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.     

Positional analysis and determination of triacylglycerol structure ofArgania spinosa seed oil

The distribution of fatty acids between the sn-1, sn-2 and sn-3 positions of triacylglycerols fromArgania spinosa seed oil of Morocco has been determined. Saturated fatty acids showed a preference for external positions. The sn-1 position contained slightly more palmitic acid than the sn-3 position, whereas stearic acid was preferentially esterified at the sn-3 position. Linoleic acid occurred predominantly in the sn-2 position with lesser amount evenly distributed between the sn-1 and the sn-3 positions, as generally found in vegetable oils. Oleic acid was distributed with a slight preference shown for the internal position, whereas the distribution between the external positions revealed a slight preference for the sn-1 position. The distribution of the triacylglycerols determined from high-performance liquid chromatography (HPLC) is at variance with that calculated from the 1-random 2-random 3-random distribution theory. This is particularly true for trioleoyl and trilinoleoylglycerols. In contrast, the agreement between theory and experiment is good for triacylglycerols containing two oleoyl and one linoleoyl chains, one oleoyl, one linoleoyl and one palmitoyl chains or one oleoyl, one palmitoyl, and one stearoyl chains.     

Stereospecific analysis of glycerolipids of egg yolk of Japanese quail (Coturnix coturnix japonica)

Phosphatidylcholine, phosphatidylethanolamine and triacylglycerol were isolated from egg yolk of the Japanese quail. Fatty acid compositions at the two and three positions of glycerol in the glycerolipids were determined by stereospecific analysis employing phospholipase A₂. The distribution of the total number of carbon atoms in the fatty acid moieties of triacylglycerol was also quantitated by high temperature gas liquid chromatography. The distribution of acyl groups in each of the positions of the phosphatidylcholine, phosphatidylethanolamine and triacylglycerol was not random, and each position has a characteristic composition. The phosphatidylcholine and phosphatidylethanolamine had distinctive fatty acid distributions for positionsn-2 of the triacylglycerol had a predominance of unsaturated fatty acids of which 18∶1 (69.9%) was the major component. Positionsn-3 contained 49.3% saturated fatty acids and was more saturated than positionsn-1 by 8.1%. The experimentally determined distribution of the carbon numbers in triacyl glycerol deviated significantly from the distribution predicted by 1-random-2-random-3-random association of the fatty acids. The data suggest that in Japanese quail there is marked preferencial synthesis of some triacylglycerols.     

Studies of triacyglycerol structure of very low density lipoproteins of normolipemic subjects and patients with type III and type IV hyperlipoproteinemia

The triacylglycerols of very low density lipoproteins (VLDL-TG) were analyzed in samples from normal subjects and patients with Frederickson’s Type III and Type IV hyperlipoproteinemia. VLDL were obtained by conventional ultracentrifugation, and the triacylglycerols were isolated by thin-layer chromatography (TLC). Representative sn-1,2(2,3)- and sn-1,3-diacylglycerols were generated by Grignard degradation of the triacylglycerols, and were resolved by TLC on borate-treated silica gel. The molecular association of the fatty acids in the diacylglycerol moieties was determined by gasliquid chromatography with mass spectrometry (GC/MS) of the tertiary-butyldimethylsilyl ethers. The positional distribution of the fatty acids was established by the Brockerhoff stereospecific analysis. The results showed a marked asymmetry in the distribution of the fatty acids in all samples, with the saturated acids predominantly in the sn-1-position and the unsaturated fatty acids distributed about equally between the sn-2- and sn-3-positions. In all instances, the molecular species composition of the sn-1,2-, sn-2,3- and sn-1,3-diacylglycerols was found to be similar to that calculated for 1-random 2-random 3-random distribution of triacylglycerols. There were marked differences in the quantitative composition of the molecular species of the VLDL-TG between normal subjects and patients, but these discrepancies were attributed to differences in the fatty acid composition of the samples.     

