Journal
JOURNAL OF BIOLOGICAL CHEMISTRY
Volume 287, Issue 13, Pages 10525-10534Publisher
AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC
DOI: 10.1074/jbc.M112.340612
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Funding
- Japan Science and Technology Agency Precursory Research for Embryonic Science and Technology
- Core Research for Evolutional Science and Technology
- Ministry of Education, Culture, Sports, Science, and Technology of Japan
- Ono Medical Research Foundation
- Program for Promotion of Basic and Applied Research for Innovations in Bio-Oriented industry
- Grants-in-Aid for Scientific Research [22116006, 23790074, 22116001, 21370051, 23227004, 23790005] Funding Source: KAKEN
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Bioactive mediators derived from omega-3 eicosapentaenoic acid (EPA) elicit potent anti-inflammatory actions. Here, we identified novel EPA metabolites, including 8,18-dihydroxyei-cosapentaenoic acid (8,18-diHEPE), 11,18-diHEPE, 12,18-diHEPE, and 17,18-diHEPE from 18-HEPE. Unlike resolvins E1 and E2, both of which are biosynthesized by neutrophils via the 5-lipoxygenase pathway, these metabolites are biosynthesized by eosinophils via the 12/15-lipoxygenase pathway. Among them, two stereoisomers of 17,18-diHEPE, collectively termed resolvin E3 (RvE3), displayed a potent anti-inflammatory action by limiting neutrophil infiltration in zymosan-induced peritonitis. The planar structure of RvE3 was unambiguously determined to be 17,18-dihydroxy-5Z, 8Z, 11Z, 13E, 15E-EPE by high resolution NMR, and the two stereoisomers were assigned to have 17,18R- and 17,18S-dihydroxy groups, respectively, using chemically synthesized 18R- and 18S-HEPE as precursors. Both 18R- and 18S-RvE3 inhibited neutrophil chemotaxis in vitro at low nanomolar concentrations. These findings suggest that RvE3 contributes to the beneficial actions of EPA in controlling inflammation and related diseases.
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