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Structure Database (LMSD)

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Common Name

15-epi-lipoxin A4

Systematic Name

(5S,6R,7E,9E,11Z,13E,15R)-5,6,15-trihydroxyicosa-7,9,11,13-tetraenoic acid

Synonyms

15-epi-LXA4
15R-LXA4

LM ID

LMFA03040010

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Lipid-derived lipoxins are produced at the site of vascular and mucosal inflammation where they down-regulate polymorphonuclear leukocyte recruitment and function. 15(R)-Lipoxin A4 (15(R)-LXA4) is derived from the aspirin-triggered formation of 15(R)-HETE from arachidonic acid .^1,2 15(R)-LXA4 inhibits LTB4-induced chemotaxis, adherence, and transmigration of neutrophils with twice the potency of LXA4 demonstrating activity in the nM range.^2,3 The anti-inflammatory effects of aspirin may be ascribed in part to the ability of 15(R)-LXA4 to regulate leukocyte function.⁴ 15(R)-LXA4 is reported to promote resolution of inflammation in LPS-treated stromal cells derived from intermediate-stage diseased supraspinatus tendons as evidenced by increased expression of the STAT-6 pathway target genes, ALOX15 and CD206.5

This information has been provided by Cayman Chemical

References

1. Dakin, S.G., Martinez, F.O., Yapp, C., et al. Inflammation activation and resolution in human tendon disease. Sci. Transl. Med. 7(311), (2015).

2. Chiang, N., Bermudez, E.A., Ridker, P.M., et al. Aspirin triggers antiinflammatory 15-epi-lipoxin A4 and inhibits thromboxane in a randomized human trial. Proc. Natl. Acad. Sci. USA 101(42), 15178-15183 (2004).

3. Fierro, I.M., Colgan, S.P., Bernasconi, G., et al. Lipoxin A4 and aspirin-triggered 15-epi-lipoxin A4 inhibit human neutrophil migration: Comparisons between synthetic 15 epimers in chemotaxis and transmigration with microvessel endothelial cells and epithelial cells. J. Immunol. 170(5), 2688-2694 (2003).

4. Clària, J., Lee, M.H., and Serhan, C.N. Aspirin-triggered lipoxins (15-epi-LX) are generated by the human lung adenocarcinoma cell line (A549)-neutrophil interactions and are potent inhibitors of cell proliferation. Mol. Med. 2(5), 583-596 (1996).

5. Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. PNAS USA 92(21), 9475-9479 (1995).

String Representations

InChiKey (Click to copy)

IXAQOQZEOGMIQS-JEWNPAEBSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,9-10,13-14,17-19,21-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9+,14-10+/t17-,18-,19+/m1/s1

SMILES (Click to copy)

C(=C/C=C/[C@@H](O)[C@@H](O)CCCC(O)=O)\C=C/C=C/[C@H](O)CCCCC