N-acylation of phosphatidylethanolamine and its biological functions in mammals

Wellner, Niels; Diep, Thi Ai; Janfelt, Christian; Hansen, Harald S.

doi:10.1016/j.bbalip.2012.08.019

Cited by 83 publications

(77 citation statements)

References 137 publications

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“…3 and Supporting Information Table S1). The concentration of NAPE species found in the investigated tissue amounting to 3 nmol/g is comparable to other published values for rat brain 1, 5, 22, 44, 45, rendering NAPE a low‐abundance lipid such as lysophosphatidic acid or sphingosine‐1‐phosphate 46, 47.…”

Section: Resultssupporting

confidence: 88%

“…N ‐Acylphosphatidylethanolamines (NAPEs) are triacylated phospholipids derived from phosphatidylethanolamine (PE) with a third, N ‐linked fatty acyl chain 1. NAPE synthesis is catalyzed by N ‐acyltransferase that transfers a fatty acyl chain from the sn‐ 1 position of phosphatidylcholine (PC) to the amino group of a PE molecule.…”

Section: Introductionmentioning

confidence: 99%

“…Increasing NAPE levels together with their product NAEs after neuronal damage 5, 6, 7 are indicative of their involvement in a neuroprotective mechanism 8, 9. Postprandial increase of NAPE levels and inhibition of food intake by their administration, may suggest a potential anorectic role 10, 11, although this is subject of controversy and has not yet been clearly shown 1.…”

Section: Introductionmentioning

confidence: 99%

“…Tissue levels of NAPE in mammals are in the range of a few nmol/g 1, and NAPEs are usually not covered by “comprehensive” HPLC, SFC, or shotgun mass spectrometric lipidomic approaches 12, 13, 14, 15, 16, 17, 18, 19, 20, but rather require specialized approaches in terms of sample preparation and identification. By hydrolysis of the sn ‐1 and sn ‐2 bonds of NAPE the resulting glycerophospho‐NAE species can be determined either by LC–MS 9, 21, GC–MS 22, 23 or HPLC coupled to fluorescence detection 24.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Quantitative analysis of N‐acylphosphatidylethanolamine molecular species in rat brain using solid‐phase extraction combined with reversed‐phase chromatography and tandem mass spectrometry

Triebl

Weissengruber

Trötzmüller

et al. 2016

J of Separation Science

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A novel method for the sensitive and selective identification and quantification of N‐acylphosphatidylethanolamine molecular species was developed. Samples were prepared using a combination of liquid–liquid and solid‐phase extraction, and intact N‐acylphosphatidylethanolamine species were determined by reversed‐phase high‐performance liquid chromatography coupled to positive electrospray tandem mass spectrometry. As a result of their biological functions as precursors for N‐acylethanolamines and as signaling molecules, tissue concentrations of N‐acylphosphatidylethanolamines are very low, and their analysis is additionally hindered by the vast excess of other sample components. Our sample preparation methods are able to selectively separate the analytes of interest from any expected biological interferences. Finally, the highest selectivity is achieved by coupling chromatographic separation and two N‐acyl chain specific selected reaction monitoring scans per analyte, enabling identification of both the N‐acyl chain and the phosphatidylethanolamine moiety. The validated method is suitable for the reliable quantification of N‐acylphosphatidylethanolamine species from rat brain with a lower limit of quantification of 10 pmol/g and a linear range up to 2300 pmol/g. In total, 41 N‐acylphosphatidylethanolamine molecular species with six different N‐acyl chains, amounting to a total concentration of 3 nmol/g, were quantified.

