Fatty acid composition of rat hearts as influenced by age and dietary fatty acids

Fatty acid composition of neutral and polar lipid fractions from rat hearts was determined in rats of different ages as their diet source changed. Piebald rats were weaned at 21 days and were fed standard lab chow. Lipids from rat hearts, mothers milk and lab chow were purified on a Sephadex G-25 fine column and separated into neutral and polar lipid fractions by silicic acid column chromatography. These lipid fractions were then hydrolyzed and methylated with BF₃ in methanol, prior to gas liquid chromatographic separation on a 1/8 in. × 10 ft aluminum column of 15% EGS on 80–100 mesh acid-washed Chromosorb W. Three major fatty acids in the neutral lipid fraction comprised 72% of total neutral lipid fatty acids from young hearts. At sexual maturity (at least 74 days old) C_18∶1 was the major fatty acid, followed by C_16∶0 and C_18∶0. The same three fatty acids comprised 83% of total polar lipid fatty acids, but C_18∶0 was the major fatty acid, followed by C_16∶0 and C_18∶1. The fatty acid composition of dietary lipids influenced the total neutral lipid fatty acid composition of the rat heart, but had little influence on the fatty acid composition of the polar lipid fraction. Presented in part at the AOCS Meeting, New Orleans, April 1970.     

GC-FID/MS Analysis of Fatty Acids in Indian Cultivars of Moringa oleifera: Potential Sources of PUFA

In the present investigation, the fatty acid profile was analysed in vegetative and reproductive parts of eight commercially cultivated Indian cultivars of Moringa oleifera and verified by gas chromatography mass spectra. In leaves, α-linolenic acid (C_18:3, cis-9,12,15) was found in the highest quantity (49–59 %) followed by palmitic acid (C_16:0) (16–18 %), and linoleic acid (C_18:2, cis-9,12) (6–13 %). The total content of saturated fatty acids and unsaturated fatty acids showed a ratio of 0.33 (cv. DHANRAJ) to 0.39 (cv. PKM-2) in leaves, 0.53 in flowers and 0.56 in tender pods. Similarly, polyunsaturated fatty acids and total monounsaturated fatty acids were found in a ratio of 5.68 (cv. DHANRAJ) to 9.71 (cv. CO-1) in leaves, 1.11 in flowers and 2.79 in tender pods. The total lipid content was recorded in the range of 1.92 % (flowers) to 4.82 % (leaves, cv. CO-1). When considering health benefits, M. oleifera leaves contain low amounts of saturated fatty acids, a high mono- and polyunsaturated fatty acid content, which can enhance the health benefits of Moringa-based products.     

Fatty acid and long chain base composition of adrenal medulla gangliosides

Five ganglioside fractions from bovine adrenal medulla were analyzed with respect to their fatty acid and long chain base compositions. The five fractions included two hematosides and three hexasamine-containing species, the latter having chromatographic properties comparable to the major gangliosides of brain. The fatty acid compositions of all five were similar: 22∶0 was the most abundant, but significant amounts of 16∶0, 18∶0, 24∶0 and 24∶1 were also present. No hydroxy fatty acids were detected. The principal long chain base in each fraction was 4-sphingenine (sphingosine), with lesser amounts of the C₁₆ and C₁₇ homologues. Minor quantities of the corresponding saturated bases were also detected. These were identified by two gas liquid chromatography methods: (a) trimethylsilyl ether derivatives, (b) aldehydes formed by periodate oxidation of the long chain bases. No 4-eicosasphingenine (C₂₀-sphingosine), characteristic of brain gangliosides, was found in any of the fractions. The results demonstrate that gangliosides of the adrenal medulla show tissue specificity in fatty acid and long chain base composition which is independent of carbohydrate structure.     

