bluuebunny/crossref_metadata_2025 huggingface dataset:
Hepatoma, host liver, and normal rat liver phospholipids as affected by diet
Authors: Wood Randall
Published: November 2006

Individual phospholipid classes derived from hepatoma, host liver, and normal liver of rats maintained on chow and fat free diets were examined in detail and the sphingomyelin and phosphoglyceride structures compared. The concentration of hepatoma sphingomyelin was higher while phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, and diphosphatidylglycerol were only one‐fourth to one‐half normal liver concentrations, irrespective of diet. Hepatoma phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, and phosphatidylinositol contained higher percentages of 18∶1 and, except phosphatidylinositol, much lower percentages of most polyunsaturated fatty acids than liver. The 1‐position of host liver phosphatidylcholine and phosphatidylethanolamine, normal liver phosphatidylcholine and phosphatidylethanolamine, and hepatoma phosphatidylcholine from animals on both diets had the same approximate fatty acid composition, but the percentage of 16∶0 in hepatoma phosphatidylethanolamine was reduced dramatically. The low percentage of 16∶0 at the 1‐position of both phosphatidylethanolamine and triglycerides suggests that the 1‐position fatty acids of these two classes may have a similar origin. The fat free diet reduced the percentage of 18∶2 in liver diphosphatidylglycerol 3‐fold and the decrease was offset by increased percentages of 16∶1 and 18∶1; whereas the very low percentage of 18∶2 in hepatoma diphosphatidylglycerol was offset by increased percentages of 18∶0 and 16∶0. Liver phosphatidylinositol and phosphatidylcholine from the animals fed the fat free diet contained the highest percentage of 20∶3, which replaced 20∶4. Hepatoma sphingomyelin contained a much higher concentration of 24∶0 and 24∶1 than liver. The hepatoma sphingomyelin also contained a C‐24 dienoic acid, which was not detected in host and normal liver. Host liver contained a higher percentage of 22∶6 than normal liver. The diglycerides derived from host liver PC contained a significantly higher percentage of carbon number 38 than normal liver. Diglycerides derived from hepatoma phosphatidylcholine and phosphatidylethanolamine exhibited a 1‐random‐2‐random distribution of fatty acids, whereas diglycerides from liver phosphatidylcholine and phosphatidylethanolamine showed pairing of specific fatty acids.
Effect of vitamin B12 status on the occurrence of branched‐chain and odd‐numbered fatty acids in the liver lipids of the baboon
Authors: Garton G. A. , Scaife J. R. , Smith A. , Siddons R. C.
Published: November 2006

Branched chain fatty acids of the anteiso series and others with methyl substitution nearer to the carboxyl group were found, together with odd numbered, straight chain fatty acids, in very small proportions in baboon liver lipids. The proportions were increased in vitamin B12‐depleted animals, especially after administration of a B12 analogue.
Effect of diet on fatty acids in the lipoprotein cholesteryl esters of type IIa and normal individuals
Authors: Newton R. S. , Pitas R. E. , Jensen R. G.
Published: November 2006

Four normal and two individuals with type IIa hyperlipoproteinemia were placed on the National Heart and Lung Institute Type IIa Diet (<300 mg of cholesterol per day, high polyunsaturated, low saturated fat diet) for 1 week and on a normal diet the following week. Plasma samples were obtained and the cholesterol contents of plasma and of very low density, low density and high density lipoproteins determined. The cholesteryl esters in one type IIa and two normal individuals were identified.

The cholesteryl esters in type IIa very low density lipoproteins from blood drawn 45 min after the last meal in each dietary period, contained less 18∶2 than from the normal. After the first dietary period, the very low density lipoprotein cholesteryl ester 18∶2 content for the type IIa was 37.2M% and for the normals, 54.7M%. After the second dietary period, the corresponding values were 49.7M% and 56.7M%. Fasting samples had lower 18∶2 contents in the low density lipoproteins from the Type IIa subject following both dietary periods and in the high density lipoproteins following the Type II diet.
Unique pathways of sterol metabolism in the Mexican bean beetle, a plant‐feeding insect
Authors: Svoboda J. A. , Thompson M. J. , Robbins W. E. , Elden T. C.
Published: November 2006

Radiolabeled sterols,14C‐cholesterol,14C‐cholestanol,3H‐stigmasterol,3H‐stigmastanol, and3H‐sitosterol, were fed to larvae of the Mexican bean beetle,Epilachna varivestis Mulsant, by coating soybean leaves. Free sterol and sterol ester fractions from treated insects were isolated and analyzed, and in each case nearly 30% or more of total radiolabeled sterols retained by the insect were found in the sterol ester fraction after 8 days. Δ5 sterols were readily reduced to stanols, and C29‐stanols thus produced were dealkylated to cholestanol. Significant amounts of labeled lathosterol were formed from Δ5‐C29 sterols; little, if any, radiolabeled cholesterol was detected in insects fed either of the labeled Δ5‐phytosterols, stigmasterol or sitosterol. Sterol metabolism of this insect thus differs considerably from that found for most phytophagous insects.
Erucic acid metabolism by rat heart preparations
Authors: Cheng Chak‐ki , Pande Shri V.
Published: November 2006

Rat heart preparations metabolized erucic acid at much slower rates than palmitic acid. This applied for activation reaction, for the conversion of acyl‐CoA to acylcarnitine, and for the utilization of acyl group for oxidation. As compared to palmityl‐CoA, erucyl‐CoA exhibited a lower affinity for carnitine palmityltransferase (EC 2.3.1 23), the respective apparent Michaelis constants were 43 and 83 μM. Presence of erucyl‐CoA or erucylcarnitine slowed the mitochondrial oxidation of palmityl groups apparently because of the slower oxidation of erucyl groups. However, presence of erucate did not inhibit the activation of palmitate. Heart mitochondria obtained from rats fed rapeseed oil (50 cal %) or corn oil diet for 3 days showed similar abilities for the coupled oxidation of various substrates and similar carnitine palmityltransferase activities. Thus a suggestion of gross mitochondrial malfunction following rapeseed oil consumption was not confirmed.
Optically active trihydroxy acids ofChamaepeuce seed oils
Authors: Mikolajczak K. L. , Smith C. R.
Published: November 2006

