Studies of the phospholipids,glycolipids and sterols of wheat endosperm

The phospholipid-glycolipid mixture, isolated chromatographically from the “free” (hexane soluble) and “bound” (hexane insoluble, water-saturated butanol extractable) lipid of wheat endosperm, was fractionated by column and thinlayer silicic acid chromatography. The components were identified by hydrolysis followed by thin-layer or paper chromatography of the products. They included a sterol-containing glycolipid, hitherto unreported in wheat. The fatty acid and sterol compositions of the phospholipidglycolipid components were determined by gasliquid chromatography. Differences were found between varieties and between components. Contribution No. 14 of the Food Research Institute, Canada Dept. of Agriculture, Ottawa, Can. Presented at the AOCS Fall Meeting, Minneapolis, 1963.     

The content and composition of sterols and sterol esters in low erucic acid rapeseed (Brassica napus)

The low temperature crystallization technique for the enrichment of “minor” components, such as sterols and sterol esters, from vegetable oils was applied to low erucic acid rapeseed oils. The recovery of free sterols and sterol esters was estimated by use of¹⁴C-cholesterol and¹⁴C-cholesterol oleate. 80% of the free sterols and 45% of the sterol esters were recovered in the liquid fraction, while in two studies total recoveries were 95% and 99%, respectively. This technique showed some selectivity toward the sterol bound fatty acids when compared to direct preparative thin layer chromatography (TLC) of the crude oil. Gas liquid chromatography (GLC) analysis of the free and esterified sterols as TMS-derivatives showed very little selectivity in the enrichment procedure. The fatty acid patterns of the sterol esters demonstrated, however, a preference in the liquid fraction for those sterol esters which have a high linoleic and linolenic acid content. The content of free sterols was 0.3–0.4% and that of sterol esters 0.7–1.2% of the rapeseed oils in both winter and summer types of low erucic acid rapeseed (Brassica napus) when the lipid classes were isolated by direct preparative TLC of the oils. The free sterols in the seven cultivars or breeding lines analyzed were composed of 44–55% sitosterol, 27–36% campesterol, 17–21% brassicasterol, and a trace of cholesterol. The esterified sterols were 47–57% sitosterol, 36–44% campesterol, 6–9% brassicasterol, and traces of cholesterol and Δ5-avenasterol. The fatty acid patterns of these esters were characterized by ca. 30% oleic acid and ca. 50% linoleic acid, whereas these acids constitute 60% and 20%, respectively, of the total fatty acids in the oil. Little or no variation in sterol and sterol ester patterns with locality within Sweden was observed for the one cultivar of summer rapeseed investigated by the low temperature crystallization technique.     

Sterol and phospholipid acyl chain alterations inSaccharomyces cerevisiae secretion mutants as a function of temperature stress

Analyses of free sterol, steryl ester and fatty acid components from yeast secretion mutants indicated that free and esterified sterol remained relatively constant over a growth range of 24 C to 34 C. The saturated fatty acid components (16∶0 and 18∶0) increased while the unsaturated fatty acids (16∶1 and 18∶1) decreased as the growth temperature increased. In secretory mutants, fatty acid composition changes are more pronounced than in the wild-type strain. A shift toward increased saturated and decreased unsaturated fatty acid was observed when cells were subjected to a 2-hr temperature upshift to 37 C. Steady-state fluorescence anisotropy data indicated that modifications to the lipid component of yeast plasma membrane produced lipid thermotropic transitions that were 3 C to 6 C higher in yeast cells subjected to thermal stress.     

Polyunsaturated fatty acids and neutral lipids in developing larvae of the oyster,Crassostrea virginica

The fatty acid composition of oyster larvae at various stages, as well as of the algal diet, were determined by gas liquid chromatography (GC). Saturated fatty acids are the major fatty acid components in all larval stages and account for 34–62%, 30–35% and 35–81% of the neutral, polar and total lipids of algal-fed larvae respectively. Weight percentage of saturated fatty acid in “starved” larvae was consistently higher (63–81%) during the whole period. The total polyunsaturated fatty acids were higher in the polar lipids than in the neutral lipids. The concentration of the ω3 fatty acids also was comparatively higher in the polar lipids than in the neutral lipids. In the total and neutral lipid fractions, the weight percentage of polyunsaturated and ω3 fatty acids was higher in the eyed than in the pre-eyed (pediveliger) larvae. Eicosapentaenoic acid (20∶5ω3) and 22∶6ω3 were not detected in lipids of “starved” and young larvae. There was an accumulation of 20∶5ω3, 22∶6ω3, and total ω3 fatty acids in the older larvae. Lipid classes were separated by thin layer chromatography (TLC). There was no qualitative change in lipid composition during larval development, but a marked increased of triacylglycerol in larvae up to the stage of maturation in algae-fed larvae. Contribution number 1195 of the Virginia Institute of Marine Science, Gloucester Point, VA 23062     

