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PubMed1996

Characterization of plasmalogen-selective phospholipase A2 from bovine brain.

Plasmalogens are hydrolyzed by a plasmalogen-selective phospholipase A2. This enzyme, purified from bovine brain, does not require Ca2+ and is localized in cytosol. It has a molecular mass of 39 kDa and is strongly inhibited by glycosaminoglycans, gangliosides, and sialoglycoproteins. These molecules may be involved in the regulation of its enzymic activity. Plasmalogen-selective phospholipase A2 plays an important role in the release of free fatty acids and platelet-activating factor during trauma.

Animals↗
PubMed1986

Age-related differences in plasmalogen content of erythrocytes from patients with the cerebro-hepato-renal (Zellweger) syndrome: implications for postnatal detection of the disease.

Phosphatidylethanolamine plasmalogen levels were determined in erythrocytes from controls and 13 patients with the cerebro-hepato-renal (Zellweger) syndrome. It was found that in Zellweger patients 20 weeks of age or younger, erythrocyte phosphatidylethanolamine plasmalogen levels were lowered whereas in older patients (except in one) normal levels were found. The results obtained suggest a close relationship between the age of the patients at sampling and the phosphatidylethanolamine plasmalogen levels in their erythrocytes. A possible explanation for these findings and the implications for the postnatal detection of Zellweger syndrome are discussed.

Brain↗
PubMed1988

Oxidation of 1-O-(alk-1-enyl)-2,3-di-O-acylglycerols: models for plasmalogen oxidation.

Alk-1-enyl diacyl glycerides, model compounds for plasmalogen lipids, were synthesized for use as substrates in oxidation studies. The neutral plasmalogen glycerides prepared included 1-O-(hexadec-1-enyl)-2,3-di-O-stearoylglycerol (4a) and 1-O-(hexadec-1-enyl)-2-O-linoleoyl-3-O-stearoylglycerol (4b). Oxidative disappearance of these glycerides was followed directly by high performance liquid chromatography (HPLC). The extent of oxidation of the side chains of these glycerides, i.e. the alkenyl ether and fatty acyl functions, was monitored by conversion of the side chains to dimethylacetal and methyl ester by methanolysis, followed by subsequent gas chromatography (GC) of the methanolysis products. Both analytical approaches show that the alkenyl ether function of neat 4a oxidizes more slowly than neat ethyl linoleate. However, the rate of alkenyl ether loss from 4a is accelerated in the presence of added ethyl linoleate. Moreover, when the linoleoyl group is incorporated into the 2-position of the alkenyl glyceride, as in 4b, the rate of loss of the alkenyl group was shown to be similar to the rate of loss of the linoleoyl group. These results suggest that oxidation of plasmalogen glycerides should not be ignored as a factor that contributes to the oxidative instability of animal tissue.

Chromatography, Gas↗
PubMed1992

Dietary ether lipid incorporation into tissue plasmalogens of humans and rodents.

Chronic feeding of 1-O-octadecyl-sn-glycerol (batyl alcohol) to patients suffering from congenital deficiency in tissue ether glycerolipids showed an increase in the plasmalogens content of their erythrocytes. However, nothing is known about the ether lipid content of other tissues in these patients. Feeding 1-O-heptadecyl-sn-glycerol to young rats showed that this uncommon ether lipid was incorporated to a high extent into the plasmalogens of all tissues except brain. Comparative studies with other precursors, such as 3-O-heptadecyl-sn-glycerol, heptadecanol and heptadecanoic acid, indicated a stereospecific incorporation of the dietary 1-O-alkyl-sn-glycerols into tissue plasmalogens without cleavage of the ether bond. Dietary ether lipids were also shown to be transferred from mothers to suckling rats, but not from pregnant rats to fetuses. The implication of these results to possible dietary ether lipid therapy for patients suffering from peroxisomal disorders is discussed.

Acyltransferases↗
PubMed2002

Characterization of trans-monounsaturated alkenyl chains in total plasmalogens (1-O-alk-1'-enyl-2-acyl glycerophospholipids) from sheep heart.

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 delta6-delta8 to delta16 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 delta9 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.

Adipose Tissue↗
PubMed1986

Plasmalogen biosynthesis in Madin-Darby canine kidney cells: selectivity in the acylation of 1-alkyl-2-lyso-sn-glycero-3-phosphoethanolamine and the subsequent desaturation step.