The effect of lyophilization on the solvent extraction of lipid classes,fatty acids and sterols from the oysterCrassostrea gigas

The lipid class compositions of adult Pacific oysters [Crassostrea gigas (Thunberg)] were examined using latroscan thin-layer chromatography/flame-ionization detection (TLC/FID), and fatty acid compositions determined by capillary gas chromatography and gas chromatography/mass spectrometry (GC/MS). The fatty acid methyl esters were separated using argentation TLC and also analyzed as their 4,4-dimethyloxazoline derivatives using GC/MS. Major esterified fatty acids inC. gigas were 16∶0, 20∶5n−3, and 22∶6n−3. C₂₀ and C₂₂ nonmethylene interrupted (NMI) fatty acids comprised 4.5 to 5.9% of the total fatty acids. The NMI trienoic fatty acid 22∶3(7,13,16) was also identified. Very little difference was found in the proportions of the various lipid classes, fatty acids or sterols between samples of adult oysters of two different sizes. However, significant differences in some of the lipid components were evident according to the method of sample preparation used prior to lipid extraction with solvents. Lyophilization (freeze drying) of samples led to a significant reduction in the amounts of triacylglycerols (TG) extracted by solvents in two separate experiments (7.0 and 52.5% extracted). Extracts from lyophilized samples had less 16∶0, C₁₈ unsaturated fatty acids, and 24-ethylcholest-5-en-3β-ol, while C₂₀ and C₂₂ unsaturated fatty acids comprised a higher proportion of the total fatty acids. There was no significant change in the amounts of polar lipids, total sterols, free fatty acids or hydrocarbons observed in extracts from lyophilized samples relative to extracts from nonlyophilized samples. Addition of water to the freezedried samples prior to lipid extraction greatly improved lipid yields and resulted in most of the TG being extracted.     

Molecular species of glycerophospholipids and sphingomyelins of human erythrocytes: Improved method of analysis

This study reports the application of modern methods of molecular species analysis in determination of the structure of both major and minor glycerophospholipids and sphingomyelins of human erythrocytes. Individual phospholipid classes were resolved from total lipid extracts by thin-layer chromatography. Diradylglycerols were released by phospholipase C and converted into trimethylsilyl ethers, which were resolved into the alkenylacyl, alkylacyl and diacylglycerol subclasses by normal phase high performance liquid chromatography. Molecular species of diradylglycerols and ceramides were quantitated according to carbon and double bond number by gas liquid chromatography using a fused silica capillary column wall-coated with bonded RTx-2330. The molecular species of ceramides were determined by GC/MS. The diradyl glycerophosphocholines contained 93.0% diacyl, 4.6% alkylacyl and 2.5% alkenylacyl, white the diradyl glycerophosphoethanolamines were made up of 48.8% diacyl, 47.8% alkenylacyl and 3.4% alkylacyl subclasses. Analysis of the molecular species showed that the long chain polyunsaturated acids were mainly combined with C₁₆ in all diradyl GPC subclasses and in diacyl GPE, while in the alkylacyl and alkenylacyl GPE and in diacyl glycerophosphoinositol and diacyl glycerophosphoserine they were combined mainly with C₁₈ saturated fatty chains. In addition to the C₁₆ and C₁₈ alkyl and alkenyl, the ether fractions also contained significant proportions of C₂₀, C₂₂ and C₂₄ chains. The molecular species of the ceramide moieties of the SPH were made up largely of mono- and diunsaturated species. Over 200 molecular species were identified and quantitated in a representative sample of human red blood cells.     

Skin surface lipids of the dog

The skin surface lipid of the dog has been reported to contain a high proportion of diol diesters having a lower mobility on thin layer chromatography than diesters from other species in spite of containing similar fatty acid and diol components. In the present study, dog skin surface lipid was separated by preparative thin layer chromatography into sterol esters (42%), wax diesters (32%), free sterols (9%), polar lipids (7%), and unidentified components (10%). The diesters contained 1,2-diols, each esterified with one long chain fatty acid and one isovaleric acid moiety. The diols were principally branched chain C₂₁ and C₂₂ compounds while the long chain fatty acids esterified with them were mainly C₂₀ and C₂₁ branched compounds. The fatty acids from the sterol esters were mostly saturated, branched chain C₁₉ to C₂₃, together with 7% of straight chain monoenoic acids, principally C₂₁ and C₂₂. There were only trace amounts of free sterols other than cholesterol, while the esterified sterols contained 96% cholesterol and 4% lathosterol.     