Positional distribution on n−3 fatty acids in triacylglycerols from rat adipose tissue during fish oil feeding

The present study was designed to investigate the metabolism of the n−3 olyunsaturated fatty acids (PUFA) in adipose tissue and its dependence upon dietary factors. Changes in the positional distribution of the fatty acids in triacylglycerols from retroperitoneal adipose tissue were studied as a function of time on rats fed for 4 wk a diet enriched with fish oil. The stereospecific analysis of triacylglycerols was based on random formation ofrac-1,2-diacylglycerols by Grignard degradation. This was followed by synthesis ofrac-phosphatidic acids and treatment with phospholipase A₂. In the triacylglycerols of the fish oil diet, 57% of the total n−3 fatty acids were in position 3,i.e., two-thirds of 22∶5n−3 and 22∶5n−3 were esterified insn-3 position, whereas 22∶6n−3 was equally distributed in positions 2 and 3. After 4 wk of feeding fish oil, the fatty acid composition of adipose tissue triacylglycerols reached a steady state. Half of the n−3 fatty acids were found in position 3, namely 75% of 22∶5n−3, 50% of 20∶5n−3 and 18∶4n−3 and 45% of 22∶6n−3, the latter being equally distributed in positions 2 and 3. This pattern of distribution resembled that found in triacylglycerols of the fish oil diet, except for a higher proportion of 20∶5n−3 in adipose tissue in position 1 at the expense of position 3. Throughout the 4-wk period of fish oil feeding, the distribution pattern of minor n−3 fatty acids (18∶4n−3 and 22∶5n−3) in adipose tissue triacylglycerols remained unchanged. On the other hand, at the onset of fish oil feeding, 20∶5n−3 and 22∶6n−3 became concentrated in position 3, but thereafter 20∶5n−3 was progressively incorporated into position 1 and 22∶6n−3 into position 2. We thus conclude that n−3 fatty acids are differentially esterified in triacylglycerols of white adipose tissue. Despite the complex sequence of hydrolysis and acylation steps involved, the positional distribution of n−3 fatty acids was found to be similar in both the fish oil diet and the stored fat, in contrast to what was observed for nonessential fatty acids.     

Comparative studies of triacylglycerol structure of very low density lipoproteins and chylomicrons of normolipemic subjects and patients with type II hyperlipoproteinemia

The triacylglycerols of very low density lipoproteins (VLDL) and of chylomicrons were analyzed in the fasting and postabsorptive states from normolipemic subjects and patients with Frederickson's Type II hyperlipoproteinemia, who subsisted on free choice diets, standard diets excluding lard, or were given a breakfast enriched in lard. The VLDL and chylomicrons were obtained by conventional ultracentrifugation, and the triacylglycerols were isolated by thin-layer chromatography (TLC). Representative sn-1,2, 2n-2-3- and sn-1,3-diacylglycerols were generated by partial Grignard degradation of the triacylglycerols and a stereospecific hydrolysis by phospholipase C of the mixed sn-1,2(2,3)-diacyl phosphatidylcholines prepared as intermediates. Representative sn-2-acylglycerols were obtained by hydrolysis with pancreatic lipase. Positional distribution of the fatty acids was established by subtracting in turn the fatty acid composition of the sn-2-position from the fatty acid composition of the sn-1,2- and sn-2,3-diacylglycerols. The molecular association of the fatty acids in the diacylglycerol moieties was determined by gas-liquid chromatography with mass spectrometry (GC/MS) of the tertiary-butyldimethylsilyl (t-BDMS) ethers. The molecular association of the fatty acids in the triacylglycerols was determined by 1-random 2-random 3-random calculation following experimental validation of the distribution. The results confirm a marked asymmetry in the positional distribution of the fatty acids in all triacylglycerol samples, with the palmitic acid predominantly in the sn-1-position, the unsaturated acids about equally divided between the sn-2-and sn-3-positions, and the stearic acid divided about equally between the sn-1- and sn-3-positions. The overall structure of the VLDL and chylomicron triacylglycerols from patients and control subjects was characterized by a noncorrelative distribution of fatty acids under all dietary conditions.     

