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PubMed1994

Plasmenylcholine (1-O-alk-1'-enyl-2-acyl-sn-glycero-3-phosphocholine) biosynthesis in guinea-pig heart and liver: cholinephosphotransferase is a bifunctional enzyme for the synthesis of phosphatidylcholine and plasmenylcholine.

Plasmenylcholine is present in significant proportion (32% of choline phosphoglycerides) in the guinea-pig heart but exists as a minor component (3% of choline phosphoglycerides) in the guinea-pig liver. In this study, the biosynthesis of plasmenylcholine in these two organs was examined. The organs were perfused with labelled choline for 15 min and chased with unlabelled choline for up to 7 h. The labelling of phosphatidylcholine was 6-fold higher than that of plasmenylcholine in the heart and about 60-fold higher in the liver. However, the same labelling ratio was maintained throughout the chase period in both organs. Alterations in the specific radioactivity of CDP-choline caused corresponding changes in the labelling of phosphatidylcholine and plasmenylcholine. Our results suggest that in guinea-pig heart and liver, CDP-choline is the immediate precursor of biosynthesis of phosphatidylcholine and plasmenylcholine. The biochemical cause for the difference in their rates of formation between the two organs was explored. The enzyme activities for the formation of both choline phosphoglycerides were determined. The two reactions share the same characteristics, and 1,2-diacylglycerol and 1-alk-1'-enyl-2-acylglcerol were found to be mutually inhibitory in a competitive fashion. The pool sizes of 1,2-diacylglycerol and 1-alk-1'-enyl-2-acylglycerol were determined, and their ratios were found to be 42 in the heart and 422 in the liver. We conclude that cholinephosphotransferase catalyses the formation of both phosphatidylcholine and plasmenylcholine in the guinea-pig tissues and the rate of plasmenylcholine biosynthesis is dependent on the availability of 1-alk-1'-enyl-2-acylglycerol. Plasmenylcholine biosynthesis is also subjected to modulation by the 1,2-diacylglycerol content of the tissue.

Animals↗
PubMed2000

Determination of the phospholipid precursor of anandamide and other N-acylethanolamine phospholipids before and after sodium azide-induced toxicity in cultured neocortical neurons.

Phospholipase D-mediated hydrolysis of N-acylethanolamine phospholipids (NAPEs) releases anandamide and other N-acylethanolamines, resulting in different actions at cellular targets in the CNS. Recently, we have demonstrated that these N-acyl lipids accumulate in cultured neocortical neurons subjected to sodium azide-induced cell injury. We here extend the information on the NAPE response, reporting on the composition of N-acylspecies of NAPE, employing a new methodological approach of HPLC-coupled electrospray ionization mass spectrometry. Exposure to sodium azide (5 mM) increased the total amount of NAPE threefold over control levels; however, no alteration of the relative composition of NAPE species was detected. The anandamide precursor (20 : 4-NAPE) constituted only 0.1% of all NAPEs detected in the neurons. Total NAPE species in control cells amounted to 956-1,060 pmol/10(7) cells. Moreover, we detected the presence of an unknown NAPE species with molecular weight identical to 20 : 4-NAPE. This may suggest the presence of a putative stereoisomer of the anandamide precursor with at least one trans-configured double bond in the N-arachidonoyl moiety. These results show that with the present method, neuronal NAPE species can be identified and quantified with respect to N-acyl composition, including a trans-isomer of the anandamide precursor. The anandamide precursor is up-regulated to the same extent as other NAPEs upon neuronal injury.

Animals↗
PubMed1989

Plasmenylethanolamine is the major storage depot for arachidonic acid in rabbit vascular smooth muscle and is rapidly hydrolyzed after angiotensin II stimulation.

The present study demonstrates that rabbit aortic intimal smooth muscle cells contain the majority of their endogenous arachidonic acid mass in plasmenylethanolamine molecular species. To demonstrate the potential significance of these plasmenylethanolamines as substrates for the smooth muscle cell phospholipases that are activated during agonist stimulation, aortic rings were prelabeled with [3H]arachidonic acid and stimulated with angiotensin II. Although the specific activities of the choline and inositol glycerophospholipid pools were similar after the labeling interval, ethanolamine glycerophospholipids had a specific activity of only 20% of the specific activity of choline and inositol glycerophospholipids. Despite the marked disparity in the specific activities of these three phospholipid classes, angiotensin II stimulation resulted in similar fractional losses (35-41%) of [3H]arachidonic acid from vascular smooth muscle choline, ethanolamine, and inositol glycerophospholipid classes. Reverse-phase HPLC demonstrated that greater than 60% of the [3H]arachidonic acid released from ethanolamine glycerophospholipids after angiotensin II stimulation originated from plasmenylethanolamine molecular species. Taken together, the results demonstrate that the major phospholipid storage depot for arachidonic acid in vascular smooth muscle cells are plasmenylethanolamine molecular species which are important substrates for the phospholipase(s) that are activated during agonist stimulation.

Angiotensin II↗
PubMed1989

Cytoplasmic requirement for peroxisome biogenesis in Chinese hamster ovary cells.