Isovaleric acid as a precursor of odd numbered iso fatty acids in Tetrahymena

Tris isovalerate-supplementedTetrahymena pyriformis W showed no qualitative change in fatty acid composition; however, an increase in polar lipids that contain odd numbered iso acids (C₁₃, C₁₅, C₁₇, C₁₉) occurred. This change was accompanied by a decrease in the proportional amount of even numbered normal acids (C₁₄, C₁₆, C₁₈). The neutral and polar lipids from cells incubated with [1-¹⁴C] isovaleric acid were found to contain radioactivity. The methyl esters of the saturated fatty acids obtained from the polar lipids by alkaline methanolysis were separated by reversed phase chromatography, the identities confirmed by gas chromatography-mass spectrometry, and the specific activities determined. Iso acids were found to be the most heavily labeled materials. In addition to ceramide, two sphingolipid components were detected. One yielded saturated fatty acids after acidic methanolysis, while the other contained >93% α-hydroxy fatty acids. Radioactivity was noted in the long chain base fraction derived from the sphingolipids. Progressive growth inhibition occurred as the isovalerate concentration was increased in the culture medium; however, the ciliates were morphologically indistinguishable from unsupplemented cells.     

Changes in flax (Linum usitatissimum L.) seed lipids during germination

Flax (Linum usitatissimum L.) seeds were germinated for 8 d under laboratory conditions, and changes in their lipid fraction were studied by various chemical and chromatographic methods. Total lipid content of the seeds was reduced fourfold at the end of the 8-d germination period as compared to ungerminated seeds on a fresh weight basis. The neutral lipids comprised the major fraction of seed lipids, and triacylglycerols predominated over all other lipid components even during the germination period. Both the spectrophotometric and thin-layer chromatography-flame-ionization detection methods of quantification showed a considerable increase in the content of free fatty acids. The glycolipid fraction of lipids increased, but the phospholipid fraction exhibited only minor changes. Lipase activity of flaxseed increased at the beginning of germination and then remained constant until the fifth day. Phosphatidylcholine was the major phospholipid of flaxseed lipids, and its content was reduced during the germination. The contents of lysophosphatidylcholine and phosphatidic acid increased from negligible amounts to 46% of the total phospholipids. Linolenic, linoleic, and oleic acids, respectively, were the predominant fatty acids of all the lipid fractions of flaxseed, and remained unchanged during the germination period. The glycolipid fraction had the lowest content of polyunsaturated fatty acids. Fatty acids C_14:0, C_20:0, C_24:0, C_20:1, C_22:1, and C_20:5 appeared after d 2 of germination in neutral, glyco- and phospholipid fractions.     

Acylglycerols Containing Trihydroxy Fatty Acids in Castor Oil and the Regiospecific Quantification of Triacylglycerols

Ricinoleate, a monohydroxy fatty acid in castor oil, has many industrial uses. Dihydroxy and trihydroxy fatty acids can also be used in industry. We report here the identification of diacylglycerols (DAG) and triacylglycerols (TAG) containing trihydroxy fatty acids in castor oil. The C₁₈ HPLC fractions of castor oil were used for mass spectrometry of the lithium adducts of acylglycerols to identify trihydroxy fatty acids and the acylglycerols containing trihydroxy fatty acids. Two DAG identified were triOH18:1–diOH18:1 and triOH18:0–OH18:1. Four TAG identified were triOH18:1–OH18:1–OH18:1, triOH18:0–OH18:1–OH18:1, triOH18:1–OH18:1–diOH18:1 and triOH18:0–OH18:1–diOH18:1. The structures of these two newly identified trihydroxy fatty acids were proposed as 11,12,13-trihydroxy-9-octadecenoic acid and 11,12,13-trihydroxyoctadecanoic acid. The locations of these trihydroxy fatty acids on the glycerol backbone were almost 100% at the sn-1,3 positions or at trace levels at the sn-2 position. The content of these acylglycerols containing trihydroxy fatty acids was at the level of about 1% or less in castor oil.     

