Plasmalogens as endogenous antioxidants: somatic cell mutants reveal the importance of the vinyl ether

Zoeller, Raphael A.; Lake, Andrew C.; Nagan, Narasimhan; Gaposchkin, Daniel P.; Legner, Margaret; Lieberthal, Wilfred

doi:10.1042/bj3380769

Cited by 178 publications

(69 citation statements)

References 37 publications

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“…The vinyl ether bond is readily susceptible to breakdown under acidic [19,20] and oxidative conditions [7,14,21]. Since PFB hydroxylamine derivatization requires acidic conditions we tested the stability of the vinyl ether bond, the acyl ester and the amide bond under derivatization conditions.…”

Section: Resultsmentioning

confidence: 99%

Quantification of Pentafluorobenzyl Oxime Derivatives of Long Chain Aldehydes by GC–MS Analysis

Brahmbhatt

Nold

Albert

et al. 2008

Lipids

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Negative ion mass spectrometric techniques for compounds having good ionization properties, such as pentafluorobenzyl derivatives, are believed to be more sensitive than positive ion methods. In this study we develop a technique of quantification of long-chain aldehydes by analysis of their pentafluorobenzyl oxime derivatives utilizing gas chromatography-mass spectrometry in the negative ion chemical ionization mode. We establish that separation of plasmalogens prior to pentafluorobenzyl derivatization is essential and achieve this separation over a silica column. We further demonstrate the sensitivity of this method and utilize this technique to identify increases in hexadecanal and octadecanal in 3-aminotriazole treated human neutrophils.

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Section: Resultsmentioning

confidence: 99%

Quantification of Pentafluorobenzyl Oxime Derivatives of Long Chain Aldehydes by GC–MS Analysis

Brahmbhatt

Nold

Albert

et al. 2008

Lipids

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“…The high PLM content (15.5-35.1% of total phospholipids) in crustacean gills is thought to play a role in ion transport processes as the gill is exposed to more oxidative stress than other tissues (Chapelle and Benson, 1986). More recent studies have demonstrated the selective degradation of PLMs when lipoproteins are exposed to reactive oxygen species (Engelmann et al, 1994;Jungens, et al, 1995), and PLMs may therefore function to protect cells against reactive oxygen species by mediating the damage (Zoeller et al, 1999). Therefore, PLMs may be a component based on the environmental and physiological conditions, which could explain the distinct DMA levels obtained in fishes, crustaceans, cephalopods, gastropods and bivalves; they may be related to their different life histories.…”

Section: Dma Levels In Octopus Vulgaris and Preymentioning

confidence: 99%

“…PLMs, whose cellular functions have not been established yet (Zoeller et al, 1999), are characterised by the presence of an aldehydic chain attached to a glycerol backbone through a vinyl ether (alkenyl) linkage (Malins and Varanasi, 1972;Horrocks and Sharma, 1980) and by a higher content of polyunsaturated fatty acids (PUFAs) than 1-alkyl-2-acyl and diacyl forms (Dembitsky, 1988). Their presence has been shown in a number of marine organisms (Rapport and Alonzo, 1960;Dembitsky, 1979;Sargent, 1989;Jeong et al, 1999;Kikuchi et al, 1999).…”

Section: Introductionmentioning

confidence: 99%

Spatial-temporal changes in dimethyl acetal (octadecanal) levels of <i>Octopus vulgaris</i> (Mollusca, Cephalopoda): relation to feeding ecology

Rosa¹,

Marques²,

Nunes³

et al. 2004

Sci. Mar.

