1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA

1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA is a phospholipid containing arachidonic acid at the sn-1 position. It is a precursor to 1-arachidonoyl glycerol (1-Monoarachidin; HY-130567) [1]. 1-Arachidonoyl-2-hydroxy-sn-glycero-3-PA binds to the LPA2/EDG4 receptor with an EC50 value of approximately 10 nM[2]. It prevents TNF-α and IL-6 secretion in wild-type but not Lpa2-/- dendritic cells stimulated by LPS[3]. It also decreases differentiation of HT-29 human colon carcinoma cells to goblet cells in the presence of sodium butyrate[4].

Product Specifications

CAS Number

[65446-08-4]

Product Name Alternative

1-Arachidonoyl-sn-glycerol 3-phosphate; 1-Arachidonoyl LPA; LPA (20:4)

UNSPSC

12352128

Target

LPL Receptor

Related Pathways

GPCR/G Protein

Applications

COVID-19-immunoregulation

Field of Research

Inflammation/Immunology

Smiles

O=P(O)(O)OC[C@H](O)COC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O

Molecular Formula

C23H39O7P

Molecular Weight

458.53

References & Citations

[1]Nakane, S., Oka, S., Arai, S., et al. 2-Arachidonoyl-sn-glycero-3-phosphate, an arachidonic acid-containing lysophosphatidic acid: occurrence and rapid enzymatic conversion to 2-arachidonoyl-sn-glycerol, a cannabinoid receptor ligand, in rat brain. Arch. Biochem. Biophys. 402 (1), 51-58 (2002) .|[2]Bandoh, K., Aoki, J., Taira, A., et al. Lysophosphatidic acid (LPA) receptors of the EDG family are differentially activated by LPA species. Structure-activity relationship of cloned LPA receptors. FEBS Lett. 478 (1-2), 159-165 (2000) .|[3]Emo, J., Meednu, N., Chapman, T.J., et al. Lpa2 is a negative regulator of both dendritic cell activation and murine models of allergic lung inflammation. J. Immunol. 188 (8), 3784-3790 (2012) .|[4]Hidaka, M., Nishihara, M., and Tokumura, A. Three lysophosphatidic acids with a distinct long chain moiety differently affect cell differentiation of human colon epithelial cells to goblet cells. Life Sci. 197, 73-79 (2018) .