LIPID MAPS

Structure Database (LMSD)

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Common Name

ent-15-epi-15-A2-IsoP

Systematic Name

9-oxo-15S-hydroxy-5Z,10,13E-prostatrienoic acid-cyclo[8S,12S]

Synonyms

(15S)-15-A2-IsoP[8S,12S]

LM ID

LMFA03110140

Formula

C₂₀H₃₀O₄

Exact Mass

Calculate m/z

334.21441

Sum Composition

FA 20:5;O2

Status

Computationally Generated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

8-iso Prostaglandin A2 (8-iso PGA2) is an isoprostane. It is produced by the non-enzymatic oxidation of arachidonic acid .^1,2 8-iso PGA2 (100 µM) induces calcium influx in HEK293 cells expressing human transient receptor potential ankyrin 1 (TRPA1) and isolated mouse trigeminal neurons.³ It potentiates glutamate-induced cytotoxicity and decreases glutathione (GSH) levels in HT22 hippocampal cells when used at concentrations of 1 and 30 µM, respectively.⁴ 8-iso PGA2 (10 µM) inhibits VEGF-induced migration and tube formation of human coronary artery endothelial cells, an effect that can be reversed by the TP receptor antagonist SQ 29,548 .⁵

This information has been provided by Cayman Chemical

References

1. Taylor-Clark, T.E., Undem, B.J., MacGlashan, D.W., Jr., et al. Prostaglandin-induced activation of nociceptive neurons via direct interaction with transient receptor potential A1 (TRPA1). Mol. Pharmacol. 73(2), 274-281 (2008).

2. Benndorf, R.A., Schwedhelm, E., Gnann, A., et al. Isoprostanes inhibit vascular endothelial growth factor-induced endothelial cell migration, tube formation, and cardiac vessel sprouting in vitro, as well as angiogenesis in vivo via activation of the thromboxane A2 receptor: A potential link between oxidative stress and impaired angiogenesis. Circ. Res. 103(9), 1037-1046 (2008).

3. Musiek, E.S., Breeding, R.S., Milne, G.L., et al. Cyclopentenone isoprostanes are novel bioactive products of lipid oxidation which enhance neurodegeneration. J. Neurochem. 97, 1301-1313 (2006).

4. Chen, Y., Zackert, W.E., Roberts, L.J., II, et al. Evidence for the formation of a novel cyclopentenone isoprostane, 15-A2t-isoprostane (8-iso-prostaglandin A2) in vivo. Biochim. Biophys. Acta 1436(3), 550-556 (1999).

5. Chen, Y., Morrow, J.D., and Roberts, L.J., II Formation of reactive cyclopentenone compounds in Vivo as products of the isoprostane pathway. J. Biol. Chem. 274(16), 10863-10868 (1999).

String Representations

InChiKey (Click to copy)

MYHXHCUNDDAEOZ-UKUWKSPLSA-N

InChi (Click to copy)

InChI=1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12-18,21H,2-3,5-6,8-11H2,1H3,(H,23,24)/b7-4-,14-12+/t16-,17-,18-/m0/s1

SMILES (Click to copy)

C(CCC/C=C\C[C@@H]1C(=O)C=C[C@@H]1/C=C/[C@@H](O)CCCCC)(=O)O