Two trihydroxy acids have been isolated fromChamaepeuce afra (Jacq.) DC, seed oil and identified as (+)‐threo‐9,10,18‐trihydroxyoctadecanoic (phloionolic) acid (9%) and (+)‐threo‐9,10‐,18‐trihydroxy‐cis‐12‐octadecenoic acid (14%). The unsaturated acid has not previously been found in nature. Nuclear magnetic resonance, infrared, thin‐layer chromatography, optical rotation, and identification of the oxidative cleavage products show that these two trihydroxy components have the structures indicated.Chamaepeuce hispanica DC. seed oil and the seed oil of an unidentifiedChamaepeuce species apparently contain these same two acids but in different proportions fromC. afra oil.
Phospholipid exchange proteins in rat intestine
Authors: Lutton C. , Zilversmit D. B.
Published: November 2006

The 105,000 g supernatant and pH 5.1 supernatant fractions from rat intestinal homogenates stimulate phosphatidylcholine exchange between [32P] phosphatidylcholine liposomes and beef heart mitochondria. This active fraction shows the characteristics of a protein. Isoelectric focusing of the intestinal pH 5.1 fraction shows two peaks of phosphatidylcholine exchange activity: one at an acidic pH (4.5–5.3), the other in a basic pH range (8–9). The second peak of activity appears to be a new phospholipid exchange protein. The anatomic distribution of phosphatidylcholine exchange activity in intestine has been investigated. Expressed per mg of protein, phosphatidylcholine exchange activity is higher in mucosa than in the intestinal wall. No significant differences have been found between villi and crypts cells or between jejunal and ileal villi. Furthermore, exchange activity per mg of protein in mucosa is unaffected by fasting or by feeding a high fat or high cholesterol diet. This suggests that phospholipid exchange activity in the absorptive cells is not a rate limiting step in the process of fat absorption.
In vitro activity of the fatty acyl desaturases of human cancerous and noncancerous tissues
Authors: Nakazawa Ichiro , Mead James F. , Yonemoto Robert H.
Published: November 2006

The microsomal desaturase activity of human cancerous and noncancerous tissues was measured in vitro using 1‐14C,‐11,14‐eicosadienoic and 1‐14C‐oleic acids as substrates. Tissues used were a case of ovarian cancer, a urinary bladder cancer, a rectal cancer, and a nonspecific colonic ulcer with appropriately normal tissues. When 11,14–20∶2 was used as substrate, radioactive tetraene and triene were produced. The tetraene was identified by radio gas chromatography as arachidonic acid (5,8,11,14–20∶4), and the triene had a retention time of 5,11,14–20∶3. Thus, the possibility arises that a Δ8 desaturase was involved. In the Δ6 desaturase, with the urinary bladder
Regulation of lipid metabolism in in vitro cultured minimal deviation hepatoma 7288C
Authors: Watson John A.
Published: November 2006

Hepatoma tissue culture (HTC) cells (derived from minimal deviation hepatoma 7288C) were cultivated in a complete medium containing either glucose, fructose or glycerol as the primary carbon source. Growth was rapid on glucose and very low on fructose containing media. Glycerol did not support any growth. Glucose‐14C (U) and fructose‐14C (U) are incorporated into the total lipid fraction of HTC cells. However the level of conversion of glucose into lipid is much greater than fructose. Tritiated water is rapidly incorporated into the saponifiable and nonsaponifiable lipid fractions of growing HTC cells. The level of incorporation is greater than that observed with glucose‐14C (U) and the difference is constant over the experimental period studied. Lipoprotein poor serum (LPPS) isolated from a calf‐fetal calf serum mixture (1∶1) supported growth at a similar rate as the unfractionated serum combination (DS). However the total lipid and total cholesterol content of the fractionated serum was one sixth and one fiftieth the level found in the whole serum mixture, respectively. The level of incorporation of glucose‐14C (U), acetate‐14C (U) and tritiated water into the nonsaponifiable fraction of HTC cells grown on LPPS was 3 to 8‐fold greater than that for DS. However mevalonate‐2‐14C incorporation was stimulated only 1.3 to 1.7‐fold. In general there was a much smaller response in the level of incorporation of radioactive metabolites into the saponifiable lipids. From these studies and additional data, it was tentatively concluded that HTC cells can respond to nutritional pertubations caused by changes in the exogenous lipid content. It was not determined if the apparent responsiveness in the lipids of the nonsaponifiable fraction is due to “feedback control” or some other regulatory mechanism.
Lipids of retina: I. Analysis of gangliosides in beef retina by thin layer chromatography
Authors: Handa Shizuo , Burton Robert Main
Published: November 2006

Lipids were extracted from beef retina by chloroform‐methanol (2∶1); the gangliosides were removed from the total lipid extract by partitioning into water and chromatographing on thin layer plates coated with silica gel. The analytical methods are described for estimating ganglioside components, i.e., N‐acetyl neuraminic acid, hexoses, hexosamine, sphingosine and fatty acids, in the presence of silica gel. Major gangliosides present in beef retina have been tentatively identified as follows: a ganglioside containing two N‐acetyl neuraminyl groups but no hexosamine; two gangliosides containing two N‐acetyl neuraminyl groups and one hexosamine; and a ganglioside with three N‐acetyl neuraminyl moieties and one hexosamine.
Effect of eicosa‐5,8,11,14‐tetraynoic acid on fatty acid composition of selected organs in the rat
Authors: Coniglio John G. , Buch David , Grogan William M.
Published: November 2006

