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1.
The fatty chain compositions of 1-O-alk-1′-enyl-2-acyl, 1-0-alkyl-2-acyl, and 1,2-diacyl glycerophospholipids of the Japanese oysterCrassostrea gigas (Thunberg) were investigated. Major fatty chains in thesn-1 position of 1-alk-1′-enyl-2-acyl ethanolamine phospholipids (EPL) were 18∶0 (64.7%) and 20∶1 (11.1%). Majorsn-1 chains of alkenylacyl choline phospholipids (CPL) were 18∶0 (63.3%) and 16∶0 (22.2%). In the case of 1-alkyl-2-acyl EPL,
the predominant fatty chains in thesn-1 position were 18∶0 (51.5%), 16∶0 (16.0%) and 20∶1 (12.5%); in the case of 1-alkyl-2-acyl CPL, the majorsn-1 chains were 16∶0 (44.0%) and 14∶0 (23.4%). Saturated fatty chains were predominant in both EPL and CPL. Prominent fatty
acids in thesn-2 position of the alkenylacyl EPL were 22∶6n−3 (29.0%), 20∶5n−3 (19.0%) and 22∶2 NMID (non-methylene interrupted dienes,
16.6%) contributing to about 65% of the total fatty acids, while alkenylacyl CPL was rich in the saturated acids 16∶0 (32.0%)
and 18∶0 (9.2%). In the alkylacyl EPL, 16∶0, 18∶1n−9, 18∶0 and 16∶1n−7 were prominentsn-2 fatty acids and accounted for 30.6%, 10.0%, 9.8%, and 8.3%, respectively. Polyunsaturated fatty acids were detected, but
were present at extremely low percentages. Majorsn-2 fatty acids in alkylacyl CPL were 16∶0 (25.4%), 22∶6n−3 (16.0%) and 20∶5n−3 (8.4%). The major fatty acids of diacyl EPL
were 20∶5n−3 (22.3%), 16∶0 (17.9%), and 18∶0 (16.1%), and those of diacyl CPL were 16∶0 (30.4%), 20∶5n−3 (17.6%) and 18∶1n−7
(7.4%). 相似文献
2.
The existence of ether-linked phospholipids, including 1-O-alk-1′-enyl-2-acyl and 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholines and ethanolamines in bonitoEuthynnus pelamis (Linnaeus) white muscle, was investigated by gas chromatography and gas chromatography-mass spectrometry. Chemical ionization
(iso-butane) mass spectrometry of trimethylsilyl ethers derived from the corresponding ether-linked glycerophospholipids proved
effective not only for determining molecular weights but also for structural identification based on the ions [M−R]+, [M−RO]+ and [M+1]+. 1-O-Alk-1′-enyl-2-acyl-sn-glycero-3-phosphocholine and ethanolamine accounted for 3.0–6.0% and 3.6–7.6% of the total glycerophospholipids, respectively.
1-O-Alkyl-2-acyl-sn-glycero-3-phosphocholine and ethanolamine were also determined for one fish and accounted for 1.4% and 0.6% of the total
glycerophospholipids, respectively. The predominant long chains in thesn-1 position of the glycerol moieties were 16∶0, 18∶0 and 18∶1 in the case of the alkenylacyl and alkylacyl components. Fatty
acid distribution of individual glycerophospholipids was also determined. 相似文献
3.
