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1.
Human milk triacylgycerols (TAG) were analyzed by tandem mass spectrometry. The SIMPLEX method and a simple linear model were
used to interpret the distribution of fatty acids between thesn-2 andsn-1,3 positions in 24 major molecular weight groups of TAG. The number of regio-isomeric pairs of TAG varied between 3 and
18 in each of these groups. Hexadecanoic (16∶0), tetradecanoic (14∶0) and dodecanoic acids (12∶0) typically occupied thesn-2 position in TAG containing less than 54 acyl carbons, whereas long-chain C18 and C20 acids were predominantly located at
the primary positions. The positions of the three fatty acids within a TAG molecule were shown to depend on the fatty acid
combination. The maximum of 12∶0 in thesn-2 position appeared at acyl carbon number (ACN) 48, the maxima of 14∶0 were at ACN 44 and ACN 50, and for 16∶0 at ACN 46
and 52. 相似文献
2.
Triacylglycerols of human milk: Rapid analysis by ammonia negative ion tandem mass spectrometry 总被引:6,自引:0,他引:6
Human milk traicylglycerols (TAG) were analyzed by ammonia negative ion chemical ionization tandem mass spectrometry. The
deprotonated molecular ions of triacylglycerols were fractionated at the first mass spectrometry (MS) stage. Twenty-nine of
the deprotonated TAG ions were further analyzed based on their collisionally activated (CA) spectra. The tandem MS analysis
covered eleven major acyl carbon number fractions, two of which contained odd carbon number fatty acids. Fatty acids of 28
different molecular weights were recorded from the daughter spectra. Hexadecanoic acid was present in all CA spectra, octadecenoic
acid in the CA spectra of all mono- and higher unsaturated TAG, and octadecadienoic acid in the CA spectra of all di- and
higher unsaturated TAG. The major fatty acid combinations in triacylglycerols were: with 0 double bonds (DB), 12∶0/12∶0/16∶0;
with 1 DB, 12∶0/16∶0/18∶1; with 2 DB, 16∶0/18∶1/18∶1; with 3 DB, 16∶0/18∶2/18∶1; with 4 DB, 18∶2/18∶1/18∶1; and with 5 DB,
18∶2/18∶2/18∶1; hexadecanoic acid typically occupied thesn-2 position. The most abundant TAG was shown to besn-18∶1–16∶0–18∶1, comprising about 10% of all triacylglycerols. 相似文献
3.
Phospholipid molecular species from human placenta lipids 总被引:1,自引:0,他引:1
The phospholipid molecular species from a large-scale preparation of human placenta lipids were analyzed. The major placental
phospholipids were choline glycerophospholipids (CPL) (53.2 wt%), sphingomyelin (21.7 wt%) and ethanolamine glycerophospholipids
(EPL) (14.6 wt%). 1,2-Diacyl-glycerophosphocholine was the most abundant subclass of CPL (91.7 mol%), while EPL contained
1,2-diacyl (54.6 mol%) and 1-alk-1′-enyl-2-acyl (43.8 mol%) subclasses. The level of polyunsaturated fatty acids (PUFA) in
total phospholipids was remarkably constant (38.4–39.9 mol%) within all placental batches tested. The long-chain PUFA, mainly
20∶4n−6 and 22∶6n−3 of the n−6 and n−3 series, respectively, were found in high proportion in all phospholipid classes, especially
in EPL (46.7 mol%) and in inositol glycerophospholipids (IPL) (39.9 mol%). CPL and serine glycerophospholipids were much richer
in 18∶1n−9 and 18∶2n−6. High levels of molecular species with arachidonic acid in thesn-2 position were found particularly in 1-alk-1′-enyl-2-acyl-glycerophospho-ethanolamine (with 24.0 mol% 16∶0 and 22.0 mol%
18∶0 insn-1 position) and in 1,2-diacyl glycerophosphoinositol with 42.6 mol% 18∶0 insn-1 position. EPL subclasses were rich in 22∶6n−3, which occurs mainly as 16∶0/22∶6n−3 (11.7 mol%) in the polasmalogen form
and as 18∶0/22∶6n−3, 16∶0/22∶6n−3 and 18∶1/22∶6n−3 in the diacyl forms. Based on their availability and composition, placental
phospholipids could be of interest, for example, for supplementing artificial milk preparations with n−3 and n−6 long-chain
PUFA for newborn infants with insufficiently developed 18∶2n−6 and 18∶3n−3 desaturation/elongation. 相似文献
4.
