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PubMed1995

Epoxidation of plasmalogens: source for long-chain alpha-hydroxyaldehydes in subcellular fractions of bovine liver.

1. Masked long-chain alpha-hydroxyaldehydes were trapped in all subcellular fractions of bovine liver by application of pentafluorbenzyloxime derivatization [van Kuijk, Thomas, Stephens and Dratz (1986) Biochem. Biophys. Res. Commun. 139, 144-149] and quantified via GLC/MS using characteristic ion traces. 2. The chain-length profile of long-chain 2-hydroxyalkanales clearly indicates their relationship to plasmalogens as precursor molecules. 3. The previously postulated existence of alpha-acyloxyplasmalogens as precursor molecules of masked long-chain alpha-hydroxyaldehydes in bovine tissue lipids [Lutz and Spiteller (1991) Liebigs Ann. Chem. 1991, 563-567] was excluded. 4. The constant oxidation rate of plasmalogens in all subcellular fractions provides conclusive evidence for a non-enzymic plasmalogen epoxidation process (probably via hydroperoxy radicals). 5. The high reactivity of alpha-hydroxyaldehydes sheds some doubt on the postulation that plasmalogens protect mammalian cells against oxidative stress as postulated previously [Morand, Zoeller and Raetz (1988) J. Biol. Chem. 263, 11590-11596; Morand, Zoeller and Raetz (1988) J. Biol. Chem. 263, 11597-11606].

Aldehydes↗
PubMed2003

Signaling events mediating activation of brain ethanolamine plasmalogen hydrolysis by ceramide.

Ceramide is a lipid second messenger that acts on multiple-target enzymes, some of which are involved in other signal-transduction systems. We have previously demonstrated that endogenous ceramide modifies the metabolism of brain ethanolamine plasmalogens. The mechanism involved was studied. On the basis of measurements of breakdown products, specific inhibitor effects, and previous findings, we suggest that a plasmalogen-selective phospholipase A2 is the ceramide target. Arachidonate-rich pools of the diacylphosphatidylethanolamine subclass were also affected by ceramide, but the most affected were plasmalogens. Concomitantly with production of free arachidonate, increased 1-O-arachidonoyl ceramide formation was observed. Quinacrine (phospholipase A2 inhibitor) and 1-O-octadecyl-2-O-methyl-rac-glycerol-3-phosphocholine (CoA-independent transacylase inhibitor) prevented all of these ceramide-elicited effects. Therefore, phospholipase and transacylase activities are tightly coupled. Okadaic acid (phosphatase 2A inhibitor) and PD 98059 (mitogen-activated protein kinase inhibitor) modified basal levels of ceramide and sphingomyelinase-induced accumulation of ceramide, respectively. Therefore, they provided no evidence to determine whether there is a sensitive enzyme downstream of ceramide. The evidence shows that there are serine-dependent and thiol-dependent enzymes downstream of ceramide generation. Furthermore, experiments with Ac-DEVD-CMK (caspase-3 specific inhibitor) have led us to conclude that caspase-3 is downstream of ceramide in activating the brain plasmalogen-selective phospholipase A2.

Animals↗
PubMed1990

Analysis of very long-chain fatty acids and plasmalogen in the erythrocyte membrane: a simple method for the detection of peroxisomal disorders and discrimination between adrenoleukodystrophy and Zellweger syndrome.

We analyzed the sphingomyelin very long-chain fatty acids (VLCFAs) and phosphatidylethanolamine (PE) plasmalogen contents of the erythrocyte membrane in patients suffering from peroxisomal disorders. In a patient with Zellweger syndrome, both a decrease in the PE plasmalogen content and an increase in the sphingomyelin VLCFAs content of the erythrocyte membrane were noted. In patients with adrenoleukodystrophy, however, there was no decrease in PE plasmalogen, although the sphingomyelin VLCFAs content of the membrane was significantly increased in comparison with control values. Analyses of both sphingomyelin VLCFAs and PE plasmalogen were carried out simultaneously, using both the same process and the same sample.

Adrenoleukodystrophy↗
PubMed2001

Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: production of the chemoattractant, 2-chlorohexadecanal.

