Anorexic contribution to increased linoleate mobilization and oxidation in lymphoma-bearing mice

To test for a regulatory defect in adipose triacylglycerol (essential) fatty acid mobilization in lymphoma-bearing mice, free [1-¹⁴C]linoleic acid/mouse serum albumin was injectediv into lymphoma-bearing and control mice, adapted to a reversed light cycle, and studied in three dietary states in the dark period. Mean daily food intake decreased in mice with small and large tumor burdens. Plasma free fatty acid (FFA) oxidation rates, which approximate FFA mobilization rates, were estimated by multicompartmental analysis (CONSAM). Oxidation of linoleate to CO₂ was reduced significantly (85%) inad libitum fed as compared to briefly fasted control mice but not in fedvs. fasted mice with large or small tumor burdens. However, plasma FFA oxidation rates to CO₂ did not differ in briefly fasted tumor-bearing and pairfed control mice. When re-fed a 250-mg test meal, briefly fasted mice with small tumors suppressed plasma free linoleic acid oxidation, as did controls. During simulated night, mildly anorexic, tumor-bearing mice with small tumor burdens mobilized essential fatty acids much faster than controls. This could explain body fat loss. The abnormally rapid rates of FFA (free linoleic acid) mobilization at night probably result from anorexia rather than from inability of food to suppress fat mobilization.     

Effect of Different Frying Methods on the Total <Emphasis Type="Italic">trans</Emphasis> Fatty Acid Content and Oxidative Stability of Oils

The main objective of this study was to determine the effect of different frying oils and frying methods on the formation of trans fatty acids and the oxidative stability of oils. Sunflower, canola and commercial frying oils, the most commonly used oils for frying potatoes in the fast food industry, were used as the frying medium. The value for total polar compounds was highest when commercial frying oil was used in the microwave oven (22.5 ± 1.1). The peroxide value, as an indicator of oil oxidation, was lowest for microwave oven frying (2.53 ± 0.03). The K₂₃₂ and K₂₇₀ values were 0.41 ± 0.04 and 0.18 ± 0.02, respectively, for commercial frying oil in the microwave oven. The lowest free fatty acid content was recorded for the commercial frying oil used in the deep‐fat fryer at 190 °C. The highest iodine value was measured for sunflower oil used in the deep‐fat fryer (148.14 ± 0.07), indicating a greater degree of unsaturation. The lowest trans fatty acid value was recorded for sunflower oil in the microwave oven (0.17 ± 0.05), with a higher overall amount of total trans fatty acids observed for oils after frying in the electrical deep‐fat fryer compared to the microwave. Sunflower oil was favourable for both frying methods in terms of the trans fatty acid content.     

Mitochondrial metabolism of (D,L)-threo-9, 10-dibromo palmitic acid

Bromination of palmitoleic or palmitelaidic acid proceeds bytrans addition and yields dibrominated products which cannot undergo β-oxidation when incubated with mitochondria isolated from hamster brown adipose tissue. These mitochondria were selected because they have a high capacity for oxidation of C₁₆ fatty acids and because they are readily uncoupled by an excess of free fatty acids of this chain length. The only metabolites which could be recovered from the incubation mixtures were dibromopalmitoylcarnitine and dibromopalmitoyl CoA. Free fatty acid was also recovered. Addition of synthetic carnitine or CoA esters of brominated fatty acids did not interfere with subsequent oxidation of palmitoylcarnitine. Addition of the free brominated fatty acids did significantly increase the rate of oxidation of subsequent additions of palmitoylcarnitine, as did other known synthetic uncouplers. These results are consistent with observations by others that feeding brominated oils leads to brominated fatty acid incorporation into tissue lipids, and indicate why this is so. They also provide a possible explanation for the hepatic damage noted in feeding experiments.     

Wirkungsmechanismus langkettiger Monoenfettsäuren im Energiestoffwechsel des Herzens

Mechanism of Long Chain Monoenoic Fatty Acids Acting on the Energy Metabolism of Heart The oxidation of 1-¹⁴C-erucic (C_22:1) and 1-¹⁴C-nervonic (C_24:1) acids was studied in comparison to 1-¹⁴C-palmitic and -oleic acids in isolated rat and pig heart mitochondria. After mitochondrial incubation with the albumin-bound fatty acids only small amounts of ¹⁴CO₂ developed from the oxidation of the long chain monoenoic acids as compared to palmitic or oleic acid. The slow down of the oxidation rate was more pronounced in rat than in pig heart mitochondria. The oxidation of palmitic or oleic acid was not found to be inhibited by the C²⁰–C²⁴-monoenoic acids, whereas palmitic or oleic acid inhibited the oxidation of erucic acid competitively. From present findings an idea may be developed of the interference on fatty acid metabolism in heart muscle by erucic and other long chain monoenoic acids.     