Alterations in chylomicron and VLDL TAG and the magnitude of postprandial lipemia were studied in healthy volunteers after
two meals of equal FA composition but different TAG-FA positional distribution. Molecular level information of individual
lipoprotein TAG regioisomers was obtained with a tandem MS method. The incremental area under the response curve of VLDL TAG
was large (P=0.021) after modified lard than after lard. In plasma TAG, the difference did not quite reach statistical significance (P=0.086). In general, there were less TAG with palmitic acid in the sn-2 position and more TAG with oleic acid in the sn-2 position in chylomicrons than in fat ingested. From 1.5 to 8 h postprandially, the proportion of individual chylomicron
TAG was constant or influenced by TAG M.W. VLDL TAG regioisomerism was similar regardless of the positional distribution of
fat ingested. Significant alterations were seen in VLDL TAG FA, in M.W. fractions, and in individual regioisomers with respect
to time. The TAG sn-14∶0-18∶1-18∶1+sn-18∶1-18∶1-14∶0, sn-16∶0-16∶1-18∶1+sn-18∶1-16∶1-16∶0, and sn-16∶1-18∶1-18∶1+sn-18∶1-18∶1-16∶1 decreased (P<0.05); and sn-16∶0-16∶0-18∶2+sn-18∶2-16∶0-16∶0, sn-16∶0-16∶0-18∶1+sn-18∶1-16∶0-16∶0, sn-16∶0-18∶1-16∶0, and sn-16∶0-18∶1-18∶2+sn-18∶2-18∶1-16∶0 increased (P<0.05) after both meals. In conclusion, positional distribution of TAG FA was found to affect postprandial lipid metabolism
in healthy normolipidemic subjects. 相似文献
5.
Molecular species of 1-O-alk-1′-enyl-2-acyl-, 1-O-alkyl-2-acyl-, and 1,2-diacyl-sn-glycero-3-phosphoethanolamine (EPL) andsn-glycero-3-phosphocholine (CPL) of Japanese oysterCrassostrea gigas were analyzed by selectedion monitoring gas chromatography/mass spectrometry using electron impact ionization. The characteristic
fragment ions, [RCH=CH+56]+ due to the alkenyl residue in thesn-1 position and [RCO+74]+ due to the acyl residue in thesn-2 position of alkenylacylglycerols, [R+130]+ due to the alkyl residue in thesn-1 position and [RCO+74]+ due to the acyl residue in thesn-2 position of alkylacylglycerols, [RCO+74]+ due to the acyl residues in thesn-1 and/orsn-2 positions of diacylglycerols, and [M−57]+ being indicative of the corresponding molecular weight, were used for structural assignments.
For alkenylacyl EPL and CPL, 19 and 16 molecular species were determined, respectively. Two molecular species, 18∶0alkenyl-22∶6n−3
and 18∶0-alkenyl-22∶2-non-methylene interrupted diene (NMID), amounted to 53.2% and 47.9%, respectively. The alkylacyl EPL
and CPL consisted of 16 and 20 molecular species, respectively, and the prominent components were 18∶0alkyl-22∶2NMID, 20∶1alkyl-20∶1n−11
(27.4%) and 20∶1alkyl-20∶2NMID (16.3%) in the former, and 16∶0alkyl-20∶5n−3 (23.0%) and 16∶0alkyl-22∶6n−3 (21.6%) in the latter.
