The positional distribution of fatty acids in the phospholipids and triglycerides ofMycobacterium smegmatis andM. bovis BCG

Position 1 of the phospholipid and triglyceride fractions isolated fromMycobacterium smegmatis andM. bovis BCG was esterified principally with C₁₈ related fatty acids (18∶0, 18∶1 and 19Br). Position 2 was occupied principally by C₁₆ fatty acids. The third position of the triglycerides was esterified with a preponderance of C₂₀+fatty acids. Seventysix per cent of position 3 fatty acids in BCG and 43% inM. smegmatis triglycerides contained fatty acids of greater than 20 carbon atoms.     

Synthesis and Surface Active Properties of Sulfonated Acrylate Esters Based on Al‐Cedre Oil

Sulfonated acrylate esters have been synthesized by using renewable raw materials such as fatty alcohols of Al‐Ceder oil. Mixed fatty acids were isolated from Al‐Ceder oil by hydrolysis; both saturated and unsaturated fatty acids were isolated from the mixed fatty acids. The methyl esters of mixed fatty acid, saturated and unsaturated acids of Al‐Cedre oil were subjected to reduction with (LiAlH4) to give the corresponding fatty alcohols. The products of the reduction process were saponified and the hydroxyl values were estimated to further confirm the reduction occurrence. The acrylate esters were synthesized by esterification of acrylic acid with fatty alcohols of C_16:0, C_18:0, C_18:1, and C_18:2 mixed saturated, mixed unsaturated and mixed fatty acids of Al‐Cedre oil, respectively. This esterification was followed by addition of NaHSO₃ to form bisulfite adducts. The structures of the prepared surfactants were characterized by IR and ¹HNMR spectroscopy. A series of useful surface parameters, stability towards acids and base hydrolysis and calcium stability have been determined.     

Molecular Species of Phospholipids with Very Long Chain Fatty Acids in Skin Fibroblasts of Zellweger Syndrome

The ratio of C_26:0/C_22:0 fatty acids in patient lipids is widely accepted as a critical clinical criterion of peroxisomal diseases, such as Zellweger syndrome and X-linked adrenoleukodystrophy (X-ALD). However, phospholipid molecular species with very long chain fatty acids (VLCFA) have not been precisely characterized. In the present study, the structures of such molecules in fibroblasts of Zellweger syndrome and X-ALD were examined using LC–ESI–MS/MS analysis. In fibroblasts from Zellweger patients, a large number of VLCFA-containing molecular species were detected in several phospholipid classes as well as neutral lipids, including triacylglycerol and cholesteryl esters. Among these lipids, phosphatidylcholine showed the most diversity in the structures of VLCFA-containing molecular species. Some VLCFA possessed longer carbon chains and/or larger number of double bonds than C_26:0-fatty acid (FA). Similar VLCFA were also found in other phospholipid classes, such as phosphatidylethanolamine and phosphatidylserine. In addition, VLCFA-containing phospholipid species showed some differences among fibroblasts from Zellweger patients. It appears that phospholipids with VLCFA, with or without double bonds, as well as C_26:0-FA might affect cellular functions, thus leading to the pathogenesis of peroxisomal diseases, such as Zellweger syndrome and X-ALD.     

Neutral lipids of chickpea flour and protein isolates

The neutral lipids composition of defatted chickpea flour and two types of protein isolates has been studied. The main compounds in neutral lipids are triacylglycerols, free fatty acids, and diacylglycerols. Other compounds present are wax esters, free fatty alcohols, and free sterols. The main fatty acids in neutral lipids are C_18:2 and C_18:1 among the unsaturated, and C_16:0 and C_18:0 among the saturated acids. Free and esterified alcohols range from C_16:0 to C_28:0, the majority being those with an even number of carbon atoms. Sterols observed are β-sito-sterol, campesterol, stigmasterol, and δ-5-avenasterol. Triacyl-glycerols are partially hydrolyzed, and the amounts of unsaturated sterols and unsaturated fatty acids are reduced as a result of the chemical treatment during production of the protein isolates.     

Fatty Acid Specificity of Candida cylindracea Lipase

Candida cylindracea lipase (SIGMA) was tested against triglycerides (TG) and wax esters (WE) of marine origin as substrates. Under the same conditions, wax esters were hydrolysed at a lower rate than the triglycerides. The C₁₄ to C₁₈ saturated and monounsaturated fatty acids were preferentially hydrolysed whereas the longer chain monoenes (20:1 and 22:1) and particularly the polyunsaturated fatty acids (18:4,20:5 and 22:6) were resistant to the hydrolysis in triglycerides as well as in wax esters. No specificity was demonstrated for the fatty alcohols in the wax esters.     

