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

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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)-dehydroxydocosabexa- 4Z,7Z,11E,13Z,15E,19Z-enoic acid formed through a double lipoxygenation mechanism instead of a previously thought epoxidation/isomerization mechanism.

Original languageEnglish (US)
Pages (from-to)2311-2314
Number of pages4
JournalJournal of lipid research
Volume46
Issue number11
DOIs
StatePublished - Nov 1 2005

Keywords

  • 10,17(S)-docosatriene
  • 10,17-dihydroxy-docosahexaenoic acid
  • Double lipoxygenation
  • Lipoxygenase
  • Nuclear magnetic resonance
  • cis, trans-geometry

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Cell Biology

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