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J Org Chem. 2011 Jul 1;76(13):5433-7. doi: 10.1021/jo2002243. Epub 2011 Jun 2.

Total synthesis and bioactivity of 18(R)-hydroxyeicosapentaenoic acid.

Author information

1
Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United States.

Abstract

Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic acid via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.

PMID:
21598971
PMCID:
PMC3253701
DOI:
10.1021/jo2002243
[Indexed for MEDLINE]
Free PMC Article

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