Stable isotope characterization of olive oils. I—Compositional and carbon-13 profiles of fatty acids

Nearly 200 olive oils produced in the Mediterranean basin, mainly in Greece, during 4 yr from 1993 to 1996, were studied by gas chromatography (GC) and on-line GC-isotope ratio mass spectrometry (GC-C-IRMS). The composition of the oils in the more abundant fatty acids (C_16:0, C_16:1, C_18:0, C_18:1, C_18:2, and C_18:3) was obtained by GC after transesterification of the triglycerides into methyl esters. Using the hyphenated GC-C-IRMS technique, the ¹³C contents of the three most abundant acids, C_16:0, C_18:1, and C_18:2, were measured with satisfactory accuracy. The results, analyzed in terms of geographical, temporal, and botanical factors, provide new criteria for the authentication of olive oils.     

The composition of beeswax alkyl esters

The alkyl esters of beeswax, after isolation from the unhydrolyzed wax by preparative layer chromatography (PLC), have been analyzed directly by high temperature GLC using 1.5% OV1 as liquid phase. In two commercial wax samples examined the ester homologues are predominantly even carbon numbered ranging from C₃₆ to C₅₄. The principal alkyl esters are C₄₀, C₄₂, C₄₄, C₄₆ and C₄₈. The GLC analysis of the ester hydrolysis products revealed that the variations in ester chain length are produced by variations in the esterified primary alcohol chain lengths. The esterified fatty acid is chiefly hexadecanoic acid. The esterified fatty acids differ in composition from the free fatty acids which are also present in the wax.     

Glyceride structure ofCardamine impatiens L. Seed oil

A group of unusual triglycerides, in which one of the acyl groups is a vicinal dihydroxy acid with one of the hydroxyl groups acetylated, has been isolated fromCardamine impatiens L. (Cruciferae) seed oil. Hydrolysis of these triglycerides with castor bean lipase facilitated isolation and identification of a mixture of C₁₈, C₂₀, C₂₂, and C₂₄ hydroxy acetoxy fatty acids. Pancreatic lipase hydrolysis data revealed that these monoacetylated dihydroxy acid residues are esterified exclusively with one of the α-positions of the glycerol moiety. The remaining acyl groups are comprised of ordinary C₁₈ unsaturated acids (which occupy 98% of the β-position), palmitic acid, and C₂₀, C₂₂, and C₂₄ monoenoic fatty acids. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Trans-6-hexadecenoic acid and the corresponding alcohol in lipids in the sea anemoneMetridium dianthus

Trans-6-hexadecenoic acid was found in polar lipids, triglycerides, was esters and diacylglyceryl ethers of the sea anemoneMetridium dianthus from Passamaquoddy Bay. The corresponding alcomaquoddy Bay. The corresponding alcohol also apparently occurs in the wax esters of this species. The long-chain (C₂₀, C₂₂) monoethylenic alcohols reported for other species of sea anemones from neighboring waters were absent and the major alcohol and glyceryl ether chain both had 16∶0 structures. The isomers of C₁₈ and C₂₀ monoethylenic fatty acids in polar lipids and triglycerides were unusual in their high proportion of theω ₇ isomer. These two lipids also contained higher proportion of the polyunsaturated fatty acids than the others.     

Medium-chain fatty acid-rich glycerides by chemical and lipase-catalyzed polyester-monoester interchange reaction

Medium-chain triglycerides (MCT) that contain caprylic acid (C_8:0) and capric acid (C_10:0) have immense medicinal and nutritional importance. Coconut oil can be used as a starting raw material for the production of MCT. The process, based on the interchange reaction between triglycerides and methyl esters of medium-chain fatty acids by chemical catalyst (sodium methoxide) or lipase (Mucor miehei) catalyst, appears to be technically feasible. Coconut oils with 25–28.3% (w/w) and 22.1–25% (w/w) medium-chain fatty acids have been obtained by chemical and lipase-catalyzed interchange reactions. Coconut olein has also been modified with C_8:0 and C_10:0 fatty acids, individually as well as with their mixtures, by chemical and lipase-catalyzed interchange reactions. Coconut olein is a better raw material than coconut oil for production of mediumchain fatty acid-rich triglyceride products by both chemical and lipase-catalyzed processes.     

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.     