For the diacyl EPL and CPL, 14 and 51 molecular species were determined, respectively. The major molecular species were 18∶0–20∶5n−3
(37.4%), 16∶0–20∶5n−3 (14.2%) and 18∶1n−7–22∶2NMID (13.2%) in the former, and 16∶0–20∶5n−3 (33.4%) and 16∶0–22∶6n−3 (22.3%)
in the latter. It was found that there were significant differences in the molecular species between the alkylacyl and diacyl
EPL and the alkylacyl and diacyl CPL; the number of molecular species was larger in CPL than in EPL, while the number of total
carbons and double bonds of the major molecular species were larger in the EPL than in the CPL. Alkenylacyl EPL were similar
to alkenylacyl CPL in molecular species composition. 相似文献
6.
Monoacylglycerol molecular species, as their di-3,5-dinitrophenylurethane derivatives, were well separated by normalphase
high-performance liquid chromatography on nitrilebonded phase. The peaks emerged in the order 20∶0, 18∶0, 16∶0, 18∶1, 16∶1,
18∶2, and 18∶3. The peaks of 1- and 2-monoacylglycerols with the same acyl group showed complete overlapping. This method
could be applied to get acyl compositions in the three positions of triacyl-sn-glycerols in their stereospecific analysis.
Presented partially at the 83rd AOCS Annual Meeting held in Toronto, Canada, May 10–14, 1992. 相似文献
7.
Human milk fat contains 20–25% palmitic acid (16∶0) and 30–35% oleic acid (18∶1). More than 60% of the plamitic acid occurs
at the sn-2 position of the glycerol backbone. Palm oil is a rich source of both palmitic and oleic acids. The structured lipid 1,3-dioleyl-2-palmitoylglycerol
(OPO) is an important ingredient in infant formula. OPO was synthesized from palm oil by a three-step method. In the first
step, low-temperature fractionation was applied to palm oil FA, yielding a palmitic acid-rich fraction (87.8%) and an oleic
acid-rich fraction (96%). The palmitic acid content was further increased to 98.3% by transforming palmitic acid into ethyl
palmitate. In the second step, esterification of ethyl palmitate and glycerol catalyzed by lipase Novozym 435 under vacuum
(40 mm Hg) was employed for the synthesis of tripalmitin. Finally, OPO was obtained by the reaction of tripalmitin. Finally,
OPO was obtained by the reaction of tripalmitin with oleic acid catalyzed by Lipase IM 60. In this final step, the TAG content
in the product acylglycerol mixture was 97%, and 66.1% oleic acid was incorporated into TAG. Analysis of the FA composition
at the sn-2 position of TAG showed 90.7 mol% of palmitic acid and 9.3 mol% of oleic acid. OPO content in the product TAG was ca. 74 mol%. Thus, an efficient method was developed for the synthesis of OPO from palm oil. 相似文献
8.
Heikki Kallio Kati Korkiasaari Olli Sjövall Jukka-Pekka Suomela Kaisa Linderborg 《Journal of the American Oil Chemists' Society》2006,83(5):407-413
TAG of butterfat were fractionated according to the type and degree of unsaturation into six fractions by silver-ion HPLC.
The fractions containing TAG with either cis-or trans-monoenoic FA were collected and fractionated further by reversed-phase HPLC to obtain fractions containing cis TAG of ACN:DB (acyl carbon number:double bonds) 48∶1, 50∶1, and 52∶1 as well as trans 48∶1, 50∶1, and 52∶1. The FA compositions of these fractions were elucidated by GC. The MW distribution of each fraction
was determined by ammonia negative-ion CI-MS. Each of the [M-H]− parent ions was fractionated further by collision-induced dissociation with argon, which gave information on the location
of cis-and trans-FA between the primary and secondary positions of TAG. The results suggest that the sn-positions of the monoenoic cis-and trans-FA depend on the two other FA present in the molecule. With 14∶0 FA in the TAG molecule, the 18∶1 FA in the sn-2 position are mostly present as cis-isomers. When there is no 14∶0 in the TAG molecule, the trans-18∶1 isomers seem to be more common in the sn-2 position. Also when other long-chain FA are present, the trans-isomers are more likely to be located in the secondary (sn-2) position. 相似文献
9.
