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Lipids

, Volume 52, Issue 9, pp 751–761 | Cite as

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

  • Amanda Lo Van
  • Baptiste Fourmaux
  • Madeleine Picq
  • Michel Guichardant
  • Michel Lagarde
  • Nathalie Bernoud-HubacEmail author
Original Article

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.

Keywords

Omega-3 fatty acids Docosahexaenoic acid Lipoxygenase Mass spectrometry Protectin DX Structured phospholipid 

Abbreviations

AceDoPC

1-Acetyl,2-DHA-glycerophosphocholine

AceDoxyPC

1-Acetyl,2-PDX-glycerophosphocholine

BBB

Blood–brain barrier

CID

Collision-induced dissociation

DCC

1,3-Dicyclohexylcarbodiimide

DMAP

4-(Dimethylamino)pyridine

DMF

Dimethylformamide

GPC

sn-Glycerophosphocholine

LOX

Lipoxygenase

LysoPtdCho-DHA

1-Lyso,2-docosahexaenoyl-glycerophosphocholine

MRM

Multiple reaction monitoring

PD1

Protectin D1

PDX

Protectin DX

sLOX

Soybean lipoxygenase

Notes

Acknowledgements

This study was supported by Lisa CARNOT Institute, National Institute of Applied Sciences-Lyon and the French Ministry of Education and Research. We thank Laurence Daniel and Valentin Ramel for their technical and supportive assistance.

Compliance with Ethical Standards

Conflict of interest

Pending patent: WO 2017006047 A1. NBH, MP, MG, and ML are associates in LipTher (http://www.lipther.com/), an emerging start up from the academic CarMeN laboratory, INSA-Lyon, whose objective is to produce AceDoPC® on a large scale.

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Copyright information

© AOCS 2017

Authors and Affiliations

  • Amanda Lo Van
    • 1
    • 2
  • Baptiste Fourmaux
    • 1
  • Madeleine Picq
    • 1
  • Michel Guichardant
    • 1
  • Michel Lagarde
    • 1
  • Nathalie Bernoud-Hubac
    • 1
    Email author
  1. 1.Univ Lyon, INSA-Lyon, Inserm UMR 1060, Inra UMR 1397, CarMeN Laboratory, INSA, Bâtiment IMBLVilleurbanne CedexFrance
  2. 2.Department of Developmental Neuroscience, Center for Neuroscience, ARTTohoku University Graduate School of MedicineSendaiJapan

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