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1.
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
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 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
4.
The contents and compositions of the 1-O-alk-1′-enyl-2-acyl, 1-O-alkyl-2-acyl, and 1,2-diacyl glycerophospholipids in the muscle and viscera of the ascidianHalocynthia roretzi, and of the gonad of the sea urchinStrongylocentrotus intermedius, which are eaten to some extent in Alaska and in Asia, were analyzed by gas-liquid chromatography. 1-O-Alk-1′-enyl-2-acyl glycerophospholipids were found in all of the samples, accounting for 64.4–69.0% of the ethanolamine glycerophospholipid
(EPL). By contrast, the levels of the 1-O-Alk-1′-enyl-2-acyl choline glycerophospholipids (CPL) were low (3.1–5.7%). CPL was rich in the 1-O-alkyl-2-acyl subclass amounting to 12.5–23.9% in the ascidian sample. The level of CPL in the sea urchin gonad was extremely
high, amounting to 46.1%. The most prominent alkyl chains in thesn-1 position of CPL from the ascidian muscle were 16∶0 (44.6%), 18∶1 (26.5%), and 18∶0 (10.7%), and of CPL from the sea urchin
gonad were 18∶0 (36.2%), 16∶0 (33.0%), and 18∶1 (17.8%). Unusually high levels of odd-numbered alkyl chains, e.g., 19∶0 andanteiso 17∶0, were detected in the CPL of all samples. The prominent alkenyl chains of EPL were 18∶0 (69.4%), 16∶0 (10.0%), and 18∶1
(8.54%) (not counting the vinyl double bond) for the sea urchin gonad. Relatively high levels of 20∶1 alkenyl chains were
also present. The glycerolsn-2 positions contained high proportions of polyunsaturated fatty acids. Thus, 20∶5n-3 (43.6%) and 22∶6n-3 (20.1%) were most
abundant in the alkylacyl CPL from the ascidian muscle and 20∶5n-3 (54.9%) and 20∶4n-6 (30.1%) in alkylacyl CPL from the sea
urchin gonad. Despite a possible interconversion of the alkyl and alkenyl chains of each class of the ether phospholipids,
they showed few features in common. 相似文献
5.
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
6.
A method is described for the quantification of the constituentO-alkyl andO-alk-1-enyl glycerols of neutral lipids or phospholipids. The method involves chemical degradation, the preparation of derivatives,
and quantification by gas chromatography using internal standards. Alk-1-enyl moieties are converted to alkyl substituted
dioxanes in the presence of 1,1-dimethoxyheptadecane as standard; alkyl glycerols are analyzed as isopropylidene derivatives
using 1-O-heptadecyl glycerol as internal standard. The method is applied to the quantification of alkyl and alk-1-enyl glycerols derived
from total lipids of rat heart, liver, testes, and brain and of various transplantable tumors, i.e. amelanotic melanoma, melanoma
B16, sarcoma T241, and Novikoff hepatoma. The levels of alkyl glycerols range from 0.11–1.07% total lipids and those of alk-1-enyl
glycerols from 0.49–5.03%. The data are compared to those obtained by other methods. 相似文献
7.
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
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.
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
10.
Lipids from bovine optic nerve were analyzed. The total content of 16.5% by weight included 27.2% nonpolar lipids, 26.1% glycolipids,
and 46.7% phospholipids by weight. Free cholesterol was the major component of the nonpolar lipid fraction. The cerebrosides,
73.5% of total glycolipids, were separated by thin layer chromatography (TLC) into two bands (upper and lower) that were present
in equal proportion. Cerebroside sulfates comprised about 27.5% of total glycolipids. Gangliosides were also detected in the
glycolipid fraction. In order of predominance, choline glycerophospholipids, ethanolamine glycerophospholipids, ethanolamine
plasmalogens, serine glycerophospholipids, sphingomyelins, and inositol glycerophospholipids were the major phospholipids.
Palmitoyl (16∶0), stearoyl (18∶0), and oleoyl (18∶1) groups were the major acyl groups in all neutral and phospholipid classes.
However, ethanolamine glycerophospholipids, serine glycerophospholipids, and inositol glycerophospholipids contained a large
percentage of 22∶6 (docosahexaenoyl) group. The major alk-1-enyl groups of the plasmalogens were 16∶0, 18∶0, and 18∶1. Steroyl
(18∶0), lignoceroyl (24∶0), and nervonoyl (24∶1) were the major acyl groups in all sphingolipids. Lower cerebroside band and
cerebroside sulfates contained large amount of hydroxylignoceroyl (cerebronoyl) and hydroxynervonoyl groups.
