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Food & Function Sep 2020Considerable attention has been paid to the absorption mechanisms of plasmalogen (Pls) because its intake has been expected to have preventive effects on brain-related...
Considerable attention has been paid to the absorption mechanisms of plasmalogen (Pls) because its intake has been expected to have preventive effects on brain-related diseases. Possible structural changes of Pls during absorption (i.e., preferential arachidonic acid re-esterification at the sn-2 position and base conversion of ethanolamine Pls (PE-Pls) into choline Pls (PC-Pls)) have previously been proposed. Since the physiological functions of Pls differ according to its structure, further elucidation of such structural changes during absorption is important to understand how Pls exerts its physiological effects in vivo. Hence, the absorption mechanism of Pls was investigated using the lymph-cannulation method and the everted jejunal sac model, with a focus on Pls molecular species. In the lymph-cannulation method, relatively high amounts of PE-Pls 18:0/20:4 and PC-Pls 18:0/20:4 were detected from the lymph even though these species were minor in the administered emulsion. Moreover, a significant increase of PE-Pls 18:0/20:4 and PC-Pls 18:0/20:4 in the intestinal mucosa was also confirmed by the everted jejunal sac model. Therefore, structural changes of PE-Pls in the intestinal mucosa were strongly suggested. The results of this study may provide an understanding of the relationship between intestinal absorption of Pls and exertion of its physiological functions in vivo.
Topics: Animals; Arachidonic Acid; Biological Transport; Esterification; Ethanolamine; Intestinal Absorption; Intestinal Mucosa; Male; Plasmalogens; Rats; Rats, Sprague-Dawley
PubMed: 32852024
DOI: 10.1039/d0fo01666g -
Stain Technology Sep 1961
Topics: Histocytochemistry; Plasmalogens
PubMed: 14037842
DOI: 10.3109/10520296109113290 -
Food Research International (Ottawa,... Jun 2024The quality of Pacific oyster (Crassostrea gigas) can be affected by many factors during depuration, in which temperature is the major element. In this study, we aim to...
The quality of Pacific oyster (Crassostrea gigas) can be affected by many factors during depuration, in which temperature is the major element. In this study, we aim to determine the quality and plasmalogen changes in C. gigas depurated at different temperatures. The quality was significantly affected by temperature, represented by varying survival rate, glycogen content, total antioxidant capacity, alkaline phosphatase activity between control and stressed groups. Targeted MS analysis demonstrated that plasmalogen profile was significantly changed during depuration with PUFA-containing plasmalogen species being most affected by temperature. Proteomics analysis and gene expression assay further verified that plasmalogen metabolism is regulated by temperature, specifically, the plasmalogen synthesis enzyme EPT1 was significantly downregulated by high temperature and four plasmalogen-related genes (GPDH, PEDS, Pex11, and PLD1) were transcriptionally regulated. The positive correlations between the plasmalogen level and quality characteristics suggested plasmalogen could be regarded as a quality indicator of oysters during depuration.
Topics: Animals; Plasmalogens; Crassostrea; Temperature; Shellfish; Proteomics; Antioxidants; Alkaline Phosphatase; Food Quality
PubMed: 38729722
DOI: 10.1016/j.foodres.2024.114356 -
Animal Reproduction Science Jun 2022Brain ethanolamine plasmalogens (EPls) are unique alkenylacyl-glycerophospholipids and the only recognized ligands of G-protein-coupled receptor 61 (GPR61), a newly...
Brain ethanolamine plasmalogens (EPls) are unique alkenylacyl-glycerophospholipids and the only recognized ligands of G-protein-coupled receptor 61 (GPR61), a newly identified receptor that colocalizes with GnRH receptors on gonadotrophs. As the chemical synthesis of EPl is challenging, only one chemosynthetic EPl, 1-(1Z-octadecenyl)- 2-oleoyl-sn-glycero-3-phosphoethanolamine (PLAPE; C18:0-C18:1), is commercially available. Therefore, we tested the hypothesis that PLAPE stimulates gonadotropin secretion from bovine gonadotrophs. We prepared anterior pituitary cells from healthy, post-pubertal heifers, cultured for 3.5 d, and then treated them with increasing concentrations (0, 0.5, 5, 50, or 500 pg/mL) of PLAPE for 5 mi, before either no treatment or GnRH stimulation. After 2 h, medium samples were harvested for FSH and LH assays. PLAPE (5-500 pg/mL) stimulated (P < 0.01) basal FSH and LH secretion, and such stimulation effects were inhibited by a SMAD pathway inhibitor. In the presence of GnRH, PLAPE at 0.5 and 5 pg/mL stimulated FSH and LH secretion (P < 0.01). However, a higher dose of PLAPE (500 pg/mL) suppressed GnRH-induced FSH and LH, and such suppressive effects were inhibited by an ERK pathway inhibitor. PLAPE stimulated gonadotropin secretion in the presence of EPls extracted from the brains of young heifers, but not old cows. Additionally, we performed in silico molecular-docking simulations using the deep-learning algorithm, AlphaFold2. The simulations revealed the presence of three binding sites for PLAPE in the three-dimensional structural model of GPR61. In conclusion, PLAPE stimulated gonadotropin secretion from bovine gonadotrophs and might act as a chemosynthetic agonist of GPR61.