Milk fatty acids consist of about 20–25% palmitic acid (16∶0), with about 70% of 16∶0 esterified to thesn-2 position of the milk triacylglycerols. Hydrolysis of dietary triacylglycerols by endogenous lipases producessn-2 monoacylglycerols and free fatty acids, which are absorbed, reesterified, and then secreted into plasma. Unesterified 16∶0
is not well absorbed and readily forms soaps with calcium in the intestine. The positioning of 16∶0 at thesn-2 position of milk triacylglycerols could explain the high coefficient of absorption of milk fat. However, the milk lipase,
bile salt-stimulated lipase, has been suggested to complete the hydrolysis of milk fat to free fatty acids and glycerol. These
studies determined whether 16∶0 is absorbed from human milk assn-2 monopalmitin by comparison of the plasma triacylglycerol total andsn-2 position fatty acid composition between breast-fed and formula-fed term gestation infants. The human milk and formula had
21.0 and 22.3% of 16∶0, respectively, with 54.2 and 4.8% 16∶0 in the fatty acids esterified to the 2 position. The plasma
triacylglycerol total fatty acids had 26.0±0.6 and 26.2±0.6% of 16∶0, and thesn-2 position fatty acids had 23.3±3.3 and 7.4±0.7% of 16∶0 in the three-month-old exclusively breast-fed (n=17) and formula-fed
(n=18) infants, respectively. Marked differences were found in the plasma total and the 2 position phospholipid percentage
of 20∶4ω6, i.e., 11.6±0.3 and 6.9±0.6 (total), 17.7±1.4 and 9.7±0.6 (sn-2 position) and percentage of 22∶6ω3, 4.6±0.3 and 2.1±0.3 (total), 5.6±0.6 and 2.0±0.2 (sn-2 position) for the breast-fed and formula-fed infants, respectively. These studies provide convincing evidence that 16∶0
is absorbed from human milk assn-2 monoacyl-glycerol. The metabolic significance of the differences in positional distribution of fatty acids in the plasma
lipids of breast-fed and formula-fed infants is not known. 相似文献
10.
This study reports a facile identification of the molecular species of enantiomeric diacylglycerols by combining chiral phase
high-performance liquid chromatography with positive chemical ionization mass spectrometry. For this purpose the 3,5-dinitrophenylurethane
(DNPU) derivatives ofsn-1,2(2,3)-diacylglycerols are separated on an (R+)-naphthylethylamine polymer column (25 cm × 0.46 cm ID) using an isocratic
solvent system made up of hexane/dichloroethane/acetonitrile (85∶10∶5, by vol) or isooctane/tert-butyl methyl ether/acetonitrile/isopropanol (80∶10∶5∶5, by vol). About 1% of the column effluent (1 mL/min) was admitted
to a quadrupole mass spectrometer (Hewlett-Packard, Palo Alto, CA)via direct liquid inlet interface, and positive chemical ionization spectra were recorded over the range of 200–900 mass units.
The DNPU derivatives of diacylglycerols yield characteristic [M-DNPU]+ and [RCO+74]+ ions for each diacylglycerol species from which the molecular weight and exact pairing of fatty acids can be unequivocally
obtained. The characteristic ions appear to be generated in nearly correct mass proportions as indicated by preliminary quantitative
comparisons.
The abbreviations 14∶0, 16∶1, 18∶2, etc. represent normal chain fatty acids of 14, 16, 18, etc. acyl carbons and 0, 1, 2,
etc. double bonds, respectively; 16∶0–18∶1, etc. represent diacylglycerols containing 16∶0 and 18∶1 fatty acids of unspecified
positional distribution;sn indicates stereospecific numbering of glycerol carbons;sn-1,2-diacylglycerols andsn-2,3-diacylglycerols are enantiomeric diacylglycerols of unspecified fatty acid composition;rac-1,2-diacylglycerols are racemic diacylglycerols representing equal amounts ofsn-1,2-andsn-2,3-enantiomers;sn-1,2(2,3)-diacylglycerols are a mixture ofsn-1,2-andsn-2,3-diacylglycerols of unspecified proportion of enantiomers and unspecified fatty acid compisition and positional distribution;
X-1,3-diacylglycerols are diacylglycerols of unspecified fatty acid composition and reverse isomer content. 相似文献
11.
