bluuebunny/crossref_metadata_2025 huggingface dataset:
Effects of surface concentration, metals and acid synergists on autoxidation of linoleic acid monolayers on silica
Authors: Porter W. L. , Levasseur L. A. , Henick A. S.
Published: November 2006

To approximate in a model system the autoxidation of monomolecular layers of lipids on the cell surfaces of freeze‐dried foods, the autoxidation of presumed monolayers of linoleic acid adsorbed from solution onto silica gel has been studied as a function of time and α‐tocopherol and acid synergist content. The method of Honn, Bezman and Daubert was used, modified by the substitution of linoleic acid for soybean oil and the use of gas chromatography to follow oxygen disappearance at 80 C. It was found that adsorption of linoleic acid onto silica gel from petroleum ether solution conforms to a Langmuir isotherm, consistent with the formation of a monolayer. Confirming the finding of Honn et al. with soybean oil, it was found that the most rapid uptake of oxygen occurred at a linoleic acid‐silica ratio close to that for the monolayer. Without included antioxidant, oxidation commences at a nearly linear rate without observable induction period. Time for consumption of one‐half mole of oxygen per mole of linoleic acid is ca. 60 min on acid‐washed silica. If very small amounts of α‐tocopherol are included in the layer, virtually no oxygen uptake measurable in this system occurs during an induction period, the length of which is approximately proportional to tocopherol content. The inflection point at the commencement of rapid oxidation is very sharp; the ensuing oxidation rate approximates that of the unprotected acid. The induction period of linoleic acid with the same tocopherol content is as much as 100% longer when exposed in monolayer than in a bulk form. However the rate after commencement of rapid oxidation is 8–10 times greater in the monolayer. Acid washing of the silica reduced its iron content by 75%. Acid washing also reduced by 60% the rate of autoxidation without α‐tocopherol and increased the length of the induction period four‐fold when α‐tocopherol was present. The effect of pretreatment of the silica by adsorption of the acid synergists, ascorbic, phosphoric, citric and ethylenediamine tetraacetic acid was qualitatively similar to the effect of acid washing. The synergists extended the induction period in increasing order as listed, EDTA producing a 100‐fold extension. For ascorbic acid the rate reduction and increase of induction period were not found on unwashed silica and were dependent on the extent of washing. These findings are consistent with synergist sequestration of metals in a complex that is ineffective in new chain generation by perioxide decomposition.
Preparation and characterization of prostanoyl carnitine
Authors: Johnson M. , Davison Pamela , Holland P. C. , Ramwell P. W.
Published: November 2006

A method is described for the preparation of prostanoyl carnitine from prostanoic acid and L‐carnitine. The crystalline compound exhibits an IR spectrum and chemical reactivity characteristic of long chain acyl carnitine esters and undergoes β‐oxidation in rat liver mitochondria in the absence of exogenous carnitine and ATP. This suggests that it may be an intermediate in the transport of prostanoic acid across the mitochondrial membrane. The data supply additional evidence that prostaglandin‐like substances are converted to the carnitine ester prior to transport in the mitochondrion.
Detection of aldehydes with 4‐amino‐5‐hydrazino‐1,2,4‐triazole‐3‐thiol as spray reagent
Authors: Rahn C. H. , Schlenk H.
Published: November 2006

A spray reagent of 4‐amino‐5‐hydrazino‐1,2,4‐triazole‐3‐thiol, 2% in aqueous 1N NaOH, was used for the detection of aldehydes on chromatograms of lipids. Purple spots are produced with aldehydes, and 1 μg of palmitaldehyde can be detected easily on thin layer chromatograms. The reagent is specific for aldehydes and does not react with ketones. The aldehyde moiety from plasmalogens is detected only after acidic hydrolysis. Purple or red stains arise also with ozonides. Simple precautions against autoxidation of the lipids should be taken to prevent formation of aldehydes which could lead to misinterpretations.
Fatty acid composition of the sterol ester fraction of human adrenal cortex in Cushing's syndrome and after treatment with aminoglutethimide
Authors: Raggatt P. R. , Engel Lewis L. , Symington T.
Published: November 2006

The lipid that accumulated in the adrenal cortex of a patient who had been treated with aminoglutethimide has been compared with the lipid in normal human adrenal cortex and identified as esters of cholesterol with fatty acids. While the concentration of free cholesterol was normal, that of esterified cholesterol was three times greater than that in normal controls. Sterols were analyzed by gas chromatography and found to consist almost wholly of cholesterol. The fatty acid composition of the cholesterol esters in adrenal cortex from patients with abnormal steroid secretion rates was determined. An increased proportion of cholesteryl arachidonate (cholesteryl‐3β‐[allcis]‐eicosa‐5,8,11,14‐tetraenoate) was found in adrenal cortex from patients with decreased steroid secretion rates and a decreased proportion in adrenal cortex from patients with steroid secretion rates raised sufficiently to cause Cushing's Syndrome.
Fractionation and analysis of rat liver14CH3‐lecithins labeled in vivo
Authors: Tinoco J. , Hopkins S. M. , McIntosh D. J. , Sheehan G. , Lyman R. L.
Published: November 2006

The14CH3‐lecithins were biosynthesized by normal adult rats injected with14CH3‐methionine. About 20% of the dose was incorporated into liver lecithins. The14CH3‐lecithins were isolated by thin‐layer chromatography. Separation of lecithins on AgNO3‐treated silica gel yielded lecithins containing a saturated fatty acid in combination with mainly one unsaturated fatty acid, namely, oleic, linoleic, eicosatrienoic, or arachidonic acid. These fractions were eluted with methanolic choline chloride, which prevented elution of AgNO3. The lecithins, after extraction into petroleum ether, were analyzed for radioactivity and for fatty acid composition. Yields were about 75%, based upon fatty acids or radioactivity applied to the plate.

