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ACS Chemical Biology Jan 2021Plasmalogens are vinyl ether-containing lipids produced by mammals and bacteria. The aerobic biosynthetic pathway in eukaryotes and bacteria is known, but the anaerobic...
Plasmalogens are vinyl ether-containing lipids produced by mammals and bacteria. The aerobic biosynthetic pathway in eukaryotes and bacteria is known, but the anaerobic pathway has remained a mystery. Here, we describe a two-gene operon (plasmalogen synthase, ) responsible for plasmalogen production in the anaerobic bacterium . While aerobic plasmalogen biosynthesis involves an oxidative conversion of an ether to a vinyl ether, anaerobic plasmalogen biosynthesis uses the reductive conversion of an ester to an aldehyde equivalent. Heterologous expression of the operon in conferred the ability to produce plasmalogens. The operon is predicted to encode a multidomain complex similar to benzoyl-CoA reductase/hydroxylacyl-CoA dehydratase (BCR/HAD) enzymes. Versions of this operon can be found in a wide range of obligate and facultative anaerobic bacteria, including many human gut microbes.
Topics: Clostridium perfringens; Enterococcus faecalis; Escherichia coli; Genes, Bacterial; Open Reading Frames; Operon; Oxidation-Reduction; Plasmalogens
PubMed: 33350306
DOI: 10.1021/acschembio.0c00673 -
Food Chemistry Jan 2021Shellfishes contain plasmalogens correlating to the functions of brain, heart, etc. Herein, a mild acid hydrolysis and hydrophilic interaction chromatography (HILIC)... (Comparative Study)
Comparative Study
Shellfishes contain plasmalogens correlating to the functions of brain, heart, etc. Herein, a mild acid hydrolysis and hydrophilic interaction chromatography (HILIC) tandem mass spectrometry method was developed for analyzing plasmalogens in six shellfish species. A total of 19 plasmalogen molecular species were successfully identified, including nine phosphatidylcholine plasmalogen (plasPC), seven phosphatidylethanolamine plasmalogen (plasPE), and three phosphatidylserine plasmalogen (plasPS). The quantitative results indicated that mussel (32 μg·mg) possessed the highest content of plasmalogens, followed by oyster (21 μg·mg) and razor clam (15 μg·mg). The statistic models showed that the plasPE P-18:0/20:5 (m/z 748), plasPE P-16:0/22:2 & P-18:0/20:2 (m/z 754) and plasPS were the most contributing difference between shellfishes. The results indicated that this method was sensitive and precise to determine plasmalogens in shellfish, and mussel was demonstrated to be a good choice for the large-scale preparation of plasmalogens.
Topics: Animals; Bivalvia; Chromatography; Food Analysis; Hydrophobic and Hydrophilic Interactions; Lipidomics; Ostrea; Phosphatidylcholines; Phosphatidylserines; Plasmalogens; Shellfish; Tandem Mass Spectrometry
PubMed: 32711269
DOI: 10.1016/j.foodchem.2020.127558 -
Journal of Alzheimer's Disease : JAD 2022The oral ingestion of scallop-derived plasmalogen (sPlas) significantly improved cognitive function in Alzheimer's disease (AD) patients.
BACKGROUND
The oral ingestion of scallop-derived plasmalogen (sPlas) significantly improved cognitive function in Alzheimer's disease (AD) patients.
OBJECTIVE
However, the effects and mechanisms of sPlas on AD with chronic cerebral hypoperfusion (CCH), a class of mixed dementia contributing to 20-30% among the dementia society, were still elusive.
METHODS
In the present study, we applied a novel mouse model of AD with CCH to investigate the potential effects of sPlas on AD with CCH.
RESULTS
The present study demonstrated that sPlas significantly recovered cerebral blood flow, improved motor and cognitive deficits, reduced amyloid-β pathology, regulated neuroinflammation, ameliorated neural oxidative stress, and inhibited neuronal loss in AD with CCH mice at 12 M.
CONCLUSION
These findings suggest that sPlas possesses clinical and pathological benefits for AD with CCH in the novel model mice. Furthermore, sPlas could have promising prevention and therapeutic effects on patients of AD with CCH.
Topics: Alzheimer Disease; Animals; Brain; Brain Ischemia; Disease Models, Animal; Humans; Mice; Pectinidae; Plasmalogens
PubMed: 35253748
DOI: 10.3233/JAD-215246 -
The Journal of Biological Chemistry Jun 2018Plasmalogens-phospholipids containing a characteristic vinyl ether group-are precursors of lipids important for cellular signaling such as arachidonic acid. Plasmalogen...
Plasmalogens-phospholipids containing a characteristic vinyl ether group-are precursors of lipids important for cellular signaling such as arachidonic acid. Plasmalogen catabolism involves cleavage of the vinyl ether bond, but the identity of the corresponding enzyme that cleaves the -1 vinyl ether bond was unknown. New research shows that cytochrome , with some help from another lipid, catalyzes the oxidative cleavage of this bond. This discovery, and the subsequent mechanistic dissection, provides exciting new directions for lipid signaling research.
Topics: Animals; Cytochromes c; Humans; Hydrolases; Lipids; Mitochondria, Heart; Oxidation-Reduction; Oxidative Stress; Plasmalogens; Vinyl Compounds
PubMed: 29858391
DOI: 10.1074/jbc.H118.003072 -
Bioscience, Biotechnology, and... May 2021A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an...
