Structure-activity relationship of lipid A: comparison of biological activities of natural and synthetic lipid A's with different fatty acid compositions

To investigate the structure-activity relationships, various biological activities, including pyrogenicity, lethal toxicity, elicitation of Shwartzman reaction, mitogenicity and tumor necrosis factor (TNF)-inducing activity, were compared among natural and synthetic lipid A's differing in fatty acid composition. In all these tests, natural lipid A's from Escherichia coli and Salmonella minnesota and synthetic LA-15-PP, which carries 3-hydroxy- and 3-acyloxy-tetradecanoyl groups at the 2, 3 and 2', 3' positions, respectively, showed the strongest activities among the tested lipid A's. In contrast, LA-16-PP, in which the amide-bound 3-hydroxytetradecanoic acid at position 2 of LA-15-PP is replaced by 3-hexadecanoyloxytetradecanoic acid, exhibited lower activity than LA-15-PP and natural lipid A's. Although LA-16-PP has been assumed to have a typical Salmonella lipid A structure (and, in fact, it has a structure corresponding to one of the components of Salmonella lipid A), the activity of this synthetic compound was not comparable to that of natural Salmonella lipid A. LA-17-PP, in which tetradecanoic acid is the sole fatty acid component, exhibited relatively strong mitogenicity and TNF-inducing activity, but very low pyrogenicity. The activities of LA-18-PP, which has ester-bound tetradecanoic acid and amide-bound 3-hydroxytetradecanoic acid, were lower than those of LA-17-PP. The results indicate that the differences in fatty acid composition of lipid A's have important influences on the biological activities studied.     

Cellular distribution and linkage of D-(-)-3-hydroxy fatty acids in Bacteroides species.

Two strains of Bacteroides asaccharolyticus and two strains of Bacteroides fragilis were analyzed for total fatty acid, total lipid fatty acid, and total bound fatty acid profiles. Extracted lipids and defatted cell residues were subjected to sequential alkaline and acid methanolyses to distinguish ester- and amide-linked fatty acids in each fraction. In the lipid fractions, all the ester-linked fatty acids were nonhydroxylated, whereas all of the amide-linked fatty acids were hydroxylated. In the nonextractable fractions, both hydroxy and nonhydroxy fatty acids were found in both ester and amide linkage, although hydroxy acids predominated. The fatty acid profiles of the bound fractions differed widely from those of the lipid fractions. Bound fatty acid represented approximately 10% of the total cellular fatty acids.     

Lipoidal Components of Bacterial Lipopolysaccharides: Nature and Distribution of Fatty Acids in Aerobacter aerogenes

The fatty acid distribution of Aerobacter aerogenes was studied by comparing the fatty acid composition of the lipoidal component of the endotoxin (lipid A) with the fatty acids of the readily extractable native lipids and total cellular fatty acids. The results for total cellular fatty acids and readily extractable native lipids were generally similar, but both quantitative and qualitative differences exist. In addition, profound differences between these two fractions and lipid A were observed. These differences included fewer fatty acids and lower concentrations of unsaturated and cyclopropane fatty acids in the lipid A. Hydroxy fatty acids persisted in the lipid A. The significance of these differences with respect to mammalian toxicity of endotoxins is discussed.     

Infrared spectroscopic study of stratum corneum model membranes prepared from human ceramides, cholesterol, and fatty acids

The outermost layer of the skin, the stratum corneum, consists of corneocytes surrounded by lipid domains. The main lipid classes in stratum corneum are cholesterol, ceramides (CER), and free fatty acids forming two crystalline lamellar phases. However, only limited information is available on whether the various lipid classes participate in the same crystalline lattices or if separate domains are formed within the lipid lamellae. In this article infrared spectroscopic studies are reported of hydrated mixtures prepared from cholesterol, human CER, and free fatty acids. Evaluation of the methylene stretching vibrations revealed a conformational disordering starting at approximately 60 degrees C for all mixtures. Examination of the rotational ordering (scissoring and rocking vibrations) of mixtures prepared from equimolar cholesterol and CER with a variation in the level of free fatty acids showed that at lower free fatty acid content orthorhombic and hexagonal domains coexist in the lipid lamellae. Increasing the fatty acid level to an equimolar cholesterol/CER/fatty acid mixture reveals the dominant presence of an orthorhombic lattice, confirming x-ray diffraction studies. Replacing the protonated free fatty acid chains by their perdeuterated counterparts demonstrates that free fatty acids and CER participate in the same orthorhombic lattice up to a level of slightly less than 1:1:0.75 cholesterol/CER/free fatty acids molar ratio but that free fatty acids also form separate domains within the lipid lamellae at equimolar ratios at room temperature. However, no evidence for this has been observed at 32 degrees C. Extrapolating these findings to the situation in stratum corneum led us conclude that in stratum corneum, fatty acids and CER participate in the orthorhombic lattice at 32 degrees C, the skin temperature.     