Specific activities differed sharply between the fractions, and arachidonoyllecithins had the highest specific activity. The sum of the activities contributed by each of the fractions agreed well with the specific activity of total lecithins, indicating the recovery of intact lecithin molecules. The recovery of intact molecules allows this procedure to be used with lecithins containing any isotopic labels.

The high specific activity of arachidonoyl‐lecithins relative to the other fractions indicates a high degree of specificity in the metabolic reactions which lead to the formation of rat liver lecithins.
Fatty acid desaturase systems of hen liver and their inhibition by cyclopropene fatty acids
Authors: Johnson A. R. , Fogerty A. C. , Pearson Judith A. , Shenstone F. S. , Bersten Audrey M.
Published: November 2006

Hen liver preparations which desaturate stearic acid at the 9,10 position to form oleic acid have been found to desaturate other saturated fatty acids of carbon chain length from 12 to 20 and 22. The 9,10‐monoenoic fatty acid of the same chain length as the substrate fatty acid is the major product formed. Minor amounts of the 10,11‐ and 11, 12‐monoenoic acids are also formed. Maximum desaturation occurred with the C14 fatty acid substrate and with the fatty acids C17 and C18, suggesting the presence of at least two desaturating systems. The cyclopropene fatty acids, sterculic and malvalic acids, inhibited the desaturation of all thefatty acids at the 9,10 position but desaturation at the 10,11 and 11, 12 positions was affected only slightly. The effect is not due to inhibition of the primary activating enzyme, the long chain acyl CoA synthetase. Sterculic acid is a more effective inhibitor than either malvalic acid or sterculyl alcohol, probably because these cyclopropene compounds do not block the desaturating site of the enzyme as completely as sterculic acid.
Intestinal versus hepatic contribution to circulating triglyceride levels
Authors: Cenedella Richard J. , Crouthamel William G. , Mengoli Henry F.
Published: November 2006

Using intravenous injected [2‐3H] glycerol, measurements wee made of the kinetics of appearance and disappearance of circulating [3H] labeled triglyceride in rats fed a fat free diet containing either no orotic acid (controls) or 2% orotic acid. Following injection of [3H] glycerol, more time is required for the initial appearance of [3H] triglyceride in the circulation of orotic acid treated rats than controls. The sustained entry of triglyceride into the circulation of orotic acid fed rats was only one‐half times as rapid as that seen for control rats. Ca. 10% as much [3H] triglyceride entered the circulation of the orotic acid treated rats as compared with controls. However, the clearance of [3H] triglyceride from the circulation of the orotic acid fed rat was only ca. one‐half times as rapid as that of the control rat. This apparently is due to differences between the lipoproteins produced by the intestines and liver, rather than to changes in the ability of the orotic acid fed animal to clear lipoprotein‐triglyceride from the circulation. Labeled lipoproteins taken from controls and injected into orotic acid treated rats were cleared from the circulation more than twice as rapidly as those taken from orotic acid fed rats and injected into controls. Considering the measured levels of plasma triglyceride synthesis and the slower turnover of the triglycerides produced by the orotic acid fed rat, the findings of this study indicate that the intestines supply 20% or more of the total plasma triglyceride in the absence of dietary fat.
In vitro incorporation of14C‐acetate into lipids of hamster flank organ (Costovertebral organ) sebaceous glands and epidermis
Authors: Lutsky Barry N. , Casmer Charles , Koziol Patricia
Published: November 2006

Following in vitro incubation of flank organs from male golden Syrian hamsters with sodium [1‐14C] acetate, sebaceous glands and appendage‐freed epidermis were obtained by treating the flank organ tissue with calcium chloride. This method permitted the study of incorporation of carbon‐14 into the lipids of these skin components. Extracted lipids were identified by thin layer chromatography and autoradiography and were quantitated by liquid scintillation counting. Mono‐, di‐, and triglycerides, free sterols, fatty acids, wax monoesters, and squalene were identified as products of sebaceous gland metabolism of labeled acetate. In marked contrast, little incorporation of14C into triglycerides by the epidermal preparations was noted, although the epidermal lipids showed higher relative proportions of free sterols and polar lipids (including phospholipids). Accumulation of sterol esters did not occur. In both preparations phosphatidylcholine represented the major labeled phospholipid.
Jimpy mouse: In vitro studies of brain sphingolipid biosynthesis
Authors: Morell Pierre , Costantino‐Ceccarini Elvira
Published: November 2006

Microsomal preparations from brains of Jimpy mice are able to synthesize only 10–20% as much galactosylceramide as preparations from control littermates. Synthesis of glucosylceramide and ketodihydrosphingosine is only slightly impaired.
7‐Methyl‐7‐hexadecenoic acid: Isolation from lipids of the ocean sunfishMola mola (Linnaeus) 1758
Authors: Ackman R. G. , Safe L. , Hooper S. N. , Paradis M. , Safe S.
Published: November 2006

A fatty acid amounting to several per cent of the acids in various samples of the liver oil of the ocean sunfishMola mola was isolated and characterized as 7‐methyl‐7‐hexadecenoic acid. This acid and the previously reported 7‐methyl‐6‐hexadecenoic acid are believed to be chiefly responsible for the 7‐methylhexadecanoic acid observed in many fatty acid mixtures of marine origin after hydrogenation.
Addition compounds of oxidizing tocopherol and soybean lecithin
Authors: Porter W. L. , Henick A. S. , Levasseur L. A.
Published: November 2006