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Section: Resultssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Quantitative analysis of N‐acylphosphatidylethanolamine molecular species in rat brain using solid‐phase extraction combined with reversed‐phase chromatography and tandem mass spectrometry

Triebl

Weissengruber

Trötzmüller

et al. 2016

J of Separation Science

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show abstract

“…The best studied of these is N-arachidonylethanolamide (anandamide), an endogenous ligand for the cannabinoid GPCR CB1 (57). Other endogenous long-chain N-acyl glycines and ethanolamines are reported to activate diverse receptors including many GPCRs (34,35,58,59). For example, N-arachidonyl-glycine activates GPR18 and T-type calcium channels; N-palmitoyl-ethanolamide activates GPR119, GPR55, and PPARα; and N-palmitoyl-glycine is believed to act through an unidentified GPCR in sensory nerves (Fig.…”

Section: Comparative Phylogenetic and Functional Analysis Of Effectormentioning

confidence: 99%

Functional metagenomic discovery of bacterial effectors in the human microbiome and isolation of commendamide, a GPCR G2A/132 agonist

Cohen

Kang

Chu

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

158

151

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The trillions of bacteria that make up the human microbiome are believed to encode functions that are important to human health; however, little is known about the specific effectors that commensal bacteria use to interact with the human host. Functional metagenomics provides a systematic means of surveying commensal DNA for genes that encode effector functions. Here, we examine 3,000 Mb of metagenomic DNA cloned from three phenotypically distinct patients for effectors that activate NF-κB, a transcription factor known to play a central role in mediating responses to environmental stimuli. This screen led to the identification of 26 unique commensal bacteria effector genes (Cbegs) that are predicted to encode proteins with diverse catabolic, anabolic, and ligand-binding functions and most frequently interact with either glycans or lipids. Detailed analysis of one effector gene family (Cbeg12) recovered from all three patient libraries found that it encodes for the production of N-acyl-3-hydroxypalmitoyl-glycine (commendamide). This metabolite was also found in culture broth from the commensal bacterium Bacteroides vulgatus, which harbors a gene highly similar to Cbeg12. Commendamide resembles long-chain N-acyl-amides that function as mammalian signaling molecules through activation of G-protein–coupled receptors (GPCRs), which led us to the observation that commendamide activates the GPCR G2A/GPR132. G2A has been implicated in disease models of autoimmunity and atherosclerosis. This study shows the utility of functional metagenomics for identifying potential mechanisms used by commensal bacteria for host interactions and outlines a functional metagenomics-based pipeline for the systematic identification of diverse commensal bacteria effectors that impact host cellular functions.

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An involvement of phospholipase A/acyltransferase family proteins in peroxisome regulation and plasmalogen metabolism

2017

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Edited by Wilhelm JustThe H-Ras-like suppressor (HRASLS) is a protein family consisting of five members in humans. Despite their discovery as tumor suppressors, we demonstrated that all these proteins are phospholipid-metabolizing enzymes, such as phospholipase (PL) A 1 /A 2 and acyltransferase. We thus proposed to rename HRASLS1-5 as PLA/acyltransferase (PLAAT)-1-5. Notably, PLAATs exhibit N-acyltransferase activity to biosynthesize N-acylated ethanolamine phospholipids, including N-acyl-plasmalogen, which serve as precursors of bioactive N-acylethanolamines. Furthermore, the overexpression of PLAAT-3 in animal cells causes disappearance of peroxisomes and a remarkable reduction in plasmalogen levels. This finding might be related to the inhibitory effect of PLAAT-3 on the chaperone activity of the peroxin PEX19. In this article, we will review our recent findings about PLAAT proteins, with special reference to their roles in peroxisome biogenesis and plasmalogen metabolism.

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N-acylation of phosphatidylethanolamine and its biological functions in mammals

Cited by 83 publications

References 137 publications

Quantitative analysis of N‐acylphosphatidylethanolamine molecular species in rat brain using solid‐phase extraction combined with reversed‐phase chromatography and tandem mass spectrometry

Quantitative analysis of N‐acylphosphatidylethanolamine molecular species in rat brain using solid‐phase extraction combined with reversed‐phase chromatography and tandem mass spectrometry

Functional metagenomic discovery of bacterial effectors in the human microbiome and isolation of commendamide, a GPCR G2A/132 agonist

An involvement of phospholipase A/acyltransferase family proteins in peroxisome regulation and plasmalogen metabolism

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