The molecular species compositions of the main diacyl phosphoglyceride classes and ether-linked subclasses from sperm of three
species of fish, sea bass Dicentrarchus labrax, Atlantic salmon Salmo salar and Chinook salmon Onchorhynchus tsawytscha, were determined. The phospholipids from sperm were highly unsaturated, dipolyunsaturated fatty acid (diPUFA) molecular species
comprised 64.6 to 71.8% of phosphatidylserine (PS), 10.1 to 17.4% of phosphatidylethanolamine (PE), and 3.3 to 10.1% of phosphatidylcholine
(PC). In sea bass sperm, di22∶6n-3 phospholipid was the predominant diPUFA molecular species, but in both salmon species 22∶5n-3/22∶6n-3
was also a major constituent of PS. Phospholipids containing 22∶6n-3 dominated in sea bass sperm with 16∶0/22∶6n-3 as a major
component of PC and PE, and 18∶0/22∶6n-3 of PE and PS in addition to di22∶6n-3 in the latter two classes. In contrast, both
salmon species contained much more 20∶5n-3 and less 22∶6n-3 so that saturated/20∶5n-3 and monounsaturated/20∶5n-3 molecular
species were more abundant than the corresponding molecules containing 22∶6n-3. Ether-linked lipids comprised 11.3–36.3% of
choline and ethanolamine phosphoglycerides in each fish species. Molecular species containing 22∶6n-3 were the major components
of 1-O-alkyl-2-acyl-glycerophosphocholine, especially 16∶0a/22∶6n-3 in sea bass and 18∶1a/∶6n-3 in the two salmon species, while
in 1-O-alk-1′-enyl-2-acyl-glycerophosphoethanolamine, 16∶0a/22∶6n-3 was the major component in both salmon and 18∶0a/22∶6n-3 in
sea bass with 18∶1a/22∶6n-3 abundant in all three species. In Atlantic salmon 1-O-alkyl-2-acylglycerophosphoethanolamine comprised 24.6% of ethanolamine glycerophospholipids which were predominantly 16∶0a/22∶6n-3
and 18∶1a/22∶6n-3. Phosphatidylinositol from sperm was dominated by stearoyl/C20 PUFA molecular species, in sea bass overwhelmingly 18∶0/20∶4n-6, while in both salmon species 18∶0/20∶4n-6 and 18∶0/20∶5n-3
were equally abundant. 相似文献
4.
In the present study, we investigated the alkenyl chains from sheep heart plasmalogens (1-O-alk-1′-enyl-2-acyl glycerophospholipids) after their conversion into trimethylene dioxyalkanyl (TMDOA) derivatives. Particular
attention was given to monounsaturated alkenyl chains (C18 mainly). For this purpose, a combination of silver ion TLC and GLC on highly polar, very long capillary columns was applied
to TMDOA derivatives. Approximately 30 different alkenyl chains could be separated, and the main observation was that the
component previously reported as a cis-9 18∶1 alkenyl chain in plasmalogens embraces in fact a wide range of trans and cis isomers, in amounts equal to 7.9 and 5.6%, respectively, of total alkenyl chains. Concerning the trans-monoenoate fraction, isomers with their ethylenic bond spanning from Δ6–Δ8 to Δ16 were tentatively identified on the basis
of their distribution profile, which was similar to that of trans-18∶1 acids prepared and isolated from sheep adipose tissue. The main trans-monoenoic C18 alkenyl chain in sheep heart plasmalogens would thus have its double bond in position 11, which seems logical, as alkenyl
chains are derived from the corresponding alcohols, themselves issued from the corresponding FA, and in this particular case,
vaccenic (trans-11 18∶1) acid. cis-Monoenoic C18 alkenyl chains also appear more complex than realized earlier, showing in particular isomers with their ethylenic bond farther
than the Δ9 position, in addition to the main isomer derived from oleic acid. Several trans-16∶1 alkenyl chains could be observed (totaling ca. 1%), but cis-16∶1 isomers were present in trace amounts only. 相似文献
5.
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
6.
In this study, the 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholine content of human platelets was determined. The distribution of arachidonate among the 1,2-diacyl,
1-O-alkyl-2-acyl, and 1-O-alk-l′-enyl-2-acyl classes of choline- and ethanolamine-containing phosphoglycerides was also assessed. The major platelet
phospholipids were choline-containing phosphoglycerides (38%), ethanolamine-containing phosphoglycerides (25%) and sphingomyelin
(18%), with smaller amounts of phosphatidylserine (11%) and phosphatidylinositol (4%). In addition to the diacyl class, the
choline-linked fraction was found to contain both 1-O-alkyl-2-acyl (10%) and 1-O-alk-l′-enyl-2-acyl (9%) species. The ethanolamine-linked fraction, on the other hand, had an elevated level of the 1-O-alk-l′-enyl-2-acyl (60%) species and a small amount of the 1-O-alkyl-2-acyl component (4%). The major fatty acyl residues found in all classes of the choline and ethanolamine phospholipids
were 16∶0, 18∶0, (Δ9), 18∶2(n−6) and 20∶4(n−6). The 1-O-alk-l and 1-O-alk-l′-enyl fraction of the ethanolamine-linked phospholipids also contained substantial amounts of 22∶4(n−6), 22∶5(n−3)
and 22∶6(n−3) acyl chains. Arachidonate comprised 44% of the acyl residues in thesn-2 position of 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholine. Corresponding values for the diacyl and 1-O-alk-l′-enyl-2-acyl species were 23% and 25%, respectively, based on all 20∶4(n−6) being linked to thesn-2 position of all classes. In the ethanolamine-linked phosphoglycerides, arachidonate constituted 60%, 20% and 68% of the
acyl groups in thesn-2 position of the 1,2-diacyl, 1-O-alkyl-2-acyl and 1-O-alk-l′-enyl-2-acyl classes, respectively. The content of 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholine appears sufficient to support the synthesis of platelet activating factor by a deacylation-reacylation
pathway in platelets. Our findings also demonstrate that human platelets contain a significant amount of 1-O-alkyl-2-arachidonyl-sn-glycero-3-phosphocholine that could possibly serve as a precursor of both platelet activating factor and bioactive arachidonate
metabolites. 相似文献
7.
