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

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.

SUBMITTER: Krishnamurthy VR

PROVIDER: S-EPMC3253701 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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

Krishnamurthy Venkata R VR Dougherty Ann A Haller Carolyn A CA Chaikof Elliot L EL

The Journal of organic chemistry 20110602 13

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 bioactiv ...[more]

PMID: 21598971

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