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1.
Metabolism of linoleate versus linoelaidate in the laying hen   总被引:1,自引:0,他引:1  
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. Presented at the AOCS Meeting, Chicago, September 1976.  相似文献   

2.
T. L. Mounts 《Lipids》1976,11(9):676-679
The metabolic fate ofcis-positional isomers of octadecenoates has been compared to that of naturally occurring oleic acid (cis-Δ9). Radioactive mixtures of tritium-labeled positional octadecenoate isomer and oleic acid-10-14C were administered to laying hens, and their eggs were analyzed for the isotopic ratios (3H/14C) incorporated into total egg lipid, triglycerides, and phospholipids. Variations in the isotopic ratios indicated the comparative metabolic utilization ofcis-positional isomers Δ8 through Δ12. Incorporation into egg lipid fractions is as follows: triglycerides: Δ9>Δ8, Δ9>Δ10, Δ9>Δ11, Δ9>12; phospholipid: Δ9>Δ8, Δ9>Δ10, Δ9<Δ11, Δ9<Δ12. Presented at the AOCS meeting in Cincinnati, September 28–October 1, 1975.  相似文献   

3.
Absorption and distribution of positionalcis andtrans octadecenoic acid isomers in lipids from rat, egg and human tissues are reviewed. Selected data on enzyme, single-cell, and whole-animal studies with positional octadecenoic acid isomers are summarized and compared.  相似文献   

4.
A. C. Lanser 《Lipids》1982,17(8):524-528
The deposition oftrans-8-octadecenoate-8(9)-3H (8t-18∶1-3H) was compared tocis-9-octadecenoate-10-14C (9c-18∶1-14C) in the major egg yolk neutral lipids and phospholipids and in organ lipids from the laying hen.trans-8-Octadecenoate was preferentially incorporated into only the phosphatidylethanolamines (PE), whereas discrimination against 8t-18∶1-3H occurred in the phosphatidylcholines (PC), triglycerides (TG) and cholesteryl esters (CE). The 1-acyl position of both PE and PC contained three times more 8t-18∶1-3H than 9c-18∶1-14C. Almost total exclusion of the 8t-18∶1-3H from the 2-acyl position of these phospholipids was found. Preferential incorporation of 9c-18∶1-14C occurred at the combined 1- and 3-acyl positions and at the 2-acyl position of yolk TG. Tissue lipid analyses indicated that there was preferential deposition of 9c-18∶1-14C into all organs. Individual liver lipid classes displayed the same relative order of discrimination against 8t-18∶1-3H as did egg yolk lipids (CE>TG>PC>PE).  相似文献   

5.
Trans octadecenoic acid methyl ester isomers were obtained from a partially hydrognated soybean oil and isolated by silver-ion high-performance liquid chromatography. Recently, the double-bond positions for nine individual trans octadecenoic acid positional isomers (Δ8 through Δ16) were confirmed by gas chromatography-electron ionization mass spectrometry after derivatization to 2-alkenyl-4,4-dimethyloxazoline. In this communication, the presence of two additional trans-18:1 fatty acid methyl ester positional isomers (Δ6 and Δ7) in the same mixture is confirmed by 13C nuclear magnetic resonance spectroscopy. The identity of the Δ5-trans-18:1 fatty acid methyl ester positional isomer is inferred. Summer student researcher.  相似文献   