Eicosa‐5,8,11,14‐tetraynoic acid or arachidonic acid or no supplement (controls) was given orally to rats maintained on a fat free diet and the fatty acid composition of total lipids of several organs determined. No changes were noted in the total fatty acid concentrations of the organs examined in the various groups. A decrease in the amount of arachidonic acid, 22∶4ω6 and 22∶5ω6 (as percent of total fatty acids), and an increase in the amount of 20∶3ω6 and linoleate were observed in total lipids of several organs. In the group receiving the arachidonate supplement, there was less linoleate and 20∶3ω6 and more arachidonate than in the controls. Both eicosa‐5,8,11,14‐tetraynoic acid and arachidonate supplements resulted in a decrease in 20∶3ω9 in most organs studied. Generally, the most marked changes were seen in liver but, of the other organs examined (heart, kidney, testis, brain, and adrenals), only the adrenals failed to show any significant differences between the controls and each of the two supplemented groups. Although the experimental conditions preclude conclusive interpretation of the changes observed, it is suggested that eicosa‐5,8,11,14‐tetraynoic acid was effective in inhibiting the conversion of linoleate to arachidonate and the conversion of arachidonate to 22∶4 and 22∶5.
Incorporation of choline‐1,2‐14C into molecular species of phosphatidylcholine by alfalfa leaflet tissue
Authors: Willemot C. , Verret G.
Published: November 2006

Alfalfa leaflet tissue incorporated choline‐1,2‐14C into at least 6 molecular speies of phosphatidylcholine. After 7 hr incubation the species containing palmitic and linoleic acids (16∶0–18∶2) and the species containing linolenic and linoleic acids (18∶3–18∶2) had the highest specific activities. After 24 hr incubation, the species containing palmitic and linolenic acids (16∶0–18∶3) and the species containing 2 linolenic acids (18∶3–18∶3) had the highest specific activities. The most likely interpretation of these data is that choline is accepted by diglycerides containing one linoleic acid residue and that this residue is then desaturated within the phosphatidylcholine molecule to linolenic acid.
Physiological and analytical variation in cholesterol and triglycerides
Authors: Warnick G. Russell , Albers John J.
Published: November 2006

Plasma cholesterol and triglyceride levels were determined, on each of two AutoAnalyzer systems in 11 healthy subjects, weekly over a 10‐week and monthly over a 12‐month period. Analytical variation was 1–2% for cholesterol and 2–5% for triglyceride. Cholesterol and triglyceride values on frozen quality control serum pools were not indicative of absolute values on fresh plasma. Even though the two AutoAnalyzer systems averaged within 1–2 mg/dl for triglyceride and cholesterol on the serum quality control pools during the 12‐month period, the two systems differed by 7–8 mg/dl on fresh or frozen plasma samples. The coefficient of physiological variation on the 10 weekly samples averaged 5% (range 3–10%) for plasma cholesterol and 18% (range 9–27%) for plasma triglyceride. Analysis of the monthly samples suggested significant (P<0.05) seasonal trends: cholesterol was highest in the winter months and lowest in October, whereas triglyceride was highest in January and February and lowest in May and December. We conclude that intra‐individual variation can be an important source of error in attempting to make a genetic diagnosis of hyperlipidemia and/or in evaluating hypolipidemic regimens in a given subject.
Preparation of specifically dideuterated octadecanoates and oxooctadecanoates
Authors: Tulloch A. P.
Published: November 2006

Sixteen methylgem dideuterooctadecanoates with two deuterium atoms at positions 2‐ to 17‐ and seven oxo esters, 8‐oxooctadecanoate‐5,5‐d2, 8‐oxooctadecanoate‐11,11‐d2, 11‐oxooctadecanoate‐8,8‐d2, 11‐oxooctadecanoate‐14,14‐d2, 12‐oxooctadecanoate‐9,9‐d2, 7‐oxooctadecanoate‐10,10‐d2 and 13‐oxooctadecanoate‐16,16‐d2 with two deuteriums on the carbon γ to the oxo group, have been synthesized. Two principal methods of introducing deuterium were used: preparation of 2,2‐dideutero acids by exchange with deuterium oxide followed by chain extension giving dideuteroxooctadecanoates, which were then reduced, as tosylhydrazones, with sodium cyanoborohydride to dideuterooctadecanoates and stepwise introduction by reduction of oxooctadecanoates with sodium borodeuteride, formation of tosylate or mesylate, reduction with lithium aluminium deuteride to tetradeuterooctadecanol and oxidation to dideuterooctadecanoic acid.
Cardiac lipids in rats and gerbils fed oils containing C22 fatty acids
Authors: Beare‐Rogers J. L. , Nera E. A. , Craig B. M.
Published: November 2006

Docosenoic acid from rapeseed oil or herring oil in the diet of the young rat promoted an accumulation of cardiac lipid. The triglyceride fraction accounted for most of the deposited fat and contained a high concentration of the docosenoic acid. Liquid rapeseed oil, partially hydrogenated rapeseed oil or partially hydrogenated herring oil increased the amount of cardiac fatty acids at 1 week and led to the development of degenerative lesions at 16 weeks. Whale or seal oils low in C22 fatty acids produced little effect on the amount of lipids in the heart of rats or gerbils. The latter species receiving 20% rapeseed oil in the diet showed a peak in cardiac lipid deposition at 4 days with similar levels of total fatty acids to that of rats, but with a lower concentration of erucic acid. Oil fromLimnanthes douglasii and hydrogenated herring oil also increased the amount of cardiac fatty acids in gerbils. A high intake of docosenoic acid was common to the animals displaying the cardiac alterations.
Ceramide, triglyceride, and sterol ester in normal human whole brain at different ages
Authors: Rouser George , Yamamoto Akira
Published: November 2006