This investigation was supported by Grants DE-03191 and 2S06-RR-08037 from the National Institutes of Health, Bethesda, MD. 相似文献
11.
A mixture ofcis-9-[1-14C] octadecenol and [1-14C] docosanol was injected into the brains of 19-day-old rats, and incorporation of radioactivity into brain lipids was determined
after 3, 12, and 24 hr. Both alcohols were metabolized by the brain but at different rates; each was oxidized to the corresponding
fatty acid, but oleic acid was more radily incorporated into polar lipids. Substantial amounts of radioactivity were incorporated
into 18∶1 alkyl and alk-1-enyl moieties of the ethanolamine phosphoglycerides and into 18∶1 alkyl moieties of the choline
phosphoglycerides. Even after the disappearance of the 18∶1 alcohol from the substrate mixture (12 hr), the 22∶0 alcohol was
not used to any measurable extent for alkyl and alk-1-enyl glycerol formation. 相似文献
12.
Hsiang Ju Lin M. S. F. Lie Ken Jie Clara Lai Hing Lee Daniel Hong Seng Lee 《Lipids》1977,12(7):620-625
A comparison of human adult and fetal adrenals with respect to their levels of glyceryl ether lipids and other lipid components
is reported. Fetal glands contained significantly lower levels of alk-1-enyl phosphoglycerides and of cholesterol. Neutral
glyceryl ether diesters, and ethanolamine and choline phosphoglycerides were isolated from adult adrenal tissue. The composition
of theO-alkyl glycerol groups in these lipid fractions was obtained by means of gas chromatography of the trimethylsilyl ethers and
diacetyl derivatives;O-alk-1-enyl glycerols were analyzed as their diacetates. About one-half of the alkyl and alk-1-enyl glycerol moieties present
in glyceryl ether diesters contained hydrocarbon side chains with 20, 22, or 24 carbon atoms. Long hydrocarbon chains (C19–24) were also found in theO-alkyl glycerol moieties present in the total lipids of fetal adrenals. 相似文献
13.
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
14.
The lipid composition of Yoshida ascites hepatoma cells was analyzed together with that of ascitic plasma and of livers and
blood plasma from host and normal rats. In comparison to normal livers, host livers showed no significant differences in the
content of the various lipid classes, but contained a higher percentage of palmitic acid and a lower proportion of arachidonic
acid in the major phospholipid classes. In addition, tumor growth induced a marked hypertriglyceridemia in host animals; changes
in the concentration of other plasma lipid classes were not statistically significant. The ascitic plasma contained small
amounts of lipids mainly constituted by cholesteryl esters and phospholipids. Yoshida hepatoma cells contained less phospholipids
in comparison to both host and normal liver, while the increased level of triglycerides and the decrease of free fatty acids
were not statistically significant. Hepatoma cells showed appreciable amounts of ether-linked lipids associated in part to
neutral lipids (as glyceryl ether diesters) and, in part, to ethanolamine and choline phosphoglycerides. The alkyl groups
in GEDE as well as in ethanolamine and choline phosphoglycerides were mainly constituted by C16∶0 and C18∶0 followed by C18∶1. The alk-1-enyl groups in ethanolamine and choline phosphoglycerides were C16∶0 and C18∶0 with only a minor proportion of C18∶1. In comparison to both host and normal liver, Yoshida hepatoma cells showed significant changes in the fatty acid composition
of neutral lipids and phospholipids. Some of the major changes consisted of an increase of monoenoic acids associated with
a decrease of arachidonic and docosahexaenoic acids in phosphatidylethanolamine, phosphatidylcholine, and phosphatidylinositol. 相似文献
15.
