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Synthesis and Identification of AceDoxyPC, a Protectin-Containing Structured Phospholipid, Using Liquid Chromatography/Mass Spectrometry

Authors
  • Lo Van, Amanda1, 2
  • Fourmaux, Baptiste1
  • Picq, Madeleine1
  • Guichardant, Michel1
  • Lagarde, Michel1
  • Bernoud-Hubac, Nathalie1
  • 1 Univ Lyon, INSA-Lyon, Inserm UMR 1060, Inra UMR 1397, CarMeN Laboratory, INSA, Bâtiment IMBL, 11 Avenue Jean Capelle, Villeurbanne Cedex, 69621, France , Villeurbanne Cedex (France)
  • 2 Tohoku University Graduate School of Medicine, Department of Developmental Neuroscience, Center for Neuroscience, ART, Sendai, Japan , Sendai (Japan)
Type
Published Article
Journal
Lipids
Publisher
Springer Berlin Heidelberg
Publication Date
Aug 03, 2017
Volume
52
Issue
9
Pages
751–761
Identifiers
DOI: 10.1007/s11745-017-4280-z
Source
Springer Nature
Keywords
License
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Abstract

Fatty acids have many health benefits in a great variety of diseases ranging from cardiovascular to cerebral diseases. For instance, docosahexaenoic acid (DHA), which is highly enriched in brain phospholipids, plays a major role in anti-inflammatory or neuroprotective pathways. Its effects are thought to be due, in part, to its conversion into derived mediators such as protectins. 1-Lyso,2-docosahexaenoyl-glycerophosphocholine (LysoPtdCho-DHA) is one of the physiological carrier of DHA to the brain. We previously synthesized a structured phosphatidylcholine to mimic 1-lyso,2-docosahexaenoyl-glycerophosphocholine, named AceDoPC® (1-acetyl,2-docosahexaenoyl-glycerophosphocholine), that is considered as a stabilized form of the physiological LysoPtdCho-DHA and that is neuroprotective in experimental ischemic stroke. Considering these, the current study aimed at enzymatically oxygenate DHA contained within AceDoPC® to synthesize a readily structured oxidized phospholipid containing protectin DX (PDX), thereafter named AceDoxyPC (1-acetyl,2-PDX-glycerophosphocholine). Identification of this product was performed using liquid chromatography/tandem mass spectrometry. Such molecule could be used as a bioactive mediator for therapy against neurodegenerative diseases and stroke.

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