Separation of neutral lipid,free fatty acid and phospholipid classes by normal phase HPLC

Normal phase high performance liquid chromatography methods are described for the separation of neutral lipid, fatty acid and five phospholipid classes using spectrophotometric detection at 206 nm. Separations were accomplished in less than 10 min for each lipid class. A mobile phase consisting of hexane/methyltertiarybutylether/acetic acid (100∶5∶0.02) proved effective in separating cholesteryl ester and triglyceride with recoveries of 100% for radiolabeled cholesteryl oleate and 98% for radiolabeled triolein. Free fatty acid and cholesterol were separated by two different mobile phases. The first, hexane/methyltertiarybutylether/acetic acid (70∶30∶0.02) effectively separated free fatty acids and cholesterol, but did not separate cholesterol from 1,2-diglyceride. A mobile phase consisting of hexane/isopropanol/acetic acid (100∶2∶0.02) effectively separated free fatty acid, cholesterol, 1,2-diglyceride and 1,3-diglyceride. Recoveries of oleic acid and cholesterol were 100% and 97%, respectively. Five phospholipid classes were separated using methylteriarybutylether/methanol/aqueous ammonium acetate (pH 8.6) (5∶8∶2) as the mobile phase. The recoveries of phosphatidylinositol, phosphatidylethanolamine, phosphatidylcholine, sphingomyelin and lysophosphatidylcholine were each greater than 96%.     

Variations in fat content and lipid class composition in ten different mango varieties

The kernels of 10 different mango varieties were extracted. The physico-chemical characteristics and lipid class composition of fats were studied. The fat content of mango kernels grown under the soil and climatic conditions of Bangladesh varied from 7.1% to 10%, depending on the variety. The total lipid extracts were fractionated into lipid classes by a combination of column and thin layer chromatography (TLC). The hydrocarbon and sterol esters varied from 0.3% to 0.7%, triglycerides from 55.6% to 91.5%, partial glycerides from 2.3% to 4% and free sterol from 0.3% to 0.6%. Free fatty acids amounted to 3.0–37% as oleic; glycolipids were 0.6–1.2% and phospholipids 0.11–0.8%. The fatty acid composition of triglyceride (TG) fractions was analyzed by gas liquid chromatography (GLC). Palmitic acid varied from 7.9 molar % to 10.0 molar %, stearic from 38.2% to 40.2%, oleic from 41.1% to 43.8%, linoleic from 6.0% to 7.6%, linolenic from 0.6% to 1.0% and arachidic acid from 1.7% to 2.6%. TLC revealed the presence of lyso-phosphatidylcholine, phosphatidylcholine, phosphatidylinositol, phosphatidylethanolamine and phosphatidic acid in the phospholipid fraction.     

Lipid composition and peroxide levels of mucosal cells in the rat large intestine in relation to dietary fat

To examine whether dietary fat alters membrane lipid composition and peroxidation of polyunsaturated fatty acids in “non-proliferative” and “proliferative” cells in the large intestine, Sprague-Dawley rats were fed diets providing a polyunsaturated-to-saturated fatty acid ratio of 1.2 or 0.3 at a high or low level of fat intake for a 25-day period. Cell populations were isolated and the effect of dietary fat on membrane polyunsaturated fatty acid content and peroxide levels was determined. Neither fat level nor fatty acid composition of diet influenced total cholesterol, total phospholipids, and percentage of phospholipid classes in membrane phospholipids. Feeding the high fat and/or high polyunsaturated-to-saturated fatty acid ratio diet increased polyunsaturated fatty acid content of mucosal cell phospholipids. Increase in polyunsaturated fatty acid content was paralleled by a decrease in the monounsaturated fatty acid content of mucosal cell phospholipids. Membrane content of total saturated fatty acids was not significantly affected by diet. Variation in phospholipid fatty acid composition between “non-proliferative” and ”proliferative” cells was observed. Lipid peroxide levels in mucosal cell lipid fractions were altered by dietary fat treatment. Animals fed high fat diets, compared to groups fed low fat diets, exhibited higher membrane peroxide levels when results are expressed as nmol/mg protein. Higher peroxide levels were observed in mucosal cells for rats fed high polyunsaturated-to-saturated fatty acid ratio diets when results were expressed per nmol of phospholipid. It is concluded that changes in fat level and fatty acid composition of the diet alters the mucosal cell membrane lipid composition in the rat large intestine and influences susceptibility of mucosal cell lipid to peroxidation. Further research is required to delineate which dietary factors—fat level, polyunsaturated-to-saturated fatty acid ratio, or both—have a primary influence on the degree of lipid peroxidation.     