6.
The lipid composition of margarines from stores in selected locations in the U.S. is reported. The lipids determined include the fatty acids, tocopherols and major plant sterols. Data are included for isomeric octadecenoic fatty acids (14 isomers or groups of isomers) and four isomeric octadecadienoic fatty acids common in partially hydrogenated vegetable fats, insofar as these are separable by capillary gas chromatography. Amounts of individual lipids found in vegetable oil margarines, spreads, imitation and diet margarines were: palmitate, 8.49 to 13.17% (normalized weight percent, calculated as triglyceride); stearate, 4.78 to 9.53%; linoleate, 6.06 to 46.39%; linolenate, 0.18 to 3.57%; α-tocopherol, 0.3 to 24.3 mg/100g; γ-tocopherol, 3.0 to 55.0 mg/100g; δ-tocopherol, 0.5 to 18.9 mg/100g; campesterol, 10.6 to 106.3 mg/100g; stigmasterol, 13.1 to 60.9 mg/100g; sitosterol, 42.3 to 412.9 mg/100g. Amounts oftrans-unsaturated octadecenoic fatty acids in these margarines varied from 10.74 to 30.06%. Small amounts of thetrans,trans, trans,cis andcis,trans isomers of linoleate also are reported.  相似文献   

7.
Kumar D. Mukherjee 《Lipids》1986,21(5):347-352
Lipids in developing seeds ofSinapis alba contain appreciable proportions of (n−7)octadecenoic (vaccenic) acid besides its (n−9) isomer (oleic acid), whereas the constituent very long chain (>C18) monounsaturated fatty acids of these lipids are overwhelmingly composed of the (n−9) isomers. Cotyledons of developingSinapis alba seed use [1-14C]acetate, [1-14C]malonate or [1,3-14C]malonyl-CoA for de novo synthesis of palmitic, stearic and oleic acids and for elongation of preformed oleic, vaccenic and stearic acids to their higher (n−9), (n−7) and saturated homologs, respectively. Moreover, elongation of preformed (n−7)palmitoleic acid to vaccenic acid is observed. Stepwise C2-additions to preformed oleoyl-CoA by acetyl-CoA or malonyl-CoA yielding (n−9)icosenoyl-CoA, (n−9)docosenoyl-CoA and (n−9)tetracosenoyl-CoA are by far the most predominant reactions catalyzed by the elongase system, which seems to have a preference for oleoyl-CoA over vaccenoyl-CoA as the primer. The pattern of14C-labeling of the very long chain fatty acids formed from either acetate or malonate shows a close analogy in the mode of elongation of monounsaturated and saturated fatty acids.  相似文献   

8.
Two deuterated fatty acids, elaidate-d 2 and oleate-d 4, were fed simultaneously to a human subject as a mixture of trielaidin-d 6 and triolein-d 12. Periodically, blood samples were drawn, and red blood cells were separated from the plasma. Red blood cells and plasma lipids were fractionated and analyzed by combined gas chromatography—multiple ion mass spectroscopy. Dual deuterium-labeling allows rate and extent of fatty acid incorporation to be followed in various plasma and red cell neutral and phospholipid fractions. Maximum amount of deuterated fat varied from 4% in cholesterol ester to 64% in phosphatidyl ethanolamine. The highest levels of deuterated fat occurred in either 6-, 8-, or 12-hr samples; generally, <1% labeled fatty acids could be detected in 72-hr samples. Because the method is based on dual-labeling, differences in the relative incorporation of both fatty acid isomers can be compared directly. Differences in rates of incorporation, rates of removal, and extent of incorporation of labeled fatty acids into blood plasma can also be determined reliably. Our experimental labeling of fats with deuterium permits for the first time the metabolism of two fatty acid isomers to be compared simultaneously in human subjects. This new method should be applicable to a variety of other lipid metabolic studies. Presented at the AOCS meeting Dallas, Texas, April 27–30, 1975.  相似文献   