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
8.
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
9.
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
10.
The phospholipid composition was determined for the amebocyte of the primitive arthropod Limulus polyphemus. The total fatty acid composition of the cells' lipids was analyzed by gas chromatography/mass spectrometry (GC/MS) of fatty
acid methyl esters (FAME). The FAME analysis revealed high levels of 20-carbon polyunsaturated fatty acids (PUFA), especially
arachidonic (20∶4n-6) and eicosapentaenoic (20∶5n-3) acids. Almost 20% of the total lipid profile was comprised of dimethyl
acetals of 16- to 20-carbon chain lengths, indicative of plasmalogens in the phospholipid pool. Phospholipids, analyzed by
high-pressure liquid chromatography, included phosphatidylethanolamine (PE), phosphatidylcholine (PC), phosphatidylserine
(PS), phosphatidylinositol (PI), sphingomyelin (SPH), and cardiolipin (CL). PE and PC levels predominated at 42.2 and 36.3%,
respectively. Smaller amounts of PS (9.0%) and PI (6.2%) were present, as well as low levels of SPH (4.6%), CL (1.6%), and
trace amounts of lysophosphatidylcholine. The major phospholipid species, PE, PC, PS and PI, were collected and their molecular
species were examined by electrospray-ionization mass spectrometry. The molecular species within the phospholipid classes
reflected the high levels of PUFA seen in the total lipid profile. PI was mainly composed of 18∶0a/20∶4. Over half of the PS consisted of 18∶0a/18∶1 and 18∶0a/20∶4. The major PE species were 20∶1p/20∶5, 20∶1p/20∶4, 18∶0p/20∶5, and 18∶0p/20∶4. PC had the largest distribution of molecular species, and its most abundant species were 16∶0e/20∶5, 16∶0e/20∶4, and 16∶0p/20∶4. The presence of 16∶0e/20∶4 is the first documentation of a specific precursor to platelet-activating factor in an invertebrate hemocyte. Note:
at the sn-1 position: [a=1=O-acyl, e=1-O-alkylether, and p=1-O-alk-1′-enyl (plasmalogen)]. 相似文献
11.
This study examined the effects of n−3 and n−6 polyunsaturated fatty acid alimentation on murine peritoneal macrophage phospholipids.
Mice were fed complete diets supplemented with either corn oil predominantly containing 18∶2n−6, borage oil containing 18∶2n−6
and 18∶3n−6, fish/corn oil mixture containing 18∶2n−6, 20∶5n−3 and 22∶6n−3, or fish/borage oil mixture containing 18∶2n−6,
18∶3n−6, 20∶5n−3 and 22∶6n−3. After two weeks, the fatty acid levels of glycerophosphoserines (GPS), glycerophosphoinositols
(GPI), sphingomyelin (SPH), and of the glycerophosphocholine (GPC) and glycerophosphoethanolamine (GPE) phospholipid subclasses
were determined. We found that mouse peritoneal macrophage GPC contain primarily 1-0-alkyl-2-acyl (range for the dietary groups, 24.6–30.5 mol %) and 1,2-diacyl (63.2–67.2 mol %), and that GPE contains 1-O-alk-1-enyl-2-acyl (40.9–47.4 mol. %) and 1,2-diacyl (44.2–51.2 mol %) subclasses. In general, fish oil feeding increased
macrophage 20∶5n−3, 22∶5n−3 and 22∶6n−3 levels while simultaneously reducing 20∶4n−6 in GPS, GPI, GPE and GPC subclasses except
for 1-O-alk-1′-enyl-2-acyl GPC. Administration of 18∶3n−6 rich diets (borage and fish/borage mixture) resulted in the accumulation
of 20∶3n−6 (2-carbon elongation product of 18∶3n−6) in most phospholipids. In general, the novel combination of dietary 18∶3n−6
and n−3 PUFA produced the highest 20∶3n−6/20∶4n−6 phospholipid fatty acid ratios. This study demonstrates that marked differences
in the responses of macrophage phospholipid classes and subclasses exist following dietary manipulation. The reduction of
20∶4n−6, while simultaneously increasing 30∶3n−6 and n−3 PUFA levels, may be important in relation to the putative beneficial
effects of 20∶3n−6 and fish oil on macrophage eicosanoid and platelet activating factor (PAF) biosynthesis. 相似文献
12.