The effect of temperature on the fatty acid and phospholipid composition ofCephalosporium falciforme andCephalosporium kiliense

The effect of temperature on the lipid composition ofCephalosporium falciforme andCephalosporium kiliense, causative agents of maduromycosis, was investigated. The fungi were grown at 28.5 C and 37 C in a chemically defined medium. The lipids were solvent extracted, purified on Sephadex, and separated into their component classes by silicic acid column chromatography. Five lipid classes were found: (a) sterol esters, (b) triacylglycerides, (c) free fatty acids, (d) sterols, and (e) phospholipids. Fatty acids were analyzed by gas liquid chromatography and phospholipids by thin layer chromatography. Temperature induced changes of varying degrees occurred in both the fatty acid phospholipid fractions of each organism.     

Lipid,sterol and fatty acid composition of antarctic krill (Euphausia superba Dana)

The lipid classes, fatty acids of total and individual lipids and sterols of Antarctic krill (Euphausia superba Dana) from two areas of the Antarctic Ocean were analyzed by thin layer chromatography (TLC), gas liquid chromatography (GLC) and gas liquid chromatography/mass spectrometry (GLC/MS). Basic differences in the lipid composition of krill from the Scotia Sea (caught in Dec. 1977) and krill from the Gerlache Strait (caught in Mar. 1981) were not observed. The main lipid classes found were: phosphatidylcholine (PC) (33–36%), phosphatidylethanolamine (PE) (5–6%), triacylglycerol (TG) (33–40%), free fatty acids (FFA) (8–16%) and sterols (1.4–1.7%). Wax esters and sterol esters were present only in traces. More than 50 fatty acids could be identified using GLC/MS, the major ones being 14∶0, 16∶0, 16∶1(n−7), 18∶1(n−9), 18∶1(n−7), 20∶5(n−3) and 22∶6(n−3). Phytanic acid was found in a concentration of 3% of total fatty acids. Short, medium-chain and hydroxy fatty acids (C≤10) were not detectable. The sterol fraction consisted of cholesterol, desmosterol and 22-dehydrocholesterol.     

Lipid changes in maturing oil-bearing plants

Seeds ofCrambe abyssinica C.D. 6619 and theBrassica napus varieties Golden and Zero-erucic were collected at different stages of maturity and the free lipid extracted with hexane. The lipid thus obtained was separated into lipid classes by silicic acid column chromatography. The lipid classes were further examined by thin-layer chromatography and the component fatty acids and sterols by gas-liquid chromatography. The relative amounts of the lipid classes in crambe and both rape varieties varied as the seed matured and a period of great change occurred about 10 days after fertilization. The greatest change was in triglycerides and phospholipids plus glycolipids. Free fatty acids, present in immature seeds, has almost disappeared at maturity. The lipid classes of crambe and both types of rape were in similar proportion at maturity. Differences in phospholipid and glycolipid composition were found between crambe and rape and between immature and mature rape. The fatty acid composition differred between lipid classes and changed with maturity. Changes in 18-carbon acids of Zero-erucic rape were concurrent with the development of erucic and eicosenoic acids in Golden rape. Contribution No. 36 of the Food Research Institute. Presented at the AOCS Meeting, Cincinnati, October 1965.     