1-O-alkyl-2,3-diacylglycerols in the skin surface lipids of the hairless mouse

A neutral lipid class was isolated by thin-layer chromatography from the skin surface lipids of the hairless mouse. The fraction migrated faster than triglycerides and had a migration rate similar to that of diacyl alkanediols (diester wax). Upon deacylation, however, the long-chain diols were identified as 1-alkylglycerol ethers based on their chromatographic properties and on the mass spectra of their nicotinylidene derivatives. Thus, the skin lipid fraction was identified as 1-O-alkyl-diacylglycerol. The alkyl moieties were all saturated and even-numbered and ranged in chainlength from C₁₆ to C₂₂ with 1-O-hexadecylglycerol amounting to 34% of the total glycerol ether moieties. The fatty acids derived from this lipid fraction were mostly monoenoic with chainlengths ranging from C₁₆ to C₂₄. The major acyl component was eicosenoic acid (20∶1) representing 61% of the total fatty acids.     

Comparative study of the molecular species of chloropropanediol diesters and triacylglycerols in milk fat

In an effort to establish the origin of the fatty acid esters of 3-chloropropanediol, which recently have been isolated in small amounts from goat milk, we compared the molecular species composition of the chlorohydrin diesters and of goat milk triacylglycerols. The chloropropanediol diesters were found to be composed of molecular species containing C₁₀−C₁₈ fatty acids and corresponded closely in carbon number to those calculated for the long chain sn-1,2-diacyl-glycerol moieties of goat milk triacylglycerols. The molecular species of goat milk total triacylglycerols contained C₄−C₁₈ fatty acids. It is suggested that triacylglycerols and chloropropanediol diesters are derived from the same pool of long chain fatty acids. A molecular distillate of bovine milk fat did not contain chloropropanediol diesters, while the available samples of human milk fat were shown to contain alkyldiacylglycerols as the major components of a neutral lipid fraction corresponding in polarity to the chloropropanediol diesters.     

Lipid composition of yoshida ascites hepatoma and of livers and blood plasma from host and normal rats

The lipid composition of Yoshida ascites hepatoma cells was analyzed together with that of ascitic plasma and of livers and blood plasma from host and normal rats. In comparison to normal livers, host livers showed no significant differences in the content of the various lipid classes, but contained a higher percentage of palmitic acid and a lower proportion of arachidonic acid in the major phospholipid classes. In addition, tumor growth induced a marked hypertriglyceridemia in host animals; changes in the concentration of other plasma lipid classes were not statistically significant. The ascitic plasma contained small amounts of lipids mainly constituted by cholesteryl esters and phospholipids. Yoshida hepatoma cells contained less phospholipids in comparison to both host and normal liver, while the increased level of triglycerides and the decrease of free fatty acids were not statistically significant. Hepatoma cells showed appreciable amounts of ether-linked lipids associated in part to neutral lipids (as glyceryl ether diesters) and, in part, to ethanolamine and choline phosphoglycerides. The alkyl groups in GEDE as well as in ethanolamine and choline phosphoglycerides were mainly constituted by C_16∶0 and C_18∶0 followed by C_18∶1. The alk-1-enyl groups in ethanolamine and choline phosphoglycerides were C_16∶0 and C_18∶0 with only a minor proportion of C_18∶1. In comparison to both host and normal liver, Yoshida hepatoma cells showed significant changes in the fatty acid composition of neutral lipids and phospholipids. Some of the major changes consisted of an increase of monoenoic acids associated with a decrease of arachidonic and docosahexaenoic acids in phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositol.     

Fatty acid composition of polar lipids in goats' milk

Silicic acid column chromatography was used to separate the polar lipids of goats' milk into glycolipid, phosphatidylethanolamine, phosphatidylserine plus phosphatidylinositol, phosphatidylcholine, and sphingomyelin fractions. Each fraction was purified by column chromatography and its fatty acid profile determined by gas liquid chromatography and mass spectrometry. The glycerophospholipids each contained 18∶1 as the predominant fatty acid (∼45%). The sphingolipids contained a high percentage of long-chain saturated fatty acids (C₂₂ to C₂₄>45%); the glycolipid fraction also contained ca. 2% 2-hydroxy fatty acids. The data represent a comprehensive cross-sectional study of the major polar lipids found in goats' milks.     