Separation of ceramides from other lipids by two dimensional thin layer chromatography, characterization of ceramide in human brain lipid extracts, and the levels of ceramide, triglyceride, and sterol ester in human brain at different ages (25 week fetus and postnatal ages of 1 day, 3 weeks, 6, 8 and 22 months, and 6, 8.5, 10, 18, 33, 55 and 98 years) are described.
Characterization of branched monounsaturated hydrocarbons ofSarcina lutea andSarcina flava
Authors: Tornabene T. G. , Markey S. P.
Published: November 2006

The exact position of the double bond and the probable branch assignments of each hydrocarbon isomer ofSarcina lutea andSarcina flava were determined by derivatives and gas chromatography and combined gas chromatography‐mass spectrometry. It was shown by mass spectral data that in all isomers the double bond position was in or near the center of the molecule and, that some of the resolved isomers contained an additional positional isomer. The hydrocarbons were identified as containing methyl branches in the iso or anteiso or both configurations, symmetrically and asymmetrically disposed on the ends of the isomers. The assignment of the methyl branches for each tetrad of four isomers as the isomers emerged from the gas chromatographic column was iso‐iso’; anteiso‐iso; anteiso‐anteiso’; and isonormal for odd carbon‐numbered chains, and iso‐iso’; anteiso‐iso; iso‐normal; and anteiso‐normal for even carbon‐numbered chains. A fifth isomer was identified as a normal‐olefin.
Role of the bases and phosphoryl bases of phospholipids in the autoxidation of methyl linoleate emulsions
Authors: Tsai Lee‐Shin , Smith Lloyd M.
Published: November 2006

Methyl linoleate, emulsified in borate buffer with sodium lauryl sulfate, was used to study the pro‐ or antioxidant effect of 0‐phosphocholine, 0‐phosphoethanolamine, 0‐phosphoserine, as well as the corresponding nonphosphoryl compounds. Oxygen uptake was calculated from rate data obtained at 37 C with an oxygen electrode. The results were similar for the corresponding phosphoryl and nonphosphoryl bases. 0‐Phosphocholine and choline had little effect at either pH 7.9 or 10.2. 0‐Phosphoethanolamine and ethanolamine significantly increased oxygen uptake at pH 7.9, but significantly decreased uptake at pH 10.2. 0‐Phosphoserine and serine decreased oxygen uptake at both pH values. The catalytic activities of the bases investigated may be attributed to their functional groups. The phosphoryl and β‐hydroxy groups exhibited no catalytic activity in the autoxidation of methyl linoleate emulsions at either pH 7.9 or 10.2. The α‐carboxyl amino group of 0‐phosphoserine and serine decelerated autoxidation at both pH values. The amino group H3N+ of the primary amine accelerated autoxidation, but the H2N: group and the reverse effect. Since the quaternary amino group (CH3)3N+ did not affect autoxidation at either pH 7.9 or 10.2, we concluded that the presence of the N−H bond may be necessary for the prooxidant activity of an amine, and that the presence of a pair of free electrons on the nitrogen of an amine is necessary for its antioxidant activity. Kinetically, the autoxidation of methyl linoleate emulsion without added base was in agreement with Farmer's proposed mechanism involving a bimolecular dissociation of hydroperoxides. However, methyl linoleate emulsion at pH 7.9 and 37 C in the presence of ethanolamine or 0‐phosphoethanolamine was autoxidized by a mechanism involving a combined mono‐ and bimolecular dissociation of hydroperoxides.
Nutrition and metabolic studies of methyl esters of dimeric fatty acids in the rat
Authors: Hsieh Alexander , Perkins Edward G.
Published: November 2006

Methyl esters of dimeric fatty acids were prepared by fractionating a mixture of conjugated linoleic and oleic acids that was heated for 24 hr at 300 C in the absence of air. Rats fed diets containing less than 1% dimers showed no significant difference (P<0.05) in the growth rate, feed efficiency, liver: body weight ratio, and lipid: liver weight ratio from those fed normal diets. A lymph cannulation study using14C labeled dimers showed that ca. 0.4% of the dimers fed were absorbed within 12 hr and were transported as free acids in the lymph. Within a 28 hr period, 2% of the labeled dimers fed by gastric intubation were oxidized to14CO2, and 1% radioactivity was recovered from the urine. The metabolism of methyl oleate appeared normal for rats prefed diets containing dimers.
Possible mechanisms of autoxidative rancidity
Authors: Loury M.
Published: November 2006

Rancidity appears as a very complex phenomenon if we consider the numerous reaction products that have been identified. Based on gas liquid chromatographic analysis of the aldehydes, alcohols, alkyl formates and hydrocarbons produced by the autoxidation of oleic acid and nonanal, an explanation of some possible reaction pathways is presented. Rancidity is described as a result of a succession of reactions, some of which are free radical in form, initiated by oleic monohydroperoxides. These yield aldehydes that are autoxidizable and also yield, by specific recurrent reactions, the wide variety of products encountered that are offensive in taste and odor.
Effect of subacute toxic levels of dietary cyclopropenoid fatty acids upon membrane function and fatty acid composition in the rat
Authors: Nixon J. E. , Eisele T. A. , Wales J. H. , Sinnhuber R. O.
Published: November 2006