Recently alpha-chloro fatty aldehydes have been shown to be products of reactive chlorinating species targeting the vinyl ether bond of plasmalogens utilizing a cell-free system. Accordingly, the present experiments were designed to show that alpha-chloro fatty aldehydes are produced by activated neutrophils and to determine their physiologic effects. A sensitive gas chromatography-mass spectrometry technique was developed to detect pentafluorobenzyl oximes of alpha-chloro fatty aldehydes utilizing negative ion chemical ionization. Phorbol 12-myristate 13-acetate activation of neutrophils resulted in the production of both 2-chlorohexadecanal and 2- chlorooctadecanal through a myeloperoxidase-dependent mechanism that likely involved the targeting of both 16 and 18 carbon vinyl ether-linked aliphatic groups present in the sn-1 position of neutrophil plasmalogens. 2-Chlorohexadecanal was also produced by fMLP-treated neutrophils. Additionally, reactive chlorinating species released from activated neutrophils targeted endothelial cell plasmalogens resulting in 2-chlorohexadecanal production. Physiologically relevant concentrations of 2-chlorohexadecanal induced neutrophil chemotaxis in vitro suggesting that alpha-chloro fatty aldehydes may have a role in neutrophil recruitment. Taken together, these studies demonstrate for the first time a novel biochemical mechanism that targets the vinyl ether bond of plasmalogens during neutrophil activation resulting in the production of alpha-chloro fatty aldehydes that may enhance the recruitment of neutrophils to areas of active inflammation.

Aldehydes↗
PubMed1997

1-Alkenyl group of ethanolamine plasmalogen derives mainly from de novo-synthesized fatty alcohol within peroxisomes, but not extraperoxisomal fatty alcohol or fatty acid.

The origin of the 1-alkenyl group of ethanolamine plasmalogen was investigated. Three candidates were examined for the fatty alcohol forming the 1-alkenyl group. [1-(14)C]Hexadecanoic acid, [1-(14)C]hexadecanol, or [1-(14)C]lignoceric acid was administered to rats treated with 0.25% clofibrate-chow for 2 weeks. At 0.5, 1, 2, 3, and 4 h after administration of the radiolabeled compound, rats were killed and ethanolamine-containing phosphoglyceride (EPG)-rich fraction was isolated from the liver. The components of the 1-radyl group in EPG-rich fraction were separated and the radioactivity was determined. The radiolabel after administration of [1-(14)C]hexadecanoic acid or [1-(14)C]hexadecanol was almost wholly incorporated into diacyl-type glycerophosphoethanolamine (GPE), and was predominantly found in hexadecanoic acid fraction. Therefore, the long-chain fatty acid may be incorporated intact into the diacyl groups, and the long-chain fatty alcohol may be similarly incorporated after oxidation to the acid. In contrast, the radiolabel after the administration of [1-(14)C]lignoceric acid was found in the 1-alkenyl group of ethanolamine plasmalogen. After hydrolysis of the 1-alkenyl group by treatment of the plasmalogen with HCl vapor, the radiolabeled products were chiefly stearaldehyde and palmitaldehyde. The above data indicate that nascent fatty alcohol de novo synthesized from acetyl-CoA derived by peroxisomal beta-oxidation is almost exclusively used as the fatty alcohol forming the 1-alkenyl group of ethanolamine plasmalogen.

Aldehydes↗
PubMed1988

Disappearance of plasmalogen-containing phospholipids in Megasphaera elsdenii.

The plasmalogen content of phospholipids isolated from Megasphaera elsdenii ATCC 17752 decreased markedly in cultures passed serially at intervals of 3 to 6 weeks. From the wild-type ratio of vinyl ether to lipid phosphorus of 0.8, clones were isolated with ratios less than 0.05. Clonal analysis, as well as the reproducibility of the phenomenon and the long time course, suggest that the loss of plasmalogens is an adaptive process. Although small variations in cell morphology and ratios of end products of fermentation were detected, plasmalogen-rich and -deficient cells were virtually indistinguishable with respect to growth rates, range of fermentable carbohydrates, activities of selected enzymes, and electrophoretic patterns in both membrane and soluble proteins. Large decreases in saturated fatty acid production accompanied the decline of plasmalogens.

Cyclopropanes↗
PubMed2002

Decreased concentrations of serum phospholipid plasmalogens indicate oxidative burden of uraemic patients undergoing haemodialysis.