The fatty acids of wax esters and sterol esters from vernix caseosa and from human skin surface lipid

Separation of sterol esters from wax esters in the lipids of vernix caseosa and adult human skin surface was accomplished by column chromatography on MgO. The fatty acids of the sterol esters and wax esters of both samples were separated into saturates and monoenes, and examined in detail by gas liquid chromatography (GLC). The saturated fatty acids of the wax esters of vernix caseosa and of adult human skin surface were remarkably similar. They ranged in chain length from at least C₁₁ to C₃₀, six skeletal types being present: straight even, straight odd, iso, anteiso, other monomethyl branched and dimethyl branched. A large number of patterns of monoenes were observed, each pattern consisting of desaturation of a specific chain at Δ6 or Δ9 plus its extension or degradation products. The mole per cent of the total Δ6 and Δ9 patterns of wax ester fatty acid monoenes of vernix caseosa were 87% and 12%, respectively, and 98% and 1%, respectively, for adult human skin surface lipid. The sterol ester fatty acids of vernix caseosa were much different from those of adult human skin surface: vernix caseosa saturates were largely branched and of lengths greater than C₁₈, whereas the saturates of adult human surface lipid resembled the wax ester fatty acids. Of the vernix caseosa monoene patterns, the mole per cent was 30% Δ6 and 70% Δ9, whereas of the adult human skin surface sterol ester fatty acids 89% were Δ6 and 11% Δ9. Chain extension was particularly pronounced in the sterol ester fatty acid monoenes of vernix caseosa amounting to 7–8 C₂ units in some cases. The fatty acids of the sterol esters of both vernix caseosa and adult human skin surface appear to be derived from the sebaceous gland and from the keratinizing epidermis, but those of the wax esters are from the sebaceous glands only.     

The high content of monoene fatty acids in the lipids of some midwater fishes: Family myctophidae

The total lipids of eleven species of Myctophids caught at depths between 20 and 700 m in the northern Pacific Ocean were analyzed using silicic acid column chromatography (lipid classes) and capillary gas chromatography (fatty acid and fatty alcohol composition). The major components in the lipid classes were triacylglycerols or wax esters; triacylglycerols were the dominant acyl neutral lipids (68.1–96.1%) in eight species, and wax esters were found as the dominant lipid (85.5–87.9%) in three species. The major fatty acids and alcohols contained in the was esters of the three fishes were 18:1n–9, 20:1n–9, 20:1n–11, and 22:1n–11 for fatty acids, and 16:0, 18:1, 20:1, and 22:1 for fatty alcohols. Fatty acids in the triacylglycerols ranging from C₁₄ to C₂₂ were predominantly of even chain length. The major components were 16:0, 16:1n–7, 18:1n–9, 20:1n–11, 22:1n–11, 20:5n–3 (icosapentaenoic acid), and 22:6n–3 (docosahexaenoic acid). In both the triacylglycerols and the wax esters, the major fatty components were monoenoic acids and alcohols. It is suggested from the lipid chemistry of the Myctophids that they may prey on the same organisms as the certain pelagic fishes such as saury and herring, because the large quantities of monoenoic fatty acids are similar to those of saury, herring, and sprats whose lipids originate from their prey organisms such as zooplanktons which are rich in monoenoic wax esters.     

Lipid composition of 30 species of yeast

The detailed composition of cellular lipid of more than 23 species of yeast has been determined quantitatively by thinchrography on quartz rods, a method previously used for estimating cellular lipids of seven species of yeast. That data was fortified by neutral and phospholipid quantitations on 30 species of yeast cells. Most of the test organisms contained 7–15% total lipid and 3–6% total phospholipid per dry cell weight, except for the extremely high accumulation of triglycerides in two species ofLipomyces. Qualitatively, 30 species of yeast cells contained similar neutral lipid constituents (triglyceride, sterol ester, free fatty acid, and free sterol) and polar lipid components (phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl serine, phosphatidyl inositol, cardiolipin, and ceramide monohexoside) without minor constituents. Based on the quantitative composition of neutral lipids, the 30 species of yeast were divided into two groups, the triglyceride predominant group and the sterol derivative group. These groupings were fairly well overlapped from the standpoint of the distribution characteristics of fatty acid. The relative polar lipid compositions also grossly resembled each other. Only one exception of polar lipid composition in yeast cells was found inRhodotorula rubra species which contained phosphatidyl ethanolamine as the most abundant phospholipid. Fatty acid distribution patterns in yeast cells consistently coincided with other reports concerning fatty acid composition of yeast cells. Correlation of lipid composition and classification of yeasts are suggested and discussed. A part of this investigation has been reported at the 14th conference of the Japan Oil Chemists' Society, Nagoya, Japan, October 1975.     