Topics: Animals; Cattle; Female; Follicle Stimulating Hormone; Gonadotrophs; Gonadotropin-Releasing Hormone; Plasmalogens
PubMed: 35580407
DOI: 10.1016/j.anireprosci.2022.106992 -
Biochemistry and Cell Biology =... Jul 1991Interest in altered ether-lipid metabolism, associated with peroxisomal disorders including adrenoleukodystrophy and Zellweger's syndrome, has highlighted present... (Review)
Review
Interest in altered ether-lipid metabolism, associated with peroxisomal disorders including adrenoleukodystrophy and Zellweger's syndrome, has highlighted present limitations in our understanding of the biosynthesis and turnover of plasmalogens. These 1-alkenyl ethanolamine phosphoglycerides are major phospholipids in brain, vascular tissue, neutrophils, and most tumors, and they constitute 15-20% of total phospholipids in cultured glioma cell. In glioma, turnover of polyunsaturated acyl chains in the sn-2 position of plasmalogens was examined in relation to selectivity for the (n - 3) and (n - 6) families. Remodeling of acyl chains was more dependent on chain length than on selectivity between families, consistent with plasmalogens enriched in polyunsaturated, but not specifically (n - 3), fatty acids. Extracellular serine was a precursor of serine and ethanolamine phosphoglycerides and was associated with plasmalogens due to decarboxylation and headgroup exchange. Incorporation of extracellular serine ceased within 8 h, even though more than 50% of the label remain in the medium. Analyses of medium and cellular water-soluble components indicated rapid conversion of serine to glycine and other metabolites not used in phospholipid biosynthesis. Thus, nutrient molecules as precursors of plasmalogens are involved in complex competitive interactions. As functions of plasmalogens are clarified, regulation of plasmalogen turnover becomes an increasingly important issue and elucidation of these processes is essential.
Topics: Adrenoleukodystrophy; Fatty Acids, Essential; Fatty Acids, Unsaturated; Glioma; Humans; Infant, Newborn; Kinetics; Microbodies; Plasmalogens; Serine; Zellweger Syndrome
PubMed: 1793558
DOI: 10.1139/o91-071 -
Journal of Bacteriology May 1975The polar lipids of Anaeroplasma contained 33.1 percent alk-1'-enyl glyceryl ether (plasmalogen) form. Phosphatidylglycerol was the major polar lipid (55.2 percent) and...
The polar lipids of Anaeroplasma contained 33.1 percent alk-1'-enyl glyceryl ether (plasmalogen) form. Phosphatidylglycerol was the major polar lipid (55.2 percent) and contained nearly all of the plasmalogen. The alk-1'-enyl glyceryl ether form accounted for 58.3 percent of the phosphatidylglycerol.
Topics: Aldehydes; Anaerobiosis; Animals; Cattle; Chromatography, Thin Layer; Fatty Acids; Glycolipids; Lipids; Mycoplasmatales; Phosphatidylglycerols; Phospholipids; Plasmalogens; Rumen; Sheep; Species Specificity
PubMed: 1168634
DOI: 10.1128/jb.122.2.785-787.1975 -
Chemistry and Physics of Lipids Jun 1995The content of plasmalogens in lipoproteins--very low density lipoprotein (VLDL), low density lipoprotein (LDL) and high density lipoprotein (HDL)--in human serum was...
The content of plasmalogens in lipoproteins--very low density lipoprotein (VLDL), low density lipoprotein (LDL) and high density lipoprotein (HDL)--in human serum was determined and compared with that after oxidation of the lipoproteins. Similarly, the content of alpha-hydroxyaldehydes produced from plasmalogens via their epoxids during lipidperoxidation (LPO) was studied. Incubation with Fe+ +/ascorbate results in a dramatic decrease in plasmalogens that correlates with an appropriate increase in alpha-hydroxyaldehydes. VLDL and LDL plasmalogens were oxidized to a greater extend (99% decrease) compared to HDL plasmalogens (35%). This finding is discussed with respect to atherogenesis and the recently postulated protective qualities of plasmalogens.
