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At least 19 recordsLinked to original sources

PubMed2003

Ingestion of plasmalogen markedly increased plasmalogen levels of blood plasma in rats.

Plasmalogens, a subclass of phospholipids, are widely distributed in human and animals, and are taken into the body as food. However, no data exist on the intestinal absorption or fate of ingested plasmalogen. Here, we determined whether dietary plasmalogen is absorbed and whether blood and tissue concentrations increased in normal male Wistar rats by using four separate experiments. Phospholipids containing more than 20 wt% of plasmalogen extracted from the bovine brain were incorporated into test diets (10-15 wt%). In experiment 1, we estimated the absorption rate by measuring the plasmalogen vinyl ether bonds remaining in the alimentary tract of rats after the ingestion of 2 g of test diet containing 91 micromol plasmalogen. The absorption rate of plasmalogen was nearly 80 mol% after 4 h, comparable to the total phospholipid content in the test diet. In experiment 2, we observed no degradation of the plasmalogen vinyl ether bonds under in vitro conditions simulating those of the stomach and small intestinal lumen. In experiment 3 we confirmed a comparable absorption (36 mol%) by using a closed loop of the upper small intestine in anesthetized rats 90 min after injecting a 10 wt% brain phospholipid emulsion. Feeding a test diet containing 10 wt% brain phospholipids for 7 d increased plasmalogen concentration threefold in blood plasma and by 25% in the liver; however, no increases were seen in blood cells, skeletal muscle, brain, lungs, kidneys, or adipose tissue (experiment 4). We concluded that dietary plasmalogen is absorbed from the intestine and contributes to a large increase in plasmalogen levels in blood plasma.

Animals↗

PubMed1998

Plasmalogen phospholipids are involved in HDL-mediated cholesterol efflux: insights from investigations with plasmalogen-deficient cells.

Plasmalogens are ether-glycerophospholipids that exist in all mammalian cells, but their physiological function remains thus far an enigma. It has been previously suggested that the association of high-density lipoprotein (HDL) with cellular phospholipid is a pre-requisite for the process of HDL-mediated cholesterol efflux (HDL-MCE). To investigate our hypothesis that plasmalogens might play a role in HDL-MCE, we used a model composed of plasmalogen-deficient cells including RAW mutant macrophages and fibroblasts from patients with rhizomelic chondrodysplasia punctata type II. In mutant macrophages, HDL-MCE was reduced by 57% compared to control macrophages, after 16 hours. A similar phenomenon was observed in plasmalogen-deficient patients fibroblasts. Incubation of plasmalogen-deficient fibroblasts with 1-0-hexadecyl-sn-glycerol, which restored plasmalogen levels to that of control cells, resulted in a 35% increase in HDL-MCE, compared to a 10% increment in controls. The novel finding that HDL-MCE is reduced in plasmalogen-deficient cells and increases following plasmalogen restoration leads us to suggest that plasmalogen has an important function in the mediation of cellular cholesterol efflux.

Animals↗

PubMed1990

Uptake of fluorescent plasmalogen analogs by cultured human skin fibroblasts deficient in plasmalogen.

One of the consequences of hereditary peroxisomal dysfunction in the cerebro-hepato-renal (Zellweger) syndrome (CHRS) is a dramatic decrease in the biosynthesis and cellular content of ether lipids. In the present study effects of reduced cellular plasmalogen levels on membrane-membrane interactions were investigated. Cultured CHRS fibroblasts were incubated with unilamellar phospholipid vesicles consisting of 1-O-alkenyl-2-acyl- or 1,2-diacyl-sn-glycerophosphocholines and ethanolamines, carrying either the trans-parinaroyl or the 1,6-diphenyl-1,3,5-hexatriene propionyl group in position 2. Transfer of the fluorogenic phospholipids from vesicles to cells was followed by measuring the concomitant increase in fluorescence intensity. Transfer of phospholipids from cells to vesicles was monitored by incubating cells, prelabeled with [3H]oleic acid, in the presence of phospholipid vesicles. Fibroblasts from healthy donors or CHRS fibroblasts supplemented with the plasmalogen precursor 1-O-hexadecylglycerol served as controls. Plasmalogen-deficient cells exhibited a significantly increased tendency to take up exogenous choline or ethanolamine plasmalogens. Cellular plasmalogens were transferred from control cells to vesicles at a higher rate if the acceptor vesicles consisted of plasmalogens as compared to diacylglycerophosphocholine. Thus, it appears as if mechanisms existed which preserve cellular plasmalogen levels during interaction with exogenous phospholipid pools. Preliminary experimental evidence suggests that the observed exchange of phospholipids between cultured fibroblasts and vesicles occurs by a protein-catalyzed process.

Biological Transport↗

PubMed1994

The discordant rates of sn-1 aliphatic chain and polar head group incorporation into plasmalogen molecular species demonstrate the fundamental importance of polar head group remodeling in plasmalogen metabolism in rabbit myocardium.

