Stereochemical assignment and anti-inflammatory properties of the omega-3 lipid mediator resolvin E3

Yosuke Isobe, Makoto Arita, Ryo Iwamoto, Daisuke Urabe, Hidenori Todoroki, Koji Masuda, Masayuki Inoue, Hiroyuki Arai

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)355-360
Number of pages6
JournalJournal of biochemistry
Volume153
Issue number4
DOIs
Publication statusPublished - 2013 Apr 1
Externally publishedYes

Keywords

  • 12/15-LOX
  • EPA
  • anti-inflammatory
  • resolvins
  • stereochemical assignments

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology

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