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Your search keyword '"N-docosahexaenoyl phosphatidylethanolamine"' showing total 2 results
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2 results on '"N-docosahexaenoyl phosphatidylethanolamine"'

1. Biosynthesis of N- Docosahexanoylethanolamine from Unesterified Docosahexaenoic Acid and Docosahexaenoyl-Lysophosphatidylcholine in Neuronal Cells.

Author

Kevala K, Lagarde M, Spector AA, and Kim HY

Subjects
Animals, Arachidonic Acids antagonists & inhibitors, Arachidonic Acids isolation & purification, Bithionol pharmacology, Carbon Isotopes, Cell Line, Tumor, Chromatography, Liquid, Endocannabinoids antagonists & inhibitors, Endocannabinoids isolation & purification, Ethanolamines antagonists & inhibitors, Ethanolamines isolation & purification, Hexachlorophene pharmacology, Kinetics, Mice, Neurons cytology, Neurons drug effects, Plasmalogens antagonists & inhibitors, Plasmalogens biosynthesis, Plasmalogens isolation & purification, Polyunsaturated Alkamides antagonists & inhibitors, Polyunsaturated Alkamides isolation & purification, Tandem Mass Spectrometry, Arachidonic Acids biosynthesis, Docosahexaenoic Acids metabolism, Endocannabinoids biosynthesis, Ethanolamines metabolism, Lysophosphatidylcholines metabolism, Neurons metabolism
Abstract

We investigated the synthesis of N- docosahexaenoylethanolamine (synaptamide) in neuronal cells from unesterified docosahexaenoic acid (DHA) or DHA-lysophosphatidylcholine (DHA-lysoPC), the two major lipid forms that deliver DHA to the brain, in order to understand the formation of this neurotrophic and neuroprotective metabolite of DHA in the brain. Both substrates were taken up in Neuro2A cells and metabolized to N- docosahexaenoylphosphatidylethanolamine (NDoPE) and synaptamide in a time- and concentration-dependent manner, but unesterified DHA was 1.5 to 2.4 times more effective than DHA-lysoPC at equimolar concentrations. The plasmalogen NDoPE (pNDoPE) amounted more than 80% of NDoPE produced from DHA or DHA-lysoPC, with 16-carbon-pNDoPE being the most abundant species. Inhibition of N- acylphosphatidylethanolamine-phospholipase D (NAPE-PLD) by hexachlorophene or bithionol significantly decreased the synaptamide production, indicating that synaptamide synthesis is mediated at least in part via NDoPE hydrolysis. NDoPE formation occurred much more rapidly than synaptamide production, indicating a precursor-product relationship. Although NDoPE is an intermediate for synaptamide biosynthesis, only about 1% of newly synthesized NDoPE was converted to synaptamide, possibly suggesting additional biological function of NDoPE, particularly for pNDoPE, which is the major form of NDoPE produced.

Published
2020
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2. Biosynthesis of N-Docosahexanoylethanolamine from Unesterified Docosahexaenoic Acid and Docosahexaenoyl-Lysophosphatidylcholine in Neuronal Cells

Author

Michel Lagarde, Karl Kevala, Hee-Yong Kim, and Arthur A. Spector

Subjects
synaptamide, Metabolite, lcsh:Chemistry, Mice, chemistry.chemical_compound, N-docosahexaenoyl phosphatidylethanolamine, Tandem Mass Spectrometry, N-Acylethanolamine, lcsh:QH301-705.5, Spectroscopy, Neurons, Carbon Isotopes, biology, Chemistry, bithionol, N-acyl phosphatidylethanolamine-phospholipase D, food and beverages, General Medicine, docosahexaenoic acid, Computer Science Applications, Lysophosphatidylcholine, Biochemistry, Ethanolamines, Docosahexaenoic acid, N-docosahexaenoyl phosphatidylethanolamine plasmalogen, lipids (amino acids, peptides, and proteins), plasmalogens, Neurotrophin, Docosahexaenoic Acids, Plasmalogen, Polyunsaturated Alkamides, Hexachlorophene, Arachidonic Acids, Neuroprotection, Article, Catalysis, Inorganic Chemistry, lysophosphatidylcholine, Biosynthesis, Cell Line, Tumor, Animals, Physical and Theoretical Chemistry, Molecular Biology, Organic Chemistry, Lysophosphatidylcholines, N-acylethanolamines, Kinetics, lcsh:Biology (General), lcsh:QD1-999, biology.protein, Chromatography, Liquid, Endocannabinoids
Abstract

We investigated the synthesis of N-docosahexaenoylethanolamine (synaptamide) in neuronal cells from unesterified docosahexaenoic acid (DHA) or DHA-lysophosphatidylcholine (DHA-lysoPC), the two major lipid forms that deliver DHA to the brain, in order to understand the formation of this neurotrophic and neuroprotective metabolite of DHA in the brain. Both substrates were taken up in Neuro2A cells and metabolized to N-docosahexaenoylphosphatidylethanolamine (NDoPE) and synaptamide in a time- and concentration-dependent manner, but unesterified DHA was 1.5 to 2.4 times more effective than DHA-lysoPC at equimolar concentrations. The plasmalogen NDoPE (pNDoPE) amounted more than 80% of NDoPE produced from DHA or DHA-lysoPC, with 16-carbon-pNDoPE being the most abundant species. Inhibition of N-acylphosphatidylethanolamine-phospholipase D (NAPE-PLD) by hexachlorophene or bithionol significantly decreased the synaptamide production, indicating that synaptamide synthesis is mediated at least in part via NDoPE hydrolysis. NDoPE formation occurred much more rapidly than synaptamide production, indicating a precursor–product relationship. Although NDoPE is an intermediate for synaptamide biosynthesis, only about 1% of newly synthesized NDoPE was converted to synaptamide, possibly suggesting additional biological function of NDoPE, particularly for pNDoPE, which is the major form of NDoPE produced.

Published
2020

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