Evidence is presented for the formation of addition compounds from tocopherol and soybean lecithin, when adsorbed in monolayer on silica from a mixed solution in chloroform and oxidized at 80 C for 72 hr. Tocopherol was present at 7 mol % of the lecithin in the monolayer. The compounds produced are analogous to linoleic acid‐tocopherol adducts previously reported by us. UV spectra of the mixed lecithin and tocopherol monolayers while in silica gel slurry in a solvent were obtained by the method previously reported by us for oxidized linoleic acid and tocopherol monolayers. The monolayer spectra show no evidence for tocopherol dimer. A minor amount of quinone is indicated, but the spectrum has a maximum at 287 nm with no other major peaks. The proposed addition compounds have been characterized by transesterification and hydrogenation, UV, IR, thin layer chromatography and gas chromatography retention behavior, mass spectrometry and elemental analysis. IR spectra of twice‐chromatographed addition compounds show specific lecithin absorption bands (5.75 μ; 10.3 μ) together with much enhanced 3.4–3.5, 6.8, 7.25 and 9.14 μ peaks, the latter two being characteristic of α‐tocopherol. The UV spectrum of the adducts showed λmaxCHCl3 287 nm, with shoulders at 276 and 300 nm. Hydrogenation removed the peaks at 287 and 276 nm, leaving a peak at 300 nm similar to that of the linoleic acid‐tocopherol adduct. Esters of the adducts prepared by transesterification and hydrogenation were similar by all our chemical, chromatographic and spectral tests to the previously characterized esters of the linoleic acid‐tocopherol adduct.
Effect of soy sterols on cholesterol synthesis in the rat
Authors: Fishler‐Mates Z. , Budowski P. , Pinsky A.
Published: November 2006

Soy sterols increased the incorporation of acetate into cholesterol by rat liver slices and prevented the depression of cholesterogenesis caused by dietary cholesterol. Acetate incorporation into cholesterol by intestinal slices was not affected by soy sterols but was decreased by cholesterol. The results with liver slices agree with the view that soy sterols, by interfering with the intestinal absorption of cholesterol, prevent the feedback inhibition of hepatic cholesterogenesis.
Sulfated bile acid in urine of patients with hepatobiliary diseases
Authors: Makino Isao , Shinozaki Kenjiro , Nakagawa Shoichi
Published: November 2006

The presence of sulfated bile acid in urine of patients with hepatobiliary diseases was recognized by using an Amberlite XAD‐2 column for extraction of bile acid and a Sephadex LH‐20 column for separation of sulfated (sulfate of either taurine or glycine conjugate) and nonsulfated bile acid (taurine and glycine conjugate). Sulfated and nonsulfated bile acid, obtained after a Sephadex LH‐20 column of urinary extract of the patient with acute hepatitis, was identified by thin layer chromatography. Sulfated bile acid showed a spot with different Rf value from that of taurine‐conjugated, glycine‐conjugated and free bile acid, and solvolysis of sulfated bile acid resulted in a compound with the same Rf value as glycodihydroxycholanoic acid. A large amount of bile acid sulfate was found in urine of patients with hepatobiliary diseases. The sulfated bile acid in these urine samples occupied from 57.1 to 93.3% of total bile acid, and consisted of both di‐and trihydroxycholanoic acid (major part, chenodeoxycholic acid). As no solvolysis was carried out in previous works, bile acid sulfate in urine, as described in this paper, was not determined at all.
Autoxidation and effects of pro‐ and antioxidants in lyophilized red blood cell membranes
Authors: Porter W. L. , Henick A. S. , Murphy F. , Colgan R. , Porfert G.
Published: November 2006

Oxygen uptake and effects of pro‐ and antioxidants have been compared at 80 C in lyophilized red blood cell (RBC) bilayer membranes (ghosts). In this dry and relatively immobile system, catalytic metals have pronounced effects. When ghosts are prepared in the usual manner, in phosphate buffer, hypotonic saline, or deionized water (DI), oxygen uptake is extremely slow and limited unless: (a) catalytic metal, e.g., cobaltous ion, is supplied in the absence of metal‐complexing buffers and (b) residual phosphate buffer is removed by repeated deionized water or hypotonic saline washes. Ghosts adsorb d‐α‐tocopherol strongly from 1% alcohol emulsion in buffer in amounts far above normal RBC concentrations, whereas synthetic antioxidant uptake seldom exceeds the normal tocopherol level. Uptake and effectiveness of antioxidants introduced by either perfusion or in the vapor phase, and resistance of ghosts to autoxidation are discussed as they relate to protection of lyophilized membranes and freeze‐dried foods.
Chain length specificity in the utilization of long chain alcohols for ether lipid biosynthesis in rat brain
Authors: Natarajan V. , Schmid H. H. O.
Published: November 2006

A mixture ofcis‐9‐[1‐14C] octadecenol and [1‐14C] docosanol was injected into the brains of 19‐day‐old rats, and incorporation of radioactivity into brain lipids was determined after 3, 12, and 24 hr. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding fatty acid, but oleic acid was more radily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated into 18∶1 alkyl and alk‐1‐enyl moieties of the ethanolamine phosphoglycerides and into 18∶1 alkyl moieties of the choline phosphoglycerides. Even after the disappearance of the 18∶1 alcohol from the substrate mixture (12 hr), the 22∶0 alcohol was not used to any measurable extent for alkyl and alk‐1‐enyl glycerol formation.
Effect of a diet rich in sunflower oil on aspects of lipid metabolism in the genetically‐obese rat
Authors: Wahle K. W. J. , Radcliffe J. D.
Published: November 2006