Acyl group specificity in the acylation of 1-alkyl-2-lyso-sn-glycero-3-phosphoethanolamine (1-alkyl-2-lyso-GroPEtn) to form 1-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine (1-alkyl-2-acyl-GroPEtn) and the subsequent desaturation of 1-alkyl-2-acyl-GroPEtn to form plasmalogens (1-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine, i.e., 1-alk-1'-enyl-2-acyl-GroPEtn) was investigated in intact Madin-Darby canine kidney (MDCK) cells and cell-free membrane preparations. We found 1-[3H]alkyl-2-lyso-GroPEtn was selectively acylated with polyunsaturated fatty acids in the order 20:4 greater than 20:5 greater than 20:3 (n-9) greater than 22:6 by cell-free membrane preparations of MDCK cells. The same pattern of acyl specificity was seen in intact MDCK cells, although the intact cells produced significantly larger amounts of 1-[3H]alkyl-2-acyl-GroPEtn containing oleic acid. There was an increased desaturation of the 1-[3H]alkyl-2-acyl-GroPEtn species containing docosahexaenoic acid to plasmalogens (1-[3H]alk-1'-enyl-2-acyl-GroPEtn) by both intact MDCK cells and the cell-free membrane preparations. The relatively rapid disappearance of the 1-[3H]alk-1'-enyl-2-docosahexaenoyl-GroPEtn species during a 20-h incubation of prelabeled intact MDCK cells suggests a more rapid turnover of this molecular species. Our results indicate there is a high selectivity in the final acylation and desaturation steps of the biosynthetic pathway for plasmalogens.

Acylation↗
PubMed1991

Stabilization of non-bilayer structures by the etherlipid ethanolamine plasmalogen.

The thermotropic phase behavior of mixtures between diradylphosphatidylethanolamines and diacylphosphatidylcholine was studied using polarized light microscopy, 31P-NMR spectroscopy and synchrotron X-ray diffraction. Multilamellar liposomes composed of alkenylacylphosphatidylethanolamine (ethanolamine plasmalogen) undergo a phase transition from a lamellar to an inverse hexagonal lipid structure at 30 degrees C, which is about 20 degrees C and 30 degrees C lower as compared to its alkylacyl- and diacyl-analog, respectively. These results indicate a higher affinity to non-bilayer structures for the ether lipids. In the presence of the bilayer stabilizing phospholipid, palmitoyloleoylphosphatidylcholine, the transition is shifted to higher temperature without any significant changes in the overall structural parameters as revealed by X-ray diffraction experiments. Again, ethanolamine plasmalogen stabilizes the inverted hexagonal phase to the highest extent, i.e. even in the presence of 40 mol% palmitoyloleoylphosphatidylcholine a pure inverse hexagonal phase is formed at 60 degrees C. Such a result was not reported so far for a diacylphosphatidylethanolamine. This property of ethanolamine plasmalogen might be predominantly explained by an optimized packing of the hydrocarbon chains in the corners and interface region of the hexagonal tubes, owing to a different conformation of the sn-2 chain, which was deduced from 2H-NMR experiments (Malthaner, M., Hermetter, A., Paltauf, F. and Seelig, J. (1987) Biochim. Biophys. Acta 900, 191-197). Data obtained by time resolved X-ray diffraction show a coexistence of lamellar and inverse hexagonal structures in the phase transition region, but do not indicate the existence of non-lamellar intermediates or disorder within the sensitivity limits of the method.

Kinetics↗
PubMed1978

A chemical study on the development of the human forebrain and cerebellum during the brain 'growth spurt' period. I. Gangliosides and plasmalogens.

Following upon previous studies on the lipid composition of the developing human brain, a further study is presented with the main object of tracing the chemical changes underlying the period of brain 'growth spurt'. Gangliosides and plasmalogens were selected as approximate markers of synaptogenesis and myelination, respectively, and these lipids were compared in cerebrum and cerebellum to establish the time, if any, at which their rate of accretion increases in a significant way. In the forebrain the rate of increase in concentration of these lipids accelerated at about the 32nd week of gestational age. Although there were too few postnatal cases to draw very firm conclusions, it seemed that the ganglioside concentration levelled off at about two months postnatal age and that the plasmalogen concentration reached a plateau between the 4th and the 6th postnatal months. In the cerebellum the concentration of gangliosides was clearly lower than that in the forebrain until about one year of age, the maximum rate of increase occurring between the last weeks of gestation and the second postnatal month. The plasmalogen concentration was somewhat higher in the cerebellum than in the forebrain but the concentration profile was similar to that followed by the gangliosides. In clear contrast with the concentration profiles in the cerebrum, in the cerebellum both lipids apparently continued to increase up to the second postnatal year. A mainly perinatal period of vulnerability is suggested for the forebrain, and a more prolonged one (probably until the second year of life) for the cerebellum.

