LIPID MAPS

Resolvin E2 (RvE2) is a member of the specialized pro-resolving mediator (SPM) family of bioactive lipids.¹ It is produced from eicosapentaenoic acid (EPA) via an 18-HEPE intermediate, which is formed by aspirin-acetylated COX-2-mediated oxidation of EPA, by 5-lipoxygenase (5-LO) in human polymorphonuclear (PMN) neutrophils.^2,3 RvE2 (20 ng/animal) inhibits increases in inflammatory exudate neutrophil infiltration in a mouse model of peritonitis induced by zymosan A .³ Hepatic RvE2 levels are increased in mice fed normal chow, as well as in a mouse model of high-fat diet-induced non-alcoholic fatty liver disease (NAFLD), by dietary supplementation with EPA.⁴ Plasma levels of RvE2 are increased by dietary supplementation with fish oil containing ω-3 polyunsaturated fatty acids (PUFAs) in patients with peripheral artery disease or chronic kidney disease.^1,5,6

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References

1. Tjonahen, E., Oh, S.F., Siegelman, J., et al. Resolvin E2: Identification and anti-inflammatory actions: Pivotal role of human 5-lipoxygenase in resolvin E series biosynthesis. Chem. Biol. 13, 1193-1202 (2006).

2. Chiang, N., and Serhan, C.N. Specialized pro-resolving mediator network: An update on production and actions. Essays Biochem. 64(3), 443-462 (2020).

3. Oh, S.F., Pillai, P.S., Recchiuti, A., et al. Pro-resolving actions and stereoselective biosynthesis of 18S E-series resolvins in human leukocytes and murine inflammation. J. Clin. Invest. 121(2), 569-581 (2011).

4. Echeverría, F., Valenzuela, R., Espinosa, A., et al. Reduction of high-fat diet-induced liver proinflammatory state by eicosapentaenoic acid plus hydroxytyrosol supplementation: Involvement of resolvins RvE1/2 and RvD1/2. J. Nutr. Biochem. 63, 35-43 (2019).

5. Ramirez, J.L., Gasper, W.J., Khetani, S.A., et al. Fish oil increases specialized pro-resolving lipid mediators in PAD (the OMEGA-PAD II trial). J. Surg. Res. 238, 164-174 (2019).

6. Barden, A.E., Shinde, S., Burke, V., et al. The effect of n-3 fatty acids and coenzyme Q10 supplementation on neutrophil leukotrienes, mediators of inflammation resolution and myeloperoxidase in chronic kidney disease. Prostaglandins Other Lipid Mediat. 136, 1-8 (2018).

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Resolvin E2: identification and anti-inflammatory actions: pivotal role of human 5-lipoxygenase in resolvin E series biosynthesis.,
Chem Biol, 2006

Pubmed ID: 17114001

InChiKey (Click to copy)

KPRHYAOSTOHNQA-NNQKPOSRSA-N

InChi (Click to copy)

InChI=1S/C20H30O4/c1-2-18(21)14-11-9-7-5-3-4-6-8-10-12-15-19(22)16-13-17-20(23)24/h3-4,7-12,14-15,18-19,21-22H,2,5-6,13,16-17H2,1H3,(H,23,24)/b4-3-,9-7-,10-8-,14-11+,15-12+/t18-,19-/m1/s1

SMILES (Click to copy)

C(CCC[C@H](O)/C=C/C=C\C/C=C\C/C=C\C=C\[C@H](O)CC)(=O)O

KEGG ID

CHEBI ID

PubChem CID

Cayman ID

Heavy Atoms 24

Rings 0