Fatty acid composition of meat from ruminants, with special emphasis on trans fatty acids

The fatty acid composition was determined in 39 samples of beef, 20 samples of veal, and 34 samples of lamb, representative of the supply of ruminant meat in Denmark. Five cuts of beef and veal and three cuts of lamb with increasing fat content were selected, and analysis of the fatty acid methyl esters was performed by gas-liquid chromatography (GLC) on a polar 50-m capillary column CP Sil 88 with flame-ionization detection. Lamb had the highest content of saturated fatty acids (52.8±1.8 g/100 g fatty acids), higher than beef and veal (45.3±3.1 and 45.4±0.8 g/100 g fatty acids, respectively). Cis monounsaturated fatty acids were 49.2±3.1, 44.9±1.8, and 37.7±1.7, and polyunsaturated fatty acids were 3.3±0.7, 5.8±2.0, and 5.0±0.1 g/100 g fatty acids in beef, veal, and lamb, respectively. Beef contained 2.1±0.8 g trans C_18:1 per 100 g fatty acids, about half that found in veal (4.0±1.2 g/100 g fatty acids) and lamb (4.5±0.6 g/100 g fatty acids). Trans C_16:1 was 0.24±0.01, 0.14±0.02, and 0.79±0.02 g/100 g fatty acids in beef, veal, and lamb, respectively. Only small variations in trans and other fatty acids could be demonstrated between cuts. The overlap between cis and trans C_18:1 by capillary GLC was verified by argentation-thin-layer chromatography followed by GLC, on three samples of veal and three samples of lamb. In veal 1.0 g, and in lamb 1.4 g trans C_18:1 per 100 g fatty acids were hidden under the cis C_18:1 peak. The mean intake of trans fatty acids from ruminant meat is estimated at 0.2 g/d.     

Polyunsaturated fatty glyceride syntheses by microbial lipases

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

Fatty Acid Composition in Ergosteryl Esters and Triglycerides from the Fungus Ganoderma lucidum

Free and esterified ergosterols are detected almost solely in fungi and are often employed as a biomarker of living fungi. In this work, the fatty acid composition and δ¹³C values of major fatty acids in triglycerides and ergosteryl esters from the fungus Ganoderma lucidum were analyzed by gas chromatography–mass spectrometer and gas chromatography–isotopic ratio mass spectrometer, respectively. The results showed that the fatty acid profiles varied in triglycerides and ergosteryl esters. The percentage of saturated fatty acids in ergosteryl esters was remarkably higher than that in triglycerides, where C_18:1^Δ9c was the predominant fatty acid and constituted 61.26 % of the total fatty acids. In contrast, C_16:0 was the predominant fatty acid and constituted 71.88 % of the total fatty acids in ergosteryl esters. The study suggests that, after fungal death, free ergosterols in the cell membrane of the dead fungus were esterified with preferentially saturated fatty acids, mainly C_16:0, from triglycerides and then stored in lipid particles for a longer period while free ergosterol markedly decreased. The δ¹³C values of C_16:0, C_18:0, C_18:1 and C_18:2 in ergosteryl esters exhibit a pronounced depletion in ¹³C compared with that in triglycerides within the range of ?1.3 to ?0.9 ‰, supporting the above inference. It is again suggested that free ergosterol in the cell membrane should be used as an indicator of living fungi, and ergosteryl esters in the lipid particles should not be included in the measurement of living fungal biomass.     

Hydrolysis of fats and oils with moist oat caryopses

To improve the economic feasibility of hydrolyzing fats and oils with moist oat caryopses, various factors affecting the efficiency of the process were studied. Caryopses produced with an impact-type dehuller exhibited greater lipase activity than those produced by a wringer-type dehuller. Abrasion of oat caryopses against each other in a fluidized bed released particles rich in lipase. Such lipase concentrates could be added to moist caryopsis reactors to speed fat hydrolysis. Beef tallow, lard, soybean oil and crambe oil were hydrolyzed more efficiently than corn oil, castor oil and milk fat. The poor hydrolysis of castor oil was attributed to the formation of esters with the hydroxy group of ricinoleic acid, and the hydrolysis of castor oil was increased by dilution of the substrate with hexane. Diglycerides inhibited the hydrolysis and accounted for the slower hydrolysis of corn oil. Hydrolysis of milk fat by moist oat caryopses resulted in preferential hydrolysis of C₆ to C₁₀ acids. Erucic acid was released from crambe oil at significantly slower rates than the other acyl groups. High conversions of fats and oils to free fatty acids could be attained by (i) exposing the fats and oils to two to three lots of moist caryopses, (ii) the use of special oat varieties with elevated lipase content, (iii) the addition of oat lipase concentrates to moist caryopsis reactors, and (iv) dilution of the substrate with hexane. Estimates of the cost of producing free fatty acids with these processes indicated that the first three should be profitable. Growth ofClostridium sporogenes spores could not be demonstrated in caryopsis reactors. During the incubation of moist oat caryopses immersed in oil, the free fatty acid content of the internal caryopsis lipid increased only slightly, but there were changes in its fatty acid composition.     