Cerebellum↗
PubMedDate not supplied

Effect of cholesterol on vesicle bilayer geometry of choline plasmalogen and comparison with dialkyl-, alkylacyl- and diacyl-glycerophosphocholines.

Small unilamellar vesicles containing alkenylacyl-, alkylacyl-, dialkyl- or diacyl-glycerophosphocholine were prepared by sonication. Their size was determined from the average internal volume after chromatography on Sepharose 2B and from 31P-NMR linewidths. Alkenylacyl glycerophosphocholine (choline plasmalogen) was found to form the largest vesicles. By addition of 30 mol% cholesterol, the size of plasmalogen vesicles, but not of those containing the alkyl and acyl analogue lipids, was significantly increased. The presence of 50 mol% sterol led to highly increased vesicle sizes of alkylacyl, dialkyl and diacyl-glycerophosphocholine. Mixtures of plasmalogens with 50 mol% cholesterol did not form unilamellar vesicles upon sonication. Bilayer thickness and surface area per phospholipid molecule were determined by small angle X-ray scattering and measurement of partial specific volumes. There is little difference between alkenylacyl glycerophosphocholine and the corresponding diacyl-analog, whereas bilayers consisting of dioleoyl glycerophosphocholine are significantly thinner. Correspondingly their molecular surface area is by about 8% larger than that of the mixed-chain diradyl glycerophosphocholine, since the partial molar volumes are similar for all vesicles tested.

Cholesterol↗
PubMed1996

Plasmalogens and their oxidative degradation products in low and high density lipoprotein.

The kinetics of the autoxidation reaction of LDL and HDL with Fe2+/ascorbate was investigated. Aldehydes derived from plasmalogens were determined by conversion to 2-alkyl-1,3-dithiolanes. Their oxidation products, 2-hydroxy-aldehydes, were trapped by reaction with pentafluorobenzylhydroxylamine. After derivatisation, the pentafluorobenzyloximes could be separated from other compounds by thin-layer chromatograpy. They were detected by gas chromatography applying an electron capture detector. LDL plasmalogens are oxidized nearly completely after 180 min while HDL plasmalogens suffer oxidation only to 5%. Oxidation of linoleic and arachidonic acid was investigated by simultaneous determination of 2-hydroxyheptanal.

Animals↗
PubMed1986

Plasmalogen deficiency in cultured skin fibroblasts from neonatal adrenoleukodystrophy.

The plasmalogen ratio (defined as area ratio of lysophosphatidylethanolamine to the diacyl form of phosphatidylethanolamine) was investigated in cultured skin fibroblasts from neonatal adrenoleukodystrophy (N = 4) and X-linked recessive (N = 3) in addition to Zellweger syndrome (N = 3) because plasmalogen was reported to be reduced in Zellweger syndrome. The ratio was markedly decreased in all cases of Zellweger syndrome studied and in three of the four cases of neonatal adrenoleukodystrophy, whereas it was normal in the X-linked cases. This is the first documentation of a plasmalogen deficiency in neonatal adrenoleukodystrophy.

Adrenoleukodystrophy↗
PubMed1988

High incorporation of dietary 1-O-heptadecyl glycerol into tissue plasmalogens of young rats.

When 1-O-heptadecyl-rac-glycerol was fed (20 mg/g of food) to 19-day-old rats for 10 days, a high incorporation of the heptadecyl group into the 1-O-alk-1'-enyl group of ethanolamine plasmalogens of all tissues was observed. For example, 62% of the alkenyl groups from liver plasmalogen was of the 17:0 variety. The analogous values for other tissues were 62% in kidney, 57% in lung, 57% in heart, 50% in intestine, 43% in erythrocytes, 25% in testis and 8% in brain. The corresponding figures in the control rats (fed normal rat chow) were only 2-3% of 17:0 for all tissues. Available evidence indicates that dietary 1-O-heptadecyl-sn-glycerol is utilized to form tissue plasmalogens without the cleavage of the ether bond. The relevance of these results to the possible dietary ether lipid therapy of patients suffering from congenital ether lipid deficiency is discussed.