The effect of subacute toxicity levels of dietary cyclopropenoid fatty acids upon several physiological parameters was determined in the rat. Diets containing 2% corn oil, 2%Sterculia foetida oil or 2% hydrogenatedSterculia foetida oil were fed.Sterculia foetida oil (50% cyclopropenoid fatty acids) fed rats exhibited retarded growth, elevated organ to body wt ratios, increased saturation of tissue lipid, and abnormal histopathology when compared to corn oil and hydrogenatedSterculia foetida oil fed rats. Growth was retarded 50%, liver/body wt doubled, and the percentage of saturated fatty acids in adipose tissue increased 2.5‐fold forSterculia foetida oil vs. corn oil comparisons. Three membrane systems were examined in corn oil andSterculia foetida oil fed rats. Erythrocyte hemolysis rate in 0.3 M glycerol was increased by 30%; induction of mitochondrial swelling by reduced glutathione was inhibited completely and microsomal codeine demethylase activity was depressed nearly 50% inSterculia foetida oil fed rats. The ability of cyclopropenoid fatty acids to inhibit fatty acyl desaturase and influence tissue and membrane lipid composition is discussed. Most of the detrimental effects observed in cyclopropenoid fatty acids fed rats may be associated with alteration of normal lipid metabolism and membrane function.
Purification of campesterol and preparation of 7‐dehydrocampesterol, 7‐campestenol and campestanol
Authors: Kircher Henry W. , Rosenstein Fumiko U.
Published: November 2006

Campesterol ([24R]‐24‐methyl‐5‐cholesten‐3β‐ol) was isolated from a soybean sterol mixture and purified on a small scale by column chromatography and on a large scale by crystallization from acetone to 97% purity. From this, 7‐dehydrocampesterol ([24R]‐24‐methyl‐5,7‐cholestadien‐3β‐ol) and campestanol ([24R]‐24‐methyl‐cholestan‐3β‐ol) were prepared. The acetates and benzoates of all four compounds also were obtained and compared to the corresponding members of the ergostane series.
Toxicity of fatty ozonides and peroxides
Authors: Cortesi Reto , Privett O. S.
Published: November 2006

Studies on the acute toxicity of the ozonides and hydroperoxides of methyl linoleate are reported. High purity preparations of these compounds were injected intravenously or administered orally to adult male rats. The lethal dose by iv injection of these compounds was virtually the same −0.07 mmol/100 g body wt. No deaths were caused in a 24 hr period by single oral dosages of these compounds of ca. 10‐fold that causing death by the iv route. The major effect of these compounds was on the lungs. The lungs became enlarged from edema and accumulation of fluid, and the animals died of lung congestion and injury similar to the effects of ozone toxicity. There was no destruction of vitamin E in the tissues of animals given lethal dosages of ozonides or peroxides intravenously, but significant changes occurred in fatty acid composition of the lipids of the serum and lung. Arachidonic acid increased at the expense of linoleic and oleic acids in these tissues. Only small amounts of peroxidic and TBA positive substances were detected in lung and serum, indicating that the injected ozonides and hydroperoxides were destroyed in the tissues.
Enzymatic oxidation of linolenic acid in aqueous wheat flour suspensions
Authors: Graveland A.
Published: November 2006

Linolenic acid oxidation by the enzyme lipoxygenase in an aqueous wheat flour suspension does not lead to accumulation of linolenic acid hydroperoxides but immediately to secondary oxidation products. The 3 most important products among these were identified as 9‐hydroxy‐trans‐10,cis‐12,cis‐15‐octadecatrienoic acid, 9‐hydroxy‐10‐oxo,cis‐12,cis‐15‐octadecadienoic acid, and 9,12,13‐trihydroxy‐trans‐10,cis‐15‐octadecadienoic acid.
The metabolism of 1‐14C arachidonic acid in pyridoxine‐deficient and pair‐fed control rats
Authors: Coniglio J. G. , Culp F. B. , Goswami A.
Published: November 2006

The metabolism of 1‐14C arachidonate was studied in pyridoxine‐deficient and pair‐fed pyridoxine‐supplemented control rats. The studies included intestinal absorption, oxidation to14CO2, organ uptakes and distribution of14C in the fatty acids of the various organs. Generally, pyridoxine deficiency resulted in little or no alteration of the metabolism of arachidonic acid 6 and 12 hrs after oral administration. A notable exception occurred in hearts of deficient animals in which the proportion of the incorporated14C activity found in fatty acids other than 20:4 was larger than that observed in hearts of pyridoxine‐supplemented animals. A significant amount of14C activity in a water‐soluble form was observed in hydrolysates of intestinal contents and of intestines of both groups. Pyridoxine‐deficient rats had larger quantities than their respective pair‐fed pyridoxine‐supplemented controls. Most of the14C activity of fatty acids of various organs was present as arachidonic acid, but significant activity was present both in fatty acids of shorter and of longer retention time than 20:4. In brain about 20% of the14C activity in fatty acids was in a fraction tentatively identified as an 18:2 isomer. In lungs about 10% of the14C activity was in a fraction tentatively identified as a 22:2 isomer and a similar quantity was observed in a polyene tentatively identified as a 22:4.
Absorption and metabolism of 1‐14C‐methyl linoleate hydroperoxide
Authors: Bergan J. G. , Draper H. H.
Published: November 2006

The absorption and metabolism of 1‐14C‐methyl linoleate hydroperoxide by rats was investigated. After intubation with 2 mg of peroxide, peak14CO2 production occurred at 90 min and 25% of the dose was expired in 24 hr. Fortyfive per cent stil remained in the gastrointestinal tract after 24 hr, most of it bound to the stomach epithelium in the form of intact peroxide. Lymph was collected from the thoracic duct 2 hr after intubation and examined for labeled metabolites. Seven per cent of the radioactivity in the lymph was present in a free 1‐14C‐hydroxy fatty acid and 31% in its methyl ester. Fifty‐seven per cent occurred in lymph triglycerides where it was equally distributed between a 1‐14C‐trienoic fatty acid and an unidentified 1‐14C‐oxy acid. The radioactivity in liver lipids was associated mainly with randomly labeled normal fatty acids. No14C‐hydroxy acids were detected in liver lipids and no evidence was obtained for the absorption of unchanged peroxide. The hydroxy and trienoic acids appear to be formed during absorption by a reduction‐dehydration reaction sequence.
Effect of essential fatty acid deficiency on lipid metabolism in isolated fat cells of epididymal fat pads of rats
Authors: Demeyer D. I. , Tan W. C. , Privett O. S.
Published: November 2006