Supercritical Carbon Dioxide Fractionation of Anhydrous Milk Fat

Supercritical carbon dioxide was used to fractionate anhydrous milk fat. Six fractions were produced at 40, 50 and 60 °C using pressure values of 10, 20, 25, 30, 33 and 36 MPa. The fractions were analyzed for fatty acids, thermal behavior, iodine and color values. Composition and yield of fatty acid methyl esters were evaluated at different fractionation conditions in relation to the original milk fat values. Short chain fatty acids (C₄–C₈), medium chain fatty acids (C₁₀–C₁₄) and total saturated fatty acids were decreased from fraction obtained in the order of 10–36 MPa, while long chain fatty acids (C₁₆–C_18:2) and total unsaturated fatty acids were increased. Fractions obtained in the raffinate stage of the fractionation exhibited higher melting behavior that obtained at the low CO₂ pressures. The higher iodine value of raffinate fraction indicated that fraction was richer in oleic acid. Fractions produced at low pressures had lower melting behavior than those obtained at high pressures. Yellowness Index and b* values increased in raffinate fraction due to concentration of carotenoids.     

Cholestane as a digestibility marker in the absorption of polyunsaturated fatty acid ethyl esters in Atlantic salmon

Salmonid fish require long-chain n−3 fatty acids in their diet. The digestibility of different chemical forms of fish oil fatty acids, fed as triacylglycerols, free fatty acids or ethyl esters, was examined in 300 g farmed Atlantic salmon (Salmo salar) using cholestane as an indicator of fat absorptionin lieu of the chromium oxide (Cr₂O₃) which is commonly used as a marker in digestibility studies. It was established that the two digestibility markers gave similar results. Conveniently, cholestane does not require a separate analysis if fatty acids are to be determined by appropriate gas-liquid chromatography. The long-chain polyunsaturated fatty acids were particularly well absorbed, the apparent digestibility being 90–98% when feeding triacylglycerols or free fatty acids. However, the digestibility of monounsaturated fatty acids (75–94%) was lower, and lower still for saturated fatty acids (50–80%). Ethyl esters of fatty acids were significantly less well absorbed (P<0.05) than were the corresponding fatty acids in free acid or triacylglycerol form. Irrespective of dietary fat type, only free fatty acids were identified in feces, indicating total hydrolysis of triacylglycerols and ethyl esters. Presented in part at the World Aquaculture Society meeting, June 10–14, 1990, Halifax, Canada.     

The biosynthesis of n-[2H7] fatty acids byArthrobacter globiformis from [U-2H15] octanoic acid

The principal fatty acids present whenArthrobacter globiformis is grown on a glycine medium free of normal fatty acids were found to be the C15 and C16 anteiso fatty acids; only a small amount of the normal fatty acids (C14 and C16) were present. Cells grown on the same medium but supplemented mented with 0.1 mg/ml [U-²H₁₅]octanoic acid were found to contain an increased amount of the normal fatty acids and these fatty acids were found to be labeled with 7 deuteriums. I concluded that the octanoic acid is degraded by β-oxidation in these cells to [U-²H₇] butyryl-CoA, which then competes with 2-methylbutyryl-CoA for the initiation of fatty acid biosynthesis.     

The composition of furan fatty acids in the crayfish

Capillary gas chromatography-mass spectrometry (GC-MS) analysis of the sterol ester fatty acid methyl esters of the crayfish hepatopancreas revealed the presence of at least 30 kinds of unusual furan fatty acids (F acids), which accounted for 28.49% of the total sterol ester fatty acids. On the other hand, only small amounts were found in triacylglycerols (0.5%) and phospholipids (0.7%). Among the F acids, 17 acids were the hitherto unknown ones, the major component being 12,15-epoxy-13,14-dimethyleicosa-12,14-dienoic acid (F₆) (41.83% of the total F acids). These novel acids possessed chain lengths of C₁₂ to C₂₂, with the largest concentration at C₂₀ (45.38%), C₁₈ (41.97%) and C₁₆ (10.35%). Odd-numbered F acids also were found, though in a very small amount (0.4%). In the living things other than the crayfish, the longest chain F acid (C₂₄) was detected in the sterol ester of the carp hepatopancreas. The bullfrog, an amphibian, and the turtle, a reptilian, were found to have F acids as well in their livers. Olefinic furan fatty acids, which were detected by GC-MS, were found to have resulted during the analytical process from cyclodehydration of the diketo-ene formed by autoxidation of the F acids.     

