1‐<i>O</i>‐alkyl‐linked phosphoglycerides of human platelets: Distribution of arachidonate and other acyl residues in the ether‐linked and diacyl species

Mueller, Howard W.; Purdon, A. D.; Smith, J B; Wykle, Robert L.

doi:10.1007/bf02534641

Cited by 122 publications

(50 citation statements)

References 34 publications

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“…In eukaryotes, the radyl group at the sn-2 position is always linked via an ester bond, but the radyl group at the sn-1 position can be an ester, vinyl ether (plasmalogen subspecies), or an alkyl ether (ether subspecies phospholipid). The presence of these subgroups of glycerophospholipids is varied for different tissues; for instance, ether lipids are common in inflammatory cell-membranes (Mueller et al, 1984), and plasmalogen species are common components of heart tissue (Scherrer & Gross, 1989) and brain (Farooqui & Horrocks, 2001). There is also significant diversity in the fatty-acyl species present in any one of the individual phospholipid classes present in a cellmembrane because of differences in chain length and degree of unsaturation of the esterified fatty acid.…”

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confidence: 98%

Electrospray mass spectrometry of phospholipids

Pulfer

Murphy

2003

Mass Spectrometry Reviews

850

764

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Phospholipids play a central role in the biochemistry of all living cells. These molecules constitute the lipid bilayer defining the outer confines of a cell, but also serve as the structural entities which confine subcellular components. Mass spectrometry has emerged as a powerful tool useful for the qualitative and quantitative analysis of complex phospholipids, including glycerophospholipids and the sphingolipid, sphingomyelin. Collision induced decomposition of both positive and negative molecular ion species yield rich information as to the polar head group of the phospholipid and the fatty-acyl substituents esterified to the glycerophospholipid backbone. This review presents the current level of understanding of the mechanisms involved in the formation of various product ions following collisional activation of molecular ion species generated by electrospray ionization of the common glycerophospholipids, including phosphatidic acid, phosphatidylethanolamine, phosphatidylcholine, phosphatidylinositol, phosphatidylglycerol, phosphatidylserine, cardiolipin, and sphingomyelin. Recent advances in the application of matrix assisted laser desorption ionization is also considered. Several applications of mass spectrometry applied to phospholipid analysis are presented as they apply to physiology as well as pathophysiology.

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mentioning

confidence: 98%

Electrospray mass spectrometry of phospholipids

Pulfer

Murphy

2003

Mass Spectrometry Reviews

850

764

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“…We employed human promyelocytic leukemia cell line, HL60, that has been widely used as a system to model human neutrophils 16,17 and the human T lymphocytes, Jurkat cells, as two target cells. The low content of oxidizable polyunsaturated fatty acid (PUFA)-containing PS in these cells permitted us to alter the phospholipid acyl chain by culture in a medium supplemented with linoleic acid (LA).…”

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confidence: 99%

Oxidatively modified phosphatidylserines on the surface of apoptotic cells are essential phagocytic ‘eat-me’ signals: cleavage and inhibition of phagocytosis by Lp-PLA2