Milk fat structure of a patient with type 1 hyperlipidemia

Structural analyses were performed on milk fat samples obtained 3–10 days postpartum from a lactating patient with primary Type 1 hyperlipidemia. The milk triacylglycerols contained 3–7% C₁₀, 14–21% C₁₂, 20–30% C₁₄, 22–26% C₁₆ and 20–30% C₁₈ (largely oleic) acids. Gas liquid chromatographic (GLC) analyses of the X-1,3- and X-1,2-diacylglycerols on polar siloxane columns showed a markedly non-random association of acyl chains. Stereospecific analyses indicated that the short chain length fatty acids were confined essentially to the sn-3-position of the triacylglycerol molecule. Furthermore, these acids were largely absent from the phosphatidylcholines and the endogenous sn-1,2-diacylglycerols of the milk fat. It is concluded that the short chain fatty acids are incorporated into the milk triacylglycerols during the final stage of biosynthesis via the phosphatidic acid pathway, and that the overall fatty acid distribution is consistent with the 1-random 2-random 3-random hypothesis.     

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.     

Polyunsaturated fatty glyceride syntheses by microbial lipases

The degree of glyceride syntheses by lipase TOYO (Chromobacterium viscosum) and lipase OF (Candida cylindracea) using individual free fatty acids C_18∶1, C_18∶2, C_18∶3, C_18∶4, C_20∶4, C_20∶5 and C_22∶6 were compared. Lipase TOYO incorporated each of the fatty acids into glycerol at levels of greater than 89%. Lipase OF incorporated most of the fatty acids at levels above 70% (docosahexaenoic acid incorporation was 63%). It was concluded that these two lipases are feasible for producing glycerides from unsaturated fatty acids.     

Δ5-Olefinic acids in the seed lipids from four Ephedra species and their distribution between the α and β positions of triacylglycerols. Characteristics common to coniferophytes and cycadophytes

The fatty acid compositions of the seed lipids from four Ephedra species, E. nevadensis, E. viridis, E. przewalskii, and E. gerardiana (four gymnosperm species belonging to the Cycadophytes), have been established with an emphasis on Δ5-unsaturated polymethylene-interrupted fatty acids (Δ5-UPIFA). Mass spectrometry of the picolinyl ester derivatives allowed characterization of 5,9- and 5,11–18∶2; 5,9,12–18∶3; 5,9,12,15–18∶4; 5,11–20∶2; 5,11,14–20∶3; and 5,11,14,17–20∶4 acids. Δ5-UPIFA with a Δ11-ethylenic bond (mostly C₂₀ acids) were in higher proportions than δ5-UPIFA with a δ9 double bond (exclusively C₁₈ acids) in all species. The total δ5-UPIFA content was 17–31% of the total fatty acids, with 5, 11, 14–20∶3 and 5, 11, 14, 17–20∶4 acids being the principal δ5-UPFIA isomers. The relatively high level of cis-vaccenic (11–18∶1) acid found in Ephedra spp. seeds, the presence of its δ5-desaturation product, 5, 11–18∶2 acid (proposed trivial name: ephedrenic acid), and of its elongation product, 13–20∶1 acid, were previously shown to occur in a single other species, Ginkgo biloba, among the approximately 170 gymnosperm species analyzed so far. Consequently, Ephedraceae and Coniferophytes (including Ginkgoatae), which have evolved separately since the Devonian period (≈300 million yr ago), have kept in common the ability to synthesize C₁₈ and C₂₀ δ5-UPIFA. We postulate the existence of two δ5-desaturases in gymnosperm seeds, one possibly specific for unsaturated acids with a δ9-ethylenic bond, and the other possibly specific for unsaturated acids with a δ11-ethylenic bond. Alternatively, the δ5-desaturases might be specific for the chain length with C₁₈ unsaturated acids on the one hand and C₂₀ unsaturated acids on the other hand. The resulting hypothetical pathways for the biosynthesis of δ5-UPIFA in gymnosperm seeds are only distinguished by the position of 11–18∶1 acid. Moreover, ¹³C nuclear magnetic resonance spectroscopy of the seed oil from two Ephedra species has shown that δ5-UPIFA are essentially excluded from the internal position of triacylglycerols, a characteristic common to all of the Coniferophytes analyzed so far (more than 30 species), with the possibility of an exclusive esterification at the sn-3 position. This structural feature would also date back to the Devonian period, but might have been lost in those rare angiosperm species containing δ5-UPIFA.     