Experimental evidence indicates that uraemic patients undergoing haemodialysis are subject to increased oxidative stress. Plasmalogens are a phospholipid subclass found in cell membranes and plasma lipoproteins, which may work as an endogenous antioxidant. Using gas chromatography, we measured reduced portions of fatty aldehyde dimethyl acetals (16:0 DMA and 18:0 DMA, representing derivatives of plasmalogens) in fatty acid patterns of fasting serum phospholipids from 30 patients with chronic renal failure (CRF) receiving repeated ambulatory haemodialysis, as compared to 99 normal control subjects (CS). The highly significant difference of mean 16:0 DMA and 18:0 DMA values between CRF patients and CS (0.53 +/- 0.15 vs. 0.67 +/- 0.13, p < 0.001 and 0.33 +/- 0.11 vs. 0.40 +/- 0.11, p < 0.01, respectively) was lost when the patients were compared to subjects older than 85 (16:0 DMA) or 75 years (18:0 DMA). Weak, but significant inverse correlations with age or triglycerides were observed in blood serum of CS for 16:0 DMA and 18:0 DMA, respectively, but not of the patients. Partial correlation analysis indicated a mutually independent association of age and triglyceride values with serum plasmalogens in CS, but not in CRF patients. In conclusion, the reduced content of serum plasmalogen phospholipids of uraemic patients undergoing haemodialysis suggests an increased oxidative stress.

Adult↗
PubMed2003

Ethanolamine plasmalogens prevent the oxidation of cholesterol by reducing the oxidizability of cholesterol in phospholipid bilayers.

The aims of the present study are to establish an appropriate system for assessing the oxidizability of cholesterol (CH) in phospholipid (PL) bilayers, and to explore the effect of ethanolamine plasmalogens on the oxidizability of CH with the system, through comparing with those of choline plasmalogens, phosphatidylethanolamine, and antioxidant alpha-tocopherol (Toc). Investigation of the effects of oxidants, vesicle lamellar forms, saturation level, and constituent ratio of PLs in vesicles on CH oxidation revealed the suitability of a system comprising unilamellar vesicles and the water-soluble radical initiator 2,2'-azobis (2-amidino-propane) dihydrochloride (AAPH). As CH oxidation in the system was found to follow the rate law for autoxidation without significant interference from oxidizable PLs, the oxidizability of CH in PL bilayers could be experimentally determined from the equation: k (p)/(2k (t))(1/2)=R (p)/[LH]R(i)(1/2) by measuring the rate of CH oxidation. It was found with this system that bovine brain ethanolamine plasmalogen (BBEP), bovine heart choline plasmalogen, and egg yolk phosphatidylethanolamine lower the oxidizability of CH in bilayers. Comparison of the dose-dependent effects of each PL demonstrated the greatest ability of BBEP to reduce the oxidizability. A time course study of CH oxidation suggested a novel mechanism of BBEP for lowering the oxidizability of CH besides the action of scavenging radicals.

Amidines↗
PubMed1985

Plasmalogen analysis in erythrocyte membranes of adrenoleukodystrophy.

Very long-chain fatty acids accumulate in both adrenoleukodystrophy and Zellweger's syndrome. Plasmalogen content is decreased in Zellweger's syndrome. We therefore analyzed plasmalogen in erythrocyte membrane glycerophospholipids of three patients with adrenoleukodystrophy and eight normal controls. There was no significant difference in the ratio of plasmalogen and diacyl forms in the phosphatidylethanolamine class of the patients and controls. This observation suggests that plasmalogen metabolism differs in adrenoleukodystrophy and Zellweger's syndrome.

Adrenoleukodystrophy↗
PubMed1999

Plasmalogens as endogenous antioxidants: somatic cell mutants reveal the importance of the vinyl ether.

Exposure of plasmalogen-deficient variants of the murine cell line RAW 264.7 to short-term (0-100 min) treatment with electron transport inhibitors antimycin A or cyanide (chemical hypoxia) resulted in a more rapid loss of viability than in the parent strain. Results suggested that plasmalogen-deficient cells were more sensitive to reactive oxygen species (ROS) generated during chemical hypoxia; the mutants could be rescued from chemical hypoxia by using the antioxidant Trolox, an alpha-tocopherol analogue, and they were more sensitive to ROS generation by plumbagin or by rose bengal treatment coupled with irradiation. In addition, the use of buffers containing 2H2O greatly enhanced the cytotoxic effect of chemical hypoxia, suggesting the involvement of singlet oxygen. We used the unique enzymic deficiencies displayed by the mutants to differentially restore either plasmenylethanolamine (the major plasmalogen species normally found in this cell line) or its biosynthetic precursor, plasmanylethanolamine. Restoration of plasmenylethanolamine, which contains the vinyl ether, resulted in wild-type-like resistance to chemical hypoxia and ROS generators, whereas increasing levels of its precursor, which bears the saturated ether, had no effect on cell survival. These findings identify the vinyl ether double bond as a crucial element in cellular protection under these conditions and support the hypothesis that plasmalogens, through the vinyl ether, act as antioxidants to protect cells against ROS. These phospholipids might protect cells from ROS-mediated damage during events such as chemical hypoxia.