Triacylglycerol and phospholipid fatty acids of the silverleaf whitefly: composition and biosynthesis

The identification and composition of the fatty acids of the major lipid classes (triacylglycerols and phospholipids) within Bemisia argentifolii Bellows and Perring (Homoptera: Aleyrodidae) nymphs were determined. Comparisons were made to fatty acids from the internal lipids of B. argentifolii adults. The fatty acids, as ester derivatives, were analyzed by capillary gas chromatography (CGC) and CGC-mass spectrometry (MS). All lipid classes contained variable distributions of eight fatty acids: the saturated fatty acids, myristic acid (14:0), palmitic acid (16:0), stearic acid (18:0), arachidic acid (20:0); the monounsaturated fatty acids, palmitoleic acid (16:1), oleic acid (18:1); the polyunsaturated fatty acids, linoleic acid (18:2), linolenic acid (18:3). Fourth instar nymphs had 5-10 times the quantities of fatty acids as compared to third instar nymphs and 1-3 times the quantities from adults. The fatty acid quantity differences between fourth and third instar nymphs were related to their size and weight differences. The percentage compositions for fatty acids from each lipid class were the same for the pooled groups of third and fourth instar nymphs. For nymphs and adults, triacylglycerols were the major source of fatty acids, with 18:1 and 16:0 acids as major components and the majority of the polyunsaturated fatty acids, 18:2 and 18:3 were present in the two phospholipid fractions, phosphatidylethanolamine and phosphatidylcholine. Evidence was obtained that whiteflies indeed synthesize linoleic acid and linolenic acid de novo: radiolabel from [2-(14)C] acetate was incorporated into 18:2 and 18:3 fatty acids of B. argentifolii adults and CGC-MS of pyrrolidide derivatives established double bonds in the Delta(9,12) and Delta(9,12,15) positions, respectively.     

Free fatty acids and sterols in the benthic spawn of aquatic molluscs, and their associated antimicrobial properties

The free lipid content of extracts from the spawn of 17 molluscs were analysed by gas chromatography/mass spectrometry. These extracts encompass the encapsulated embryos and extraembryonic structures from benthic gelatinous egg masses and leathery egg capsules covering five taxonomic groups. Palmitic and stearic acids were the dominant saturated fatty acids and oleic acid was the principal unsaturated acid found in the spawn. Cholesterol was the dominant sterol and the only sterol found in the spawn from every species. Extracts from gelatinous egg masses were found to contain proportionally more fatty acids compared to leathery egg capsules. No unsaturated fatty acids were found in any of the leathery egg capsules, including five neogastropods and one littorinimorph. Unsaturated fatty acids were present in all of the gelatinous egg masses, including two other littorinimorphs. This is the first study to demonstrate that unsaturated fatty acids possess significant bacteriolytic activity against four aquatic pathogens. Encapsulated Anaspidea egg masses contain relatively high concentrations of these unsaturated fatty acids and a lipid mixture modeled on these extracts was strongly bacteriolytic at concentrations down to 0.0001 mg/ml. By comparison, lipid mixtures modeled on extracts from the spawn of four other molluscan taxa with higher proportions of saturated fatty acid and cholesterol, were only partially active against some of the bacteria at 0.1 mg/ml. Thus, unsaturated fatty acids could explain the antimicrobial activity previously reported in lipid extracts of some, but not most, molluscan spawn. MDS ordination and ANOSIM revealed significant taxonomic differences in the composition of free lipids from molluscan spawn, suggesting that lipid analyses may be useful in future systematic studies of the Mollusca.     

