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Originally published In Press as doi:10.1074/jbc.M300218200 on February 17, 2003

J. Biol. Chem., Vol. 278, Issue 17, 14677-14687, April 25, 2003
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Novel Docosatrienes and 17S-Resolvins Generated from Docosahexaenoic Acid in Murine Brain, Human Blood, and Glial Cells
AUTACOIDS IN ANTI-INFLAMMATION*

Song HongDagger , Karsten GronertDagger , Pallavi R. Devchand, Rose-Laure Moussignac, and Charles N. Serhan§

From the Center for Experimental Therapeutics and Reperfusion Injury, Department of Anesthesiology, Perioperative and Pain Medicine, Brigham and Women's Hospital and Harvard Medical School, Boston, Massachusetts 02115

Docosahexaenoic acid (DHA, C22:6) is highly enriched in brain, synapses, and retina and is a major omega -3 fatty acid. Deficiencies in this essential fatty acid are reportedly associated with neuronal function, cancer, and inflammation. Here, using new lipidomic analyses employing high performance liquid chromatography coupled with a photodiode-array detector and a tandem mass spectrometer, a novel series of endogenous mediators was identified in blood, leukocytes, brain, and glial cells as 17S-hydroxy-containing docosanoids denoted as docosatrienes (the main bioactive member of the series was 10,17S-docosatriene) and 17S series resolvins. These novel mediators were biosynthesized via epoxide-containing intermediates and proved potent (pico- to nanomolar range) regulators of both leukocytes reducing infiltration in vivo and glial cells blocking their cytokine production. These results indicate that DHA is the precursor to potent protective mediators generated via enzymatic oxygenations to novel docosatrienes and 17S series resolvins that each regulate events of interest in inflammation and resolution.


* This work was supported in part by National Institute of Health Grants GM38765 and P01-DE13499 (to C. N. S.) and DK60583 (to K. G.).The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

Dagger Both authors contributed equally to this work.

§ To whom correspondence should be addressed: Center for Experimental Therapeutics and Reperfusion Injury, Thorn Medical Research Bldg., 7th Floor, Brigham and Women's Hospital, Boston, MA 02115. Tel.: 617-732-8822; Fax: 617-582-6141; E-mail: cnserhan@zeus.bwh.harvard.edu.


Copyright © 2003 by The American Society for Biochemistry and Molecular Biology, Inc.
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[Abstract] [Full Text] [PDF]


Home page
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[Abstract] [Full Text] [PDF]


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[Abstract] [Full Text] [PDF]


Home page
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J. Immunol., February 1, 2006; 176(3): 1848 - 1859.
[Abstract] [Full Text] [PDF]


Home page
J. Biol. Chem.Home page
A. Ariel, P.-L. Li, W. Wang, W.-X. Tang, G. Fredman, S. Hong, K. H. Gotlinger, and C. N. Serhan
The Docosatriene Protectin D1 Is Produced by TH2 Skewing and Promotes Human T Cell Apoptosis via Lipid Raft Clustering
J. Biol. Chem., December 30, 2005; 280(52): 43079 - 43086.
[Abstract] [Full Text] [PDF]


Home page
J. Lipid Res.Home page
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J. Lipid Res., November 1, 2005; 46(11): 2311 - 2314.
[Abstract] [Full Text] [PDF]


Home page
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J. Biol. Chem., April 15, 2005; 280(15): 15267 - 15278.
[Abstract] [Full Text] [PDF]


Home page
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Y. Lu, S. Hong, E. Tjonahen, and C. N. Serhan
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J. Lipid Res., April 1, 2005; 46(4): 790 - 802.
[Abstract] [Full Text] [PDF]


Home page
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G. L. Bannenberg, N. Chiang, A. Ariel, M. Arita, E. Tjonahen, K. H. Gotlinger, S. Hong, and C. N. Serhan
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Home page
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[Abstract] [Full Text] [PDF]


Home page
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S. D. Freedman, P. G. Blanco, M. M. Zaman, J. C. Shea, M. Ollero, I. K. Hopper, D. A. Weed, A. Gelrud, M. M. Regan, M. Laposata, et al.
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[Abstract] [Full Text] [PDF]


Home page
Am. J. Physiol. Renal Physiol.Home page
B. McMahon and C. Godson
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Am J Physiol Renal Physiol, February 1, 2004; 286(2): F189 - F201.
[Abstract] [Full Text] [PDF]


Home page
NEJMHome page
J. H. Dwyer, H. Allayee, K. M. Dwyer, J. Fan, H. Wu, R. Mar, A. J. Lusis, and M. Mehrabian
Arachidonate 5-Lipoxygenase Promoter Genotype, Dietary Arachidonic Acid, and Atherosclerosis
N. Engl. J. Med., January 1, 2004; 350(1): 29 - 37.
[Abstract] [Full Text] [PDF]


Home page
J. Immunol.Home page
C. N. Serhan, A. Jain, S. Marleau, C. Clish, A. Kantarci, B. Behbehani, S. P. Colgan, G. L. Stahl, A. Merched, N. A. Petasis, et al.
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J. Immunol., December 15, 2003; 171(12): 6856 - 6865.
[Abstract] [Full Text] [PDF]


Home page
J. Lipid Res.Home page
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Synaptic lipid signaling: significance of polyunsaturated fatty acids and platelet-activating factor
J. Lipid Res., December 1, 2003; 44(12): 2221 - 2233.
[Abstract] [Full Text] [PDF]


Home page
Am. J. Physiol. Heart Circ. Physiol.Home page
B. Nohe, T. Johannes, H.-J. Dieterich, K. Mayer, M. Merfels, F. Grimminger, and W. Seeger
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Am J Physiol Heart Circ Physiol, November 1, 2003; 285(5): H2248 - H2250.
[Full Text] [PDF]


Home page
J. Biol. Chem.Home page
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[Abstract] [Full Text] [PDF]




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