Molecular analysis of intact preen waxes of Calidris canutus (Aves: Scolopacidae) by gas chromatography/mass spectrometry

The intact preen wax esters of the red knot Calidris canutus were studied with gas chromatography/mass spectrometry (GC/MS) and GC/MS/MS. In this latter technique, transitions from the molecular ion to fragment ions representing the fatty acid moiety of the wax esters were measured, providing additional resolution to the analysis of wax esters. The C₂₁−C₃₂ wax esters are composed of complex mixtures of hundreds of individual isomers. The odd carbon-numbered wax esters are predominantly composed of even carbon-numbered n-alcohols (C₁₄, C₁₆, and C₁₈) esterified predominantly with odd carbon-numbered 2-methyl fatty acids (C₇, C₉, C₁₁, and C₁₃), resulting in relatively simple distributions. The even carbon-numbered wax esters show a far more complex distribution due to a number of factors: (i) Their n-alcohol moieties are not dominated by even carbon-numbered n-alcohol moieties are not dominated by even carbon-numbered n-alcohols esterified with odd carbon-numbered 2-methyl fatty acids, but odd and even carbon-numbered n-alcohols participate in approximately equal amounts; (ii) odd carbon-numbered methyl-branched alcohols participate abundantly in these wax ester clusters; and (iii) with increasing molecular weight, various isomers of the 2,6-, 2,8-, and 2,10-dimethyl branched fatty acids also participate in the even carbon-numbered wax esters. The data demonstrate that there is a clear biosynthetic control on the wax ester composition although the reasons for the complex chemistry of the waxes are not yet understood.     

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.     

Über die Zusammensetzung des Samenöles aus Traubenholunder (Sambucus racemosa L.)

Composition of the Seed Oil of Clustered Elder (Sambucus racemosa L.) The seeds of clustered elder (Sambucus racemosa L.) contain 28% of an oil. Its separation to groups of components was carried out by adsorption chromatography. Single groups of substances were further analysed by TLC and GLC in combination with physico-chemical methods (IR and MS). Thus the following substances were found and identified: n-alkanes (C₁₇–C₃₃), 2-methyl- and 3-methylalkanes, squalene, a mixture of esters, triglycerides, β-sitosterol, campesterol and a mixture of diglycerides. The conditions for the separation of esters by silica gel column chromatography were also found. The mixture of esters was thus separated into a group of aliphatic wax esters (C₃₄–C₄₄) and four groups of esters of steroidal alcohols (mainly β-sitosterol and campesterol) with aliphatic unsaturated acids (predominantly C_18:1, C_18:2 and C_18:3). In the triglycerides representing the main fraction of the oil (93%), the acids C_16:0, C_18:1, C_18:2 and C_18:3 are present. The same acids were also found in diglycerides.     

The fatty acid composition of clothes soil

Summary Organic soil that had gradually accumulated on cotton garments and was unremovable by normal washing procedures was analyzed for free and combined fatty acids by gas-liquid chromatography. The fatty acid composition of this material was similar to sebum and hair fat and was remarkably uniform although from several different sources and geographical locations. The predominant fatty acids were C₁₅, C₁₆, and C₁₈ straight-chain acids. More than 30% of the total fatty acid was palmitic acid. The amount of oleic acid was considerably less than is reported for hair and skin fat. No linoleic acid or linolenic acid was detected. The small amount of unsaturated acids is probably the result of their oxidation to polymers and other oxidation products. The amount of free fatty acids was very small because they were converted to insoluble heavy metal soaps. Most of the combined fatty acids were present as esters,i.e., triglycerides.     

Modification of goat milk fat triglycerides by immobilized lipase

The lipid fraction of goat milk was subjected to transesterification using a commercially available immobilized lipase to decrease the amount of short- and medium-chain fatty acids (C₄–C₁₄) by enrichment of the reaction mixture with long-chain (C_18:1 and C_18:2) fatty acids. Aliquots were taken during, transesterification at different reaction times and analyzed for triglycerides and their fatty acid components. The gas chromatographic analyses of triglycerides (previously isolated by thinlayer chromatography) showed that at 6 h reaction under the experimental conditions led to the greatest reduction of the low molecular weight triglycerides (C₂₂–C₃₈) and concomitantly to the greatest increase in the higher molecular weight triglycerides (C₄₈–C₅₄). These changes correlated with the variations observed in the fatty acids of the triglyceride fraction.     

Lipid Studies of Pimpinella acuminata

The seed oil of Pimpinella acuminata species of the family Umbelli-ferae was extracted with chloroform : methanol (2:1) for the separation of different classes of lipids as hydrocarbons (1.7%), sterol esters (traces), triglycerides (74.1%), free fatty acids (6.6%), 1,3-diglycerides (1.6%), 1,2-diglycerides (1.6%), sterols (1.8%), mono-glycerides (2.0%), phosphatidyl ethanolamine (0.8%), phosphatidyl choline (1.2 %), lyso phosphatidyl ethanolamine (0.4%), phosphatidyl inositol (1.2%) and unknown (7.0%). The fatty acids as determined by application of gas liquid chromatography is C₁₀-C₂₂, whereas C_16:0, C_18:0-C_18:2 and C_18:2 are predominantly present in all polar and non-polar lipid classes.     

