Journal
JOURNAL OF BIOCHEMISTRY
Volume 156, Issue 6, Pages 315-321Publisher
OXFORD UNIV PRESS
DOI: 10.1093/jb/mvu044
Keywords
anti-inflammation; lipidomics; 12; 15-lipoxygenase; omega-3 polyunsaturated fatty acid
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Funding
- Japan Science and Technology Agency Precursory Research for Embryonic Science and Technology (PRESTO)
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- programme for Promotion of Basic and Applied Research for Innovations in Bio-Oriented industry
- Grants-in-Aid for Scientific Research [14J12409] Funding Source: KAKEN
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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.
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