Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1

Makoto Arita, Francesca Bianchini, Julio Aliberti, Alan Sher, Nan Chiang, Song Hong, Rong Yang, Nicos A. Petasis, Charles N. Serhan

Research output: Contribution to journalArticle

596 Citations (Scopus)

Abstract

The essential fatty acid eicosapentaenoic acid (EPA) present in fish oils displays beneficial effects in a range of human disorders associated with inflammation including cardiovascular disease. Resolvin E1 (RvE1), a new bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis. Results of bioaction and physical matching studies indicate that the complete structure of RvE1 is 5S,12R,18R-trihydroxy-6Z,8E,10E, 14Z,16E-EPA. At nanomolar levels, RvE1 dramatically reduced dermal inflammation, peritonitis, dendritic cell (DC) migration, and interleukin (IL) 12 production. We screened receptors and identified one, denoted earlier as ChemR23, that mediates RvE1 signal to attenuate nuclear factor-κB. Specific binding of RvE1 to this receptor was confirmed using synthetic [3H]-labeled RvE1. Treatment of DCs with small interference RNA specific for ChemR23 sharply reduced RvE1 regulation of IL-12. These results demonstrate novel counterregulatory responses in inflammation initiated via RvE1 receptor activation that provide the first evidence for EPA-derived potent endogenous agonists of antiinflammation.

Original languageEnglish
Pages (from-to)713-722
Number of pages10
JournalJournal of Experimental Medicine
Volume201
Issue number5
DOIs
Publication statusPublished - 2005 Mar 7
Externally publishedYes

Fingerprint

Anti-Inflammatory Agents
Lipids
Eicosapentaenoic Acid
Interleukin-12
Inflammation
5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic acid
Synthetic Chemistry Techniques
Essential Fatty Acids
Fish Oils
RNA Interference
Peritonitis
Dendritic Cells
Cell Movement
Cardiovascular Diseases
Skin

ASJC Scopus subject areas

  • Immunology

Cite this

Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1. / Arita, Makoto; Bianchini, Francesca; Aliberti, Julio; Sher, Alan; Chiang, Nan; Hong, Song; Yang, Rong; Petasis, Nicos A.; Serhan, Charles N.

In: Journal of Experimental Medicine, Vol. 201, No. 5, 07.03.2005, p. 713-722.

Research output: Contribution to journalArticle

Arita, M, Bianchini, F, Aliberti, J, Sher, A, Chiang, N, Hong, S, Yang, R, Petasis, NA & Serhan, CN 2005, 'Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1', Journal of Experimental Medicine, vol. 201, no. 5, pp. 713-722. https://doi.org/10.1084/jem.20042031
Arita, Makoto ; Bianchini, Francesca ; Aliberti, Julio ; Sher, Alan ; Chiang, Nan ; Hong, Song ; Yang, Rong ; Petasis, Nicos A. ; Serhan, Charles N. / Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1. In: Journal of Experimental Medicine. 2005 ; Vol. 201, No. 5. pp. 713-722.
@article{e625daf102214e739eea7a937095124b,
title = "Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1",
abstract = "The essential fatty acid eicosapentaenoic acid (EPA) present in fish oils displays beneficial effects in a range of human disorders associated with inflammation including cardiovascular disease. Resolvin E1 (RvE1), a new bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis. Results of bioaction and physical matching studies indicate that the complete structure of RvE1 is 5S,12R,18R-trihydroxy-6Z,8E,10E, 14Z,16E-EPA. At nanomolar levels, RvE1 dramatically reduced dermal inflammation, peritonitis, dendritic cell (DC) migration, and interleukin (IL) 12 production. We screened receptors and identified one, denoted earlier as ChemR23, that mediates RvE1 signal to attenuate nuclear factor-κB. Specific binding of RvE1 to this receptor was confirmed using synthetic [3H]-labeled RvE1. Treatment of DCs with small interference RNA specific for ChemR23 sharply reduced RvE1 regulation of IL-12. These results demonstrate novel counterregulatory responses in inflammation initiated via RvE1 receptor activation that provide the first evidence for EPA-derived potent endogenous agonists of antiinflammation.",
author = "Makoto Arita and Francesca Bianchini and Julio Aliberti and Alan Sher and Nan Chiang and Song Hong and Rong Yang and Petasis, {Nicos A.} and Serhan, {Charles N.}",
year = "2005",
month = "3",
day = "7",
doi = "10.1084/jem.20042031",
language = "English",
volume = "201",
pages = "713--722",
journal = "Journal of Experimental Medicine",
issn = "0022-1007",
publisher = "Rockefeller University Press",
number = "5",

}

TY - JOUR

T1 - Stereochemical assignment, antiinflammatory properties, and receptor for the omega-3 lipid mediator resolvin E1

AU - Arita, Makoto

AU - Bianchini, Francesca

AU - Aliberti, Julio

AU - Sher, Alan

AU - Chiang, Nan

AU - Hong, Song

AU - Yang, Rong

AU - Petasis, Nicos A.

AU - Serhan, Charles N.

PY - 2005/3/7

Y1 - 2005/3/7

N2 - The essential fatty acid eicosapentaenoic acid (EPA) present in fish oils displays beneficial effects in a range of human disorders associated with inflammation including cardiovascular disease. Resolvin E1 (RvE1), a new bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis. Results of bioaction and physical matching studies indicate that the complete structure of RvE1 is 5S,12R,18R-trihydroxy-6Z,8E,10E, 14Z,16E-EPA. At nanomolar levels, RvE1 dramatically reduced dermal inflammation, peritonitis, dendritic cell (DC) migration, and interleukin (IL) 12 production. We screened receptors and identified one, denoted earlier as ChemR23, that mediates RvE1 signal to attenuate nuclear factor-κB. Specific binding of RvE1 to this receptor was confirmed using synthetic [3H]-labeled RvE1. Treatment of DCs with small interference RNA specific for ChemR23 sharply reduced RvE1 regulation of IL-12. These results demonstrate novel counterregulatory responses in inflammation initiated via RvE1 receptor activation that provide the first evidence for EPA-derived potent endogenous agonists of antiinflammation.

AB - The essential fatty acid eicosapentaenoic acid (EPA) present in fish oils displays beneficial effects in a range of human disorders associated with inflammation including cardiovascular disease. Resolvin E1 (RvE1), a new bioactive oxygenated product of EPA, was identified in human plasma and prepared by total organic synthesis. Results of bioaction and physical matching studies indicate that the complete structure of RvE1 is 5S,12R,18R-trihydroxy-6Z,8E,10E, 14Z,16E-EPA. At nanomolar levels, RvE1 dramatically reduced dermal inflammation, peritonitis, dendritic cell (DC) migration, and interleukin (IL) 12 production. We screened receptors and identified one, denoted earlier as ChemR23, that mediates RvE1 signal to attenuate nuclear factor-κB. Specific binding of RvE1 to this receptor was confirmed using synthetic [3H]-labeled RvE1. Treatment of DCs with small interference RNA specific for ChemR23 sharply reduced RvE1 regulation of IL-12. These results demonstrate novel counterregulatory responses in inflammation initiated via RvE1 receptor activation that provide the first evidence for EPA-derived potent endogenous agonists of antiinflammation.

UR - http://www.scopus.com/inward/record.url?scp=12344321136&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=12344321136&partnerID=8YFLogxK

U2 - 10.1084/jem.20042031

DO - 10.1084/jem.20042031

M3 - Article

VL - 201

SP - 713

EP - 722

JO - Journal of Experimental Medicine

JF - Journal of Experimental Medicine

SN - 0022-1007

IS - 5

ER -