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

被引：85

作者：

Chen, P. ^{[1
]}

Fenet, B. ^{[2
]}

Michaud, S. ^{[1
]}

Tomczyk, N. ^{[3
]}

Vericel, E. ^{[1
]}

Lagarde, M. ^{[1
]}

Guichardant, M. ^{[1
]}

机构：

[1] Univ Lyon, Insa Lyon, RMND, IMBL,Inserm,UMR 870,Inra 1235, F-69621 Villeurbanne, France

[2] UCB Lyon 1, ESCPE, CCRMN, Lyon, France

[3] Waters Corp, Manchester M22 5PP, Lancs, England

来源：

FEBS LETTERS | 2009年 / 583卷 / 21期

关键词：

Docosahexaenoic acid; 15-Lipoxygenase; 10,17-Dihydroxy-docosahexaenoic acid; Double lipoxygenation; Ion mobility separation; DOCOSAHEXAENOIC ACID; OXIDATIVE STRESS; ARACHIDONIC-ACID; BRAIN; LEUKOCYTES; CELLS; DOCOSATRIENES; BIOSYNTHESIS; LIPOXYGENASE; LEUKOTRIENES;

D O I：

10.1016/j.febslet.2009.10.004

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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)-dihydroxydocosahexa-4Z,7Z, 11E, 13Z, 15E,19Z-enoic acid. The use of O-18(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. (C) 2009 Federation of European Biochemical Societies. Published by Elsevier B. V. All rights reserved.

引用

页码：3478 / 3484

页数：7

共 22 条

[1] The docosatriene Protectin D1 is produced by TH2 skewing and promotes human T cell apoptosis via lipid raft clustering [J].

Ariel, A ;

Li, PL ;

Wang, W ;

Tang, WX ;

Fredman, G ;

Hong, S ;

Gotlinger, KH ;

Serhan, CN .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2005, 280 (52) :43079-43086

[2] Brain response to injury and neurodegeneration - Endogenous neuroprotective signaling [J].

Bazan, NG ;

Marcheselli, VL ;

Cole-Edwards, K .

NEUROPROTECTIVE AGENTS, 2005, 1053 :137-147

[3]

Bazan NG, 2005, BRAIN PATHOL, V15, P159

[4]

Bazan NG, 2008, ADV EXP MED BIOL, V613, P39

[5] STUDIES ON THE MECHANISM OF FORMATION OF THE 5S, 12S-DIHYDROXY-6,8,10,14(E,Z,E,Z)-ICOSATETRAENOIC ACID IN LEUKOCYTES [J].

BORGEAT, P ;

DELACLOS, BF ;

PICARD, S ;

DRAPEAU, J ;

VALLERAND, P ;

COREY, EJ .

PROSTAGLANDINS, 1982, 23 (05) :713-724

[6] A one-step method of 10,17-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid synthesis by soybean lipoxygenase [J].

Butovich, IA .

JOURNAL OF LIPID RESEARCH, 2006, 47 (04) :854-863

[7] On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family [J].

Butovich, IA .

JOURNAL OF LIPID RESEARCH, 2005, 46 (11) :2311-2314

[8] IMPROVED SPECTRAL RESOLUTION IN H-1-NMR SPECTROSCOPY BY HOMONUCLEAR SEMISELECTIVE SHAPED PULSE DECOUPLING DURING ACQUISITION [J].

HAMMARSTROM, A ;

OTTING, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8847-8848

[9] Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins -: Mediator lipidornic analysis [J].

Hong, S ;

Tjonahen, E ;

Morgan, EL ;

Lu, Y ;

Serhan, CN ;

Rowley, AF .

PROSTAGLANDINS & OTHER LIPID MEDIATORS, 2005, 78 (1-4) :107-116

[10] Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells -: Autacoids in anti-inflammation [J].

Hong, S ;

Gronert, K ;

Devchand, PR ;

Moussignac, RL ;

Serhan, CN .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (17) :14677-14687

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