The Content and Composition of Total,Free, and Esterified Sterols of Lotus Plumule Oil by GC–MS/FID

This study investigated the content and composition of total, free, and esterified sterols of three varieties of lotus plumule oil (Hunan lotus, Jiangxi lotus, and Fujian lotus) using GC–MS/FID. The fatty acid composition of sterol fatty acid esters (SFAE) was also analyzed and compared with that of triglycerides. Results showed that total sterol of lotus plumule oil (12.10–14.21 g/100 g) was higher than that of other plant oils (corn germ oil, 1.11 g/100 g; rapeseed oil, 0.78 g/100 g). No significant difference was found among the total sterol contents of the three types of lotus plumule oils (p > 0.05). Most sterol existed in ester forms (81.8–89.1%) rather than in free forms (8.4–10.1%). β‐Sitosterol (71.4–73.4%), and campesterol (6.2–7.5%) were the predominant fractions of free sterols. β‐Sitosterol (41.3–53.7%) and ?5‐avenasterol (27.1–31.1%) were the predominant fractions of esterified sterols, followed by campesterol (12.1–13.0%) and ?7‐avenasterol (3.4–3.7%). Linoleic acid (63.6–65.8%), oleic acid (8.3–10.4%), and behenic acid (9.0–9.9%) were the main fatty acids of SFAE, which were different from those of triglycerides. The results from this study suggest that lotus plumule oil may be a good resource of SFAE and can be used as a supplemental ingredient in functional foods.     

θ3 fatty acids in freshwater fish from south brazil

Lipid and fatty acid levels in the edible flesh of 17 freshwater fish from Brazil’s southern region were determined. Analyses of fatty acid methyl esters were performed by gas chromatography. Palmitic acid (C_16:0) was the predominant saturated fatty acid, accounting for 50–70% of total saturated acids. Oleic acid (C_18:1θ9) was the most abundant monounsaturated fatty acid. Linoleic acid (C_18:2θ6), linolenic acid (C_18:3θ3), and docosahexaenoic acid (C_22:6θ3) were the predominant polyunsaturated fatty acids (PUFA). The data revealed that species such as truta, barbado, and corvina were good sources of eicosapentaenoic acid (C_20:5θ3) and docosahexaenoic acid (C_22:6θ3), and that most freshwater fish examined were good sources of PUFA θ3.     

Characterization of skin-surface lipids from the monkey (Macaca fascicularis)

Skin-surface lipids from the monkeyMacaca fascicularis are composed of sterol esters (38%), cholesterol (4%) and two types of wax diesters, identified as Type II (IIa and IIb, 17% and 40%, respectively). Type IIa contained diesters of 1,2-alkanediols esterified with two molecules of long-chain (C₁₄−C₃₄) fatty acids having straight and branched chains. In the diesters IIa, fatty acids shorter than C₁₉ predominated in position 1, and fatty acids longer than C₂₀ predominated in position 2. Type IIb contained diesters of 1,2-alkanediols esterified with C₄ and C₅ branched-chain fatty acids (predominantly isovaleric acid) at position 1 and long-chain (C₁₄−C₂₇) acids, having straight and branched chains, at position 2. The shortchain acids were converted to 2-nitrophenylhydrazides and analyzed by high-performance liquid chromatography (HPLC). Ammonia chemical ionization (CI)-gas chromatography (GC)-mass spectrometry (MS) resolved the intact diesters IIb into 12 peaks corresponding to molecular weights ranging from 597 to 748, and showed that the molecular species, such as C₂₁−C₁₆−C₅ (diol, fatty acid in position 2, fatty acid in position 1), C₂₂−C₁₆−C₅ and C₂₃−C₁₆−C₅, were prevalent. The fatty acids from both diesters were mostly (>98%) saturated. The 1,2-alkanediols from both diesters consisted of C₁₆−C₂₆ saturated straight- and branched-chain components. The acyl groups of sterol esters contained 86% C₁₄−C₃₄ branched-chain acids. The unsaturated fatty acids (5.4%) belonged to a straight-chain monoenoic series having extremely long chains (C₁₈−C₃₄). The branched-chain structures in the fatty acids and diols were iso and anteiso. These results show the species-specific profile for the skin-surface lipid synthesis.