Cardiac fatty acids in rats fed marine oils

Cardiac fatty acids were studied in young rats fed marine oils for 1 week. When the diet contained 0, 0.5, 1, 2, 4, 8 or 16% by weight of partially hydrogenated oil from Norwegian capelin, the concentration of fatty acids in the cardiac tissue was elevated only at the highest level. The amount of the lipid and the content of docosenoic acid in the heart were less than those observed with 15% partially hydrogenated oil from Canadian herring. Nonhydrogenated Peruvian anchovy oil lacking docosenoic acid produced no change in the amount of fat deposited. The extent of fatty acid accumulation in the heart was related to the dietary C₂₂ acids.     

Structure-activity relationship of unsaturated fatty acids as mosquito ovipositional repellents

Various straight-chain unsaturated fatty acids from C₁₄ to C₂₄ were evaluated for their ovipositional repellency against gravid females of the southern house mosquitoCulex quinquefasciatus Say, and the relationship between the structures of the fatty acids and their ovipositional repellency was determined. A double bond withZ configuration was prerequisite for an unsaturated fatty acid to be highly repellent;E isomers were less active or even inactive. No relationship was found between the repellency and the number of double bonds in the unsaturated fatty acids. In C₁₈ monounsaturated fatty acids, (Z)-9 acid was more active than (Z)-11 and (Z)-6 acids, indicating that a double bond at the 9 position rendered an acid highly repellent. Among (Z)-9-alkenoic acids of different chain lengths, the most repellent was C₁₈ acid which was also more active than (Z)-11-C₂₀, (Z)-13-C₂₂, and (Z)-15-C₂₄ acids. Oleic[(Z)-9-octadecenoic]acid, which met all these criteria, was the most ovipositionally repellent among the unsaturated fatty acids tested.Diptera: Culicidae.     

Competitive adsorption among sesame oil components in a concentrated miscella system

Competitive adsorption of free fatty acids and carotenoids adsorption from sesame oil miscellas on vegetable carbon was studied by regression analysis. The equations obtained indicated that unsaturated carbonyls, free fatty acids (FFA₀), and carotenoids interacted to determine fatty acid and carotenoid adsorption. The driving force for carotenoid adsorption, the carotenoid concentration (C₀), was affected by a quadratic function of free fatty acid concentration [i.e., (FFA₀/C₀)²]. As FFA₀/C₀ increased, carotenoid adsorption efficiency was reduced, possibly because the accessible adsorption sites for carotenoids were occupied by fatty acids. Unsaturated carbonyls promoted free fatty acid adsorption, probably in the pores that were readily accessible for fatty acids. However, when the carbonyl concentration increased in the oil miscella, carbonyls were adsorbed instead of fatty acids. The results indicated how different oil molecules interact and affect adsorption (i.e., free fatty acids and carotenoids). Therefore, the adsorption process of vegetable oils (i.e., bleaching) has to be considered a multicomponent adsorption system.     

Structuring of Chicken Fat by Monoacylglycerols

In this study, we investigated the effect of monoacylglycerol (MAG) as a structuring agent on the physicochemical, microstructure and rheological properties of chicken fat. The fatty acid composition, oxidative stability, free fatty acids (FFA), slip melting point (SMP), solid fat content (SFC), kinetics of crystallization, microstructure and rheological properties of the samples were evaluated. The addition of MAG at a 0.5 % level did not affect the fatty acid composition, induction period of oxidation at 110 °C (IP_ox110), SFC curve or rheological properties of chicken fat (p > 0.05). However, structured samples containing 3.0 and 5.0 % MAG had higher saturated fatty acid (SFA) content, SFC, SMP, FFA content and IP_ox110 (p < 0.05). The addition of MAG led to a reduction in the IP of oxidation at 60 °C (IP_ox60) and increased the oxidation rate of fats, as measured by the Schaal oven test. Samples containing 3–5 % MAG had higher SFC content, higher loss, storage and complex moduli, higher complex viscosity, and a lower induction period of crystallization (IP_cryst) and tan δ than chicken fat. Investigations by polarized light microscopy confirmed the presence of increased crystal content in samples containing higher MAG levels. These results show that structured chicken fats have the potential for application in the production of soft tub margarine and Iranian vanaspati.     