Although recent studies have demonstrated the existence of the requisite enzymic machinery necessary for the shuttling of vinyl ether linkages through polar head group remodeling, the relative rates of plasmalogen de novo synthesis and polar head group remodeling are unknown. Pulse-chase radiolabeling of perfused rabbit hearts with [1-3H]hexadecanol demonstrated the rapid and progressive incorporation of radiolabel into plasmenylethanolamine (e.g., after 0.5 h of radiolabeling, 10% of [1-3H]hexadecanol incorporated into ethanolamine glycerophospholipid was in plasmenylethanolamine, and after 1.5 h, 21% was in plasmenylethanolamine) with no detectable radiolabeling of plasmenylcholine until 3 h after the pulse. Furthermore, perfusion of hearts with [1',2'-alkyl-3H2]1-O-alkyl-GPC resulted in the rapid incorporation of radiolabel into plasmanylcholine, but not plasmenylcholine, even after extended perfusion intervals. In contrast, both radiolabeled choline and ethanolamine were rapidly incorporated into plasmalogens through polar head group remodeling at rates that were over 300-fold greater than that of plasmalogen de novo synthesis (e.g., an incorporation rate of 31 nmol/gdry.h for ethanolamine but only 93 pmol/gdry.h for hexadecanol into plasmenylethanolamine was manifest). Similarly, sn-2 remodeling of plasmalogen molecular species with arachidonic or oleic acid also occurred at rates that were over 100-fold greater than that of de novo plasmalogen biosynthesis. Collectively, these results underscore the fundamental importance of rapid polar head group remodeling of plasmalogen molecular species in the synthesis and maintenance of plasmenylcholine and plasmenylethanolamine pools in intact contracting myocardium.

Animals↗

PubMed1987

Deuterium nuclear magnetic resonance studies on the plasmalogens and the glycerol acetals of plasmalogens of Clostridium butyricum and Clostridium beijerinckii.

Deuterium nuclear magnetic resonance was used to investigate the structure of different lipid fractions isolated from the anaerobic bacteria Clostridium butyricum and Clostridium beijerinckii. The fractions isolated from C. butyricum were (1) phosphatidylethanolamine/plasmenylethanolamine and (2) the glycerol acetal of plasmenylethanolamine, and from C. beijerinckii similar fractions containing principally (1) phosphatidyl-N-monomethylethanolamine, along with its plasmalogen, and (2) the glycerol acetal of this plasmalogen were isolated. The third fraction from both species consisted largely of the acidic lipids phosphatidylglycerol and cardiolipin along with plasmalogen forms of these lipids. Palmitic acid with deuterium labels at C-2, C-3, or C-4 or oleic acid with deuterium labels at C-2 and C-9,10 was added to the growth medium and incorporated to various extents in the lipid fractions. Biochemical analysis showed that palmitic acid and oleic acid were preferentially bound to the sn-2 and sn-1 positions, respectively, of the glycerol backbone when both fatty acids were added to the medium. From the 2H NMR spectra, the hydrocarbon chain ordering near the lipid-water interface could be determined and appeared to be similar for all three lipid fractions. The deuterium quadrupole splitting and order parameter were low at the C-2 segment and increased by almost a factor of 2 at positions C-3 and C-4 for cells fed with deuterated palmitic acid along with unlabeled oleic acid. These results agree with previous findings on pure diacyl lipids in which the sn-2 chain was found to adopt a bent conformation at the carbon segment C-2. However, two unusual quadrupole splittings could be detected for the plasmalogens.(ABSTRACT TRUNCATED AT 250 WORDS)

Acetals↗

PubMed1997

Plasmalogens and oxidative stress: evidence against a major role of plasmalogens in protection against the superoxide anion radical.

Although ether-linked phospholipids have been known to be constituents of biological membranes for a long time, their physiological function has remained an enigma through the years. Inspired by the suggestion of Zoeller and coworkers that plasmalogens, which are specific types of ether-linked phospholipids characterized by the occurrence of an alpha, beta-unsaturated ether bond at the sn-1 position, are involved in the protection of cells against reactive oxygen species, we studied reactive oxygen species metabolism in cultured human skin fibroblasts. Menadione was used as intracellular generator of reactive oxygen species and cytochrome c as extracellular indicator for the production of reactive oxygen species. The finding that identical results were obtained in control and plasmalogen-deficient fibroblasts leads us to conclude that plasmalogens do not play a major role in protection against reactive oxygen species.

Anions↗

PubMed1984

Biosynthesis of phospholipids in Clostridium butyricum: kinetics of synthesis of plasmalogens and the glycerol acetal of ethanolamine plasmalogen.

The biosynthesis of the plasmalogen forms of phosphatidylethanolamine (plasmenylethanolamine) and phosphatidylglycerol (plasmenylglycerol) and of the glycerol acetal of plasmenylethanolamine has been studied in cultures of Clostridium butyricum IFO 3852. When growing cells were pulsed with [32P]orthophosphate, there was a lag of 5 to 7 min between the rapid incorporation of label into the acylphosphatides and the rapid incorporation of label into the corresponding plasmalogens. The labeling of the glycerol acetal of plasmenylethanolamine was even slower. In pulse-chase experiments with 32Pi, the kinetics of labeling indicated precursor-product relationships between phosphatidylethanolamine and plasmenylethanolamine and between the latter and its glycerol acetal. A precursor-product relationship was also seen between phosphatidylglycerol and cardiolipin, but the kinetics of labeling of the alkenyl-containing forms of these lipids were not consistent with direct precursor-product relationships with the acyl lipids. In the presence of hydroxylamine and 32Pi, both phosphatidylserine and plasmenylserine accumulated 32P in a ratio of ca. 15:1. Upon release of the inhibition of phosphatidylserine decarboxylase, label appeared in the following sequence: phosphatidylethanolamine, plasmenylethanolamine, and the glycerol acetal of plasmenylethanolamine. Acyl phosphatidylglycerol was identified as a major phospholipid (17% of lipid phosphorus) in C. butyricum grown in low-phosphate (1.13 mM) medium with 50 mM Tris buffer. Of the acyl phosphatidylglycerol, 13% was acid labile. There appear to be two plasmalogen forms of acyl phosphatidylglycerol. One of these has a single alkenyl ether group, and the other has alkenyl ether groups on both glycerols.

Clostridium↗

PubMed1963