LIPID MAPS

Structure Database (LMSD)

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Common Name

Resolvin E1-d4

Systematic Name

5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-eicosapentaenoic 6,7,14,15-d4 acid

Synonyms

RvE1-d4
5S,12R,18R-trihydroxy-EPA-d4
5S,12R,18R-trihydroxy-6Z,8E,10E,14Z,16E-EPA-d4
5,12,18R-triHEPE-d4

LM ID

LMFA03140014

Formula

C₂₀H₂₆D₄O₅

Exact Mass

Calculate m/z

354.234432

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Resolvin E1-d4 (RvE1-d4) is intended for use as an internal standard for the quantification of RvE1 by GC- or LC-MS. RvE1 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 epoxide intermediate, which is formed by aspirin-acetylated COX-2-mediated oxidation of EPA and 5-lipoxygenase (5-LO), by leukotriene A4 (LTA4) hydrolase in human polymorphonuclear (PMN) neutrophils. RvE1 activates chemokine-like receptor 1 (CMKLR1; EC50 = 0.137 nM in a reporter assay). RvE1 (20 ng/animal) inhibits increases in inflammatory exudate neutrophil infiltration in a mouse model of peritonitis induced by zymosan A. It increases survival and prevents decreases in colon length in a mouse model of TNBS-induced colitis when administered at a dose of 50 µg/kg.² RvE1 (50 µg/kg) inhibits ovalbumin-induced increases in eosinophil and total cell numbers, as well as IL-13 and IgE levels in bronchoalveolar lavage fluid (BALF) in an ovalbumin-sensitized mouse model of asthma.³

This information has been provided by Cayman Chemical

References

1. 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).

2. Arita, M., Yoshida, M., Hong, S., et al. Resolvin E1, an endogenous lipid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis. Proc. Natl. Acad. Sci. USA 102(21), 7671-7676 (2005).

3. Aoki, H., Hisada, T., Ishizuka, T., et al. Resolvin E1 dampens airway inflammation and hyperresponsiveness in a murine model of asthma. Biochem. Biophys. Res. Commun. 367(2), 509-515 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

AOPOCGPBAIARAV-VUOMCXAQSA-N

InChi (Click to copy)

InChI=1S/C20H30O5/c1-2-17(21)11-8-5-9-14-18(22)12-6-3-4-7-13-19(23)15-10-16-20(24)25/h3-9,11-13,17-19,21-23H,2,10,14-16H2,1H3,(H,24,25)/b4-3+,9-5-,11-8+,12-6+,13-7-/t17-,18+,19-/m1/s1/i5D,7D,9D,13D

SMILES (Click to copy)

C(CCC[C@H](O)/C(/[2H])=C(/[2H])\C=C\C=C\[C@H](O)C/C(/[2H])=C(/[2H])\C=C\[C@H](O)CC)(=O)O