9.
Fatty acids ofSterculia foetida were added to the medium used to maintain the Morris hepatoma 7288C in culture. The effect of this supplement on the lipid composition was examined. Overall, monoene levels were decreased with 18∶1 levels reduced by 40%. Saturated fatty acid levels were increased, with stearate (18∶0) levels 220% of control values. No effect occurred on the level of polyunsaturates (18∶2, 20∶4, 22∶5, 22∶6). These changes in fatty acid makeup were observed in both neutral and phospholipid fractions, and all lipid classes were affected. Triglycerides were most affected with a 66% decrease in 18∶1. There appeared to be little specificity of effect in the phospholipids with 18∶1 levels decreased 40–60% in all classes. All classes were therefore dependent on an endogenous supply of 18∶1. Examination of the distribution of geometrical isomers of 18∶1 reveals that in all lipid classes, except diphosphatidylglycerol (DPG), the ratio of Δ11 to Δ9 isomer decreased toward the isomeric distribution displayed by total medium lipids. In DPG, although 18∶1 levels were lowered, the isomeric distribution increased. DPG, synthesized and found in the mitochondria, may use a separate pool of 18∶1 during synthesis. Cyclopropene fatty acids (sterculic and malvalic) were incorporated into both neutral and phospholipid fractions with preferential incorporation into triglycerides. Cyclopropene fatty acids were not selectively incorporated into any phospholipid species. Sphingomyelin did not incorporate cyclopropene fatty acids, indicating that a different class of acyltransferase is used in the formation of this phospholipid class.  相似文献   

10.
M. Nikolopoulou  J. C. Vary 《Lipids》1987,22(10):698-703
Bacillus megaterium QM B1551 spore lipids were extracted by an improved technique, and the phospholipid and fatty acid compositions were determined. Phospholipids accounted for 65% of the total fatty acids; the neutral lipid fraction contained 15% and the remaining fatty acids were in the interphase, aqueous phase and pellet from the lipid extraction. Each phospholipid had similar fatty acid compositions as did the delipidated pellet. However, the aqueous phase and, to some extent, the interphase had unique fatty acid compositions. Also, fatty acids were found acylated to proteins, which was observed by electrophoresis of delipidated proteins from spores grown in [1-14C]palmitate. Therefore, spores contain unique non-phosphatide fatty acid components that can now be analyzed.  相似文献   

11.
Specific differences between the acyl composition of lipids on the helminthParatenuisentis ambiguus and its host eel, as shown previously, prompted us to study the lipid metabolism in this intestinal fish parasite. Adults and larvae ofP. ambiguus were fed various lipid precursors, e.g., fatty acids, long-chain alcohols and 1-O-alkylglycerols, which may occur as common nutrients of intestinal parasites. Incorporation of [1-14C]palmitic acid into neutral and polar lipids was found to be similar under aerobic and near-anaerobic conditions. In adult parasites maintained in culture medium supplemented with glucose, [1-14C]palmitic acid was incorporated mainly into triacylglycerols and phosphatidylcholines, whereas [1-14C]oleic acid was incorporated preferentially into triacylglycerols. In fasted adults, as well as in larvae, [1-14C]oleic acid was mainly transferred to phosphatidylcholines. Lipolytic activity was detected in adult parasites that had been incubated with radioactive trioleoylglycerol. [1-14C]Hexadecan-1-ol was oxidized inP. ambiguus at a high rate to labeled palmitic acid, which was incorporated into various lipid classes ofP. ambiguus. Small but significant proportions of radioactivity from hexadecan-1-ol were incorporated into ether glycerolipids of the parasite. A more direct precursor in ether glycerolipid metabolism, i.e.,rac-1-O-[1′-14C] hexadecylglycerol, was incorporated into alkyl and 1′-alkenyl moieties of choline and etha-nolamine etherglycerophospholipids ofP. ambiguus in high yield. High proportions of labeled diacylglycerols, triacylglycerols and steryl esters were detected in surface lipids as well as lipid extracts of the culture media after incubation ofP. ambiguus with [1-14C]palmitic or [1-14C]oleic acids. The results suggest that palmitic acid and oleic acid are incorporated into neutral and polar lipids ofP. ambiguus maintained in glucose medium quite differently with oleic acid showing a strong preference for triacylglycerols. However, the incorporation of palmitic acid in glucose-fed parasites was similar to that of oleic acid in fasted parasites, as well as in larvae. This may be explained by partial fatty acid depletion in fasted worms and rapid cell division in larvae, respectively.  相似文献   