et al. 2014

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Diversified anionic phospholipids, phosphatidylserines (PS), externalized to the surface of apoptotic cells are universal phagocytic signals. However, the role of major PS metabolites, such as peroxidized species of PS (PSox) and lyso-PS, in the clearance of apoptotic cells has not been rigorously evaluated. Here, we demonstrate that H 2 O 2 was equally effective in inducing apoptosis and externalization of PS in naive HL60 cells and in cells enriched with oxidizable polyunsaturated species of PS (supplemented with linoleic acid (LA)). Despite this, the uptake of LA-supplemented cells by RAW264.7 and THP-1 macrophages was more than an order of magnitude more effective than that of naive cells. A similar stimulation of phagocytosis was observed with LA-enriched HL60 cells and Jurkat cells triggered to apoptosis with staurosporine. This was due to the presence of PSox on the surface of apoptotic LA-supplemented cells (but not of naive cells). This enhanced phagocytosis was dependent on activation of the intrinsic apoptotic pathway, as no stimulation of phagocytosis occurred in LA-enriched cells challenged with Fas antibody. Incubation of apoptotic cells with lipoprotein-associated phospholipase A 2 (Lp-PLA 2 ), a secreted enzyme with high specificity towards PSox, hydrolyzed peroxidized PS species in LA-supplemented cells resulting in the suppression of phagocytosis to the levels observed for naive cells. This suppression of phagocytosis by Lp-PLA 2 was blocked by a selective inhibitor of Lp-PLA 2 , SB-435495. Screening of possible receptor candidates revealed the ability of several PS receptors and bridging proteins to recognize both PS and PSox, albeit with diverse selectivity. We conclude that PSox is an effective phagocytic 'eat-me' signal that participates in the engulfment of cells undergoing intrinsic apoptosis.

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“…For example, fish oil metabolites (i.e., TxA3, PGA3, and LTB5) are less effective than arachidonate metabolites (i.e., TxA2, PGA2, and LTB4) in having a platelet-aggregating effect in the body. This would explain the depressed platelet reactivity found in subjects consuming large amounts of fish oils [37,47].…”

Section: Functional Rolementioning

confidence: 99%

“…14, No. 2,1993 Arachidonate regulation Ethanolamine plasmalogens have also been indicated a storage terminals for polyunsaturated fatty acids (PUFA), especially arachidonic acid [37,38]. This may have important implications, because arachidonic acid is known for its role in the biosynthesis of eicosanoids [39].…”

Section: Functional Rolementioning

confidence: 99%

The Biosynthesis and Functions of plasmalogens.

Garg

Haerdi

1993

J. Clin. Biochem. Nutr.

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SummaryThe biosynthesis of plasmalogen (alkenyl acyl glycerophosphoryl choline or ethanolamine) is independent of diacyl glycerophospholipid synthesis and requires the coordinated activities of peroxisomal, cytosolic, and endoplasmic reticulum enzymes. This would indicate that the plasmalogens may have a unique role(s) to play in cellular functions, one different from that of the diacyl glycerophospholipids. Several functions have been assigned to plasmalogens such as antioxidants, arachidonic acid storage terminals, receptor mediators, substrate for the biosynthesis of platelet-activating-factor (PAF), and determinant of physicochemical properties of biomembranes. Except for serving as a substrate for biologically active PAF biosynthesis, none of the proposed functions have been fully validated. The purpose of this review article is to provide up-to-date knowledge of the biosynthetic pathway and functions of plasmalogens.Key Words: plasmalogens, alkyl-acylphosphoglycerides, alkenyl-acylphosphoglycerides, functions, ether-linked phospholipidsMany years have passed since ether-linked phospholipids were first discovered in tissue membrane. Their actual structure, however, was not identified until the 1960's [1]. Two sub-classes exist, differing in the moiety present at the sn-1-position of the glycerol backbone [2]. A saturated 0-alkyl linkage and an alpha, beta-unsaturated O-alkenyl linkage (vinyl ether linkage) are the distinguishing features of these two molecules. This review will focus on the latter product, alkenyl acyl glycerophosphoryl ethanolamine (choline), which has also been given the trivial name of plasmalogen. As mentioned, both ethanolamine and choline may be present in the plasmalogen molecule at the sn-3 position. Ethanolamine

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1‐O‐alkyl‐linked phosphoglycerides of human platelets: Distribution of arachidonate and other acyl residues in the ether‐linked and diacyl species

Cited by 122 publications

References 34 publications

Electrospray mass spectrometry of phospholipids

Electrospray mass spectrometry of phospholipids

Oxidatively modified phosphatidylserines on the surface of apoptotic cells are essential phagocytic ‘eat-me’ signals: cleavage and inhibition of phagocytosis by Lp-PLA2

The Biosynthesis and Functions of plasmalogens.

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