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

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...

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Main Author:	Igor A. Butovich
Format:	Article
Language:	English
Published:	Elsevier 2005-11-01
Series:	Journal of Lipid Research
Subjects:	10,17(S)-docosatriene 10,17-dihydroxydocosahexaenoic acid lipoxygenase double lipoxygenation nuclear magnetic resonance cis,trans-geometry
Online Access:	http://www.sciencedirect.com/science/article/pii/S0022227520328686

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spelling	doaj-b63cf3cecab24223a2f8e81fd011ca492021-04-27T04:43:26ZengElsevierJournal of Lipid Research0022-22752005-11-01461123112314On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid familyIgor A. Butovich0To whom correspondence should be addressed.; Department of Ophthalmology, University of Texas Southwestern Medical Center, Dallas, TX 75390-9057Potato 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.http://www.sciencedirect.com/science/article/pii/S002222752032868610,17(S)-docosatriene10,17-dihydroxydocosahexaenoic acidlipoxygenasedouble lipoxygenationnuclear magnetic resonancecis,trans-geometry
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Igor A. Butovich
spellingShingle	Igor A. Butovich On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family Journal of Lipid Research 10,17(S)-docosatriene 10,17-dihydroxydocosahexaenoic acid lipoxygenase double lipoxygenation nuclear magnetic resonance cis,trans-geometry
author_facet	Igor A. Butovich
author_sort	Igor A. Butovich
title	On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
title_short	On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
title_full	On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
title_fullStr	On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
title_full_unstemmed	On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family
title_sort	on the structure and synthesis of neuroprotectin d1, a novel anti-inflammatory compound of the docosahexaenoic acid family
publisher	Elsevier
series	Journal of Lipid Research
issn	0022-2275
publishDate	2005-11-01
description	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.
topic	10,17(S)-docosatriene 10,17-dihydroxydocosahexaenoic acid lipoxygenase double lipoxygenation nuclear magnetic resonance cis,trans-geometry
url	http://www.sciencedirect.com/science/article/pii/S0022227520328686
work_keys_str_mv	AT igorabutovich onthestructureandsynthesisofneuroprotectind1anovelantiinflammatorycompoundofthedocosahexaenoicacidfamily
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On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family

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