Normal-phase HPLC resolution of sn-1,2(2,3)- and x-1,3-DAG generated by partial Grignard degradation from natural TAG was carried out with both (R)-(−) and (S)-(+)-1-(1-naphthyl)ethylurethane derivatives. The diastereomeric sn-1,2- and sn-2,3-DAG derivatives were resolved using two Supelcosil LC-Si (5 μm, 25 cm × 4.6 mm i.d.) columns in series and an isocratic
elution with 0.37% isopropanol in hexane at a flow rate of 0.7 mL/min. The DAG were detected by UV absorption at 280 nm and
were identified by electrospray ionization MS in the positive ion mode following postcolumn addition of chloroform/methanol/30%
ammonium hydroxide (75∶24.5∶0.5, by vol) at 0.6 mL/min. Application of the method to a stereospecific analysis of the molecular
species of TAG of rat VLDL showed that the TAG composition of VLDL circulating under basal conditions differs markedly from
that of VLDL secreted by the liver during inhibition of serum lipases. The inhibition of serum lipases resulted in a significant
proportional decrease in 16∶0 and PUFA and an increase in 18∶0 and oligoenoic FA in the sn-1-position, whereas the FA compositions in the sn-2- and sn-3-positions were much less affected. 相似文献
12.
The effect of dietary TAG structure and fatty acid acyl TAG position on palmitic and linoleic acid metabolism was investigated
in four middle-aged male subjects. The study design consisted of feeding diets containing 61 g/d of native lard (NL) or randomized
lard (RL) for 28 d. Subjects then received an oral dose of either 1,3-tetradeuteriopalmitoyl-2-dideuteriolinoleoyl-rac-glycerol or a mixture of 1,3-dideuteriolinoleoyl-2-tetradeuteriopalmitoyl-rac-glycerol and 1,3-hexadeuteriopalmitoyl-2-tetradeuteriolinoleoyl-rac-glycerol. Methyl esters of plasma lipids isolated from blood samples drawn over a 2-d period were analyzed by GC-MS. Results
showed that absorption of the 2H-fatty acids (2H-FA) was not influenced by TAG position. The 2H-FA at the 2-acyl TAG position were 85±4.6% retained after absorption. Substantial migration of 2H-16∶0 (31.2±8.6%) from the sn-2 TAG position to the sn-1,3 position and 2H-18∶2n−6 (52.8±6.4%) from the sn-1,3 position to the sn-2 position of chylomicron TAG occurred after initial absorption and indicates the presence of a previously unrecognized isomerization
mechanism. Incorporation and turnover of the 2H-FA in chylomicron TAG, plasma TAG, and plasma cholesterol esters were not influenced by TAG acyl position. Accretion of
2H-16∶0 from the sn-2 TAG position in 1-acylphosphatidylcholine was 1.7 times higher than 2H-16∶0 from the sn-1,3 TAG positions. Acyl TAG position did not influence 2H-18∶2n−6 incorporation in PC. The concentration of 2H-18∶2n−6-derived 2H-20∶4n−6 in plasma PC from subjects fed, the RL diet was 1.5 times higher than for subjects fed the NL diet, and this result
suggests that diets containing 16∶0 located at the sn-2 TAG position may inhibit 20∶4n−6 synthesis. The overall conclusion is that selective rearrangement of chylomicron TAG structures
diminishes but does not totally eliminate the metabolic and physiological effects of dietary TAG structure. 相似文献
13.