Stable Cell Surface Expression of GPI‐Anchored Proteins,but not Intracellular Transport,Depends on their Fatty Acid Structure

Glycosylphosphatidylinositol‐anchored proteins (GPI‐APs) are a class of lipid anchored proteins expressed on the cell surface of eukaryotes. The potential interaction of GPI‐APs with ordered lipid domains enriched in cholesterol and sphingolipids has been proposed to function in the intracellular transport of these lipid anchored proteins. Here, we examined the biological importance of two saturated fatty acids present in the phosphatidylinositol moiety of GPI‐APs. These fatty acids are introduced by the action of lipid remodeling enzymes and required for the GPI‐AP association within ordered lipid domains. We found that the fatty acid remodeling is not required for either efficient Golgi‐to‐plasma membrane transport or selective endocytosis via GPI‐enriched early endosomal compartment (GEEC)/ clathrin‐independent carrier (CLIC) pathway, whereas cholesterol depletion significantly affects both pathways independent of their fatty acid structure. Therefore, the mechanism of cholesterol dependence does not appear to be related to the interaction with ordered lipid domains mediated by two saturated fatty acids. Furthermore, cholesterol extraction drastically releases the unremodeled GPI‐APs carrying an unsaturated fatty acid from the cell surface, but not remodeled GPI‐APs carrying two saturated fatty acids. This underscores the essential role of lipid remodeling to ensure a stable membrane association of GPI‐APs particularly under potential membrane lipid perturbation.      

Lipid Class and Fatty Acid Composition of the Protozoan Parasite of Oysters, Perkinsus marinus Cultivated in Two Different Media

The meront stage of the oyster protozoan parasite, Perkinsus marinus, cultivated in two media with different fatty acid profiles was analyzed for its fatty acid and lipid class composition. The composition of fatty acids in the prezoosporangium stage of the parasite as well as that of the host oyster were investigated. Although the lipid class composition of meronts was dominated by phospholipids and triacylglycerol, there was no triaclgycerol detected in either culture medium. Despite the difference in fatty acid composition of the two media, the fatty acid composition of meronts in each medium was dominated by 14:0, 16:0, 18:0, 18:1(n-9), 20: (n-9), 18:2(n-6) and 20:4(n-6), a profile that differed from its host. The quantities of total lipids and fatty acids in meronts increased as the number of meronts increased and far exceeded the initial amounts in the media and in the initial cell inoculum. The meronts harvested 25 d post-inoculation, had about 3 to 6 times higher total lipids and 4 to 13 times higher fatty acids than the amounts contained in the media. The fatty acid profiles of both prezoosporangia and oysters resembled each other and consisted primarily of 16:0, 20:4(n-6), 20:5(n-3), 22:2delta7,15, and 22:6(n-3). These results indicate that during meront proliferation, the parasite synthesizes certain fatty acids and lipid classes. For development from meront to prezoosporangium, the parasite may rely on its host for lipid resources.     

Comparative study of lipid A from pertussis microbes differing in the toxicity of their O-antigens. I. Chemical composition and stability of the bond between lipid A and the specific polysaccharide in B. pertussis lipopolysaccharide]

Data presented in this work indicated that antigens, contrastive by toxicity, obtained by Boiven's method and O'Neill and Tood's method from two strains of Bordetella pertussis differed by stability of lipid A binding with the specific polysaccharide. The influence of duration of the lipopolysaccharide hydrolysis on the fatty acid content in lipid A, and of heptose in the specific polysaccharide was demonstrated. Lipid A fatty acid composition was studied. It is supposed that bound fatty acids are presented as C14 and C19--C22. There was a correlation between the antigen toxicity and the stability of lipid A bond with the specific polysaccharide. Stability of the lipopolysaccharide complex bond depended on heptose and lipid A content and on the composition and the amount of fatty acids in the lipid A preparations.     

Lipid composition of the electron transport membrane of Haemophilus parainfluenzae