A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through 8 steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are (1) regio- and Z-selective vinyl ether formation via the alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification-oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase high-performance liquid chromatography purification.
Topics: Chemistry Techniques, Synthetic; Esterification; Oxidation-Reduction; Plasmalogens; Stereoisomerism
PubMed: 33705523
DOI: 10.1093/bbb/zbab037 -
Journal of Psychiatry & Neuroscience :... Jan 2010Plasmalogens, which are key structural phospholipids in brain membranes, are decreased in the brain and serum of patients with Alzheimer disease (AD). We performed this...
BACKGROUND
Plasmalogens, which are key structural phospholipids in brain membranes, are decreased in the brain and serum of patients with Alzheimer disease (AD). We performed this pilot study to evaluate the relation between the levels of circulating plasmalogens and Alzheimer Disease Assessment Scale-Cognitive (ADAS-Cog) scores in patients with AD.
METHODS
We evaluated participants' ADAS-Cog scores and serum plasmalogen levels. For the 40 included AD patients with an ADAS-Cog score between 20 and 46, were tested their ADAS-Cog score 1 year later. The levels of docosahexaenoic acid plasmalogen were measured by use of liquid chromatography-tandem mass spectrometry.
RESULTS
We found that the ADAS-Cog score increased significantly in AD patients with circulating plasmalogen levels that were
plasmalogen levels at baseline (> 75%). LIMITATIONS
This was a pilot study with 40 patients, and the results require validation in a larger population.
CONCLUSION
Our study demonstrates that decreased levels of plasmalogen precursors in the central nervous system correlate with functional decline (as measured by ADAS-Cog scores) in AD patients. The use of both ADAS-Cog and serum plasmalogen data may be a more accurate way of predicting cognitive decline in AD patients, and may be used to decrease the risk of including patients with no cognitive decline in the placebo arm of a drug trial.
Topics: Aged; Aged, 80 and over; Alzheimer Disease; Apolipoproteins E; Chromatography, Liquid; Cognition; Docosahexaenoic Acids; Female; Humans; Male; Pilot Projects; Plasmalogens; Psychiatric Status Rating Scales; Tandem Mass Spectrometry; Time Factors
PubMed: 20040248
DOI: 10.1503/jpn.090059 -
The British Journal of Nutrition Jul 2003Plasmalogen is a subclass of phospholipids that is widely distributed in man and animals. Many physiological roles have been proposed for this lipid; however, there have...
Plasmalogen is a subclass of phospholipids that is widely distributed in man and animals. Many physiological roles have been proposed for this lipid; however, there have been no reports on the intestinal absorption of plasmalogen. In the present study, we examined lymphatic absorption of plasmalogen after the duodenal infusion of emulsified brain phospholipids (BPL) containing plasmalogen (22 mol % of total phospholipids) and soyabean lecithin (SPL) (100 g emulsified phospholipid/l). Male Wistar rats with implanted cannulas in the mesenteric lymph duct and the duodenum were kept in a Bollman-type restraining cage, and were infused the emulsion after 1 d recovery with duodenal infusion of a glucose-NaCl solution. Lymphatic plasmalogen output was increased at 2-4 h after the switch to BPL emulsion, and peaked at 4-6 h. However, no increases were observed after SPL infusion. Lymphatic recovery of plasmalogen for 8 h was 198 nmol, which was 0.22 mol % of the total plasmalogen disappeared from the intestine. We did not detect any increases in long-chain fatty aldehydes, which are the degradation product of plasmalogen, either in the blood or the small intestine. We conclude that a small percentage but a significant amount of the plasmalogen was absorbed into the lymph.
Topics: Animals; Duodenum; Intestinal Absorption; Lymph Nodes; Male; Mesentery; Plasmalogens; Rats; Rats, Wistar
PubMed: 12844372
DOI: 10.1079/bjn2003879 -
Insect Biochemistry and Molecular... Aug 2012Herbivorous insect species are constantly challenged with endogenous and exogenous oxidative stress. Consequently, they possess an array of antioxidant enzymes and small...
Herbivorous insect species are constantly challenged with endogenous and exogenous oxidative stress. Consequently, they possess an array of antioxidant enzymes and small molecular weight antioxidants. Lipid-soluble small molecular antioxidants, such as tocopherols, have not been well studied in insects but may play important antioxidant roles. In this study, we identified plasmalogen phosphatidylethanolamines (pPEs) as well as α-, β/γ-, δ-tocopherol in the larvae of the silkworm Bombyx mori by LCMS analyses and examined their distribution. Plasmalogen are reported to inhibit the metal ion induced oxidation. The composition of tocopherols was the same among gut contents, gut tissues, and the other tissues. However, plasmalogens, a unique class of glycerophospholipids rich in polyunsaturated fatty acids and containing a vinyl ether bond at the sn-1 position, were mainly distributed in gut tissues. Plasmalogens might protect gut tissues from oxidation stress.
Topics: Animals; Antioxidants; Bombyx; Gastrointestinal Tract; Larva; Plasmalogens; Tocopherols
PubMed: 22580185
DOI: 10.1016/j.ibmb.2012.04.006 -
Journal of Bacteriology Jun 1988The 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 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.
Topics: Cyclopropanes; Phospholipids; Plasmalogens; Veillonellaceae; Vinyl Compounds
PubMed: 3372481
DOI: 10.1128/jb.170.6.2770-2774.1988 -
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