12.
The distribution of hydroperoxides among lipid fractions (namely neutral lipids, glycolipids, sphingolipids, and phospholipids) of the oleaginous fungus Cunninghamella echinulata was studied during the growth cycle. The lipid hydroperoxide content of total lipids increased during growth. Neutral lipids contained a small amount of hydroperoxides (0.78×10–4–5×10–4 µmol/mg), glycolipids plus sphingolipids contained large amounts of hydroperoxides (14×10–4–17.6×10–4 µmol/mg), while the hydroperoxide content of phospholipids increased greatly during growth (from 4.6×10–4 to 38×10–4 µmol/mg). In addition, the distribution of lipid hydroperoxides among the major phospholipid classes indicated that the neutral phospholipids, namely phosphatidylcholine and phosphatidylethanolamine, were more susceptible to peroxidation than the anionic ones (i.e. phosphatidylinositol and phosphatidylserine). A novel parameter, namely “specific lipid peroxidizability”, which is able to evaluate the susceptibility to peroxidation (peroxidizability) of each lipid fraction/class due to the nature of the lipid itself, was introduced. By using this parameter it was found that peroxidizability depended on the nature of the individual lipid rather than on its polyunsaturated fatty acid content.  相似文献   

13.
This study examined the effects of linolenic acid‐rich vs. linoleic acid‐rich feeding system on the occurrence of individual CLA isomers in the rumen and duodenum digesta of German Holstein and German Simmental bulls using Ag+‐HPLC/DAD. The diet affected the biosynthesis of individual CLA isomers in the rumen of the bulls of both breeds. The isomer t‐11,c‐13 CLA was detected as the most abundant isomer in the rumen of linolenic acid‐rich diet‐fed bulls, up to six times higher compared to linoleic acid‐rich diet‐fed bulls. However, the main isomer in muscle lipid, c‐9,t‐11 CLA, was produced to a low extent in the rumen of linolenic acid‐rich diet‐fed bulls compared to higher concentrations of this isomer in the rumen of linoleic acid‐rich diet‐fed bulls. The isomers t‐7,c‐9 CLA and t‐8,c‐10 CLA were not present in the rumen samples of bulls fed both diets; however, abundant t‐7,c‐9 CLA was identified in the duodenum. The CLA isomers t‐12,t‐14 CLA and t‐11,t‐13 CLA were identified as the main t,t CLA isomers in the rumen, and were significantly enhanced in the rumen of linolenic acid‐rich diet‐fed compared to linoleic acid‐rich diet‐fed bulls. In contrast to c‐9,t‐11 CLA, the t,t CLA isomers seem to be biosynthesized predominantly in the rumen, further transported via the duodenum and finally deposited in the tissue lipids mainly in linolenic acid‐rich diet‐fed bulls. This was shown earlier for muscle and subcutaneous fat samples from the same animal experiment.  相似文献   

14.
Three isomeric tetraaryl cyanate esters containing biphenyl moieties {bis‐[4‐(4′‐cyanatophenyl)phenyl]propane, 2,2‐bis‐[4‐(3′‐cyanatophenyl)phenyl]propane, and 2,2‐bis‐[4‐(2′‐cyanatophenyl)phenyl]propane} and three isomeric triaryl cyanate esters {2‐(4′‐hydroxyphenyl)‐2‐[4′‐(4‐hydroxyphenyl)phenyl]propane, 2‐(4′‐hydroxyphenyl)‐2‐[4′‐(3‐hydroxyphenyl)phenyl]propane, and 2‐(4′‐hydroxyphenyl)‐2‐[4′‐(2‐hydroxyphenyl)phenyl]propane} were synthesized from their corresponding bisphenols. The structures of the monomers were confirmed with IR and 1H‐NMR spectroscopy. The curing behavior was investigated with differential scanning calorimetry. Cyanate esters were cured thermally in the absence of a catalyst and were characterized by dynamic mechanical analysis. The results were compared to the properties of commercial bisphenol A polycyanurate. Of the three tetraaryl isomers, 2,2‐bis‐[4‐(2′‐cyanatophenyl)phenyl]propane had the highest melting point, and its corresponding resin had the lowest glass‐transition temperature (Tg). The para isomer displayed the highest Tg value of the three novel tetraaryl resins. The triaryl dicyanate isomers were low‐melting solids, with the ortho and meta isomers existing as liquids at room temperature. The Tg value of the para‐triaryl isomer was the highest of the three triaryl isomers and was about the same as that of bisphenol A polycyanurate. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011  相似文献   