The individual molecular species composition of diacyl, alkylacyl and alkenylacyl glycerophospholipids was determined in mouse
peritoneal macrophages. A marked deterogeneity in the relative composition (mol%) of macrophage ether and ester phospholipid
individual species was noted. High concentrations of 16∶0–20∶4 were found in ether phospholipids such as alkenylacyl glycerophosphoethanolamine
(GPE; 27.5 mol%) and alkylacyl glycerophosphocholine (GPC; 16.6%) as compared to mol % levels of 16∶0–20∶4 in diacyl GPE (5.7%)
and diacyl GPC (8.1%), respectively. Interestingly, alkenylacyl GPE was highly enriched in 1-ether (16∶0) relative to alkylacyl
GPC. The predominant diacyl molecular species in glycerophosphoinositol (GPI) and glycerophosphoserine (GPS) were 18∶0–20∶4
(59.1%) and 16∶0–18∶1 (41.1%), respectively. It is noteworthy that the level of 18∶0–20∶4 was several times higher in diacyl
GPI (59.1%) than in diacyl GPS (11.1%), diacyl GPE (25.7%), and diacyl GPC (3.7%). The most abundant molecular species in
diacyl GPC and diacyl GPE were 16∶0–18∶1 (29.9%) and 18∶0–20∶4 (25.7%), respectively. The abundance of 20∶4 in ether phospholipids,
specifically 16∶0–20∶4 and 18∶0–20∶4, in alkylacyl GPC is significant in view of the role these antecedents play in the biosynthesis
of platelet-activating factor (PAF) and 20∶4-derived eicosanoids in stimulated macrophages. The unique molecular species composition
of the peritoneal macrophage distinguishes this cell type from others. 相似文献
14.
The molecular species composition of the major glycerophospholipids from white matter of human brain were determined by high-performance
liquid chromatography of the 3,5-dinitrobenzoyl derivatives of the corresponding diradylglycerols. In phosphatidylcholine
(PC) and phosphatidylserine (PS), molecular species containing only saturated fatty acids (SFA) and monounsaturated fatty
acids (MUFA) comprised 85.7 and 82.4% of the respective totals, with 18∶0/18∶1 predominant in PS and 16∶0/18∶1 in PC. These
molecular species were also abundant in phosphatidylethanolamine (PE), but in this phospholipid species containing polyunsaturated
fatty acids (PUFA), largely 18∶0/22∶6n−3 and 18∶0/20∶4n−6, accounted for over half the total; 18∶1/18∶1 was also abundant
in PE. In contrast, 1-O-alk-1′-enyl-2-acylsn-glycero-3-phosphoethanolamine (GPE) had much more SFA- and MUFA-containing species, predominantly 16∶0a/18∶1, 18∶0a/18∶1
and 18∶1a/18∶1, with low amounts of species containing 20∶4n−6 and 22∶6n−3. In alkenylacyl GPE, 22∶4n−6 was the major PUFA
and 16∶0a/22∶4n−6 and 18∶1a/22∶4n−6 the main PUFA-containing species. There was six times more 22∶6n−3, twice as much 20∶4n−6
and half the amount of 22∶4n−6 in PE as compared to alkenylacyl GPE.
Molecular species are abbreviated as follows:e.g., 16∶0/18∶1 PE is 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine; the corresponding alkenylacyl species, 1-O-hexadec-1′-enyl-2-oleoyl-sn-glycero-3-phosphoethanolamine is 16∶0a/18∶1. 相似文献
15.
Nakagawa Yasuhito Waku Keizo Hirose Akihiko Kawashima Yoichi Kozuka Hiroshi 《Lipids》1986,21(10):634-638
The effect of administeringp-chlorophenoxyisobutyric (clofibric) acid to rats on the molecular species composition of diacyl-glycerophosphocholine (GPC)
of rat liver microsomes was studied. Microsomal choline glycerophospholipids were converted to 1,2-diradyl-3-acetylglycerol
and were separated into molecular species by reverse-phase high performance liquid chromatography. Diacyl-GPC consisted of
17 different molecular species. The predominant species were arachidonoyl derivatives, such as 18∶0–20∶4 (22.2% of the total)
and 16∶0–20∶4 (22.0%). Administration of clofibric acid to rats caused a marked increase in 16∶0–18∶1 species of diacyl-GPC
from 8% to 30%, making these the predominant species of diacyl-GPC in clofibric acid-fed rats. Also, a significant decrease
(50% of controls) in 18∶0–18∶2 and 18∶0–20∶4 species was observed, whereas the decrease in molecular species containing 16∶0
at the 1-position such as 16∶0–18∶2 and 16∶0–20∶4 was small (approximately 85% of control). The results show that clofibric
acid caused marked changes in the molecular species composition of diacyl-GPC. The participation of 1-acyl-GPC acyltransferase
and stearoyl-CoA desaturase in the regulation of the molecular species composition of diacyl-GPC is discussed. 相似文献
16.