Animals↗
PubMed1979

Bradykinin-stimulated release of [3H]arachidonic acid from phospholipids of HSDM1C1 cells: comparison of diacyl phospholipids and plasmalogens as sources of prostaglandin precursors.

Ethanolamine plasmalogens (1-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamines) of many tissues contain high levels of arachidonate at their 2-position, and in certain tissues have been implicated as possible donors of arachidonate required in the synthesis of prostaglandins and thromboxanes. In the present study, [3H]arachidonate-labeled phospholipids of HSDM1C1 cells, a cell line derived from a mouse fibrosarcoma, were examined to determine the donor of the arachidonic acid released upon bradykinin stimulation of the synthesis of PGE2. HSDM1C1 cells labeled with [3H]arachidonic acid for 24 hr in serum-free medium were used in most of the experiments and had the following distribution of label among the cellular lipids; phosphatidylcholine (33%), phosphatidylinositol (20%), diacyl-sn-glycero-3-phosphoethanolamine (15%), ethanolamine plasmalogen (15%), and less polar lipids )16%). Bradykinin treatment stimulated a rapid hydrolysis of [3H]arachidonate from the cellular lipids and conversion of the released acid to PGE2, which was secreted into the medium. The label was released predominantly from phosphatidylinositol and possibly from phosphatidylcholine with no detectable change in the labeling of diacyl- or 1-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine. The ethanolamine plasmalogens, therefore, do not appear to be involved in the stimulated release of arachidonate in the HSDM1C1 cells. Indomethacin blocked the bradykinin-stimulated synthesis of PGE2 and to a lesser degree inhibited the release of [3H]arachidonate from the cellular lipids into the medium.

Animals↗
PubMed1982

A reappraisal of the dog-heart infarct plasmalogen, its conception as a bis-phosphatidic acid and current recognition as an N-acyl phosphatidyl ethanolamine.

1. We have re-examined the lipids from myocardial infarcts of cat, dog, rabbit and man, mainly through TLC methods, and confirm the identity of cat and dog "infarct plasmalogen" as an N-acyl phosphatidyl ethanolamine (NAPE). This substance was not detected in infarcts of rabbit and man. 2. We have extended our observations on a similar phosphatide, as the plasmalogen form, naturally occurring in the brain and optic nerve of fish. 3. Supporting evidence for the NAPE identity was provided from non-plasmalogen forms isolated from peas and lentils. 4. NAPE in all of its forms was shown to be a reluctant substrate for the phospholipase A2 of snake venoms. 5. Co-chromatography problems involving NAPE, semi-lyso cardiolipin and bis-phosphatidic acid are documented and their relationship to the infarct phenomenon discussed.

Animals↗
PubMed2004

Electrospray ionization tandem mass spectrometry of glycerophosphoethanolamine plasmalogen phospholipids.

Collision-induced dissociation (CID) of the [M + H]+ of glycerophospholipids typically results in abundant fragment ions that are related to the polar head group or loss of the polar head group. An exception to this general rule occurs for glycerophosphoethanolamines (GPEtn), which are a class of phospholipids that can have an acyl, 1-O-alkyl, or 1-O-alk-1'-enyl group as a substituent at the sn-1 position. The CID of the [M + H]+ of diacyl-GPEtn typically results in the expected loss of the phosphoethanolamine head group (141 Da). Therefore, constant neutral loss of 141 Da has been used as a diagnostic tool for the determination of GPEtn species in complex lipid mixtures. One disadvantage in using constant neutral loss of 141 Da in order to determine GPEtn content in lipid mixtures is that plasmalogen GPEtn does not undergo neutral loss of phosphoethanolamine to the same extent as diacyl-GPEtn. The current studies have used positive ion mode electrospray tandem mass spectrometry to study the collision-induced dissociation of various GPEtn plasmalogens present in the phospholipid membranes of human neutrophils. The CID of the [M + H]+ of plasmalogen GPEtn resulted in two prominent fragment ions; one that was characteristic of the sn-1 position and one that was characteristic of the sn-2 position. These two ions were used to detect specific molecular species of GPEtn containing esterified arachidonate (precursors of m/z 361) present in the human neutrophil.

Humans↗
PubMed1997

Effect of hyperoxia on the composition of the alveolar surfactant and the turnover of surfactant phospholipids, cholesterol, plasmalogens and vitamin E.