The principal lipids associated with the electron transport membrane of Haemophilus parainfluenzae are phosphatidylethanolamine (78%), phosphatidylmonomethylethanolamine (0.4%), phosphatidylglycerol (18%), phosphatidylcholine (0.4%), phosphatidylserine (0.4%), phosphatidic acid (0.2%), and cardiolipin (3.0%). Phospholipids account for 98.4% of the extractible fatty acids. There are no glycolipids, plasmalogens, alkyl ethers, or lipo amino acid esters in the membrane lipids. Glycerol phosphate esters derived from the phospholipids by mild alkaline methanolysis were identified by their staining reactions, mobility on paper and ion-exchange column chromatography, and by the molar glycerol to phosphate ratios. Eleven diacyl phospholipids can be separated by two-dimensional thin-layer chromatography. Each lipid served as a substrate for phospholipase D, and had a fatty acid to phosphate ratio of 2:1. Each separated diacyl phospholipid was deacylated and the glycerol phosphate ester was identified by paper chromatography in four solvent systems. Of the 11 separated phospholipids, 3 were phosphatidylethanolamines, 2 were phosphatidylserines, and 2 were phosphatidylglycerols. Phosphatidylcholine, cardiolipin, and phosphatidic acid were found at a single location. Phosphatidylmonomethylethanolamine was found with the major phosphatidylethanolamine. Three distinct classes of phospholipids are separable according to their relative fatty acid compositions. (i) The trace lipids consist of two phosphatidylethanolamines, two phosphatidylserines, phosphatidylcholine, phosphatidic acid, and a phosphatidylglycerol. Each lipid represents less than 0.3% of the total lipid phosphate. These lipids are characterized by high proportions of the short (C(10) to C(14)) and long (C(19) to C(22)) fatty acids with practically no palmitoleic acid. (ii) The major phospholipids (93% of the lipid phosphate) are phosphatidylethanolamine, phosphatidylmonomethylethanolamine, and phosphatidylglycerol. These lipids contain a low proportion of the short (C(19)) fatty acids. Palmitic and palmitoleic acids represent over 80% of the total fatty acids. (iii) The fatty acid composition of the cardiolipin is intermediate between the other two classes. Both palmitoleic and the longer fatty acids represent a significant proportion of the total fatty acid.     

Improving the tolerance of Escherichia coli to medium-chain fatty acid production

Microbial fatty acids are an attractive source of precursors for a variety of renewable commodity chemicals such as alkanes, alcohols, and biofuels. Rerouting lipid biosynthesis into free fatty acid production can be toxic, however, due to alterations of membrane lipid composition. Here we find that membrane lipid composition can be altered by the direct incorporation of medium-chain fatty acids into lipids via the Aas pathway in cells expressing the medium-chain thioesterase from Umbellularia californica (BTE). We find that deletion of the aas gene and sequestering exported fatty acids reduces medium-chain fatty acid toxicity, partially restores normal lipid composition, and improves medium-chain fatty acid yields.     

Changes in the fatty acid composition of steelhead trout, Salmo gairdnerii Richardson, associated with parr-smolt transformation

Fatty acids from the several lipid classes of selected steelhead trout (Salmo gairdnerii) parr and smolt tissues, previously separated by thin-layer chromatography, were analyzed by gas-liquid chromatography. The fatty acid composition of the parr was markedly different from that of the smolt; the former being characterized by relatively low amounts of polyunsaturated fatty acids and relatively high amounts of linoleic acid, much like the typical freshwater lipid pattern. The fatty acid composition of the smolt was characterized by large proportions of long-chain polyunsaturated fatty acids. Generally, the fatty acid composition of the smolt resembled the typical seawater lipid pattern. The change in fatty acid composition of the smolt is anticipatory to seawater entry and is independent of diet and water temperature. These alterations suggest that the assumption of a polyunsaturated lipid pattern during parr-smolt transformation (smoltification) is preadaptive to seawater entry.     

Die Gefriertrocknung von Rinderkot

Fatty acids in fish can arise from two sources: synthesis de novo from non‐lipid carbon sources within the animal, or directly from dietary lipid. Acetyl‐CoA derived mainly from protein can be converted to saturated fatty acids via the combined action of acetyl‐CoA carboxylase and fatty acid synthetase. The actual rate of fatty acid synthesis de novo is inversely related to the level of lipid in the diet. Freshwater fish can de‐saturate endogenously‐synthesized fatty acids to monounsaturated fatty acids via a A9 desaturase but lack the necessary enzymes for complete de novo synthesis of polyunsaturated fatty acids which must therefore be obtained preformed from the diet. Most freshwater fish species can desaturate and elongate 18:2(n‐6) and 18:3(n‐3) to their C20 and C22 homologues but the pathways involved remain ill‐defined. Cyclooxygenase and lipoxygenase enzymes can convert C20 polyunsaturated fatty acids to a variety of eicosanoid products. The dietary ratio of (n‐3) to (n‐6) polyunsaturated fatty acids influences the pattern of eicosanoids formed. The ß‐oxidation of fatty acids can occur in both mitochondria and peroxisomes but mi‐tochondrial ß‐oxidation is quantitatively more important and can utilise a wide range of fatty acid substrates.     

Effect of glutamic acid on the fatty acid and lipid composition of Choanephora cucurbitarum.