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
13.
Kiyoshi Satouchi Kaoru Hirano Masamitsu Sakaguchi Hisaaki Takehara Fumito Matsuura 《Lipids》1993,28(9):837-840
The phospholipid and the fatty chain compositions of diacyl, alkylacyl and alkenylacyl glycerophospholipids of the free-living
nematode,Caenorhabditis elegans, were investigated. The phospholipids were comprised of 54.5% ethanolamine glycerophospholipid (EGP), 32.3% choline glycerophospholipid
(CGP), 8.1% sphingomyelin and 5.1% others. The most abundant fatty acid in CGP was eicosapentaenoic acid (20∶5n−3). The fatty
acids in CGP were more unsaturated than those in EGP. Alkenylacyl and alkylacyl subclasses accounted for 1.0 and 2.6%, respectively,
of CGP and 14.0 and 19.6%, respectively, of EGP. At least 80% of the alkenyl and alkyl groups were 18∶0 chains and the remaining
were odd numbered chains. The potential presence of platelet-activating factor (PAF) was examined by bioassay, but PAF-like
activity was not detected in the extracts of this nematode. 相似文献
14.
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
15.
The incorporation of [1-14C]18∶3n−3, (LNA) and [1-14C]-22∶6n−3 (DHA), and the metabolismvia the desaturase/elongase pathways of [1-14C]LNA, and [1-14C]20∶5n−3 (EPA) were studied in brain cells from newly-weaned (1-month-old) and 4-month-old turbot. The rank order of the
extent of net incorporation of both LNA and DHA into glycerophospholipids was total diradyl glycerophosphocholines (CPL)>
total diradyl glycerophosphoethanolamines (EPL)> phosphatidylserine (PS) and phosphatidylinositol (PI) and was independent
of the polyunsaturated fatty acid added, the age of the fish and the time of incubation. However, the rate of incorporation
of LNA into total lipid, CPL, EPL and PS was significantly greater than the rate of incorporation of DHA, and there was a
significantly greater amount of DHA incorporated into EPL than LNA. There was no significant difference between the amounts
of LNA and DHA incorporated into total lipid, CPL, PS and PI. Therefore, little preferential uptake and incorporation of DHA
into brain cells was apparent. In 24-h incubations, on average 1.1% and 8.5% of radioactivity from [1-14C]LNA and [1-14C]EPA, respectively, were recovered in the DHA fraction. Therefore, LNA cannot contribute significantly to brain DHA levels
in the turbot but EPA can. There were no significant differences between the amounts of radioactivity from either [1-14C]LNA or [1-14C]EPA recovered in the individual products/intermediates of the desaturase pathways in brain cells from 30-day-old and 120-day-old
turbot. 相似文献
16.
A simple method is presented to esterify 1-O-hexadecyl-rac-glycerol using lipases in different organic solvents. The following fatty acids were used: C14∶0, C16∶0, C18∶0, C18∶1, and C18∶2. Monoesterification was achieved by using a limiting amount of the fatty acid. Both the 1-O-hexadecyl-3-O-acylglycerol and the 2-O-acylglycerol were obtained in a total yield of 75% and a ratio of 7∶1 in dichloromethane after 3 d. Chromatographic data
for the monoesters, useful for the identification of the natural products, are given (gas-liquid chromatography, thin-layer
chromatography, reverse-phase thin-layer chromatography). The structure was confirmed by a chemical synthesis of 1-O-hexadecyl-2-O-hexadecanoylglycerol. The 3-O-glyceride was also formed by acyl migration, as the minor component. The monoesters were separated by column chromatography
and characterized by 1H and 13C nuclear magnetic resonance spectra. 相似文献
17.