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SUMMARY: The present study aimed to identify and quantify the dimethyl acetal (DMA) levels in the muscle of Octopus vulgaris Cuvier, 1797, and to investigate the possible influence of octopus feeding ecology on their spatial and seasonal variations. The research was performed over one year in three areas of the Portuguese coast: Viana do Castelo, Cascais and Tavira. Significantly higher values of DMA were detected in Tavira (p<0.05), an area where the importance of bivalves in the octopus' diet was higher. The biochemical analyses performed in several prey items, belonging to five major taxonomic groups identified in octopus stomachs, revealed significant differences in DMA levels (p<0.05). The highest values were obtained in bivalves (1.15 mg 100 g -1 dry weight), followed by gastropods (0.74 mg 100g -1 dw), cephalopods (0.67 mg 100 g -1 dw), crustaceans (0.23 mg 100 g -1 dw) and osteichthyes (0.10 mg 100 g -1 dw). Therefore, based on these findings it can be speculated that the higher DMA levels in O. vulgaris obtained in Tavira throughout the year were evidence of its feeding ecology. Since DMAs are derived from ether glycerophospholipids, including plasmalogens (PLMs), the importance and role of this phospholipid class is discussed.Key words: Octopus vulgaris, dimethyl acetal, plasmalogens, phospholipids, feeding ecology. RESUMEN: CAMBIOS ESPACIO-TEMPORALES EN LOS NIVELES DE DIMETIL ACETAL (OCTADENAL) DE OCTOPUS VULGARIS(MOLLUSCA: CEPHALOPODA): RELACIÓN CON LA ECOLOGÍA TRÒFICA. -El presente trabajo ha tenido como objetivo la identificación y la cuantificación del nivel de dimetil acetal (DMA) en el músculo de Octopus vulgaris Cuvier, 1797, e investigar la influencia de la ecología alimentaria del pulpo en los variaciones espacio-temporales de este compuesto. El estudio ha sido realizado durante un año en tres zonas de la costa portuguesa: Viana do Castelo, Cascais y Tavira. Se han obtenido valores significativamente superiores del DMA (p<0.05) en Tavira, un área donde la importancia relativa de los bivalvos en la dieta fue superior. Los análisis bioquímicos realizados en distintos tipos de presas, pertenecientes a los cinco grupos taxonómicos identificados en los contenidos estomacales del pulpo, han revelado la existencia de diferencias significativas en los niveles de DMA entre los grupos (p<0,05). Los valores más elevados han sido obtenidos en los bivalvos (1.15 mg 100 g -1 ), seguidos de los gasterópodos (0.74 mg 100 g -1 ), cefalópodos (0.67 mg 100 g -1 ), crustáceos (0.23 mg 100 g -1 ) e osteichthies (0.10 mg 100 g -1 ). En base a estos resultados se puede especular que los valores más elevados obtenidos en Tavira a lo largo de todo el año constituyen una evidencia de la ecología alimentar del pulpo. Dado que los DMA son derivados de los eter glicerofosfolípidos, donde se incluyen los plasmalogénos (PLM), se discute la importancia y el papel funcional de esta clase de fosfolípidos.

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“…Plasmalogens (PIs), a subclass of glycerophospholipids possessing a vinyl-ether bond at the sn-1 position, are biosynthesized and regulated in peroxisomes [4][5][6]. Therefore, plasma Pls may reflect the systemic functional state of peroxisomes, and serve as potential biomarkers for diseases related to oxidative stress and aging [7][8][9]. Human plasma Pls are synthesized mainly in the liver and secreted into the blood as lipoprotein components.…”

Section: Introductionmentioning

confidence: 99%

Extrinsic effectors regulating genes for plasmalogen biosynthetic enzymes in HepG2 cells

Maeba¹,

Nakahara²

2017

Biomed Res Clin Prac

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Plasma plasmalogens (Pls) may serve as potential biomarkers not only for rare peroxisomal diseases but also for general disorders related to oxidative stress and aging. Recent clinical observational studies demonstrated that low levels of plasma Pls are risk factors for atherosclerosis and dementia. Serum levels of Pls showed a strong positive correlation with high-density lipoprotein (HDL) cholesterol concentration, suggesting that Pls may be involved in metabolism or the function of HDL. Increasing the levels of plasma Pls may serve as a novel therapeutic strategy for preventing diseases associated with oxidative stress and aging. Therefore, we and other groups elevated plasma Pl levels in laboratory animals or humans through administration of myo-inositol, monounsaturated long-chain fatty acids, and the hypolipidemic agent, statin. However, their effects on the gene expression of Pl biosynthetic enzymes remain unknown. To gain insight into the manipulation of Pl biosynthesis and the relationship between Pl biosynthesis and HDL metabolism, we examined target gene expression by real time reverse transcription polymerase chain reaction (RT-PCR) in hepatoma HepG2 cells treated with various test substances. Monounsaturated long-chain fatty acids such as oleic acid and erucic acid, myo-inositol, and the Pl precursor alkylglycerol, all of which supply materials or coenzymes for Pl biosynthesis, unexpectedly reduced the expression of the genes for Pl biosynthetic enzymes. These results suggest the presence of strict regulation of Pl homeostasis. In contrast, pitavastatin induced peroxisome biogenesis and promoted the expression of peroxisomal Pl biosynthetic enzymes and HDL metabolism-associated proteins such as apoprotein A1 and ATP-binding cassette transporter A1. This was likely through enhancement of peroxisome proliferator-activated receptor (PPAR) expression. These findings suggest that there may be a physiological relationship between Pl biosynthesis and HDL metabolism via peroxisomal status.

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Plasmalogens as endogenous antioxidants: somatic cell mutants reveal the importance of the vinyl ether

Cited by 178 publications

References 37 publications

Quantification of Pentafluorobenzyl Oxime Derivatives of Long Chain Aldehydes by GC–MS Analysis

Quantification of Pentafluorobenzyl Oxime Derivatives of Long Chain Aldehydes by GC–MS Analysis

Spatial-temporal changes in dimethyl acetal (octadecanal) levels of <i>Octopus vulgaris</i> (Mollusca, Cephalopoda): relation to feeding ecology

Extrinsic effectors regulating genes for plasmalogen biosynthetic enzymes in HepG2 cells

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