Lipogenesis, lipolysis, and stimulation of glucose conversion into lipid by insulin or prostaglandin E1 were studied in isolated fat cells of the epididymal fat pads of rats fed a fat‐free diet or this diet supplemented with 10% hydrogenated coconut oil or 10% safflower seed oil. Changes in fatty acid composition, characteristic of an essential fatty acid deficiency, were well advanced in the neutral lipid but had only started in the polar lipid of the fat cells of the epididymal fat pads of animals 3 months after weaning. Cellularity of the epididymal fat pads, as indicated by protein to lipid ratio of the fat cells, was influenced greatly by hydrogenated coconut oil in the diet irrespective of an essential fatty acid deficiency. Lipogenesis was increased in the fat cells of the animals fed the hydrogenated coconut oil diet 5 weeks after weaning but was not significantly different from that of the safflower fed animals 3 months after weaning. Incorporation of glucose into lipid, oxidation to CO2, and basal lipolysis were not significantly different in the fat cells of the essential fatty acid deficient animals from those fed safflower oil 3 months after weaning, except in animals of the fat‐free group based upon cell lipid. However, conversion of glucose to free fatty acid was significantly greater in the isolated fat cells of animals fed either the hydrogenated coconut oil or the fat‐free diet than in those of animals fed the safflower oil supplement. The incorporation of glucose into lipid by isolated fat cells was stimulated significantly by insulin in young animals fed a fat‐free diet, but the effect on lipogenesis appeared to be reversed in the fat cells of animals receiving safflower seed oil 3 months after weaning. Prostaglandin E1 also appeared to stimulate the incorporation of glucose into lipid in the fat cells of the older animals receiving safflower seed oil. Differences in osmolarity produced large differences in utilization of glucose and release of lipid from isolated fat cells, but no significant differences were observed between the cells from animals fed the fat‐free diet and those from the controls fed safflower oil. The results demonstrated the effects of diets containing fat or no fat on enzyme activities and membrane properties of fat cells of the epididymal fat pads of essential fatty acid deficient rats.
Synthesis of 1,2 dilinoleoyl and 1,2 dipalmitoylsn‐3‐glycerophosphorylcholine
Authors: Gordon D. T. , Jensen R. G.
Published: November 2006

The synthesis of 1,2 dilinoleoylsn‐3‐glycerophosphorylcholine (1,2‐18∶2‐sn‐3‐GPC) and 1,2 dipalmitoylsn‐3‐glycerophosphorylcholine (1,2‐16∶0‐sn‐3‐SPC) is described. Synthesis was accomplished by acylating free glycerophosphorylcholine (GPC) with the anhydride and potassium salt of the desired acid. Purification of 1,2‐16∶0‐sn‐3‐GPC was accomplished by crystallization, while purification of 1,2‐18∶2‐sn‐3‐GPC required the use of alumina column chromatography and then crystallization from acetone at −7C.
Ascarosides of the ovaries and eggs ofAscaris lumbricoides (Nematoda)
Authors: Tarr George E. , Fairbairn Donald
Published: November 2006

Nearly all ascarosides in the ovaries ofA. lumbricoides occurred as esters. Among 15 identified esters, 13 occurred at concentrations exceeding 0.1% of the total ascarosides. Each ester consisted of one or two moles of glycone (ascarylose) and several homologs of long chain aglycone. The acid residues consisted of 95.6 mol % acetate and 4.4 mol % propionate. When present, propionate occurred only at the 2′ position of the glycone, which was always esterified. Esters with more than one free hydroxyl group were scarce, 89 wt % of the ascarosides being completely esterified. Monol aglycones contained 25–32 carbon atoms. The C29 homolog was most abundant, and ca. 25 wt% of these aglycones were branched and even‐numbered. Diol aglycones were unbranched C29–35 homologs, C31 and C33 being about equally abundant in diol ascarosides and C33 most common in diol diascarosides. Within each ascaroside class the proportions of different homologs were correlated with the extent of esterification. Free ascarosides of the ascaroside layer of the egg shell, which are formed from the ovarian esters, consisted of 12% monol ascaroside, 10% diol ascaroside, 8% diol diascaroside and 70% diol ascaroside containing an acetylated aglycone. The absence from ascaroside esters of the α‐methyl butyrate and α‐methyl valerate residues which are plentiful in ovarian triglycerides and waxes suggests considerable biosynthetic specificity.
Sphingolipids of the fungiPhycomycetes blakesleeanus andFusarium lini
Authors: Weiss Benjamin , Stiller Richard L. , Cecil R. , Jack M.
Published: November 2006

Ceramides and cerebrosides isolated fromPhycomyces blakesleeanus andFusarium lini together comprise ca. 0.2–0.3% of the cell dry weight, which is ca. 7–8% of the wet weight. The long chain bases obtained from these sphingolipids are (A) 16‐methyl‐4‐hydroxy heptadecasphinganine; (B) 4‐hydroxy octadecasphinganine; (C) 17‐methyl‐4‐hydroxy octadecasphinganine; (D) 18‐methyl‐4‐hydroxy nonadecasphinganine; (E) 19‐methyl‐4‐hydroxy eicosasphinganine; (F) 20‐methyl‐4‐hydroxy heneicosasphinganine; (G) 20‐methyl‐4‐hydroxy heneicosa‐X1‐sphingenine; (H) 20‐methyl‐4‐hydroxy‐heneicosa‐X2‐sphingenine; (I) 4‐hydroxy docosasphinganine; (J) 4‐hydroxy docosa‐X1‐sphingenine; and (K) 4‐hydroxy docosa‐X2‐sphingenine (The position, geometry and nature of unsaturation are unknown. The subscripts indicate the presence of two different unsaturated bases.) The occurrence in biological materials other than mushrooms of bases (D), (F), (G), (H), (I), (J) and (K) has not been previously reported. (The nomenclature used is that recommended by IUPAC‐IUB Commission on Biochemical Nomenclature. The configurations at carbon atoms 2, 3 and 4 are unknown in all cases.) The major normal fatty acids are palmitate, stearate, octadecenoate and octadecadienoate inP. blakesleeanus and stearate inF. lini. The predominant hydroxy fatty acids are hydroxypentadecanoate and hydroxypalmitate inP. blakesleeanus and hydroxy stearate inF. lini. The hexose from the cerebrosides of both fungi is glucose, except cerebroside II ofP. blakesleeanus which contains glucose and galactose.
Pyrolysis of saturated triglycerides
Authors: Nichols Patrick C. , Holman Ralph T.
Published: November 2006