The molecular species composition of phosphatidylinositol (PI) purified from four different tissues from cod was found to
show large tissue-specific differences. In brain 18∶0/20∶5 was the most abundant species (40.8%) followed by 18∶1/20∶5 (13.5%).
In retina, 24–26% each of PI was the 16∶0/22∶6 and 18∶0/20∶4 species with 16–18% each of 18∶0/20∶5 and 18∶0/22∶6. In liver,
almost half of the PI was 18∶0/20∶4 with 18% 18∶1/20∶4. In contrast, muscle contained almost 40% of 18∶0/22∶6 with 10–14%
each of 18∶0/20∶4, 18∶0/20∶5 and 18∶1/22∶6.
Molecular species are abbreviated as follows:e.g., 18∶0/20∶4 PI is 1-stearoyl-2-eicosatetraenoyl-sn-glycero-3-phosphoinositol. 相似文献
17.
Ethanolamine glycerophospholipids from the brains of both trout and cod comprised 36–38% of 1-O-alk-1′-enyl-2-acyl-glycerophosphoethanolamine (GPE) determined using two methods. In 1-O-alk-1′-enyl-2-acyl-GPE from trout brain, the main molecular species were 18∶1a/18∶1, 18∶0a/18∶1 and 16∶0a/18∶1, which totalled
63.3%, while polyunsaturated fatty acid (PUFA) containing species totalled only 18.2%. 1-O-Alk-1′-enyl-2-acyl-GPE from cod brain was much more unsaturated with PUFA containing species totalling 52.6%, of which 18∶0a/20∶5n−3,
18∶1a/20∶5n−3 and 18∶1a/22∶6n−3 were predominant. In cod 18∶1a/18∶1, 18∶0a/18∶1 and 16∶0a/18∶1 were the only other species
present at over 5% each, totalling 31.8%. In both cod and trout, small amounts of species containing 22∶4n−6 were found. The
results of this and earlier studies indicate that there is considerable specificity of composition at the level of molecular
species between different lipid classes and subclasses.
Molecular species of 1-O-alk-1′-enyl-2-acyl-GPE are abbreviated as follows:e.g., 16∶0a/18∶1 GPE is 1-O-hexadec-1′-enyl-2-oleoyl-sn-glycero-3-phosphoethanolamine. The corresponding diacyl species, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine, is abbreviated as 16∶0/18∶1. 相似文献
18.
Ether lipid content and fatty acid distribution in rabbit polymorphonuclear neutrophil phospholipids
This study was undertaken to determine if rabbit neutrophils contain sufficient ether-linked precursor for the synthesis of
1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (platelet activatin factor) by a deacylation-reacylation pathway. The phospholipids from rabbit
peritoneal polymorphonuclear neutrophils were purified and quantitated, and the choline-containing and ethanolamine-containing
phosphoglycerides were analyzed for ether lipid content. Choline-containing phosphoglycerides (37%), ethanolamine-containing
phosphoglycerides (30%), and sphingomyelin (28%) were the predominant phospholipid classes, with smaller amounts of phosphatidylserine
(5%) and phosphatidylinositol (<1%). The choline-linked fraction contained high amounts of 1-O-alkyl-2-acyl-(46%) and 1,2-diacyl-sn-glycero-3-phosphocholine (54%), with a trace of the 1-O-alk-1′-enyl-2-acyl species. The ethanolamine-linked fraction contained high amounts of 1-O-alk-1′-enyl-2-acyl-(63%) and 1,2-diacyl-sn-glycero-3-phosphoethanolamine (34%), and a low quantity of the 1-O-alkyl-2-acyl species (3%). The predominant 1-O-alkyl ether chains found in thesn-1 position of the choline-linked fraction were 16∶0 (35%), 18∶0 (14%), 18∶1 (26%), 20∶0 (16%), and 22∶0 (9%). The major 1-O-alk-1′-enyl ether chains found in thesn-1 position of the ethanolamine-linked fraction were 14∶0 (13%), 16∶0 (44%), 18∶0 (27%), 18∶1 (12%) and 18∶2 (3%). The major
acyl groups in thesn-1 position of 1,2-diacyl-sn-glycero-3-phosphocholine and 1,2-diacyl-sn-glycero-3-phosphoethanolamine were 16∶0, 18∶0 and 18∶1. The most abundant acyl group in thesn-2 position of all classes of choline- and ethanolamine-linked phosphoglycerides was 18⩺2. Although this work does not define
the biosynthetic pathway for platelet activating factor, it does show that there is ample precursor present to support its
synthesis by a deacylation-reacylation pathway. 相似文献
19.
