.     

Some chemical processes utilizing oleic safflower oil

Oleic safflower seed (UC-1) produces an oil containing approximately 80% oleic acid and 12% linoleic acid. The oil is a source of high quality oleic acid, and fatty acids from the oil may be used without further separation in some applications where technical oleic acid is now used, since oleic safflower free fatty acids have a a higher oleic acid content than good commercial grades of oleic acid. A high purity oleic acid can be produced by urea fractionation. Ozonization of the oil followed by reductive cleavage yields pelargonaldehyde and nearly colorless aldehyde oils. Ozonization of a crude mixture of oleic safflower acids followed by oxidative cleavage provides high yields of azelaic acid and pelargonic acid. In contrast, ozonization of free fatty acids from polyunsaturated vegetable oils produces azelaic acid and mixtures of lower molecular weight carboxylic acids with smaller amounts of pelargonic acid. Furtherore, ozone consumption is lower and reaction time is shorter when oleic safflower acids are used in place of more highly unsaturated fatty acids.     

Impact of development periods on chemical properties and bioactive components of safflower (Carthamus tinctorius L.) varieties

This study aimed to determine the chemical properties (fatty acid composition, oil content, sterol and tocopherol compositions) of the oils extracted from the seeds of safflower (Dinçer, Remzibey, Balci, Linas, Yenice, Olas) varieties harvested in different periods from flowering to ripening period. In parallel with the increase of harvest time, the humidity rate decreased, while the oil ratios increased. It was determined that palmitic (16:0) and stearic (18:0) acids, which are significant saturated fatty acids, and oleic (18:1) and linoleic (18:2) acids, which are unsaturated fatty acids, are quite high in the oils of all safflower varieties. These fatty acids showed significant changes from the first harvest to the last harvest. The total saturated fatty acid ratios decreased, while the amount of unsaturated fatty acids increased as the maturation progressed. The first and latest harvest samples of Dinçer, Remzibey, Balcı, Linas, Yenice, Olas cultivars were selected and their sterol and tocopherol compositions were examined. The highest level of sterol in all cultivars was β-sitosterol and the amount of sterols decreased towards full maturity. It was determined that α-tocopherol was the dominant tocopherol found in the safflower oils and the amount of tocopherol increased towards full maturity.     

Preferential degradation of noncholine phosphatides in soybean lecithin by thermalization

Purified soybean lecithin and the gum derived from soybean oil processing were heated separately in bulk at 125 to 200°C for 60 min, or at 175°C for 30, 60, 90 and 120 min, and the products were analyzed by thin-layer chromatography and high-performance liquid chromatography. It was found that the noncholine phosphatides are preferentially degraded relative to phosphatidylcholine, and that these phosphatides are broken down in the order phosphatidyl-ethanolamine (PE)>phosphatidylinositol (PI)>phosphatidic acid (PA) with increasing temperature. At 175°C, the heating time required to degrade the noncholine phosphatides was between 30 and 60 min. Diglycerides were the principal products of thermalization at 77% of the total material, indicating that the 3-phosphoester linkage is the most heat-labile portion of the noncholine phosphatide molecules. Cleavage of the fatty acids from positions 1 and 2 of the phosphatides was minimal, as indicated by the relatively low amount of free fatty acids (8% of the total) when the lecithin was heated at 180°C for 90 min. The appearance of brown discoloration, characteristic of heated lecithin, coincided mainly with the decomposition of PE.