Journal
JOURNAL OF BIOCHEMISTRY
Volume 153, Issue 4, Pages 355-360Publisher
OXFORD UNIV PRESS
DOI: 10.1093/jb/mvs151
Keywords
EPA; anti-inflammatory; 12/15-LOX; resolvins; stereochemical assignments
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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
- program for Promotion of Basic and Applied Research for Innovations in Bio-Oriented industry
- Grants-in-Aid for Scientific Research [12J10348, 23790005, 22116006, 25460007, 23227004] Funding Source: KAKEN
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Uncontrolled inflammation is now considered to be a link between many widely occurring diseases. Thus, controlling the innate inflammatory response and its local chemical mediators has been receiving increasing attention. We recently identified a novel family of eicosapentaenoic acid (EPA)-derived mediators produced by eosinophils, denoted as resolvin E3 (RvE3), that possess potent anti-inflammatory actions both in vitro and in vivo. Carbons at 17 and 18 positions are asymmetric and thus the molecule has a total of four potential stereoisomers. Here, we assigned the stereochemistry of the conjugated double bonds and chirality of alcohols present in two natural isomers of RvE3 with four different stereoisomers prepared by total organic synthesis. The complete structures of two natural isomers of RvE3 were determined to be 17R,18S- and 17R,18R-dihydroxy-5Z,8Z,11Z,13E,15E-EPA, respectively. These natural isomers prepared by total organic synthesis displayed a potent anti-inflammatory action by limiting neutrophil infiltrations both in vitro and in vivo. The unnatural stereoisomers were much less active compared with the natural isomers, demonstrating the stereoselective action of RvE3.
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