The deposition oftrans-12-octadecenoate-12(13)-3H (12t-18∶1-3H) was compared tocis-9-octadecenoate-10-14C (9c-18∶1-14C) in the major egg yolk neutral lipids and phospholipids.trans-12-Octadecenoate was preferentially incorporated into cholesteryl esters (CE), phosphatidylcholines (PC), and phosphatidylethanolamines
(PE) but was discriminated against in triglycerides (TG). Isotopic ratios indicate that 5.9 and 5.6 times more 12t-18∶1-3H than 9c-18∶1-14C was esterified at the 1-acyl position of PE and PC, respectively. The combined 1- and 3-acyl positions of TG and the 2-acyl
position of TG, PE and PC were each preferentially esterified with 9c-18∶1-14C. 相似文献
18.
Giuseppe Fregapane Douglas B. Sarney Sydney G. Greenberg Dorothy J. Knight Evgeny N. Vulfson 《Journal of the American Oil Chemists' Society》1994,71(1):87-91
5-O-Acyl-1,2-O-isopropylidene-D-xylofuranose and 6-O-acyl1,2∶3,4-di-O-isopropylidene-D-galactopyranose were enzymatically prepared from the corresponding monosaccharide acetals and commercial
(crude) fatty acid mixtures. Subsequent acid-catalyzed hydrolysis of the isopropylidene group(s) gave monosaccharide esters
with overall yields of 59–88%, where the monoester content was at least 80% (galactose oleate) and typically 90% for the other
preparations. In contrast to sugar fatty acid esters prepared by conventional, high-temperature (trans)esterification, the
enzymatically obtained monosaccharide esters contained no appreciable quantities of undersirable side products, and the only
contaminants were monosaccharides and fatty acids. 相似文献
19.
Satyesh C. Pakrashi Pradeep K. Duffa Basudeb Achari Suniti Misra Amalesh Choudhury Subhashis Chattopadhyay Amitabha Ghosh 《Lipids》1989,24(5):443-447
Total lipids from hepatopancreas of the horseshoe crabs,Tachypleus gigas andCarcinoscorpius rotundicauda, obtained in 7.6 and 3.3% wet weight respective yields, were fractionated by various chromatographic techniques and identified
by gas-liquid chromatography and spectroscopic methods. Fatty acid-containing lipids were rich in 16∶0 (8.0–25%), 18∶1ω9 (6.9–22%)
and 18∶2ω6 (6.8–18.5%); appreciable amounts of 16∶1ω7, 18∶3ω3, 20∶5ω3 and 22∶6ω3 were also present. The level of 26∶0 in the
hydrocarbon fractions was unusually high (64 and 68%). Carbon chain lengths of major wax esters were 44, 46 and 48 forT. gigas and 38, 40 and 42 forC. rotundicauda. 1-O-Alkyl diglycerides were 7.2 and 9.1% of the total lipids in the two species and contained 14∶0(20%), 16∶0(60%) and 18∶0(20%)
alkyl chains along with a relatively higher percentage (32–35%) of saturated fatty acids. High levels of cholesterol (>50%
of total sterol) in the free and combined state were encountered in both samples, phospholipid contents being 40 and 35%,
respectively, and contained highest levels of unsaturated fatty acids. 相似文献
20.
Lida T Nakamori R Yabuta R Yada S Takagi Y Mano N Ikegawa S Goto J Nambara T 《Lipids》2002,37(1):101-110
A facile and efficient synthesis of the carboxyl-linked glucosides of bile acids is described. Direct esterification of unprotected
bile acids with 2,3,4,6-tetra-O-benzyl-d-glucopyranose in pyridine in the presence of 2-chloro-1,3,5-trinitrobenzene as a coupling agent afforded a mixture of the
α- and β-anomers (ca. 1∶3) of the 1-O-acyl-d-glucoside benzyl ethers of bile acids, which was separated effectively on a C18 reversedphase chromatography column (isolated yields of α- and β-anomers are 4–9% and 12–19%, respectively). Subsequent hydrogenolysis
of the α- and β-acyl glucoside benzyl ethers on a 10% Pd−C catalyst in acetic acid/methanol/EtOAc (1∶2∶2, by vol) at 35°C
under atmospheric pressure gave the corresponding free esters in good yields (79–89%). Chemical specificities such as facile
hydrolysis and transesterification of the acyl glucosides in various solvents were also discussed. 相似文献