Fatty acid composition at the 2-position of ether-linked and diacyl ethanolamine and choline phosphoglycerides of human brain tumors

The acyl composition of ethanolamine and choline phosphoglycerides from a series of human brain tumors was determined and compared to that of normal human gray matter. Six glioblastomas, one astrocytoma, one oligodendroglioma, and one meningioma were analyzed. The total fatty acid composition of ethanolamine phosphoglycerides generally had a higher percentage of 18∶1, 18∶2ω6, and 22∶5ω3 and a lower percentage of 22∶6ω3 than that of normal gray matter. Choline phosphoglycerides from the tumors also contained a higher than normal percentage of 18∶2ω6. Separate analysis of the acyl groups at the 2 position of the diacyl and ether-linked components of the phosphoglycerides revealed that the diacyl component of ethanolamine phosphoglyceride from the tumors had lower than normal amount of 22∶6ω3 and a higher than normal amount of 18∶1 and 18∶2ω6. The acyl composition of ether-linked ethanolamine phosphoglycerides genearally contained a higher percentage of 20∶4ω6 and a lower percentage of 18∶1 compared to the corresponding fraction from normal gray matter. The astrocytoma analyzed had fatty acid profiles similar to those of the control with the exception of a greater 18∶2ω6 content. These data demonstrate that the composition of the acyl moiety at the 2 position of diacyl and ether-linked phosphoglycerides of brain tumors differs from the corresponding component from normal gray matter and that the ether-linked ethanolamine phosphoglycerides provide an important pool of polyunsaturated fatty acids from brain tumor phospholipids.     

Incorporation of n−3 fatty acids of fish oil into tissue and serum lipids of ruminants

This study examines the biohydrogenation and utilization of the C₂₀ and C₂₂ polyenoic fatty acids in ruminants. Eicosapentaenoic (20∶5n−3) and docosahexaenoic (22∶6n−3) acids were not biohydrogenated to any significant extent by rumen microorganisms, whereas C₁₈ polyenoic fatty acids were extensively hydrogenated. The feeding of protected fish oil increased the proportion of 20∶5 from 1% to 13–18% and 22∶6 from 2% to 7–9% in serum lipids and there were reductions in the proportion of stearic (18∶0) and linoleic (18∶2) acids. The proportion of 20∶5 in muscle phospholipids (PL) increased from 1.5% to 14.7% and 22∶6 from 1.0% to 4.2%; these acids were not incorporated into muscle or adipose tissue triacylglycerols (TAG). In the total PL of muscle, the incorporated 20∶5 and 22∶6 substituted primarily for oleic (18∶1) and/or linoleic (18∶2) acid, and there was no consistent change in the porportion of arachidonic (20∶4) acid.     

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.     

Composition and structure of triacylglycerols in brown adipose tissue of rats fed fish oil

This study examines the incorporation of highly unsaturated n−3 fatty acids (HUFA) into triacylglycerols (TAG) of brown adipose tissue (BAT), and their effect on the positional distribution of saturated (SFA) and of unsaturated (UFA) 16- or 18-carbon fatty acids. To this end, rats were fed a fish oil diet for up to four weeks. The stereospecific analysis of TAG was based on generation ofsn-1,2- andsn-2,3-acylglycerols by Grignard degradation, followed by synthesis of phosphatidic acid and specific hydrolysis with phospholipase A₂. From the end of the first week of fish oil feeding, a steady-state in the fatty acid composition of TAG in BAT was reached. HUFA concentration increased 30-fold, mainly at the expense of n−9 UFA and of SFA. The amount of SFA decreased selectively at position 3, where these fatty acids were progressively replaced by n−3 HUFA. By contrast, the amount of UFA decreased at all positions, and their positional distribution was not affected. About 60% of HUFA was incorporated at position 3. Nearly twice as much 22∶6n−3 was incorporated into TAG than had been previously observed in white adipose tissue (WAT) [Leray, C., Raclot, T., and Groscolas, R. (1993)Lipids 28, 279–284]. At the steady-state, the distribution of HUFA was characterized by high proportions of 22∶6n−3 and 20∶5n−3 in position 3. Moreover, in each position of TAG, a steady level was reached rapidly (within 1 wk). It is concluded that, during fish-oil feeding, fatty acids in TAG of BAT show characteristic time-course changes that lead to a characteristic composition and a tissue-specific positional distribution. This suggests that adipose tissue has its own specificity in controlling the build-up of TAG stores, which is likely to be regulated by the specificity of acylating enzymes as well as molecular rearrangements.     