Saturated monoacid triglycerides were pyrolyzed in a flowing atmosphere of helium at 630–650 C, and the products were colleted at low temperature. They were fractionated by thin layer chromatography, according to polarity, and were further resolved and analyzed by gas chromatography, mass spectrometry and IR spectrometry. Alkanes, alkenes, ketones, esters, free acids and cyclic products were identified. Among the latter are probably lactones and substituted dioxanes and dioxolanes, for which structures have been postulated. The parent acid of the triglyceride and the cyclic residual products, after loss of one acid group from the triglyceride, were prominent products. Many products of pyrolysis had structures similar to the major ions produced in the mass spectrum of the triglyceride.
Observations on the role of vitamin E in the toxicity of oxidized fats
Authors: Privett O. S. , Cortesi Reto
Published: November 2006

Studies are reported on the relative effects of in vivo oxidation produced by diets devoid of vitamin E and the consumption of oxidized fat. Rats of the Sprague‐Dawley strain were raised from weaning on a sucrose‐casein diet containing minerals and vitamins in the required amounts, supplemented with 10% of safflower oil, menhaden oil, hydrogenated coconut oil or no fat. Animals of ca. 185 g of the group fed the 10% safflower oil were then switched for 4 weeks to safflower or menhaden oil‐supplemented diets that were allowed to oxidize by exposing them to room temperature in the dark for 2–8 days. For comparison with effects of in vivo oxidation, animals were raised from weaning on similar fresh diets devoid of vitamin E. Consumption of oxidized fat was accompanied by loss of weight, effects on the size of the organs, changes in triglyceride levels and production of TBA‐reacting substances in the tissues. There was no effect on the induced swelling of liver mitochondria or the susceptibility of erythrocytes to hemolysis in these animals. Growth was also suppressed in the animals fed the vitamin E‐free diets, and in vivo oxidation in these animals produced marked effects on the membrane properties of erythrocytes and liver mitochondria.
Simultaneous partial purification of sterol ester hydrolase and lipase from rabbit pancreas
Authors: Morin Robert J.
Published: November 2006

Sterol ester hydrolase and lipase from rabbit pancreatic aqueous extracts were partially purified simultaneously by a rapid method consisting of an initial 50% ammonium sulfate precipitation, followed by chromatography with sodium taurocholate on a 10% agarose gel column (0.5 million exclusion limit), followed by precipitation of both enzymes with heparin and MnCl2. Sterol ester hydrolase was 39‐fold purified and lipase 42‐fold purified, as compared to the initial extract. The enzymes could be partially separated by a DEAE ion exchange procedure, and exhibited different quantitative responses to several activators and inhibitors.
Metabolism of linoleate versus linoelaidate in the laying hen
Authors: Lanser Alan C. , Mounts T. L. , Emken E. A.
Published: November 2006

The metabolic fate in the laying hen of linoelaidic acid, thetrans,trans‐geometric isomer of linoleic acid, was compared to that of the naturally occurringcis,cis linoleate. In two experiments, mixtures of radioisotope‐labeled linoleate and linoelaidate were orally administered to a set of three laying hens. A third mixture consisting of linoleate‐3H and linoleate‐14C was fed to three hens to measure biological isotope effects. Isotopic ratios (3H/14C) of the neutral lipid and phospholipid fractions isolated from egg yolks and of the octadecadienoic acids from these fractions were compared to those of the administered mixtures. The3H/14C ratiosindicate that linoelaidic acid and linoleic acid are equally incorporated into egg yolk neutral lipids and phospholipids. Arachidonic acid was found exclusively in the phospholipid fraction and was radiolabeled with the isotope from thecis,cis octadecadienoate isomer only. Further detailed analysis of individual neutral lipid components indicated: (a) discrimination against thetrans,trans isomer in cholesteryl esters and (b) no discrimination against either isomer in triacylglycerols.
Tissue variation in hydrocarbon composition in the rabbit
Authors: Ferretti Aldo , Flanagan Vincent P.
Published: November 2006

This study, which deals with the distribution of hydrocarbons in seven types of rabbit tissues, was done for the purpose of providing information that might help shed light on the biological relevance of the hydrocarbons in mammalian metabolism. Liver, kidneys, brain, spleen, skeletal muscle, perinephric adipose, and a sample of blood serum were collected from a single animal for analysis of their hydrocarbon composition. The analytical methodology consisted of solvent extraction, saponification (adipose), elution chromatography on hydrated alumina, and combined gas chromatography‐mass spectrometry. Hydrocarbons were detected in all of the tissues examined at concentrations estimated to range from 0.1 to 0.01% of the total lipid extracted. Three quite distinct distribution modes were recognized. The bulk of the identified components consisted of normal, saturated, nonterpenoid hydrocarbons in the C16 to C33 range. Squalene, phytene, phytadiene, and pristane were the only terpenoids detected. Nonterepenoid branched (iso andanteiso) hydrocarbons were identified unequivocally and in significant amounts in the muscle only. The adipose was the only tissue which was relatively rich in monoalkenes, and its overall hydrocarbon composition closely resembled that of the feed. The results of the study are not consistent with metabolic inertness. The observed qualitative and quantitative differences might reflect function and metabolic activities of the individual organs in a way yet to be elucidated.
The effects of original and randomized rapeseed oils containing high or very low levels of erucic acid on cardiac lipids and myocardial lesions in rats
Authors: Hung S. , Umemura T. , Yamashiro S. , Slinger S. J. , Holub B. J.
Published: November 2006