Lipids of the Antarctic sei whale,Balaenoptera borealis

The blubber, liver, and muscle of the Antarctic sei whale were analyzed for total lipid content, composition of lipid by classes and positional distribution of fatty acids in individual lipids. The major glycerolipids (triglycerides, phosphatidylcholine, and phosphatidylethanolamine) were fractionated by silver nitrate thin layer chromatography. The phospholipid fractions were analyzed for fatty acid positional distribution. The whale stomach contained almost exclusively the amphipodParathemisto gaudichaudi. Its lipids were also studied and compared with the lipids of the body tissues. The results indicate that the stomach content lipids are subjected to modifications before being deposited in the blubber, liver, and muscle. According to the silver nitrate thin layer chromatographic studies, liver and blubber triglycerides resemble each other in their patterns of positional distribution of fatty acids and in molecular species composition. The phospholipids of liver and blubber also exhibited closely related fatty acid distribution patterns. In general, while the proportions of lipid classes and their predominant fatty acids varied from tissue to tissue, the patterns according to which the lipids had been synthesized seemed to be common. “...And beneath the effulgent Antarctic skies I have boarded the Argo-Navis, and joined the chase against the starry Cetus far beyond the utmost stretch of Hydrus and the Flying Fish.” (1).     

Improved Methods for the Fatty Acid Analysis of Blood Lipid Classes

Two improved methods have been developed for preparation of fatty acid methyl esters (FAME) from major O-ester lipid classes in blood, i.e., cholesterol ester, triacylglycerol, and glycerophospholipids. The methods involve simple operations, and use neither harmful solvents such as chloroform or benzene nor highly reactive volatile reagents such as acetyl chloride. The FAME synthesis reaction proceeds under mild temperature conditions. The methods include (1) extraction of lipids from 0.2 ml of blood with 0.2 ml of tert-butyl methyl ether and 0.1 ml of methanol, (2) separation of the total lipids into lipid classes using a solid-phase extraction column or thin-layer chromatography, and (3) methanolysis of each lipid class at room temperature or at 45 °C. In all the operations, solvent concentration is performed only once prior to gas–liquid chromatography (GC). No noticeable differences in composition determined by GC have been found between FAME prepared by the present methods and those prepared by a conventional method involving lipid extraction with chloroform/methanol. The mild reaction and simplified procedures of the present methods enabled safe and reproducible analysis of the fatty acid compositions of the major ester-lipid classes in blood.     

Wax esters of barracudina lipid: A potential replacement for sperm whale oil

A sample of barracudina, a small fish potentially available in large quantities off Nova Scotia, contained 17.7% body lipid of which 10% was triglyceride and 85% wax ester. The triglyceride, of calculated iodine value 48, was unusually rich in 14:0 (25.8%), 18:0 (4.3%), 20:0 (1.19%), 22:0 (0.45%) and 24:0 (0.75%). The wax ester fatty acids had a calculated iodine value of 126 and a “normal” marine oil fatty acid composition. The wax ester fatty alcohols contained 42.2% hexadecanol, 29.5% octadecenols, 8.2% eicosenols and 3.8% docosenols. Certain interrelationships between fatty alcohols and fatty acids are indicated by details of composition. The potential exploitation of barracudina lipid as a substitute for sperm oil in some uses appears possible.     

Sterol and fatty acid composition of neutral lipids ofParatenuisentis ambiguus and its host eel

The sterol composition of free sterol and steryl ester fractions of the fish parasiteParatenuisentis ambiguus was determined. In addition, the fatty acid composition of various neutral lipid classes, i.e., wax esters, steryl esters, triacylglycerols and free fatty acids, as well as the composition of the 1-O-alkyl moieties of total ether glycerolipids of the parasite, were investigated. The results of these studies were compared with those obtained on the intestinal tract tissue of its host, the eel (Anguilla anguilla). Cholesterol is the major sterol in bothP. ambiguus andA. anguilla. However, the sterols ofP. ambiguus contain high proportions (>20%) of other sterols, such as campesterol and various dehydrosterols. [e.g., 7-dehydrocholesterol and cholesta-5,22(E)-dienol]. The presence of these minor sterols agrees with the known biotransformations of exogenous sterols in various helminths. Considerable differences are found in the fatty acid composition of neutral lipid fractions, as well as the total lipid extract from the endoparasite as compared to the host tissue. In particular, eicosapentaenoic acid (20∶5n−3), other polyunsaturated fatty acids, such as 20∶4n−6, 22∶5n−3 and 22∶6n−3, as well as long-chain saturated fatty acids, such as 20∶0, are generally enriched in the neutral lipid fractions of the parasite as compared to those of infected eel intestine. The analysis of ether glycerolipids revealed that 1-O-hexadecyl (16∶0) and 1-O-hexadecenyl (16∶1) moieties were present in similar proportions in the ether lipids of bothP. ambiguus and eel intestine, whereas 1-O-octadecyl (18∶0) moieties are more prominent in the parasite and 1-O-octadecenyl (18∶1) moieties in the eel. The results of these studies show thatP. ambiguus has specific mechanisms for the regulation of the sterol and fatty acid composition of its neutral lipids. Dedicated to Professor Helmut K. Mangold on the occasion of his 70th birthday.     