Aspects of the lipid metabolism of male, obese and lean Zucker rats were compared using animals which had been fed ad libitum for 32 days on a diet (HS) which contained 200 g sunflowerseed oil/kg or one (LS) which contained 50 g/kg of the oil. When compared with the LS diet, the HS diet decreased the characteristic lipid accretion in the liver of obese rats from 126 mg (LS) to 81 mg (HS)/g wet weight; corresponding values for the lean rats were 39 mg and 56 mg/g wet weight of liver, respectively. The HS diet depressed lipid synthesis de novo by liver homogenates and decreased the Δ9‐desaturase activity of liver microsomes from obese and clean rats by about 50%. Δ9‐Desaturase activity in vitro was also depressed by the addition of linoleic acid to liver microsomes from both obese and lean rats fed ad libitum on a standard laboratory diet. Depressed Δ9‐desaturase activity, due to ingestion of the HS diet, was reflected in lower ratios of 16∶1/16∶0 and 18∶1/18∶0 fatty acids in tissue lipids from obese and lean rats. Ingestion of the HS compared with the LS diet resulted in increased proportions of 18∶2ω6 in liver lipids and adipose tissue triacylglycerols of obese and lean rats. The HS diet also increased the proportions of 20∶4ω6 in adipose triacylglycerols of obese and lean rats and in liver lipids of obese animals but not in their lean littermates.
Hypertriglyceridemia in ehrlich ascites carcinomatous mice: Tumor and mouse strain differences
Authors: Kannan R. , Baker N.
Published: November 2006

Ehrlich ascites carcinoma growth in mice induces hypertriglyceridemia. The degree of hypertriglyceridemia found in one laboratory (Spector's) was much greater than we observed in our laboratory. Moreover, major differences were reported with respect to fasting (no effect on tumor extracellular fluid triglyceride levels in Spector's tumor‐bearing mice; marked decrease in ours). We have obtained tumorous CBA mice from Spector's laboratory and have studied them simultaneously with our Swiss‐Webster mice. Triglyceride levels of the above two groups and from two controlled crossover groups, included to evaluate the influence of mouse and tumor strains on hypertriglyceridemia, were determined. The CBA mice had intense hypertriglyceridemia and high triglyceride levels in tumor extracellular fluid regardless of the subline source of ascites tumor. On the other hand, only mild hyperlipidemia was induced with both strains of tumor in Swiss‐Webster mice. Thus, the variations in plasma and tumor extracellular fluid triglyceride levels probably arise from the mouse strains and not from variations in the tumor subline. Fasting caused a decrease in both plasma and tumor extracellular fluid triglyceride concentrations in CBA, as well as in Swiss‐Webster mice. A mouse strain difference was also evident from a significant decrease in wet weights of adipose tissues like epididymal fat, inguinal fat, and intermuscular fat with tumor growth in the CBA strain which was not observed in the Swiss‐Webster strain at the corresponding stage of tumor growth. Study of these strain differences may lead to an understanding of factors that regulate hyperlipidemia.
Ketone bodies serve as important precursors of brain lipids in the developing rat
Authors: Yeh Yu‐Yan , Streuli Victoria L. , Zee Paulus
Published: November 2006

Ketone bodies are readily oxidized for energy by extrahepatic tissues. Since oxidation of ketone bodies produces acetyl coenzyme A (AcCoA), and hence could be an important source of immediate precursors for fatty acid synthesis, we investigated, in whole‐brain homogenates of developing rats, the preferential utilization of [3‐14C]acetoacetate (AcAc), [3‐14C]β‐hydroxybutyrate (β‐OHB), and [U‐14C]glucose for production of CO2 and lipids, including phospholipids, glycerides, cholesterol, and free fatty acids. Throughout the postnatal period, the rate of AcAc oxidation was 2–3 and 2–6 times the rate for β‐OHB and glucose, respectively. The eynthesis of lipids from AcAc was 7‐ to 11‐fold higher than from glucose. The brain's capacity for lipid synthesis from β‐OHB was similar to that from AcAc during the first 8 days of life; however, during the next 10 days, the synthesis of lipids from β‐OHB decreased to 60% of AcAc‐dependent synthesis. The high rate of lipid synthesis from ketone bodies was accompanied by increased activities of cytoplasmic acetoacetyl CoA synthetase and acetoacetyl CoA thiolase in the developing brain. During the entire postnatal development, the proportion of radioactivity claimed by lipids vs. CO2 from [3‐14C]AcAc was 44–62% vs. 38–56%; from [3‐14C]β‐OHB, 50–81% vs. 19–50%; and from [U‐14C]glucose, 14–43% vs. 57–86%. Phospholipids accounted for more than two‐thirds of total lipids synthesized from either ketone bodies or glucose, while diglycerides plus cholesterol and free fatty acids accounted for most of the remainder. Addition of glucose to the incubation medium did not alter lipid production from AcAc throughout the suckling period, but moderately depressed energy production in the brain of 16‐ to 20‐day‐old rats. It is clear that in cell‐free preparations from the brain of developing rats, ketone bodies are preferred over glucose as precursors for both energy and lipids, mainly phospholipids. These results suggest that ketone bodies are important for the growth and development of the brain.
Glyceride structure variation in soybean varieties: I. Stereospecific analysis
Authors: Fatemi S. H. , Hammond E. G.
Published: November 2006