Edward N. Lambremont 《Lipids》1972,7(8):528-533
When14C-labeled acetate, fatty acids or fatty alcohols were injected into or fed to the tobacco budworm, acyl, alkyl and alk-1-enyl
moieties of the phospholipids incorporated radioactivity. Fatty acids were the principal precursor in acyl bond formation
and fatty alcohols in the synthesis of alkyl and alk-1-enyl glyceryl ethers. Detailed analysis of the etherlinked phosphoglycerides
revealed that most of the radioactivity was in the ethanolamine phosphoglycerides, and very little14C was found in the choline phosphoglycerides. In experiments of a short duration, the alkyl glyceryl ethers incorporated more
radioactivity than the alk-1-enyl glyceryl ethers. The reverse was found with long term experiments, when the alk-1-enyl ethers
had higher radioactivity. In addition to demonstrating the synthesis of ether-linked ethanolamine phosphoglycerides, the data
suggested that fatty alcohols and acids were interconverted by insects and that the alk-1-enyl ethers were derived from the
alkyl ethers.
Presented at the AOCS Meeting, Houston, May 1971.
The following abbreviations and terminology will be used: PE, PC, PI and PS for the generic terms ethanolamine, choline, inositol
and serine phosphoglycerides, respectfully. Alkyl glyceryl ether for 1-alkyl-2-acyl-sn-glycerol-3-phosphoryl-, and alk-1-enyl glyceryl ether for 1-alk-1′-enyl-2-acyl-sn-glycerol-3-phosphoryl-(commonly called plasmalogen). These are adapted from the tentative rules published inJ. Lipid Res. 8:522–528 (1967). 相似文献
16.
Molecular architecture and biophysical properties of phospholipids during thermal adaptation in fish: An experimental and model study 总被引:1,自引:0,他引:1
Elfrieda Fodor Richard H. Jones Csaba Buda Klara Kitajka Indranil Dey Tibor Farkas 《Lipids》1995,30(12):1119-1126
Phospholipids from livers of carps (Cyprinus carpio L.) adapted to winter (5°C) and summer (25°C) temperatures were isolated, and the fatty acid composition of total phospholipids,
as well as molecular species composition of diacyl phosphatidylcholines and ethanolamines, were determined. Order parameter
of 5-doxyl stearic acid and steady-state fluorescence anisotropy of different anthroyloxy fatty acids—[2-, 12(N-9-anthroyloxy)stearic acid and 16(N-9-anthroyloxy)palmitic acid—embedded in native and synthetic (16∶0/16∶0, 16∶0/22∶6, 18∶0/22∶6, 18∶1/22∶6, 20∶4/20∶4, 22∶6/22∶6
phosphatidylcholines and 16∶0/18∶1, 18∶1/22∶6 phosphatidylethanolamines) phospholipid vesicles was also determined between
−30 and 30°C and 5 and 30°C, respectively. There is an accumulation of 1-monoenoic, 2-polyenoic diacyl phosphatidylcholine
and ethanolamine with a concomitant reduction of 1-stearoyl,2-docosahexaenoyl species in the cold-adapted state. Despite a
30% accumulation of long-chain polyunsaturated fatty acids in phospholipids in cold, there is only a 5°C downshift in the
solid-gel to liquid-crystalline phase transition temperature (−8 vs. −13°C). Vesicles from total phospholipids of cold-adapted
fish proved to be more disordered in all segments than from the warmadapted ones when assayed using 2,12-(N-9-anthroyloxy)stearic and 16-(N-9-anthroyloxy)palmitic acid. Vesicles made from purified phosphatidylcholines showed the same pattern, but they were more
disordered than the corresponding total phospholipids. This could be modelled using mixed phospholipid vesicles made of synthetic
16∶0/22∶6 phosphatidylcholine (75%) and either 18∶1/22∶6 phosphatidylethanolamine (25%) vs. 16∶0/18∶1 phosphatidylethanolamine
(25%) and comparison of the anisotropy parameters of 100% 16∶0/22∶6 and 100% 18∶1/22∶6 phosphatidylcholine vesicles. Mixing
either 16∶0/18∶1 (25%) or 18∶1/22∶6 (25%) phosphatidylethanolamines to 18∶0/22∶6 (75%) phosphatidylcholine shifted down or
up, respectively, the transition temperature of vesicles compared to 100% 18∶0/22∶6 vesicles assayed by electron spin resonance
spectroscopy using 5-doxylstearic acid. It is concluded that it is not the gross amount of long-chain polyunsaturated fatty
acids in phospholipids, but rather their specific combination withcis Δ9 monounsaturated fatty acids in the positionsn-1, especially in phosphatidylethanolamines, that is important in determining the physical properties of biomembranes in relation
to adaptational temperature. 相似文献
17.