The fatty acid composition of the total, neutral, sterol, free fatty acid, and polar-lipid fractions in the mycelium of Choanephora curcurbitarum was determined. The major fatty acids in all lipid fractions were palmitic, oleic, linoleic, and gamma-linolenic acid. Different lipid fractions did not show any particular preference for any individual fatty acid; however, the degree of unsaturation was different in different lipid fractions. Free fatty acid and polar lipid fractions contained a higher proportion of gamma-linolenic acid than did triglyceride and sterol fractions. Addition of glutamic acid to the malt-yeast extract and medium resulted in the biosynthesis of a number of long-chain fatty acids beyond the gamma-linolenic acid. These fatty acids, e.g., C22:1, C24:0, and C26:0, were never observed to be present in the fungus when grown on a malt-yeast extract medium without glutamic acid. Furthermore, thin-layer chromatographic analysis showed a larger and denser spot of diphosphatidyl glycerol from the mycelium grown on glutamic acid medium than from the control mycelium. The possible significance of this finding is discussed.     

Cellular Lipid and Fatty Acid Compositions of Burkholderia pseudomallei Strains Isolated from Human and Environment in Viet Nam

Viet nam is known as an endemic area of melioidosis but its etiologic agent originated in Viet nam was not extensively studied. For the first time, we analyzed the cellular lipid and fatty acid compositions of 15 Vietnamese isolates of Burkholderia pseudomallei, 10 from humans and 5 from the environment. Cellular lipid compositions were analyzed by two-dimensional thin-layer chromatography on silica gel G plates. Cellular fatty acid methyl esters were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The major lipids in all the isolates were phosphatidylglycerol (PG), two forms of phosphatidylethanolamine (PE-1 and PE-2), and two forms of ornithine-containing lipid (OL-1 and OL-2). PE-1 contained non-hydroxy fatty acids at both sn-1 and ?2 positions, while PE-2 possessed 2-hydroxy fatty acids and non-hydroxy fatty acids in a ratio of 1: 1. Since snake venom phospholipase A₂ digestion of PE-2 liberated 2-hydroxy fatty acids, it was confirmed that these acids are at the sn-2 position of glycerol moiety. In both OL-1 and OL-2, amide-linked fatty acid was 3-hydroxy palmitic acid (3-OH-C16: 0), while ester-linked fatty acids were non-hydroxy acids in OL-1 and 2-hydroxy acids in OL-2. The total cellular fatty acid compositions of the test strains were characterized by the presence of 2-hydroxy palmitic (2-OH-C16: 0), 2-hydroxy hexadecenoic (2-OH-C16: 1), 2-hydroxy octadecenoic (2-OH-C18: 1), 2-hydroxy methylene octadecanoic (2-OH-C19CPA), 3-hydroxy myristic (3-OH-C14: 0) and 3-hydroxy palmitic (3-OH-C16: 0) acids. There were significant differences in the concentration of hexadecenoic (C16: 1), methylene hexadecanoic (C17CPA), octadecenoic (C18: 1) and methylene octadecanoic (C19CPA) acids among the Vietnamese isolates of B. pseudomallei. However, no significant difference was observed in cellular lipid and fatty acid components between strains of human and environmental origins.     

The transfer of fatty acids across the sheep placenta

Maternal and fetal plasma concentrations of free fatty acids, triacylglycerols and phospholipids and the profile of their fatty acids were measured in three catheterized and unanaesthetized sheep. Fetal concentrations of all three lipid fractions were low and did not correlate with maternal concentrations. There were no measurable umbilical venous-arterial differences. Linoleic acid concentrations were low in both mother and fetus. The fatty acid composition of fetal adipose tissue, liver, lung and cerebellum of five animals was analysed. Again linoleic acid levels were very low, but phospholipids contained 2-8% arachidonic acid. [14C] linoleic acid and [3H] palmitic acid were infused intravenously into three ewes. Only trace amounts of labelled fatty acids were found in fetal plasma and these were confined to the free fatty acids. 14C-label was incorporated into fetal tissue lipids, but most of this probably was due to fetal lipid synthesis from [14C] acetate or other water-soluble products of maternal [14C] linoleic acid catabolism. It is concluded that only trace amounts of fatty acids cross the sheep placenta. They are derived mainly from the maternal plasma free fatty acids and might just be sufficient to be the source of the small amounts of essential fatty acids found in the lamb fetus, but are insignificant in terms of energy supply or lipid storage.     