Stereospecific analysis of soybeans and related species showed that there was little palmitic or stearic acid on thesn‐2‐position, and thesn‐1‐position is consistently richer in palmitic, stearic, and linolenic acids than thesn‐3‐position. Thesn‐3‐position is enriched in oleic acid and thesn‐2‐position with linoleic. Plots of the percentage of fatty acids on the glycerol positions vs. the percentage in the whole oil revealed a soybean variety that had a deviant distribution that is probably genetically controlled.
Hydrolysis ofbis‐phosphatidic acid from developing soybean by phospholipase A2
Authors: Morton W. T. , Stearns E. M. , Schmid H. H. O.
Published: November 2006

bis‐Phosphatidic acid from developing soybean was completely hydrolyzed with phospholipase A2 (lyophilized venom from Ophiophagus hannah) to yield lyso‐bis‐phosphatidic acid and free fatty acids. It is suggested that soybean bis‐phosphatidic acid is derived from sn‐3‐glycerophospho‐sn‐3′‐glycerol.
Composition of novel triesters from the skin of the rhino mutant mouse
Authors: Logani Mahendra K. , Nhari David B. , Davies Ronald E.
Published: November 2006

Composition of two novel triesters, derived from the skin of the rhino mutant mouse, is described. Chemical and spectroscopic analysis of the products of pancreatic hydrolysis of the triesters showed that these are comprised predominantly of isomer I (92.7 mole %). The syntheses of two reference compounds, 1‐O‐hexadecanoyl‐2‐[(14‐hexadecanoyloxy)O‐tetradecanoyl] 1,2‐hexadecanediol (Ia) and 2‐O‐hexadecanoyl‐1‐[(14‐hexadecanoyloxy)O‐tetradecanoyl]‐1,2‐hexadecanediol (IIa), corresponding in their structures to isomers I and II of the triester, wax have also been described.
Differential biosynthesis of molecular species of 1,2‐diacyl‐sn‐glycerols and phosphatidylcholines in cold and warm acclimated goldfish (Carassius auratus L.)
Authors: Holub B. J. , Piekarski J. , Leatherland J. F.
Published: November 2006

The initial incorporation of glycerol‐3H into the molecular species of liver 1,2‐diacyl‐sn‐glycerols and phosphatidylcholines was studied in vivo using goldfish acclimated to 10 C and 30 C. A 1.5‐ and 2.2‐fold higher proportion of the total radioactivity in the diacylglycerols from cold acclimated fish was found to be associated with the trienoic and pentaenoic species, respectively, when compared to warm acclimated fish. In the phosphatidylcholines, 1.9‐ and 1.3‐fold greater percentages of the newly‐incorporated radioactivity were found in tetraenoic and pentaenoic molecules, respectively, from cold relative to warm acclimated fish which suggests a preferential synthesis of these molecules relative to other molecular species in response to a lowering of environmental temperature. The present results indicate, therefore, that environmental temperature influences the complement of molecular species of diacyglycerols and phosphatidylcholines which fish produce by way of de novo biosynthesis in vivo.
Myristicin. The major volatile component in mature seed ofPortenschlagia ramosissima
Authors: Bohannon Maerean B. , Kleiman Robert
Published: November 2006

Portenschlagia ramosissima (Port.) vis. (Umbelliferae) seed contains 15% essential oils, 70% of which is the aromatic ether myristicin. These structural assignments were made from nuclear magnetic resonance, combined gas chromatography‐mass spectrometry (GC‐MS), and infrared and ultraviolet data. GC‐MS data also indicate the presence of pinene, cymene, terpinene, elemicin, methyl eugenol, and a variety of sesquiterpene hydrocarbons.
Linolenic acid deficiency: Changes in fatty acid patterns in female and male rats raised on a linolenic acid‐deficient diet for two generations
Authors: Tinoco J. , Babcock R. , Hincenbergs I. , Medwadowski B. , Miljanich P.
Published: November 2006

Rats were fed for two generations a purified, linolenic acid‐deficient diet in which the only source of lipid was purified methyl linoleate. This diet contained about 38 mg linolenic acid/kg diet. Control rats were given the same diet supplemented with methyl linolenate (2,500 mg/kg diet). Male and female rats ranged in age from weanling pups to adults. Lipids were extracted from liver, brain, kidney, spleen, heart, muscle, gastrointestinal tract, lung, ovary, testis, adrenal, plasma, erythrocytes, retina, and adipose tissue. Fatty acids of major phospholipid classes (choline phosphoglycerides, ethanolamine phosphoglycerides, and mixed serine phosphoglycerides plus inositol phosphoglycerides) or of total lipid extracts were measured by gas liquid chromatography. Growth rates and organ weights were similar in control and linolenic acid‐deficient rats. The major effect of the deficiency was to lower the proportions of n−3 fatty acids, especially 22∶6 n−3, in all the organs analyzed. Docosahexaenoic acid (22∶6 n−3) was mainly replaced by 22∶5 n−6 in deficient rats. The greatest changes in composition were found in brain, heart, muscle, retina, and liver.
Lipids of the Antarctic sei whale,Balaenoptera borealis
Authors: Bottino Nestor R.
Published: November 2006

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.
The 6,9,12,15,18‐heneicosapentaenoic acid of seal oil
Authors: Mayzaud P. , Ackman R. G.
Published: November 2006

A heneicosapentaenoic acid isolated from seal oil has been identified as all‐cis‐heneicosa‐6,9,12,15,18‐pentaenoic acid (21∶5ω3). The gas liquid chromatographic retention times of the methyl ester on four different liquid phases were identical to those of synthetic 21∶5ω3, and the mass spectra of the pyrrolidide derivatives were very similar. The ω3 structure, unusual in an odd‐chain polyethylenic acid, suggests as the origin α‐oxidation of 22∶5ω3, but ω‐oxidation of the 21∶6 hydrocarbon common in marine algae is also discussed.
Triglyceride synthesis from dihydroxyacetone phosphate and palmitate by microsomes from mammary glands of lactating mice
Authors: Ananda Rao G. , Abraham S.
Published: November 2006