Experimental and clinical studies have provided evidence for the involvement of oxygen free radicals in development of acute and chronic lung diseases. Hyperoxia is very often an indispensable therapeutic intervention which seems to impose oxidative stress on lung tissue. We measured the effect of hyperoxia (80% O2 for 20 h) (1) on the lipid composition of pulmonary surfactant treated in vitro, (2) on surfactant lipid synthesis and secretion of type II pneumocytes in primary culture, (3) on the lipid composition and on the SP-A content of rat lung lavages and (4) on the turnover of phospholipids, cholesterol, plasmalogens and vitamin E in type II pneumocytes, lamellar bodies and lavages of adult rat lungs. (1) Hyperoxia of lung lavages in vitro reduces the vitamin E content significantly but does not change the relative proportion of PUFA or the content of plasmalogens. (2) Hyperoxia does not affect the biosynthesis or secretion of surfactant lipids and plasmalogens by type pneumocytes in primary culture. (3) Hyperoxic treatment of rats increases the SP-A content and reduces the vitamin E content significantly but does not change the concentration of other lipid components of lung lavage. (4) The vitamin E turnover, measured in type II pneumocytes, lamellar bodies and lung lavages, is increased 2-fold in these fractions. In contrast, the turnover of surfactant cholesterol and surfactant lipids does not change. (5) Hyperoxia caused an increase of the vitamin E uptake by type II pneumocytes resulting in a vitamin E enrichment of lamellar bodies. From these results we conclude that type II pneumocytes are able to regulate the turnover of lipophilic constituents of the alveolar surfactant independently of each other. Hyperoxia caused type II pneumocytes to increase the vitamin E content of lamellar bodies. The lipid and SP-A content of alveolar fluid can be regulated independently each other.

Animals↗
PubMed2003

Ethanolamine plasmalogen and cholesterol reduce the total membrane oxidizability measured by the oxygen uptake method.

To investigate the effects of ethanolamine plasmalogen, phosphatidylethanolamine, cholesterol, and alpha-tocopherol on the oxidizability of membranes, various large unilamellar vesicles (LUVs) including these lipids and antioxidant were examined for their total membrane oxidizabilities, evaluated as R(p)/R(i)(1/2) value (where R(p) is rate of oxygen consumption and R(i)(1/2) is the square root of rate of chain initiation) by the oxygen uptake method with water-soluble radical initiator and inhibitor. Incorporation of bovine brain ethanolamine plasmalogen (BBEP) into vesicles as well as cholesterol led to lower the total membrane oxidizability dose-dependently. The effect of BBEP was more efficient in the presence of cholesterol in vesicles. On the other hand, diacyl counterpart, egg yolk phosphatidylethanolamine, and a typical radical scavenger, alpha-tocopherol, had no effect on the membrane oxidizability. Alpha-tocopherol only prolonged an induction period dose-dependently in the present oxidizing system, suggesting a novel antioxidant mechanism of ethanolamine plasmalogens besides the action of scavenging radicals.

Animals↗
PubMed2001

Chronic myo-inositol increases rat brain phosphatidylethanolamine plasmalogen.

BACKGROUND: Oral myo-inositol (12--18 g/day) has shown beneficial effect in placebo-controlled studies of major depression, panic disorder, and obsessive compulsive disorder, and preliminary data suggest it also may be effective in bipolar depression. Evidence linking antidepressant activity to membrane phospholipid alterations suggested the examination of acute and chronic myo-inositol effects on rat brain membrane phospholipid metabolism. METHODS: With both (31)P nuclear magnetic resonance (NMR) and quantitative high-performance thin-layer chromatography (HPTLC; hydrolysis) methods, rat brain phospholipid levels were measured after acute (n = 20, each group) and chronic myo-inositol administration (n = 10, each group). With (31)P NMR, we measured myo-inositol rat brain levels after acute and chronic myo-inositol administration. RESULTS: Brain myo-inositol increased by 17% after acute myo-inositol administration and by 5% after chronic administration, as compared with the control groups. Chronic myo-inositol administration increased brain phosphatidylethanolamine (PtdEtn) plasmalogen by 10% and decreased brain PtdEtn by 5%, thus increasing the ratio PtdEtn plasmalogen (PtdEtn-Plas)/PtdEtn by 15%. Phosphatidylethanolamine plasmalogen levels quantified by (31)P NMR and HPTLC were highly correlated. The validity and reliability of the (31)P NMR method for phospholipid analysis were demonstrated with phospholipid standards. CONCLUSIONS: The observed alteration in the PtdEtn-Plas/PtdEtn ratio could provide insights into the therapeutic effect of myo-inositol in affective disorders.

Animals↗