Comparison of the phospholipid and triacylglycerol fatty acid profile of rat serum, skeletal muscle and heart

Although several studies have analyzed the fatty acid profile of phospholipids (PL) and, to a lesser degree, triacylglycerols (TG) in one or more tissues concurrently, a systematic comparison of the fatty acid composition of different tissues and/or lipid classes is lacking. The purpose of the present study was to compare the fatty acid composition of major lipid classes (PL and TG) in the rat serum, soleus muscle, extensor digitorum longus muscle and the heart. Lipids were extracted from these tissues and analyzed by a combination of thin-layer chromatography and gas chromatography. We found many significant differences in various tissues and lipid classes. Serum had the most distinct fatty acid profile in PL but this "uniqueness" was less apparent in TG, where differences among tissues were in general less frequent than in PL. These two skeletal muscles exhibited similar fatty acid composition in both lipid classes despite their different muscle fiber type composition, denoting that fiber type is not a major determinant of the fatty acid composition of rat skeletal muscle. The fatty acid profile of heart PL was the most different from that of the other tissues examined. PL were rich in polyunsaturated fatty acids, whereas TG were rich in monounsaturated fatty acids. Although the reasons for the differences in fatty acid profile among the tissues examined are largely unknown, it is likely that these differences have an impact upon numerous biological functions.     

Oleic acid prevents detrimental effects of saturated fatty acids on bovine oocyte developmental competence

Mobilization of fatty acids from adipose tissue during metabolic stress will increase the amount of free fatty acids in blood and follicular fluid and, thus, may affect oocyte quality. In this in vitro study, the three predominant fatty acids in follicular fluid (saturated palmitic and stearic acid and unsaturated oleic acid) were presented to maturing oocytes to test whether fatty acids can affect lipid storage of the oocyte and developmental competence postfertilization. Palmitic and stearic acid had a dose-dependent inhibitory effect on the amount of fat stored in lipid droplets and a concomitant detrimental effect on oocyte developmental competence. Oleic acid, in contrast, had the opposite effect, causing an increase of lipid storage in lipid droplets and an improvement of oocyte developmental competence. Remarkably, the adverse effects of palmitic and stearic acid could be counteracted by oleic acid. These results suggest that the ratio and amount of saturated and unsaturated fatty acid is relevant for lipid storage in the maturing oocyte and that this relates to the developmental competence of maturing oocytes.     

Superoxide dismutase deficiency and the toxicity of the products of autooxidation of polyunsaturated fatty acids in yeast

Mutants of Saccharomyces cerevisiae, deficient in cytosolic superoxide dismutase and catalase activities were used to study the role of various oxygen species in the process of lipid peroxidation in yeast cells. Lipid peroxidation does not occur normally in yeast, because this organism is unable to form fatty acids with more than one double bond, whereas under physiological conditions, only fatty acids with at least two double bonds undergo this process. The fatty acid content of cellular lipids was modified by growing the cells in anoxia in the presence of oleic or linolenic acid. Toxic effects of oxygen were observed almost exclusively in those cells of yeast mutants deficient in superoxide dismutase, which contain linolenic acid in cellular lipids. Hypersensitivity of the mutant cells, however, results mainly from toxic effects of the products of autooxidation of extracellular fatty acids. These facts suggest that superoxide dismutases are in some way involved in preventing toxic effects of the products of lipid peroxidation and to some extent prevent the process of lipid peroxidation.     

Yolk lipids and their fatty acids in the wild and captive ostrich (Struthio camelus)

A comparative study has been made of the major lipid fractions and their fatty acid compositions in the yolk of eggs from ostriches under wild and farmed conditions. There were no differences in the lipid contents and proportions of the lipid fractions between the two groups of yolks. In both groups of yolks triacylglycerol and phospholipid were the major fractions. In the eggs from the wild ostriches, all the lipid fractions displayed substantial concentrations of C18 polyunsaturated fatty acids, triacylglycerol being particularly rich in linolenic acid and phospholipid rich in linoleic acid; phospholipid displayed substantial concentrations also of C20 and C22 polyunsaturates. There were considerable differences in the fatty acid compositions between the yolks. Those from the farmed birds displayed lower proportions of C18 polyunsaturates, particularly linolenic acid, throughout the lipid fractions. Compensatory increases were displayed most obviously in the concentrations of oleic acid and palmitoleic acid as well as other acids. The distinctive and extensive changes in fatty acid composition, particularly relating to the polyunsaturates, are discussed with respect to overall dietary requirements and specificities for embryo metabolism and possible effects on reproductive performance.