Both di‐ and triglycerides were synthesized when microsomes isolated from mammary glands of lactating mice were incubated with dihydroxyacetone phosphate (DHAP), (1‐14C)palmitate, ATP, CoASH, GSH, KF, MgCl2, and NADPH. When NADH replaced NADPH, glyceride synthesis was very low. In the absence of either NADPH or NADH, DHAP was acylated to palmityl‐DHAP. Since microsomes do not have glycerol 3‐phosphate NAD:oxidoreductase activity, we inferred that glycerol 3‐phosphate (GP) is not an intermediate in triglyceride biosynthesis from DHAP. This reductase, present in the cytosol, was active only with NADH. With the same concentration of either GP or DHAP, microsomes yielded essentially similar amounts of di‐ and triglycerides. Mitochondria, while capable of synthesizing palmityl‐DHAP, did not produce di‐ and triglycerides.
Kinetics of a micelle specific palmitoyltransferase isoenzyme of rabbit mammary gland
Authors: Caffrey Martin , Kinsella John E.
Published: November 2006

Palmityl‐CoA: monopalmityl‐sn‐glycerol 3‐phosphate palmitoyltransferase [EC 2.3.1.‐] in rabbit mammary gland microsomes is composed of two isoenzymic species. The α form (LPAT‐α) is active with monomeric substrates and inhibited by micelles while the β form (LPAT‐β) is active only with micelles. By combining the effects of time, temperature, and Tween 80 which selectively inhibited LPAT‐α, the substrate saturation curve for the LPAT‐β isoenzyme has been successfully determined. Both theoretical and experimental curves are in good agreement.
Oxygenated fatty acid constituents of soybean phosphatidylcholines
Authors: Sessa D. J. , Gardner H. W. , Kleiman R. , Weisleder D.
Published: November 2006

Bitter‐tasting phosphatidylcholines from hexane‐defatted soybean flakes were chromatographically separable from ordinary soy phosphatidylcholines (SPC). The bitter‐tasting SPC contain 32% oxygenated fatty acids in addition to palmitic, stearic, oleic, linoleic, and linolenic acids. Identification of these oxygenated acids was based on infrared, ultraviolet, proton nuclear magnetic resonance, and mass spectral characteristics of methyl ester derivatives which were separated and purified by column and thin layer chromatography. The fatty acid methyl esters identified were (a) 15, 16‐epoxy‐9, 12‐octadecadienoate, (b) 12, 13‐epoxy‐9‐octadecenoate, both with double bonds and epoxide groups predominantly ofcis configuration; (c) 13‐oxo‐9,11‐and 9‐oxo‐10, 12‐octadecadienoates; (d) 13‐hydroxy‐9, 11‐ and 9‐hydroxy‐10, 12‐octadecadienoates; (e) 9, 10, 13‐trihydroxy‐11‐ and 9,12,13‐trihydroxy‐10‐octadecenoates. In addition, trace amounts of (f) 11‐hydroxy‐9,10‐epoxy‐12‐and 11‐hydroxy‐12,13‐epoxy‐9‐octadecenoates; (g) 13‐oxo‐9‐hydroxy‐10‐and 9‐oxo‐13‐hydroxy‐11‐octadecenoates; (h) 9,10‐dihydroxy‐12‐ and 12, 13‐dihydroxy‐9‐octadecenoates; and (i) 9,12,13‐dihydroxyethoxy‐10‐ and 9,10,13‐dihydroxyethoxy‐11‐octadecenoates were indicated by mass spectrometry. Dihydroxyethoxy compounds (i) were possibly formed upon extraction of the SPC from flakes by 80% ethanol. Except for the first two epoxy compounds, labelled a and b, the oxygenated fatty acids are similar to the products formed by homolytic decomposition of linoleic acid hydroperoxide. The first two compounds with predominantlycis configuration may occur by action of fatty acid hydroperoxides on an unsaturated fatty acid.
Atherogenesis in swine fed several types of lipid‐cholesterol diets
Authors: Goldsmith Dale P. J. , Jacobi Herbert P.
Published: November 2006

Eighteen‐month‐old Nebraska strain minipigs were fed diets containing 2% cholesterol and 20% corn oil, lard, or coconut oil for 12 to 18 months. Concentrations of serum total lipid, total cholesterol, and total phospholipid increased 200 to 300% with each diet. Changes in serum concentrations of Sf 20+ and Sf 0–20 lipoproteins varied with diets fed. Serum concentration of high density lipoprotein was increased in all cases. Intima concentration of Sf 0–20 lipoprotein fraction was elevated by feeding the corn oil diet. There was no development of atherosclerosis as a result of feeding the corn oil‐cholesterol diet, but there was an increase in atherosclerosis as a result of feeding the lard or coconut oil diet. There were no correlations between fatty acid patterns of several lipid fractions from serum and corresponding lipid fractions from aortic intima of corn oil fed animals.
The circadian cycles of plasma corticosterone and adrenal cholesteryl esters in the normal and EFA‐deficient female rat
Authors: Young Angela K. , Walker Brian L.
Published: November 2006

