Acyl chain-dependent effect of lysophosphatidylcholine on endothelial prostacyclin production

Riederer, Monika; Ojala, Pauli J.; Hrzenjak, Andelko; Graier, Wolfgang F.; Malli, Roland; Tritscher, Michaela; Hermansson, Martin; Watzer, Bernhard; Schweer, Horst; Desoyé, Gernot; Heinemann, Ákos; Frank, Saša

doi:10.1194/jlr.m006536

Cited by 47 publications

(45 citation statements)

References 59 publications

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“…Additionally, LPC was also reported to stimulate the release of arachidonic acid (AA), a pro-inflammatory fatty acid and precursor of a variety of pro-inflammatory eicosanoid derivatives, from human endothelial cells [6]. In neutrophils, LPCs express their inflammatory actions by inducing mobilization of cytosolic calcium, activating NADPH oxidase leading to superoxide formation [7,8]. Moreover, LPC stimulates macrophages to induce Toll-like-2 receptor (TLR 2 )-dependent NF-kB activation and cytokine formation.…”

Section: Introductionmentioning

confidence: 99%

Prevention of 1-palmitoyl lysophosphatidylcholine-induced inflammation by polyunsaturated acyl lysophosphatidylcholine

2012

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Section: Introductionmentioning

confidence: 99%

Prevention of 1-palmitoyl lysophosphatidylcholine-induced inflammation by polyunsaturated acyl lysophosphatidylcholine

2012

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“…related to acyl-chain length and degree of unsaturation (Brkić et al, 2012;Rao et al, 2013). For instance, among the various species of LPCs in plasma, 16:0-, 18:1-and 20:4-LPC induce an increase of endothelial prostacyclin production in vitro (1.4-, 3-and 8.3-fold, respectively) although C18:2-LPC is inactive (Riederer et al, 2010). Moreover, several studies have contributed to show that LPLs are convenient carriers for optimal transport of docosahexaenoic acid (DHA, C22:6 v3) to the brain where it plays a number of important functions (Bernoud et al, 1999;Lagarde et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Lipase-catalyzed production of lysophospholipids

Mnasri

Hérault

Gauvry

et al. 2017

OCL

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-Lysophospholipids, such as lysophosphatidic acid or lysophosphatidylcholine, are important bioactive lipids, involved in various normal and pathological cellular processes. They also have industrial and pharmaceutical uses such as emulsifiers or components of drug delivery systems. Lipases, which natural substrates are long chain triacylglycerols, are important biocatalysts for organic synthesis mainly due to their broad substrate specificity and their ability to display high catalytic activity in organic media. This paper describes the various lipase-catalyzed reactions implemented for the production of lysophospholipids. They include hydrolysis or alcoholysis of phospholipids and acylation of the glycerophosphoryl moiety. Special emphasis is made on our work dealing with the production of lysophospholipids rich in dososahexaenoic acid, an important dietary polyunsaturated fatty acid via the hydrolysis of phospholipids extracted from the microalga Isochrysis galbana.Keywords: lipase / lysophospholipid / hydrolysis / esterification / docosahexaenoic acid Résumé -Synthèse de lysophospholipides catalysée par des lipases. Les lysophospholipides, comme par exemple l'acide lysophosphatidique ou la lysophosphatidylcholine, sont des médiateurs lipidiques impliqués dans de nombreux processus cellulaires. Ils sont également employés au niveau industriel comme émulsifiants ou dans les formulations galéniques, par exemple. Les lipases, dont les substrats naturels sont les triacylglycérols à longues chaînes, sont des biocatalyseurs très utilisés en synthèse organique, du fait de leur large spécificité de substrats et de leur activité catalytique élevée en milieu organique. Cet article décrit les différentes approches développées pour la synthèse des lysophospholipides mettant en oeuvre les lipases, à savoir l'hydrolyse ou l'alcoolyse de phospholipides et l'acylation de la partie glycerophosphoryle correspondant au lysophospholipide recherché. En particulier, nos travaux, portant sur la synthèse de lysophospholipides riches en acide docosahexaénoique par hydrolyse de phospholipides issus de la microalgue Isochrysis galbana, sont présentés.

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“…Such free LPC might appear in vivo during excessive lipolysis when albumin and other carrier plasma proteins are saturated with FA and LPC [20]. We found previously that 10 µM LPC 18:1 when applied in the absence of serum is not toxic to cultured endothelial cells or aortic rings [29], [30]. In the present study we show that 10 µM LPC 18:1 applied in the absence of serum impacts NO bioavailability and ROS production similarly to 60 µM LPC applied with 5% FBS.…”

Section: Discussionmentioning

confidence: 96%

Oleoyl-Lysophosphatidylcholine Limits Endothelial Nitric Oxide Bioavailability by Induction of Reactive Oxygen Species

et al. 2014

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Previously we reported modulation of endothelial prostacyclin and interleukin-8 production, cyclooxygenase-2 expression and vasorelaxation by oleoyl- lysophosphatidylcholine (LPC 18:1). In the present study, we examined the impact of this LPC on nitric oxide (NO) bioavailability in vascular endothelial EA.hy926 cells. Basal NO formation in these cells was decreased by LPC 18:1. This was accompanied with a partial disruption of the active endothelial nitric oxide synthase (eNOS)- dimer, leading to eNOS uncoupling and increased formation of reactive oxygen species (ROS). The LPC 18:1-induced ROS formation was attenuated by the superoxide scavenger Tiron, as well as by the pharmacological inhibitors of eNOS, NADPH oxidases, flavin-containing enzymes and superoxide dismutase (SOD). Intracellular ROS-formation was most prominent in mitochondria, less pronounced in cytosol and undetectable in endoplasmic reticulum. Importantly, Tiron completely prevented the LPC 18:1-induced decrease in NO bioavailability in EA.hy926 cells. The importance of the discovered findings for more in vivo like situations was analyzed by organ bath experiments in mouse aortic rings. LPC 18:1 attenuated the acetylcholine-induced, endothelium dependent vasorelaxation and massively decreased NO bioavailability. We conclude that LPC 18:1 induces eNOS uncoupling and unspecific superoxide production. This results in NO scavenging by ROS, a limited endothelial NO bioavailability and impaired vascular function.

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Acyl chain-dependent effect of lysophosphatidylcholine on endothelial prostacyclin production

Cited by 47 publications

References 59 publications

Prevention of 1-palmitoyl lysophosphatidylcholine-induced inflammation by polyunsaturated acyl lysophosphatidylcholine

Prevention of 1-palmitoyl lysophosphatidylcholine-induced inflammation by polyunsaturated acyl lysophosphatidylcholine

Lipase-catalyzed production of lysophospholipids

Oleoyl-Lysophosphatidylcholine Limits Endothelial Nitric Oxide Bioavailability by Induction of Reactive Oxygen Species

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