Distinctive medium chain wax esters,triglycerides, and diacyl glyceryl ethers in the head fats of the pacific beaked whale,Berardius bairdi

Lipids were extracted from the mandibular fat body (jaw), the fatty forehead (melon), and the dorsal blubber of a Pacific beaked whale (Berardius bairdi) and separated into lipid classes by preparative thin layer chromatography. The head fats were mixtures of wax esters and triglycerides with a very small amount of diacyl glyceryl ether. The blubber fat contained 97% was ester and 3% triglyceride. Gas liquid chromatography (GLC) of the intact lipid classes indicated an unusually low C₂₆–C₃₀ range for most of the jaw and melon wax esters compared to the more normal C₃₂–C₄₀ molecules found in the blubber. Distinctive lower molecular weight C₂₄–C₄₀ triglycerides occurred in the head fats vs. the usual C₄₄–C₅₈ range in the blubber. Most diacyl glyceryl ethers were in the C₃₅–C₄₆ range, below the molecular weight of hexadecyldipalmitoyl glyceryl ether (C₄₈). GLC of the derived fatty acid methyl esters showed that the lower molecular weight neutral lipids in the head fats were due to high levels of iso-10∶0, n−10∶0, iso-11∶0, iso-12∶0, n−12∶0, and iso-13∶0 acids. The wax ester fatty alcohols and the alkoxy chains of the glyceryl ethers were mostly the C₁₄–C₂₀ chain lengths commonly observed in marine organisms. The distinctive medium chain neutral lipids in the jaw and melon fats of this whale may be related to the postulated acoustical role of these tissues in echolocation.     

Molecular species of glycerophospholipids and sphingomyelins of human plasma: Comparison to red blood cells

In addition to diacyl glycerophosphocholine and sphingomyelin, human plasma also contains small amounts of other glycerophospholipids, which may have special metabolic function. The structure and origin of these minor plasma lipids has not been determined. Knowledge of the detailed composition of the phospholipids of red blood cells (Myheret al., Lipids 24, 1989) permits evaluation of one of the possible sources. This study reports the detailed analyses of plasma glycerophospholipids made in parallel to those of the erythrocyte lipids obtained from the same blood using HPLC and GLC methods. The proportions of the major phospholipid classes in the plasma and erythrocytes were similar to published values, including the essential absence of diradyl glycerophosphoserine from plasma. Plasma diradyl glycerophosphocholine contained 93.0% diacyl, 3.4% alkylkacyl and 3.6% alkenylacyl, whereas the diradyl glycerophosphoethanolamine consisted of 71.8% alkenylacyl, 19.9% diacyl and 8.3% alkylacyl subclasses. The diradyl glycerophosphoinositol was 100% diacyl. The content of the minor subclasses of plasma diradyl glycerophosphocholine is similar to that of the red cells, but the ether content of the diradyl glycerophosphoethanolamine is higher in plasma than in cells. The lipid ether subclasses of plasma glycerophospholipids also contained a higher proportion of the C₂₀, C₂₂ and C₂₄ alkyl and alkenyl chains than those of the cells. Furthermore, the C₁₆ and C₁₈-containing species in diradyl glycerophosphoethanolamine subclasses varied with the nature of the polyunsaturated acid, whereas in diradyl glycerophosphocholine subclasses the polyunsaturated acids were combined with the C₁₆ and C₁₈ acids in equal proportions. The significant differences in the molecular species of glycerophospholipids and sphingomyelin between plasma and red cells would appear to limit any direct transfer or equilibration of their lipid components.     

Studies on Mirabilis jalapa (Four O'clock Plant) Seed Oil

Mirabilis jalapa of Nyctaginaceae plant family yields 4–5% of fatty oil. The oil is investigated for its glycerides and fatty acid composition by gas liquid chromatography. The fatty acids in the seed oil constitute C_16:0, 18.3%;C_18:1,55.3%;C_18:2,11.5%;C_18:3,14.9%. The triglyceride components were also determined by separating the triglycerides according to their degree of unsaturation by means of thin-layer chromatography on silica gel impregnated with silver nitrate. The fatty acid composition of the different triglyceride fractions was determined. Moreover, the triglycerides were separated according to their carbon number by gas liquid chromatography.     