In female rats subjected to a 12 hr light‐12 hr darkness schedule and fed a semipurified diet containing 10% corn oil, plasma corticosterone concentration showed a monophasic circadian cycle with minimum and maximum concentrations at the start of the light and dark periods, respectively. Adrenal total cholesteryl ester concentration was inversely related to plasma corticosterone, as were those of several of the individual esters; changes in cholesteryl ester concentration appeared to follow rather than precede changes in plasma corticosterone. There was preferential depletion of the cholesteryl esters of 18∶1, 18∶2ω6, and 20∶4ω6 during glucocorticoid secretion. [Abbreviations: EFA, essential fatty acid (s);X:YωZ, fatty acid with X carbon atoms and Y olefinic bonds with the terminal double bond Z carbon atoms from the methyl group.] In female rats fed hydrogenated coconut oil (EFA‐deficient), a monophasic cycle for plasma corticosterone was also observed, but the peak was much broader than that recorded for rats fed corn oil, although minima and maxima occurred at similar times for the two groups. No significant cycle of adrenal total cholesteryl esters was evident in the deficient rats, but the 20∶3ω9 and 22∶3ω9 esters did decrease significantly during the period of high plasma corticosterone concentration. Preferential net decreases in adrenal cholesteryl esters during corticosteroidogenesis were more apparent in normal than in EFA‐deficient rats.
Apoproteins in association with intralipid incubations in rat and human plasma
Authors: Robinson Stuart F. , Quarfordt Steven H.
Published: November 2006

Intralipid was incubated with rat and human plasma and examined for changes in lipid and apoprotein composition. Upon incubation in rat plasma, Intralipid acquired an apoprotein complement similar to that found in chylomicrons following plasma incubation or in chylomicrons after alimentary lipemia. Since the apoproteins of lipoproteins probably govern their metabolism, these results suggest that Intralipid and chylomicrons undergo similar metabolic fates. This pattern is characterized by a predominance of Apo E (the arginine‐rich apoprotein) and Apo C. Incubation of Intralipid with human plasma showed the uptake of Apo A‐I and Apo A‐IV as well. Density fractionation of the plasma into separate lipoprotein classes facilitated identification of high density lipoprotein as the major apoprotein donor to the Intralipid. When rat lipoprotein‐free plasma (δ>1.21) was incubated with Intralipid, a different apoprotein pattern appeared in the particles of Sf>400 depending on whether the entire Intralipid preparation or only the Sf>400 fraction alone was incubated. The difference consisted of a virtual total absence of the arginine‐rich protein on the Sf>400 particles in whole Intralipid incubations. Density fractionation of the Sf<400 particles of Intralipid and recombination of these fractions with the Sf>400 fraction before incubation revealed the major inhibitory fraction to be δ<1.006 (Sf 20–400).
Characterization of branched‐chain fatty acids from fallow deer perinephric triacylglycerols by gas chromatography‐mass spectrometry
Authors: Smith A. , Duncan W. R. H.
Published: November 2006

Branched‐chain fatty acids of perinephric triacylglycerols of semi‐feral fallow deer (Dama dama dama) were analyzed by high resolution gas chromatography‐mass spectrometry. Of the total fatty acids, 15.50% were Branched‐chain components including 8.96% iso acids, mostly 14‐methylpentacanoic acid, 2.85% anteiso acids and 1.73% of other monomethyl‐substituted acids; dimethyl‐branched acids with an iso structure (1.05%) and with an anteiso structure (0.18%) were also present. Whereas the predominant iso acids and methyl‐substituted iso acids had chain lengths of 13 and 15 carbon atoms, the anteiso acids and methyl‐substituted anteiso acids had chain lengths of 14 and 16 carbon atoms. Methyl substitution occurred on the even numbered carbon atoms relative to the carboxyl group. The general composition is also given of the fatty acids comprising the triacylglycerols of subcutaneous (rump area) and perinephric adipose tissue.
Comparison of lipid status in the hearts of piglets and rats on short term feeding of marine oils and rapeseed oils
Authors: Opstvedt J. , Svaar H. , Hansen P. , Pettersen J. , Langmark F. T. , Barlow S. M. , Duthie I. F.
Published: November 2006

A series of 4 experiments with piglets and one experiment with rats has been conducted to establish the cardiac lipid status of weanling (3 weeks old) male animals fed fats with different contents of docosenoic fatty acids. Experimental fats were rapeseed oil (RSO) (48.0% 22∶1), refined fish oil (RFO) (14.6% 22∶1), partially hydrogenated fish oil (PHFO) (14.3% 22∶1) and lard (0% 22∶1) combined with sunflower seed oil (SFO) in different proportions in diets with 21% total fat. Lipidosis could not be detected in piglets as increased heart weights, by chemical assay for myocardial contents of triglycerides, or by accumulation of docosenoic fatty acids or nonesterified fatty acids (NEFA). In rats, diets with RSO at a level of 16% increased myocardial triglyceride and docosenoic fatty acid contents about 7 times while the effect on cardiac NEFA was inconsistent. Histological examinations of the hearts revealed stainable intracellular fat droplets in some piglets fed 16% RSO for 8 to 13 days, but not after 2,4 and 6 and 16, 19 and 22 days of feeding. After 10 days of feeding, mild to moderate histological lipidosis was found in piglets fed diets containing 2% or more of 22∶1 fatty acids, with no significant difference between RSO, RFO and PHFO in this respect. The same diets in rats gave about 5 times more histological lipidosis than in piglets. This is attributed to a difference in species response, the rat reacting in a more pronounced manner than the piglet. The cardiac lipidosis no‐effect level in piglets corresponded to a daily intake of docosenoic fatty acids of 0.4 g per kg body weight. Mild lipidosis was also found in a few animals on docosenoic acid‐free diets.
Cholesteryl ester and triacylglycerol fatty acids in type V hyperlipidemia
Authors: Jensen R. G. , Clark R. M. , Gerrior S. A. , Fey M. B. , Gotto A. M.
Published: November 2006

