Identification of 14,2

Yoshiyuki Yokokura, Yosuke Isobe, Shinnosuke Matsueda, Ryo Iwamoto, Tomomi Goto, Takeshi Yoshioka, Daisuke Urabe, Masayuki Inoue, Hiroyuki Arai, Makoto Arita

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Docosahexaenoic acid (DHA) exhibits anti-inflammatory activity related to some of its oxygenated metabolites, such as D-series resolvins, protectin and maresin. Here, we analysed the lipids in inflammatory exudates using liquid chromatography-tandem mass spectrometry and identified a novel DHA metabolite, 14,20-dihydroxy-DHA (14,20-diHDHA) and showed that it is biosynthesized by eosinophils through the 12/15-lipoxygenase pathway. The chemical structure of the dominant 14,20-diHDHA isomer, which is endogenously biosynthesized by eosinophils, was identified as 14S,20R-diHDHA using chemically synthesized stereoisomers. Nanogram doses of 14,20-diHDHA displayed a potent anti-inflammatory action by limiting neutrophil infiltration in zymosan-induced peritonitis. The in vivo formation and potent anti-inflammatory action of 14,20-diHDHA may contribute to the protective effects of DHA.

Original languageEnglish
Pages (from-to)315-321
Number of pages7
JournalJournal of biochemistry
Volume156
Issue number6
DOIs
Publication statusPublished - 2014 Dec 1
Externally publishedYes

Keywords

  • 15-lipoxygenase
  • anti-inflammation
  • lipidomics 12
  • omega-3 polyunsaturated fatty acid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

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