Topics: Aldehydes; Ascorbic Acid; Epoxy Compounds; Humans; Lipid Peroxidation; Lipoproteins; Lipoproteins, HDL; Lipoproteins, LDL; Lipoproteins, VLDL; Mass Spectrometry; Oxidation-Reduction; Peroxides; Plasmalogens
PubMed: 7634364
DOI: 10.1016/0009-3084(94)02448-e -
Biochimica Et Biophysica Acta.... Jun 2024Sea cucumber phospholipids, including the plasmalogen (PlsEtn) and plasmanylcholine (PakCho), have been shown to play a regulatory role in lipid metabolism disorders,...
Sea cucumber phospholipids, including the plasmalogen (PlsEtn) and plasmanylcholine (PakCho), have been shown to play a regulatory role in lipid metabolism disorders, but their mechanism of action remains unclear. Therefore, high-fat diet (HFD) and palmitic acid were used to establish lipid accumulation models in mice and HepG2 cells, respectively. Results showed that PlsEtn can reduce lipid deposition both in vivo and in vitro. HFD stimulation abnormally activated lipophagy through the phosphorylation of the AMPK/ULK1 pathway. The lipophagy flux monitor revealed abnormalities in the fusion stage of lipophagy. Of note, only PlsEtn stimulated the dynamic remodeling of the autophagosome membrane, which was indicated by the significantly decreased LC3 II/I ratio and p62 level. In all experiments, the effect of PlsEtn was significantly higher than that of PakCho. These findings elucidated the mechanism of PlsEtn in alleviating lipid accumulation, showed that it might be a lipophagy enhancer, and provided new insights into the high-value utilization of sea cucumber as an agricultural resource.
Topics: Animals; Diet, High-Fat; Plasmalogens; Sea Cucumbers; Lipid Metabolism; Mice; Humans; Hep G2 Cells; Male; Mice, Inbred C57BL; Autophagy
PubMed: 38609006
DOI: 10.1016/j.bbalip.2024.159495 -
Current Medicinal Chemistry 2009Plasmalogens are a specific glycerophospholipid class containing a vinyl ether moiety at the sn-1-position of the glycerol backbone. The high susceptibility of this... (Review)
Review
Plasmalogens in biological systems: their role in oxidative processes in biological membranes, their contribution to pathological processes and aging and plasmalogen analysis.
Plasmalogens are a specific glycerophospholipid class containing a vinyl ether moiety at the sn-1-position of the glycerol backbone. The high susceptibility of this vinyl ether bond to oxidative damage and traces of acids may indicate the possible function of plasmalogens in biological systems: The regarded cell-internal antioxidative defense of membranes by protecting other phospholipids or lipoprotein particles against oxidative stress is controversial. Reactive oxygen species preferably affect the vinyl ether function as well as the olefinic acyl residues at the sn-2-position of plasmalogens. This review is dedicated to the role of plasmalogens in different cells and tissues as spermatozoal cells or brain tissue. The first chapter of this review will discuss the molecular structure and chemistry of plasmalogen molecules, their distributions in cells and tissues and the species-specificity. In the second chapter their functions as lipid mediators will be considered and the controversial antioxidative function will be discussed. The supposed function of plasmalogens as "scavengers" for reactive oxygen species (ROS) in biological membranes is challenged by the finding that plasmalogen oxidation products as alpha-hydroxyaldehydes and plasmalogen epoxides accumulate in all chronic diseases as atherosclerosis and myocardial infarction, upon aging as well as in Alzheimers disease and other neuropathological conditions. All these conditions, characterized by increased membrane instability and oxidative damage, will be reviewed in chapter three. Chronically proceeding processes can be described by permanently invading polymorphonuclear neutrophils into inflammatory loci. The degranulation of the azurophilic granula in polymorphonuclear leukocytes causes the release of highly reactive substances, for instance the myeloperoxidase-generated hypochlorous acid (HOCl) acting as effective oxidant. Therefore, special attention will be paid to neutrophil-derived HOCl. The last chapter deals with currently used methods of detecting plasmalogens and their degradation products. Although chromatographic methods will be also discussed, special attention will be given to (31)P NMR spectroscopy and soft ionization techniques of mass spectrometry as electrospray ionization or matrix-assisted laser desorption and ionization time-of-flight mass spectrometry.
Topics: Aging; Animals; Cell Membrane; Disease; Humans; Inflammation; Oxidation-Reduction; Plasmalogens
PubMed: 19519379
DOI: 10.2174/092986709788682164 -
Neurology Jul 1985Very long-chain fatty acids accumulate in both adrenoleukodystrophy and Zellweger's syndrome. Plasmalogen content is decreased in Zellweger's syndrome. We therefore...
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.
Topics: Adrenoleukodystrophy; Adult; Child; Diffuse Cerebral Sclerosis of Schilder; Erythrocyte Membrane; Female; Humans; Male; Middle Aged; Plasmalogens
PubMed: 4010945
DOI: 10.1212/wnl.35.7.1051