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Journal of Lipid Research, Vol. 46, 2311-2314, November 2005
Copyright © 2005 by American Society for Biochemistry and Molecular Biology

Rapid Communication

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

Igor A. Butovich¹

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

Published, JLR Papers in Press, September 8, 2005. DOI 10.1194/jlr.C500015-JLR200

¹ To whom correspondence should be addressed. e-mail: igor.butovich{at}utsouthwestern.edu

ABSTRACT

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] which was formed apparently through a double lipoxygenation mechanism. 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 very likely 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.

Abbreviations: COSY, correlation spectroscopy; DHA, docosahexaenoic acid (-3 C22:6); LOX, lipoxygenase; ptLOX, potato tuber lipoxygenase; sLOX, soybean lipoxygenase; 10,17(S)-diHDHA, 10,17(S)-dihydroxydocosahexaenoic acid; 17(S)-HDHA, 17(S)-hydroxydocosahexaenoic acid; 17(S)-HPDHA, 17(S)-hydroperoxydocosahexaenoic acid

Supplementary key words 10,17(S)-docosatriene • 10,17-dihydroxydocosahexaenoic acid • lipoxygenase • double lipoxygenation • nuclear magnetic resonance • cis,trans-geometry

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