Lysophosphatidylinositol

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Structural formula
Structure of lysophosphatidylinositol
General
Surname Lysophosphatidylinositol
other names

((2 R ) -2-Hydroxy-3- {hydroxy - [(2 R , 3 R , 5 S , 6 R ) -2,3,4,5,6-pentahydroxycyclohexyl] oxyphosphoryl} oxypropyl) hexadecanoate

Molecular formula C 25 H 49 O 12 P
External identifiers / databases
CAS number 796963-91-2 ( sodium salt )
PubChem 71296207
Wikidata Q19317959
properties
Molar mass 572.62 g mol −1
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lysophosphatidylinositol (LPI) is the lysophosphatide of phosphatidylinositol-4,5-bisphosphate .

properties

As a lysophosphatide, lysophosphatidylinositol, compared to phosphatidylinositol-4,5-bisphosphate, has a free hydroxyl group near the phosphate group instead of one of the two ester bonds to the glycerol . The hydrolytic cleavage of phosphatidylinositol-4,5-bisphosphate to form lysophosphatidylinositol is catalyzed by phospholipase A2 . Lysophosphatidylinositol is a neurotransmitter in the endocannabinoid system and, in addition to the 2-arachidonyl derivative, one of the endogenous ligands of the G protein-coupled receptor GPR55 . In the brown rat brain, an average of about 51% of the fatty acids contained in lysophosphatidylinositol are stearic acid , and another 22% are arachidonic acid. Lysophosphatidylinositol is involved in the vasodilation in the brain and in the release of calcium ions in the endothelial cells (a second messenger ) of the arteries.

literature

  • J. Chun, EJ Goetzl, T. Hla, Y. Igarashi, KR Lynch, W. Moolenaar, S. Pyne, G. Tigyi: International Union of Pharmacology. XXXIV. Lysophospholipid Receptor Nomenclature. In: Pharmacological Reviews 54, pp. 265-269 (2002).
  • A. Yamashita, S. Oka, T. Tanikawa, Y. Hayashi, Y. Nemoto-Sasaki, T. Sugiura: The actions and metabolism of lysophosphatidylinositol, an endogenous agonist for GPR55. In: Prostaglandins & other lipid mediators. Volume 107, December 2013, pp. 103-116, doi : 10.1016 / j.prostaglandins.2013.05.004 , PMID 23714700 .

Individual evidence

  1. ↑ a b Data sheet L-α-Lysophosphatidylinositol sodium salt from soybean, ≥98.0% (TLC) from Sigma-Aldrich , accessed on February 20, 2015 ( PDF ).
  2. ↑ S. Oka, K. Nakajima, A. Yamashita, S. Kishimoto, T. Sugiura: Identification of GPR55 as a lysophosphatidylinositol receptor. In: Biochemical and biophysical research communications. Volume 362, Number 4, November 2007, pp. 928-934, doi : 10.1016 / j.bbrc.2007.08.078 , PMID 17765871 .
  3. ^ A b S. Oka, T. Toshida, K. Maruyama, K. Nakajima, A. Yamashita, T. Sugiura: 2-arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55. In: Journal of biochemistry. Volume 145, Number 1, January 2009, pp. 13-20, doi : 10.1093 / jb / mvn136 , PMID 18845565 .
  4. ↑ R. Piñeiro, M. Falasca: lysophosphatidylinositol signaling: new wine from bottle to old. In: Biochimica et Biophysica Acta . Volume 1821, Number 4, April 2012, pp. 694-705, doi : 10.1016 / j.bbalip.2012.01.009 , PMID 22285325 .
  5. ↑ YM AlSuleimani, CR Hiley: The GPR55 agonist lysophosphatidylinositol mediates vasorelaxation of the rat mesenteric resistance artery and induces calcium release in rat mesenteric artery endothelial cells. In: British journal of pharmacology. [Electronic publication before printing] February 2015, doi : 10.1111 / bph.13107 , PMID 25652040 .