The acyl and Alk-1-enyl groups of the major phosphoglycerides from ox brain myelin and mouse brain microsomal,mitochondrial and myelin fractions 总被引:1,自引:0,他引:1
The major phosphoglycerides from ox brain myelin and mouse brain microsomal, mitochondrial and myelin fractions were separated
by preparative thin layer chromatography. Alk-1-enyl groups from the alk-1-enyl acyl glycerophosphorylethanolamines were reacted
with 1,3-propanediol to form the 1,3-dioxolane derivatives. Acyl groups were converted to the methyl ester derivatives and
the acyl groups from alk-1-enyl acyl glycerophosphorylethanolamines and diacyl glycerophosphorylethanolamines were also determined
separately. The acyl and alk-1-enyl group compositions of the phosphoglycerides from microsomal and mitochondrial fractions
were quite similar. The ethanolamine and serine phosphoglycerides contained large amounts of 18∶0, 18∶1, 20∶4 and 22∶6 acyl
groups. The choline phosphoglycerides had small amounts of polyunsaturated acyl groups and large amounts of 16∶0, 18∶1 and
18∶0 acyl groups. The mitochondrial cardiolipins contained unusual amounts of several acyl groups including 18∶1, 52%; 18∶2,
6%; and 16.1, 4%. A large portion of the mouse brain 18∶2 is in that fraction. The myelin phosphoglycerides were deficient
in saturated and 22∶6 groups and markedly enriched in 18∶1 and 20∶1 groups when compared with the corresponding microsomal
or mitochondrial phosphoglycerides.
Presented in part at the AOCS Meetings, New York, October 1968 and San Francisco, April 1969. 相似文献
18.
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
19.
Eric M. Carey 《Lipids》1982,17(9):656-661
The alk-1-enyl group of 1-alk-11-enyl-2-acyl-glycerophospholipids (plasmalogens) rapidly combines with mercuric chloride. At 0 C, there was a 1∶1 stoichiometry
for Hg binding to the reactive enol group of plasmalogens. Aldehydes were not released, indicating that the alkenyl ether
bond was not cleaved. Hg binding to less reactive double bonds in unsaturated fatty acids was not significant. Quantitative
estimation of bound Hg afforded a rapid and sensitive assay for alkenylacyl lipids and gave values similar to those obtained
with other methods of analysis. The proportion of plasmalogens in bovine myelin glycerophosphatides and in ethanolamine glycerophosphatide
was 35 and 75%, respectively. Plasmalogens account for 23.3% of the total glycerophospholipid of rat erythrocytes. 相似文献
20.
The neutral and polar lipid composition ofEntomophthora coronata was determined qualitatively. The fungus was grown on a chemically nondefined medium (Sabouraud dextrose yeast extract) and
a chemically defined medium for a period up to 26 days. The lipids were characterized by thin-layer, column, gas chromatography,
and selective sprays,32P-labeling, and mass spectrometry. The neutral lipids consist of monoglycerides, diglycerides, cholesterol, free fatty acids,
triglycerides, and cholesteryl esters. The polar lipids consist of phospholipids (phosphatidyl ethanolamine, phosphatidyl
choline, lysophosphatidyl ethanolamine, lysophosphatidyl choline, and spingomyelin), a number of glycolipids including cerebrosides,
and many unrecognizable lipids, most of which are present in trace amounts. The cerebrosides and spingomyelin are present
in significant amounts, and their concentration increased with age of the culture. The major fatty acids (>10%) of the total,
neutral, and polar lipids of the mycelia are 14∶0, 16∶0, 18∶1, 18∶3(γ), and 24∶1. The polar lipids of total culture (unsaturation
index 0.88) and of the conidia (unsaturation index 1.48) are considerably more unsaturated than the corresponding neutral
lipids (unsaturated index 0.50 and 0.49). The mycelial polar lipids, compared to the neutral lipids, possess less 14∶0 and
18∶1 but contain a greater percentage of 16∶0, 18∶2, 18∶3(γ), 24∶0, and 24∶1. The major fatty acid of the conidia (>10%) are
13∶0, 14∶0, 18∶1, 18∶2, 18∶3(γ), and 20∶4. Their polar lipids have a higher proportion of 18∶2, 18∶3(γ), and 20∶4. The cerebrosides
possess 24.1 in high relative proportion (30.1%).
Presented at the AOCS Meeting, Atlantic City, October 1971. 相似文献