Hybrids constructed by fusion of wild-type Chinese hamster ovary cells (CHO-K1) to peroxisome-deficient CHO mutants (ZR-78.1) contain normal peroxisomes, demonstrating that the mutation(s) are recessive. "Nuclear hybrids" prepared by fusion of CHO-K1 karyoplasts to mutant ZR-78.1 occasionally fail to regain intact peroxisomes (approximately 1/300 cells). These peroxisome-deficient nuclear hybrids closely resemble the original mutant cells by biochemical criteria, but their modal chromosome number is 36-38, the same as that of CHO hybrids generated from intact cells. When the peroxisome-deficient nuclear hybrids are fused to wild-type cytoplasts, a fraction of the fusion products (at least 70%) continue to propagate normal peroxisomes indefinitely. Peroxisome biogenesis cannot be reinitiated in cells of mutant ZR-78.1 by fusion to wild-type cytoplasts. Our results suggest that a wild-type nucleus by itself is necessary but not sufficient for restoration of normal peroxisome biogenesis and that a cytoplasmic component of wild-type cells, possibly a normal peroxisome, is also required.

Animals↗
PubMed2001

A novel plasmal conjugate to glycerol and psychosine ("glyceroplasmalopsychosine"): isolation and characterization from bovine brain white matter.

A novel plasmal conjugate of glycosphingolipid having cationic lipid properties was isolated from the white matter of bovine brain. Linkage analysis of galactosyl residue by methylation, liquid secondary ion, and electrospray ionization mass spectrometry of intact and methylated derivatives, and by (1)H- and (13)C-NMR spectroscopy, identified the structure unambiguously as an O-acetal conjugate of plasmal to the primary hydroxyl group of glycerol and to the 6-hydroxyl group of galactosyl residue of beta-galactosyl 1-->1 sphingosine (psychosine). This novel compound is hereby termed "glyceroplasmalopsychosine"; its structure is shown below (see text).

Animals↗
PubMed1985

Biochemical studies on cell fusion. I. Lipid composition of fusion-resistant cells.

A series of stable cell mutants of mouse fibroblasts were previously isolated (Roos, D. S. and R. L. Davidson, 1980, Somatic Cell Genet., 6:381-390) that exhibit varying degrees of resistance to the fusion-inducing effect of polyethylene glycol (PEG), but are morphologically similar to the parental cells from which they were derived. Biochemical analysis of these mutant cell lines has revealed differences in whole cell lipid composition which are directly correlated with their susceptibility to fusion. Fusion-resistant cells contain elevated levels of neutral lipids, particularly triglycerides and an unusual ether-linked lipid, O-alkyl, diacylglycerol. This ether lipid is increased approximately 35-fold over parental cells in the most highly PEG-resistant cell line. Fusion-resistant cells also contain more highly saturated fatty acyl chains (ratio of saturated to polyunsaturated fatty acids [S/P ratio] approximately 4:1) than the parental line (S/P ratio approximately 1:1). Cells which are intermediate in their resistance to PEG have ether lipid and fatty acid composition which is intermediate between the parental cells and the most fusion-resistant mutants. In a related communication (Roos, D. S. and P. W. Choppin, 1985, J. Cell. Biol., 100:1591-1598) evidence is presented that alteration of lipid content can predictably control the fusion response of these cells.

Animals↗
PubMed1975

Analysis and quantification of ether lipids by chromatographic methods.

Chromatographic methods, especially thin-layer chromatography (TLC) and gas-liquid chromatography (GLC) are widely used in investigations of the occurrence, molecular structure and metabolism of ether lipids. The application of such techniques to structural analysis and quantification, in combination with methods for the degradation and derivatization of ether lipids, is discussed.

Alkenes↗
PubMed1986

Long term survival of a patient with the cerebro-hepato-renal (Zellweger) syndrome.

A 13-year-old girl with severe mental retardation, tapetoretinal degeneration, an extinguished electroretinogram and sensoneurinal hearing loss is described. In early life the diagnosis of Zellweger (cerebro-hepato-renal) syndrome was considered because of hypotonia, craniofacial dysmorphia, abnormal liver functions and pipecolic aciduria. Biochemical studies in fibroblasts from the patient revealed a general peroxisomal dysfunction comparable to the findings in Zellweger Syndrome. As the clinical presentation of this patient is essentially different from that in classical Zellweger patients, who usually die early in life, we recommend the study of peroxisomal functions in all patients with severe mental retardation, tapetoretinal degeneration and sensoneurinal hearing loss.

Abnormalities, Multiple↗
PubMed1979

Turnover rates of the molecular species of alkenyl ether phospholipids of Ehrlich ascites tumor cells.

[1-14C]Glycerol was injected into the peritoneal cavity of mice bearing Ehrlich ascites tumor cells and the lipids were extracted from the cells after selected periods. 1-O-Alkenyl-2-acyl-3-acetylglycerols were prepared from the ethanolamine phosphoglycerides and fractionated by AgNO3-impregnated thin-layer chromatography into five molecular species. Bands 1--5 obtained in this way can be designated as saturated, monoene, diene, tetraene and hexaene species, respectively. Band 5, composed mainly of hexaene species was predominant among those derived from alkenyl ether phospholipids. The specific radioactivities of the fractionated species were determined. Hexaene molecular species turned over most rapidly and disaturated and tetraene species turned over at a high rate, while monoene and diene molecular species turned over very slowly.

Animals↗