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J. Lipid Res.
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A more recent version of this article appeared on November 1, 2005

Papers In Press, published online ahead of print September 8, 2005
J. Lipid Res., doi:10.1194/jlr.C500015-JLR200
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Submitted on June 30, 2005
Revised on August 19, 2005
Accepted on August 19, 2005

On the structure, synthesis and mechanism of formation of neuroprotectin D1-a novel anti-inflammatory compound of docosahexaenoic acid family

Igor A. Butovich

Department of Ophthalmology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9057

Corresponding Author: igor.butovich{at}utsouthwestern.edu

Potato tuber lipoxygenase was shown to convert 17(S)-hydro(pero)xydocasahexaenoic acid in 10,17(S)-dihydro(pero)xydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid (10,17(S)-diHDHA). No traces of 10,17(S)-dihydro(pero)xydocosahexa-4Z,7Z,11E,13E,15Z,19Z -enoic acid were found among the reaction products. It is concluded that a described earlier “neuroprotectin D1” (or “10,17(S)docosatriene”) – a novel and potent anti-inflammatory compound derived from docosahexaenoic acid – was, in fact, 10,17(S)-dihydroxydocosahexa-4Z,7Z,11E,13Z,15E,19Z-enoic acid formed through a double lipoxygenation mechanism instead of a previously thought epoxidation/isomerization mechanism.


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