13(R)-HODE

Description

13(R)-HODE is the opposite enantiomer of the 13(S)-HODE produced when linoleic acid is incubated with soybean lipoxygenase. The presence of 13(R)-HODE in the supernatants and membranes of cultured bovine endothelial cells has been attributed to COX metabolism.¹ 13(R)-HODE is a weak (IC₅₀ = 2.7 μM) inhibitor of U-46619-induced platelet aggregation.²

Definition

ChEBI: 13(R)-HODE is a 13-HODE in which the stereocentre at position 13 has S-configuration. It is a conjugate acid of a 13(R)-HODE(1-).

References

1. Baer, A.N., Costello, P.B., and Green, F.A. Stereospecificity of the hydroxyeicosatetraenoic and hydroxyoctadecadienoic acids produced by cultured bovine endothelial cells Biochim. Biophys. Acta 1085(1),45-52(1991).
2. Lagarde, M., Boutillon, M.M., Guichardant, M., et al. Further studies on the anti-thromboxane A₂ activity of monohydroxylated fatty acids Biochem. Pharmacol. 38,1863-1864(1989).