Positional analyses of triacylglycerol fatty acids in the milk fat of the antarctic fur seal (Arctocephalus gazella)

The positional distribution of fatty acids has been determined for the milk triacylglycerols of the Antarctic fur seal,Arctocephalus gazella. Of particular interest was the positional distribution of the polyunsaturated n−3 fatty acids in milk triacylglycerols (TG). In adipocytes of pinnipeds, TG are synthesized with the n−3 fatty acids primarily in thesn-1,3 positions. To determine the positional distribution, extracts of enzymatically digested lipids were separated by thin-layer chromatography, and the constituent fatty acids were separated and quantified by gas-liquid chromatography. Monoenoic and saturated fatty acids comprised over 75% of the total, the ratio of monoenoic to saturated fatty acids being 2∶1. The percent content of the long-chain n−3 fatty acids, 20∶5, 22∶5 and 22∶6, ranged between 15–20%. The positional analyses revealed that at thesn-2 position of milk TG, saturated fatty acids were in excess (57%), and the content of n−3 fatty acids was less than 5%. More than 80% of the n−3 fatty acids in milk were located in thesn-1,3 positions. The data indicate that in pinnipeds TG are synthesized in the mammary gland and adipose tissue with fatty acids having similar positional distributions.     

Evidence that palmitic acid is absorbed assn-2 monoacylglycerol from human milk by breast-fed infants

Milk fatty acids consist of about 20–25% palmitic acid (16∶0), with about 70% of 16∶0 esterified to thesn-2 position of the milk triacylglycerols. Hydrolysis of dietary triacylglycerols by endogenous lipases producessn-2 monoacylglycerols and free fatty acids, which are absorbed, reesterified, and then secreted into plasma. Unesterified 16∶0 is not well absorbed and readily forms soaps with calcium in the intestine. The positioning of 16∶0 at thesn-2 position of milk triacylglycerols could explain the high coefficient of absorption of milk fat. However, the milk lipase, bile salt-stimulated lipase, has been suggested to complete the hydrolysis of milk fat to free fatty acids and glycerol. These studies determined whether 16∶0 is absorbed from human milk assn-2 monopalmitin by comparison of the plasma triacylglycerol total andsn-2 position fatty acid composition between breast-fed and formula-fed term gestation infants. The human milk and formula had 21.0 and 22.3% of 16∶0, respectively, with 54.2 and 4.8% 16∶0 in the fatty acids esterified to the 2 position. The plasma triacylglycerol total fatty acids had 26.0±0.6 and 26.2±0.6% of 16∶0, and thesn-2 position fatty acids had 23.3±3.3 and 7.4±0.7% of 16∶0 in the three-month-old exclusively breast-fed (n=17) and formula-fed (n=18) infants, respectively. Marked differences were found in the plasma total and the 2 position phospholipid percentage of 20∶4ω6, i.e., 11.6±0.3 and 6.9±0.6 (total), 17.7±1.4 and 9.7±0.6 (sn-2 position) and percentage of 22∶6ω3, 4.6±0.3 and 2.1±0.3 (total), 5.6±0.6 and 2.0±0.2 (sn-2 position) for the breast-fed and formula-fed infants, respectively. These studies provide convincing evidence that 16∶0 is absorbed from human milk assn-2 monoacyl-glycerol. The metabolic significance of the differences in positional distribution of fatty acids in the plasma lipids of breast-fed and formula-fed infants is not known.     