The nutritional status of the very lowerucate rapeseed oil,Brassica napus var. ‘Tower,’ was compared with that of the high‐erucate oil,Brassica napus var. ‘Target’, as well as with corn oil. The effect of randomization on the nutritional qualities of rapeseed oil was investigated as well. The feeding of diets containing the original and randomized ‘Tower” oil or the original ‘Target’ oil, at the 20% level by weight, gave growth rates which were not significantly different from that for corn oil. However, the randomized ‘Target’ oil gave growth rates which were significantly less than all other groups. The growth results could not be explained simply on the basis of food consumption. The level of triglycerides in the hearts of rats fed the very low‐erucate oils was not significantly different from the corn oil group. Triglyceride concentrations in the hearts of animals given the high‐erucate oils were 7–12 times greater than all other groups. The level of total fatty acids in tissue phospholipids was the same regardless of dietary treatment. Fatty acid compositions of the tissue lipids were the same in animals fed either the original or randomized rapeseed oils. A much higher incidence of focal myocardial necrosis was found in animals receiving high‐erucate rapeseed oil relative to animals given the corn oil. The incidence in rats fed diets containing very low‐erucate rapeseed oil was intermediate between these latter two extremes.
Gas chromatographic separation of cholesteryl esters of fatty acids of different degrees of unsaturation
Authors: Takagi Toru , Sakai Akira , Itabashi Yutaka , Hayashi Kenji
Published: November 2006

Cholesteryl esters prepared from the fatty acid methyl esters of linseed oil, pig liver lipids, and Japanese anchovy oil have been separated on the basis of their chain lengths and number of double bonds by gas lipid chromatography on a cyanosiloxane SILAR 10C column. The equivalent chain lengths of cholesteryl esters having acyl groups with 14–22 carbons and 0–6 double bonds are presented. A significant influence of the column temperature on the equivalent chain lengths of the polyenoic fatty acid cholesteryl esters has been found. Separation of the cholestanyl and epicholestanyl esters of linseed oil fatty acids, respectively, under the same conditions is also described.
Hydrocarbon gases produced during in vitro peroxidation of polyunsaturated fatty acids and decomposition of preformed hydroperoxides
Authors: Dumelin Erich E. , Tappel Al L.
Published: November 2006

Hydrocarbon gases have been used previously as an index of lipid peroxidation in vivo and in vitro. In vitro experiments are reported on the formation of hydrocarbon gases from peroxidizing ω‐3 and ω‐6 fatty acids. Hydrocarbon gases were not related during a 20‐hr peroxidation phase but were released following the decomposition of hydroperoxides by addition of excess ascorbic acid. The major hydrocarbon gas products in iron, copper, or hematin catalyzed peroxidation systems were ethane or ethylene from linolenic acid, and pentane from linoleic acid and arachidonic acid. Calculations of the ratios of hydrocarbon gases formed were based on fatty acid decrease and/or change in diene conjugation and peroxide values. Depending on the fatty acid, catalyst, and calculation basis used, pentane formation was a high as 1.3 mol %, ethanol 4.3 mol %, and ethylene 10.6 mol %.
Determination of lipid conjugated dienes with tetracyano‐ethylene‐14C: Significance for study of the pathology of lipid peroxidation
Authors: Waller Robert L. , Recknagel Richard O.
Published: November 2006

A method for quantitative analysis of conjugated diene unsaturation has been developed utilizing tetracyanoethylene‐14C (TCNE‐14C) in a Diels‐Alder condensation. The amount of C14 found in the Diels‐Alder adduct has been shown to be a measure of conjugated diene content. The method has proven successful in analysis of a variety of triglycerides, phospholipids, and peroxidized tissue lipids. In the course of this work, a method for removing the fatty acid substituents from phospholipids using lithium aluminum hydride was developed. TCNE‐14C analysis for conjugated dienes in rat liver microsomal lipids after dosing with CCl4 or BrCCl3 has provided conclusive evidence that the increase in ultraviolet absorption at 233 nm of these lipids is due to conjugated dienes.
Hypercholesterolemia and triglyceride secretion rates in monkeys fed different dietary fats
Authors: Nicolosi R. J. , Hayes K. C. , el Lozy M. , Herrera M. G.
Published: November 2006

The influence of hypercholesterolemia on the triglyceride secretion rate was studied in both squirrel and cebus monkeys fed coconut oil, corn oil, or safflower oil. The triglyceride secretion rate (TGSR) was determined in vivo following the administration of Triton WR1339, which blocks the clearance of very low density lipoprotein (VLDL). Thus, the increase observed in circulating triglyceride after Triton administration presumably reflects hepatic triglyceride (VLDL) secretion in the fasted state. The VLDL‐TGSR was lowest in hypercholesterolemic monkeys and highest in those fed unsaturated fat diets and having a low serum cholesterol. In all instances, TGSR was inversely correlated with the plasma cholesterol concentration. While a definitive explanation for these observations must await further investigation, the possibility that circulating low density lipoprotein (LDL) acts to feed back on VLDL secretion is discussed. The decreased TGSR associated with the diet‐induced cholesterolemia also implies clearance of VLDL is impaired under these conditions.