Fatty acids and sterols in oils from canola screenings

One sample of canola seed (variety Tower) and five samples of screenings were commercially processed to yield first an “expeller oil” and subsequently an “extractor oil” by the hexane extraction of the residue. The screening samples contained 25–50% intact or broken canola seed. The balance included 21–31% weed seeds (especially lambsquarter and stinkweed), hulls, fragments of the embryo, and chaff. All the oil samples were analyzed for sterol and fatty acid composition. The extractor screening samples had slightly higher sterol contents than the corresponding expeller samples, while the Tower samples gave the lowest values. The averages (in mg/g oil or extract) for the extractor screening samples were: brassicasterol, 1.0; campesterol, 4.1; and β-sitosterol, 7.3. For expeller screening samples the average were: 0.9, 3.6 and 6.2 and for the Tower oils they were, respectively, 0.9, 3.8, 5.3 and 0.9, 3.5, 4.7. The fatty acid compositions of the screening samples for both extractor and expeller oils were similar to that of the Tower oil except for the higher proportions of docosenoic acid (22:1) and eicosenoic acid (20:1) and the more obvious presence of three C₁₈ conjugated dienes totalling up to 0.6% of one screening oil sample. The docosenoic acid level (mainly erucic acid) ranged from 3.0 to 7.0% for the extractor oils and from 2.5 to 8.0% for the expeller samples, compared to 0.1% for the two Tower oils. The oil contents of the screenings ranged from 20 to 30%, and the fatty acids and sterols appear to be nutritionally useful and innocuous in all respects. Presented in part at the ISF/AOCS World Congress, New York, April–May 1980.     

Lipid changes in maturing oil-bearing plants. III. Changes in lipid classes in flax and safflower oils

Seeds from Raja flax and Indian safflower were collected at increasing stages of maturity and the free lipid extracted from them with hexane. The true lipid material obtained in this manner was separated into lipid classes by silicic acid column chromatography using a diethyl ether-hexane gradient and methanol for the phospholipids. Thin-layer chromatography was used to establish the homogeneity of each lipid class. The composition of the lipid classes was examined by a combination of gas-liquid, silicic acid-impregnated paper and thin-layer chromatography. With both flax and safflower, the relative amounts of the different lipid classes were shown to vary as the seed matured; the phospholipids showed the greatest degree of change. Free fatty acid, mono- and diglycerides were not encountered; acidity, when present, was not due to lipid material. Differences within lipid classes were also investigated. Presented at AOCS meeting in Chicago, Ill., 1961. Contribution No. 84 from the Genetics and Plant Breeding Research Institute, Research Branch, Canada Department of Agriculture, Ottawa.     

Effects of dietary oil related to the toxic oil syndrome on the lipids of guinea pig liver microsomes

The potential effects of oil specimens related to cases of toxic oil syndrome (TOS) on the liver microsomal lipid composition from guinea pigs were investigated. For four weeks, animals were fed diets supplemented with either “case oil” (oil related to cases of TOS) or “control oil” (oil unrelated to cases of TOS), either previously heated or not. Results were compared with those from guinea pigs fed the same diet with no oil. The administration of case oil produced changes in liver microsomal lipid composition. Statistically significant differences were also found between heated case and heated control oils. The cholesterol/phospholipid molar ratios and the major phospholipid class distribution were unaffected under these diet conditions. However, increases in the relative contents of linoleic and arachidonic acids and, simultaneously, a reduction in palmitic and palmitoleic acid levels were observed by diet effects. Heated oil administration decreased the saturated/unsaturated ratios in all cases. Our data suggest that changes observed in the fatty acid composition are attributable to the free fatty acid contents of administered oils. The toxic constituents of case oil seem to be able to alter the liver microsomal lipid composition.