Adequate accumulation of polyunsaturated essential fatty acids, in particular docosahexaenoic acid (22∶6n−3), into membrane
phospholipids is critical for optimal fetal brain development. This process is maximal during the period of rapid neurite
outgrowth, neuritogenesis, which precedes the major growth phase, myelination. There is no information about differential
changes during gestation to individual brain phospholipid molecular species which contain 22∶6n−3. Such details of brain development
would be concealed by total fatty acid analysis of isolated phospholipid classes. We have detailed phosphatidylcholine (PC)
and phosphatidylethanolamine (PE) molecular species compositions in developing fetal guinea pig brain. Total brain PC concentration
increased substantially between 40 and 68 (term) d of gestation, corresponding to myelination, while PE increased in a biphasic
manner between 25–35 d, which was coincident with onset of neuritogenesis, and 40–68 d. Fetal brain development was accompanied
by complex changes in the concentration of individual phospholipid molecular species. During early gestation (25–40 d) 22∶6n−3
was enriched in both PC and PEsn−1 16∶0 molecular species. However, between 40 d and term there was no further increase in brain PC 22∶6n−3 content, while
brain PE was significantly enriched in both PE 18∶1/22∶6 and PE18∶0/22∶6. We hypothesize that accumulation of 22∶6n−3 intosn−1 18∶1 and 18∶0 species represents establishment of a 22∶6n−3-containing membrane PE pool which may be turned over more slowly
thansn−1 16∶0 species. Identification of specific changes in membrane phospholipids which are associated with defined events in
brain development may provide a basis for assigning functional roles to individual molecular species. 相似文献
20.
The effect of the water-soluble fraction (WSF) of crude oil on lipid contents, lipid classes, FA, and PC molecular species
was studied in high-phospholipid (hepatopancreas) and low-phospholipid (egg) tissues of a freshwater crustacean. After a 21-d
exposure to a sublethal concentration of WSF, a significant decrease in shrimp total lipids was observed, although no alterations
could be detected in the hepatopancreas or egg lipid contents. TAG/phospholipid ratios increased in the hepatopancreas and
decreased in the eggs, suggesting alterations either in the mobilization of TAG to phospholipid pools or in the energy balance.
The FA composition of phosphoglycerides in the hepatopancreas and eggs was dominated by PUFA, whereas the n−3/n−6 ratio was
not affected by WSF exposure, although there was a significant increase in hepatopancreas 18∶1n−9. Analysis of the PC molecular
species by HPLC-ELSD showed the presence of 15 species, with 16∶0/18∶1, 18∶1/18∶2, 16∶0/20∶5, and 16∶1/20∶5 being the major
species in the hepatopancreas. The PC molecular species in the eggs showed a different pattern, dominated by 16∶0/18∶1 and
18∶1/18∶2. Of the PC molecular species, 10 contained 22∶6n−3, 20∶5n−3, and 20∶4n−6. Small amounts of di-PUFA species were
also found. Exposure to WSF altered the PC molecular species in both tissues. The four major hepatopancreas molecular species
and most of the ones containing PUFA decreased. This was compensated for by an increase in 16∶1/18∶1 (152%) and 18∶1/18∶1
(50%). The two major egg PC molecular species decreased, whereas the PUFA-containing ones increased. The contrasting responses
of both tissues of WSF contamination suggests the presence of different homeostatic mechanisms. 相似文献