Animals↗
PubMed1992

Mutants in a macrophage-like cell line are defective in plasmalogen biosynthesis, but contain functional peroxisomes.

We have used a fluorescence-activated cytotoxicity protocol, 9-(1'-pyrene)nonanol (P9OH)/UV selection (Morand, O. H., Allen, L.-A. H., Zoeller, R. A., and Raetz, C. R. H. (1990) Biochim. Biophys. Acta 1034, 132-141), to isolate a series of plasmalogen-deficient mutants in a murine, macrophage-like cell line, RAW 264.7. Three of these mutants, RAW.7, RAW.12, and RAW.108, displayed varying degrees of plasmalogen deficiency (48, 17, and 14% of wild-type levels, respectively), and all three mutants were deficient in peroxisomal dihydroxyacetone phosphate (DHAP) acyltransferase activity (5% of wild-type). Unlike previously described Chinese hamster ovary (CHO) cell mutants, the RAW mutants contained intact, functional, peroxisomes and normal levels of alkyl-DHAP synthase activity, a peroxisomal, membrane-bound enzyme. In RAW.7 and RAW.108 cells, the loss of peroxisomal DHAP acyltransferase is the primary lesion. RAW.12 displayed not only a deficiency in the DHAP acyltransferase activity, but also displayed a second lesion in the biosynthetic pathway, a deficiency in delta 1'-desaturase activity (plasmanylethanolamine desaturase, EC 1.14.99.19), the final step in plasmenylethanolamine biosynthesis. The deficiencies expressed in the mutants represent unique lesions in plasmalogen biosynthesis. Since the RAW cell line is a macrophage-like responsive cell line, these mutants can be used to examine the role of plasmalogens in cellular functions such as arachidonic acid metabolism, prostaglandin synthesis, protein secretion, and signal transduction.

Acyltransferases↗
PubMed1988

Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation.

Chinese hamster ovary cells (CHO-K1) photosensitized with 12-(1'-pyrene)dodecanoic acid (P12) are killed when exposed to long wavelength ultraviolet (UV) light (greater than 300 nm). Mutants deficient in plasmalogen biosynthesis are hypersensitive to this treatment. We now demonstrate that plasmenylethanolamine is rapidly and preferentially destroyed when CHO-K1 cells, photosensitized either with P12 or merocyanine 540, are irradiated with light of the appropriate wavelength. Using [2-14C]ethanolamine, [1-14C]hexadecanol, or [U-14C]hexadecanol to follow the turnover of plasmenylethanolamine, we show that 2-monoacylglycerophosphoethanolamine, formic acid, and pentadecanal are formed during P12/UV treatment of CHO-K1 cells, but not of mutant cells deficient in plasmalogen synthesis. The decomposition of plasmenylethanolamine is O2-dependent, is enhanced in D2O, and is reduced in the presence of sodium azide. The process may be explained, in part, by the cycloaddition of singlet oxygen to the vinyl ether linkage of plasmenylethanolamine, generating a dioxetane intermediate that would be expected to decompose under physiological conditions to the observed products. An additional possibility is the formation of an allylic hydroperoxide at the 1'-carbon of the alkyl moiety by an "ene" reaction of singlet oxygen, or by radical-mediated oxidation, followed by metabolism or chemical decomposition of the hydroperoxide. Given the P12/UV hypersensitivity of plasmalogen-deficient mutants, we suggest that plasmalogens might protect animal cell membranes from singlet oxygen and/or radical-initiated oxidation by functioning as scavengers and decomposing to products that can be reutilized.

Animals↗
PubMed1978

The action of piracetam on the formation of ethanolamine-plasmalogen by neuronal microsomes of the developing rat brain.

In search of a common biochemical denominator of the action of the nootropic drug 2-oxo-pyrrolidine-1-acetamide (piracetam, Normabrain, Nootrop) the effects of the substance on the neuronal respiratory chain were investigated. The activity of the electron transport system of the respiratory chain was measured by the conversion of the ether to the enolether bond (plasmalogen) of ethanolamine containing glycerophosphatides. Piracetam enhances the formation of ethanolamine-plasmalogen from the corresponding ether lipid by neuronal microsomes and thus resembles the action of cytochrome b5. The addition of antibody against cytochrome b5 was able to inhibit the piracetam-dependent stimulation of the plasmalogen biosynthesis. Thus it appears that the stimulatory effect of piracetam on the formation of ethanolamine-plasmalogen is mediated by an increased synthesis or turnover of cytochrome b5.