15.
Essential fatty acid (EFA)-deficient rats were injected intraportally with a labeled solution containing3H arachidonic acid and14C-linoleic acid during a 1 min period. Livers were quickly frozen, pulverized, and the lipids extracted and fractioned by thin layer chromatography. The incorporation of3H and14C into liver lipids was measured, and the per cent distribution of radioactivity into the different lipid fractions determined and compared with those previously obtained from normal rats. In contrast with normal rats, ca. 70% of the3H arachidonic acid and14C-linoleic acid incorporated into total lipids from EFA-deficient rats was recovered in the phospholipid fraction. From the results of this experiment, it is suggested that a more active deacylation-reacylation cycle in EFA-deficiency could be responsible for this increase.  相似文献   

16.
Miriam D. Rosenthal 《Lipids》1981,16(3):173-182
The accumulation of neutral lipids by human skin fibroblasts grown in medium supplemented with fatty acids has been investigated. GM-10 cells incorporated exogenous fatty acids into both phospholipids and neutral lipids. More [14C] oleate, linoleate, or linolenate was incorporated into triacylglycerol than was [14C] palmitate or stearate. Supplementation of medium containing delipidized serum with unsaturated fatty acids resulted in far more stimulation of [14C] glycerol incorporation into triacylglycerol than did supplementation with saturated fatty acids. Palmitate- and stearate-fed cells incorporated sizable amounts of [14C] fatty acids and [14C] glycerol into diacylglycerol as well as triacylglycerol, especially at higher fatty acid concentrations. Increased oleate supplementation from 10–300 μM resulted in increased triacylglycerol synthesis and accumulation of discrete cytoplasmic lipid droplets; palmitate concentrations above 70 μm were toxic. Micrographs of the palmitate-fed cells showed electron translucent slits, suggesting solid depositions of saturated fat, rather than the discrete osmiophilic droplets found in oleate-fed cells. Although GM-10 cells can synthesize fully saturated triacylglycerols, these data suggest that in cells fed saturated fatty acids, solid depositions of neutral lipids may sequester diacylglycerols and thus limit triacylglycerol synthesis.  相似文献   

17.
Monotrans geometrical isomers of 20∶5 n−3 and 22∶6 n−3 were detected in liver lipid of rats fed heated linseed oil. The isomers were identified as being 20∶5 δ5c, 8c, 11c, 14c, 17t and 22∶6 δ4c, 7c, 10c, 13c, 16c, 19t. These fatty acids were isolated as methyl esters by preparative high-performance liquid chromatography (HPLC) on reversed phase columns followed by silver nitrate thin layer chromatography (AgNO3-TLC). The structures were identified using partial hydrazine reduction, AgNO3-TLC of the resulting monoenes, oxidative ozonolysis of each monoene band, and gas-liquid chromatography (GLC) of the resulting dimethyl esters and monomethyl esters. Fourier-transform-infrared spectrometry confirmed thetrans geometry in isolated 20∶5 and 22∶6 isomers. The isomers of eicosapentaenoic and docosahexaenoic acids in liver lipids probably resulted from desaturation and elongation of 18∶3 δ9c, 12c, 15t, a geometrical isomer of linolenic acid present in the heated dietary oil.  相似文献   

