Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation

Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical charact...

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Bibliographic Details
Published in:FEBS letters 2009-11, Vol.583 (21), p.3478-3484
Main Authors: Chen, P., Fenet, B., Michaud, S., Tomczyk, N., Véricel, E., Lagarde, M., Guichardant, M.
Format: Article
Language:English
Subjects:
10,17-Dihydroxy-docosahexaenoic acid
15-Lipoxygenase
Arachidonate 15-Lipoxygenase
Arachidonate 15-Lipoxygenase - metabolism
BSTFA
Carbon
Carbon - chemistry
DHA
Docosahexaenoic acid
Docosahexaenoic Acids
Docosahexaenoic Acids - chemistry
Docosahexaenoic Acids - metabolism
Docosahexaenoic Acids - pharmacology
Dose-Response Relationship, Drug
Double lipoxygenation
Food and Nutrition
Gas Chromatography-Mass Spectrometry
Glycine max - enzymology
heptafluorobutyryl imidazole
HFBI
Humans
Hydroxides
Hydroxides - chemistry
Ion mobility separation
Life Sciences
Magnetic Resonance Spectroscopy
N,O-Bis(trimethylsilyl)-trifluroroacetamide
Platelet Aggregation
Platelet Aggregation - drug effects
sLOX
soybean lipoxygenase
Soybeans
Stereoisomerism
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Summary:Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical characterization (e.g. GC–MS, HPLC and LC–MS/MS) indicated that PDX is 10(S),17(S)-dihydroxy-docosahexa-4 Z,7 Z,11 E,13 Z,15 E,19 Z-enoic acid. The use of 18O 2 and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with E,Z,E geometry (PDX) instead of E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations.
ISSN:0014-5793
1873-3468
DOI:10.1016/j.febslet.2009.10.004