Adenine Nucleotides↗
PubMedDate not supplied

[Plasmalogen forms of phospholipids in the subcellular fractions of the rabbit brain].

Data are presented on plasmalogen and diacylic forms of phospholipids-phosphatidylethanolamine and phosphatidylcholine-in different parts of the brain, as well as in different subcellular fractions from the brain of rabbits. Studies were made on 4 brain structures (forebrain, midbrain, cerebellum, medulla oblongata) and 5 subcellular fractions (myelin, nuclei, microsomes, mitochondria, synaptosomes). It was shown that among brain structures, the medulla oblongata has the highest plasmalogen content. The latter being also the highest in myelin fraction. Fatty aldehydes and fatty acids of myelinic plasmalogens are most unsaturated. Nuclear fraction is more similar to myelin than other ones. With respect to relative content and plasmalogen composition, microsomal, mitochondrial and synaptosomal fractions differ from myelin and nuclear fractions.

Aldehydes↗
PubMed2001

Plasmalogen levels in serum from patients with impaired carbohydrate or lipid metabolism and in elderly subjects with normal metabolic values.

The precise role played by plasmalogen phospholipids (PL) of lipoproteins and cell membranes is not well understood. However, they might act as endogenous antioxidants in defending cell membranes and lipoproteins from reactive oxygen species. A decline of plasmalogen concentrations has been observed in some tissues in normal aging and in some pathologic conditions. For healthy adults, we had reported negative correlations of age with serum plasmalogen PL derived heaxadecanal dimethylacetal (16:0DMA) or octadecanal dimethylacetal (18:0DMA) values. To mark off these age associated changes from disturbances in glucose or lipid metabolism, this study compares the 16:0DMA and 18:0DMA data of serum PL from 118 elderly subjects, aged 57-94 years, and grouped according to the disturbance of glucose or lipid metabolism. Using a new synthetic test mixture of 16:0DMA with oleic acid butylester as a quality control in gas chromatography, the highest 16:0DMA values were found in hypercholesterolemic subjects. However, related to the bulk of serum PL, were the plasmalogens possibly act as antioxidants, the highest values of 16:0DMA/PL were found in controls. A negative correlation of serum triglycerides (TG) with 16:0DMA was detected (n=118). The data suggest a closer association of low DMA values with elevated TG levels as compared to elevated plasma glucose or other serum lipid levels.

Journal Article↗
PubMed1963

Incorporation of isobutyrate and valerate into cellular plasmalogen by Bacteroides succinogenes.

Wegner, G. H. (University of Wisconsin, Madison) and E. M. Foster. Incorporation of isobutyrate and valerate into cellular plasmalogen by Bacteroides succinogenes. J. Bacteriol. 85:53-61. 1963.-Bacteroides succinogenes was found to require both a branched-chain volatile fatty acid (e.g., isobutyric) and a straight-chain acid (e.g., valeric) for growth. The organism used the acids as precursors for the synthesis of long-chain fatty acids and fatty aldehydes, which in turn were employed in the synthesis of phospholipid, mainly ethanolamine plasmalogen. Isobutyric acid was incorporated primarily into branched-chain C(14) and C(16) acids (tentatively identified as 12-methyl tridecanoic and 14-methyl pentadecanoic acids, respectively), and into fatty aldehydes. Valeric acid was used mainly for the synthesis of n-C(13) and n-C(15) fatty acids and fatty aldehydes. Apparently the two short-chain fatty acids were built up by the addition of two-carbon units to form the long-chain acids and aldehydes of the plasmalogen.

Aldehydes↗
PubMed1996

Simple analysis of plasmalogens in erythrocytes using gas chromatography/mass spectrometry with selected-ion monitoring acquisition.

Plasmalogens are a unique class of ether-phospholipids whose role, even though not fully defined, is essential. Their biosynthesis starts in peroxisomes, therefore, plasmalogen analysis is fundamental in the study of peroxisomal disorders. The present work reports a simple method for plasmalogen determination in erythrocytes for use in the study of peroxisomal disorders in humans; the procedure is based on two other methods that have previously been reported and employs GC/MS for separation and detection.

Acetals↗