18.
Potassium permanganate oxidation in neutral medium of isomeric Δ13-docosenoic acids (erucic and brassidic acids) yielded mainly a mixture of two structurally isomeric hydroxy-keto acids, 13(14)-hydroxy-14(13)-ketobehenic acids. The constitutions of the individual hydroxy-keto acids have been established by oxidative cleavage with lead tetraacetate. The higher melting acid has been characterised as 14-hydroxy-13-ketobehenic acid, m. p. 79°–80° C, and the other low-melting isomer as 13-hydroxy-14-ketobehenic acid, m. p. 76°–77° C.  相似文献   

19.
Placental transport of 9-trans [1-14C] octadecenoic (elaidic) and 9-trans,12-trans [1-14C] octadecadienoic (linoelaidic) acids was demonstrated in rats. On the 18th day of gestation, a14C-labeled albumin complex of elaidic or linoelaidic acid was injected into the jugular vein of pregnant rats. For comparison, 9-cis [1-14C] octadecenoic (oleic) or 9-cis,12-cis [1-14C] octadecadienoic (linoleic) acid also was injected into the maternal circulation of rats. All animals were sacrificed 1 hr following injection. Lipid composition and distribution of label were determined in maternal plasma, placental and fetal tissues. Differences in specific activities of plasma, placental and fetal total lipids indicated a decreasing concentration gradient for bothcis andtrans isomers of octadecenoic and octadecadienoic acids. Distribution of radioactivity in various lipid components was determined by thin layer chromatography. Irrespective of the label, the highest percentage of total radioactivity was carried by triglycerides (TG) in maternal plasma (∼60–80%), and was incorporated mainly in phospholipids (PL) of fetal tissues (∼50–60%). A nearly equal distribution of the label was found between PL and TG of placental lipids (∼40%). Radioactivity of fatty acid methyl esters (FAME) determined by radiogas liquid chromatography indicated that after injection of linoelaidate, radioactivity of maternal plasma, placental and fetal tissue FAME was associated only witht,t-18∶2. Following injection of elaidate, all the radioactivity in placental FAME was associated witht-18∶1; however, in fetal tissues, the label was distributed between 16∶0 andt-18∶1. These findings suggest that, in contrast to linoelaidic acid, rat fetal tissues can metabolize elaidic acid via β oxidation to form acetyl CoA and palmitic acid.  相似文献   

20.
Hepatic metabolism of the two main isomers of CLA (9cis-11 trans, 10trans-12cisC18∶2) was compared to that of oleic acid (representative of the main plasma FA) in 16 rats by using the in vitro method of incubated liver slices. Liver tissue samples were incubated at 37°C for 17h under an atmosphere of 95% O2/5%CO2 in a medium supplemented with 0.75 mM of FA mixture (representative of circulating nonesterified FA) and with 55 μM [1-14C]9cis-11 trans C18∶2, [1-14C]10trans-12cis C18∶2, or [1-14C]oleate. The uptake of CLA by hepatocytes was similar for both isomers (9%) and was three times higher (P<0.01) than for oleate (2.6%). The rate of CLA isomer oxidation was two times higher (49 and 40% of incorporated amounts of 9cis-11 trans and 10trans-12 cis, respectively) than that of oleate (P<0.01). Total oxidation of oleate and CLA isomers into [14CO2] was low (2 to 7% of total oxidized FA) compared to the partial oxidation (93 to 98%) leading to the production of [14C] acid-soluble products. CLA isoemrs escaping from catabolism were both highly desaturated (26.7 and 26.8%) into conjugated 18∶3. Oleate and CLA isomers were mainly esterified into neutral lipids (30%). They were slowly secreted as parts of VLDL particles (<0.4% of FA incorporated into cells), the extent of secretion of oleate and of 10trans-12 cis being 2.2-fold higher than that of 9cis-11 trans (P<0.02). In conclusion, this study clearly showed that both CLA isomers were highly catabolized by hepatocytes, reducing their availability for peripheral tissues. Moreover, more than 25% of CLA escaping from catabolism was converted into conjugated 18∶3, the biological properties of which remain to be elucidated.  相似文献   

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