Triacylglycerols of human milk: Rapid analysis by ammonia negative ion tandem mass spectrometry

Human milk traicylglycerols (TAG) were analyzed by ammonia negative ion chemical ionization tandem mass spectrometry. The deprotonated molecular ions of triacylglycerols were fractionated at the first mass spectrometry (MS) stage. Twenty-nine of the deprotonated TAG ions were further analyzed based on their collisionally activated (CA) spectra. The tandem MS analysis covered eleven major acyl carbon number fractions, two of which contained odd carbon number fatty acids. Fatty acids of 28 different molecular weights were recorded from the daughter spectra. Hexadecanoic acid was present in all CA spectra, octadecenoic acid in the CA spectra of all mono- and higher unsaturated TAG, and octadecadienoic acid in the CA spectra of all di- and higher unsaturated TAG. The major fatty acid combinations in triacylglycerols were: with 0 double bonds (DB), 12∶0/12∶0/16∶0; with 1 DB, 12∶0/16∶0/18∶1; with 2 DB, 16∶0/18∶1/18∶1; with 3 DB, 16∶0/18∶2/18∶1; with 4 DB, 18∶2/18∶1/18∶1; and with 5 DB, 18∶2/18∶2/18∶1; hexadecanoic acid typically occupied thesn-2 position. The most abundant TAG was shown to besn-18∶1–16∶0–18∶1, comprising about 10% of all triacylglycerols.     

Comparative studies on the fatty acid composition of moderately and extremely thermophilic bacteria

The fatty acids of three strains of extremely thermophilic bacteria and three strains of moderately thermophilic bacteria were examined by gas liquid chromatography. All the thermophiles contained straight, iso, and ante-iso branched fatty acids. Iso C_17∶0 acid was abundant in both the moderately thermophilic strains (10–33%) and the extremely thermophilic strains (50–61%). The pair of fatty acids iso C_15∶0 and iso C_17∶0 was the predominant pair in both the moderately (34–64%) and extremely (76–87%) thermophilic strains. The pair of fatty acids ante-iso C_15∶0 and ante-iso C_17∶0 was present in larger amount in moderately (25–34%) than in extremely (8.5–15%) thermophilic strains. No hydroxy cyclopropane, or unsaturated fatty acids were found. One extreme thermophile,Flavobacterium thermophilum HB-8 was grown at 6 different culture temperatures from 49–82 C, and the changes of its fatty acid composition were studied. The ratios of iso C_17∶0/iso C_15∶0 and ante-iso C_17∶0/ante-iso C_15∶0 were much greater at higher culture temperatures, indicating chain elongation.     

A comparison of the positional distribution of fatty acids in milk triglycerides of the extant monotremes platypus (Ornithorhynchus anatinus) and echidna (Tachyglossus aculeatus)

Milk triglycerides from the platypus were subjected to fatty acid and stereospecific analysis to determine the positional distribution of fatty acids in the triglycerides. Of the major fatty acids, 12∶0 was preferentially esterified at thesn-3 position, 14∶0 and 16∶0 were selectively associated with thesn-2 position, and 18∶0 was located predominantly at thesn-1 position. The unsaturated fatty acids, 14∶1, 16∶1, 18∶1, 18∶2 and 18∶3, were preferentially esterified at thesn-3 position. The fatty acid distribution pattern of the platypus, a monotreme, is similar to that of marsupials and eutherians but is in contrast to the only other extant monotreme, the echidna.     

Altered microsomal phospholipid composition in the streptozotocin diabetic rat

Streptozotocin diabetes in the rat alters liver microsomal membrane fatty acid composition. The present study was undertaken to determine if such changes in fatty acid composition were due to changes in the amount of individual phosphoglycerides or to disproportionate changes in fatty acid composition in any of the individual phosphoglycerides. The diabetic animals showed a small increase in total microsomal phospholipid, which is due to a selective increase in the phosphatidylethanolamine fraction. The changes in fatty acid composition in the total lipid extract (decreased palmitoleic, oleic and arachidonic acids and increased linoleic and docosahexaenoic acids) from the diabetic animals were present in both the major phosphoglycerides, phosphatidylcholine and phosphatidylethanolamine, with very little change in fatty acid composition in the phosphatidylserine and inositol fraction. Further studies are necessary to delineate the cause of the abnormal membrane phospholipid composition in the diabetic animal. Abbreviations: The abbreviated fatty acid nomenclature refers to the number of carbon atoms in the chain, the number of unsaturated bonds, and the position of the first unsaturated bond counting from the terminal methyl group; thus arachidonic acid, 5,8,11,14-eicosatetraenoic acid, is 20∶4ω6.