Leaf Epicuticular Wax Chemicals of the Japanese Knotweed Fallopia japonica as Oviposition Stimulants for Ostrinia latipennis

Extraction, fractionation, and gas chromatography−mass spectrometry analyses guided by bioassays have shown that n-alkanes and free fatty acids in leaf epicuticular wax of the Japanese knotweed Fallopia (Reynoutria) japonica stimulate oviposition in the Far-Eastern knotweed borer, Ostrinia latipennis (Lepidoptera: Crambidae). n-Alkanes made up 48.1% of the total amount of epicuticular wax, and their carbon chain length was in the C₁₆−C₃₃ range, with n-nonacosane (n-C₂₉) most abundant, followed by n-C₂₇, n-C₂₅, and n-C₃₁. Free fatty acids with C₉−C₂₂ accounted for 22.3%, and hexadecanoic acid was predominant. A mixture of authentic n-alkanes and fatty acids of the composition found in the epicuticular wax, a mixture of n-alkanes, and a mixture of fatty acids significantly enhanced oviposition. Thus, it was demonstrated that both n-alkanes and free fatty acids in leaf epicuticular wax of F. japonica are naturally occurring oviposition stimulants for O. latipennis.     

Analysis of 4-methyloctanoic acid and other medium chain-length fatty acid constituents of ovine tissue lipids

Medium chain-length (C₆−C₉) fatty acids in depot, intramuscular, kidney, and liver lipids from pasture-fed sheep and subcutaneous and intramuscular lipids from barley-fed sheep were analyzed with emphasis on the 4-methyloctanoic acid (hircinoic acid) content. Within individual animals, the level of hircinoic acid in the subcutaneous fat was usually higher than that either in the deeper depot fats or in the intramuscular fat. Variation of hircinoic acid levels between animals was greatest in the subcutaneous fat and least in the perinephric fat. There were usually higher levels of both branched and odd carbon chain fatty acids in the lipids of barley-fed sheep than in the corresponding lipids of pasture-fed sheep.     

Dietary fat and the fatty acid composition of tissue lipids

Some characteristics of the fatty acid composition of animal tissue lipids are described and the origins of tissue fatty acids are discussed briefly. The effect of dietary fat on composition of tissue lipids is discussed. Types of dietary fatty acids for which experimental work is described include polyunsaturated fatty acids, short-chain fatty acids, fatty acids with chain length greater than C₁₈,trans unsaturated fatty acids, fatty acids with conjugated double bonds, acetylenic fatty acids, branched-chain fatty acids and oxygenated fatty acids. The individuality of fatty acids is discussed in relation to their roles as components of tissue lipids.     

Fatty acid-specific, regiospecific, and stereospecific hydroxylation by cytochrome P450 (CYP152B1) from Sphingomonas paucimobilis: Substrate structure required for α-hydroxylation

Fatty acid α-hydroxylase from Sphingomonas paucimobilis is an unusual cytochrome P450 enzyme that hydroxylates the α-carbon of fatty acids in the presence of H₂O₂. Herein, we describe our investigation concerning the utilization of various substrates and the optical configuration of the α-hydroxyl product using a recombinant form of this enzyme. This enzyme can metabolize saturated fatty acids with carbon chain lengths of more than 10. The K _m value for pentadecanoic acid (C₁₅) was the smallest among the saturated fatty acids tested (C₁₀–C₁₈) and that for myristic acid (C₁₄) showed similar enzyme kinetics to those seen for C₁₅. As shorter or longer carbon chain lengths were used, K _m values increased. The turnover numbers for fatty acids with carbon chain lengths of more than 11 were of the same order of magnitude (10³ min⁻¹), but the turnover number for undecanoic acid (C₁₁) was less. Dicarboxylic fatty acids and methyl myristate were not metabolized, but monomethyl hexadecanedioate and ω-hydroxypalmitic acid were metabolized, though with lower turnover values. Arachidonic acid was a good substrate, comparable to C₁₄ or C₁₅. The metabolite of arachidonic acid was only α-hydroxyarachidonic acid. Alkanes, fatty alcohols, and fatty aldehydes were not utilized as substrates. Analysis of the optical configurations of the α-hydroxylated products demonstrated that the products were S-enantiomers (more than 98% enantiomerically pure). These results suggested that this P450 enzyme is strictly responsible for fatty acids and catalyzes highly stereo- and regioselective hydroxylation, where structure of ω-carbon and carboxyl carbon as well as carbon chain length of fatty acids are important for substrate-enzyme interaction.