The fatty acid compositions of plasma cholesteryl esters (CE) and triacylglycerols (TG) from seven healthy individuals and five patients with type V hyperlipoproteinemia were determined. Very low density (VLDL), low density (LDL) and high density lipoproteins (HDL) were isolated. The lipids were extracted from the lipoproteins and the triacylglycerols and cholesteryl esters separated for analysis. The fatty acid compositions of triacylglycerols from healthy and type V individuals were very similar. The cholesteryl esters from type V patients had increased contents of palmitic and decreased amounts of linoleic and arachidonic acids as compared to the normal individuals. The fatty acid composition of the cholesteryl esters from the high density lipoproteins had the greatest deviation. The fatty acid compositions of the triacylglycerols from the two groups were similar. However, the triacylglycerols in all lipoprotein fractions contained more palmitic and oleic and less linoleic and arachidonic acids than the cholesteryl esters.
Polyenoic acid metabolism in cultured human skin fibroblasts
Authors: Aeberhard Ernesto E. , Corbo Lucille , Menkes John H.
Published: November 2006

The incorporation of [1‐14C]linoleic acid, and [1‐14C]linoleic acid into cellular lipids of cultured human skin fibroblasts was studied. Cultured cells took up both labeled fatty acids at nearly the same rate and incorporated them into a variety of lipid classes. At the end of 1 hr incubation with [1‐14C]linoleic acid, radioactivity was found in the triacylglycerol (TG) and choline phosphoglyceride (CPG) pools preferentially. Incorporation into the TG fraction decreased rapidly, while the uptake into CPG, serine phosphoglyceride (SPG), and ethanolamine phosphoglyceride (EPG) fractions increased progressively with longer incubation times. Similar results were obtained with [1‐14C]linoleic acid as precursor. At the end of 24 hr, desaturation and chain elongation of 18∶3 n−3 was more extensive than conversion of 18∶2 n−6 to higher polyenoic acids. During pulse‐chase experiments with either fatty acid precursor, the incorporated radioactivity was progressively lost from cellular lipids, particularly from the TG and CPG fractions, but continued to increase in the SPG and EPG pools. The similar labeling pattern of cellular phospholipids with linoleic or linolenic acids, and data from pulse‐chase studies suggest that a direct transfer of fatty acids from CPG to EPG is a likely pathway in fibroblast cultures. Incorporation into the EPG pool during the pulse‐chase experiments paralleled extensive desaturation and elongation of linoleic acid into 20∶4 n−6, and 22∶4 n−6; and of linolenic acid into 22∶5 n−3 and 22∶6 n−3.
Effects of feeding ethyl‐dihomo‐γ‐linolenate on rabbit renomedullary lipid composition and prostaglandin production in vitro
Authors: Knapp H. R. , Oelz O. , Whorton A. R. , Oates J. A.
Published: November 2006

Feeding the ethyl ester of dihomo‐γ‐linolenic acid for 25 days to rabbits resulted in increased PGE1 (20to30‐fold) and PGE2 (1.5‐fold) output by a hormone responsive, in vitro, renal papilla preparation. The relative amount of PGE1 increased from <5% of PGE2 in controls to 25–35% of PGE2 in the papillae of 20∶3ω6‐supplemented animals. During the study renomedullary triglycerides in the 20∶3ω6‐supplemented animals increased 2.8‐fold compared to animals fed an equal amount of a control fatty acid mixture, and in addition to a marked enrichment in 20∶3ω6, also contained increased proportions of 20∶4ω6 and longer chain polyenes. The increase in triglyceride content found in the renal medulla was not seen in the renal cortex or liver. There was no increase in renomedullary phospholipid content during the study, and phopholipids of treated animals contained increased proportions of 20∶3ω6 and 20∶4ω6, but not longer chain polyenes. The results indicate that enriching the prostaglandin precursor pool by feeding 20∶3ω6 can alter the type and amount of prostaglandin released by the renal papilla, at least in vitro. Also, the selective changes in amount and long chain polyene content of renomedullary triglycerides during the study suggest some special functions for this lipid class in prostaglandin precursor metabolism. *** DIRECT SUPPORT *** A00M6131 00010
Synthesis and characterization of [1‐13C]‐and d8‐arachidonic acid
Authors: Do Un Hoi , Sundaram M. G. , Ramachandran S. , Bryant Robert W.
Published: November 2006

Methyld8‐ and [1‐13C] 5,8,11,14‐eicosatetraenoate (arachidonate) were prepared from a common synthetic precursor, 4,7,10,13‐nonadecatetrayn‐1‐ol. The purified products were characterized by gas chromatography‐mass spectrometry. Mass spectra oft‐butyldimethylsilyl esters ofd8‐and [1‐13C]‐arachidonic acid showed a most intense [M‐57]+ peak at high mass. The isotopic purity of methyl [1‐13C] arachidonate was 99% and that of methyld8‐arachidonate was 56%. Whend8‐arachidonic acid was prepared by direct deuteration of 5,8,11,14‐eicosatetraynoic acid, the isotopic purity of the sample was 86%.
Molecular species composition of phosphatidylcholines during the development of the avian embryo brain
Authors: Gonzalez‐Ros Jose M. , Ribera A.
Published: November 2006

A comparative approach has been used to investigate the molecular species composition of phosphatidylcholine (PC) and its age variation throughout several developmental stages of chick and duck embryo brains. The brain PC consist of 15 major molecular species which do not undergo appreciable variation in their relative abundance either during embryonic development or between equivalent stages of maturation in the 2 avian species. In fact, a highly invariable molecular architecture of PC is shown in the developing organ. Molecular species containing saturated or monounsaturated fatty acids were dominant in all stages of development of the avian embryo brain. Among these molecular species, 1,2‐dipalmitoyl‐sn‐glycero‐3‐phosphocholine, 1‐palmitoyl‐2‐oleoyl‐sn‐glycero‐3‐phosphocholine accounted for 75–80% of the total PC.