Fatty Acid Composition in Ergosteryl Esters and Triglycerides from the Fungus Ganoderma lucidum

Free and esterified ergosterols are detected almost solely in fungi and are often employed as a biomarker of living fungi. In this work, the fatty acid composition and δ¹³C values of major fatty acids in triglycerides and ergosteryl esters from the fungus Ganoderma lucidum were analyzed by gas chromatography–mass spectrometer and gas chromatography–isotopic ratio mass spectrometer, respectively. The results showed that the fatty acid profiles varied in triglycerides and ergosteryl esters. The percentage of saturated fatty acids in ergosteryl esters was remarkably higher than that in triglycerides, where C_18:1^Δ9c was the predominant fatty acid and constituted 61.26 % of the total fatty acids. In contrast, C_16:0 was the predominant fatty acid and constituted 71.88 % of the total fatty acids in ergosteryl esters. The study suggests that, after fungal death, free ergosterols in the cell membrane of the dead fungus were esterified with preferentially saturated fatty acids, mainly C_16:0, from triglycerides and then stored in lipid particles for a longer period while free ergosterol markedly decreased. The δ¹³C values of C_16:0, C_18:0, C_18:1 and C_18:2 in ergosteryl esters exhibit a pronounced depletion in ¹³C compared with that in triglycerides within the range of ?1.3 to ?0.9 ‰, supporting the above inference. It is again suggested that free ergosterol in the cell membrane should be used as an indicator of living fungi, and ergosteryl esters in the lipid particles should not be included in the measurement of living fungal biomass.     

Lipid composition of commercially canned single-strength orange juice

The lipid composition of commercially canned single-strength orange juice ranged from 84–101 mg/100 ml juice (overall mean 95 ± 6). Phospholipid phosphorus, expressed as mg/100 ml juice, showed a range of from 1.56–1.95, while phospholipid phosphorus/lipid values (as µg-P/mg lipid) were within a very narrow range, 18.9 ± 1.1. The percentage distribution of lipid classes in these juices was 24–35% neutral lipids, 18–23% resin acids and glycolipids, and 43–53% phospholipids and other polar lipids. Five fatty acids, i.e. C₁₆, C_16:1, C_18:1, C_18:2, and C_18:3, accounted for over 93% of all fatty acids. The relative percentages of C_18:2 and C_18:3 differed between seasonal juices. The lipid composition does not warrant inclusion in nutritional labeling; however, lipid levels may be useful in detecting adulteration.     

Identification of Acylglycerols Containing Dihydroxy Fatty Acids in Castor Oil by Mass Spectrometry

Ricinoleate, a monohydroxy fatty acid, in castor oil has many industrial uses. Dihydroxy fatty acids can also be used in industry. The C₁₈ HPLC fractions of castor oil were analyzed by electrospray ionization mass spectrometry of lithium adducts to identify the acylglycerols containing dihydroxy fatty acids and the dihydroxy fatty acids. Four diacylglycerols identified were diOH18:1-diOH18:1, diOH18:2-OH18:1, diOH18:1-OH18:1 and diOH18:0-OH18:1. Eight triacylglycerols identified were diOH18:1-diOH18:1-diOH18:1, diOH18:1-diOH18:1-diOH18:0, diOH18:2-diOH18:1-OH18:1, diOH18:1-diOH18:1-OH18:1, diOH18:1-diOH18:0-OH18:1, diOH18:2-OH18:1-OH18:1, diOH18:1-OH18:1-OH18:1 and diOH18:0-OH18:1-OH18:1. The locations of fatty acids on the glycerol backbone were not determined. The structures of these three newly identified dihydroxy fatty acids were proposed as 11,12-dihydroxy-9-octadecenoic acid, 11,12-dihydroxy-9,13-octadecadienoic acid and 11,12-dihydroxyoctadecanoic acid. These individual acylglycerols were at the levels of about 0.5% or less in castor oil and can be isolated from castor oil or overproduced in a transgenic oil seed plant for future industrial uses.     

Characteristics and Composition of Seeds and Oil of Couroupita guianensis Aubl. From Gujarat,India

The seeds of Couroupita guianensis Aubl. contain 32% oil and 19.0 % protein. The seed oil has iodine value of 126.1, saponification value of 185.7, peroxide value of 0.8 and acid value of 2.4. The fatty acid composition (wt%) as determined by gas liquid chromatography (GLC) is: C_8:0, 0.3; C_10:0, 1.5; C_12:0, 0.6;C_14;0,1.2;C_14:1,0.9;C_16:0,6.3;C_16:1,1.0;C_18:0,3.4;C_18:1,3.3 and C_18:2,81.5.