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Lysophosphatidylinositol

From Wikipedia, the free encyclopedia
Lysophosphatidylinositol
Names
IUPAC name
[(2R)-2-hydroxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]-oxyphosphoryl]oxypropyl] hexadecanoate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C25H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)35-16-18(26)17-36-38(33,34)37-25-23(31)21(29)20(28)22(30)24(25)32/h18,20-26,28-32H,2-17H2,1H3,(H,33,34)/t18-,20?,21-,22+,23-,24-,25?/m1/s1
    Key: UOXRPRZMAROFPH-IESLQMLBSA-N
  • CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC1[C@@H]([C@H](C([C@H]([C@H]1O)O)O)O)O)O
Properties
C25H49O12P
Molar mass572.629 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Lysophosphatidylinositol (LPI,lysoPI), orL-α-lysophosphatidylinositol, is anendogenouslysophospholipid andendocannabinoidneurotransmitter.[1] LPI, along with its 2-arachidonoyl- derivative,2-arachidonoyl lysophosphatidylinositol (2-ALPI), have been proposed as the endogenousligands ofGPR55.[2][3][4][5] Recent studies have shown that the fatty acyl composition of LPI influences neuroinflammatory responses in primary neuronal cultures, highlighting its potential role in neuroinflammation.[6]

See also

[edit]

References

[edit]
  1. ^Li X, Wang L, Fang P, et al. (May 2018)."Lysophospholipids induce innate immune transdifferentiation of endothelial cells, resulting in prolonged endothelial activation".The Journal of Biological Chemistry.293 (28):11033–11045.doi:10.1074/jbc.RA118.002752.PMC 6052225.PMID 29769317.
  2. ^Oka S, Nakajima K, Yamashita A, Kishimoto S, Sugiura T (November 2007). "Identification of GPR55 as a lysophosphatidylinositol receptor".Biochemical and Biophysical Research Communications.362 (4):928–34.Bibcode:2007BBRC..362..928O.doi:10.1016/j.bbrc.2007.08.078.PMID 17765871.
  3. ^Henstridge CM, Balenga NA, Ford LA, Ross RA, Waldhoer M, Irving AJ (January 2009)."The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation".The FASEB Journal.23 (1):183–93.doi:10.1096/fj.08-108670.PMID 18757503.S2CID 27142069.
  4. ^Piñeiro, Roberto; Falasca, Marco (2012)."Lysophosphatidylinositol signalling: New wine from an old bottle".Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids.1821 (4):694–705.doi:10.1016/j.bbalip.2012.01.009.PMID 22285325.
  5. ^Oka S, Toshida T, Maruyama K, Nakajima K, Yamashita A, Sugiura T (January 2009). "2-Arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55".Journal of Biochemistry.145 (1):13–20.doi:10.1093/jb/mvn136.PMID 18845565.
  6. ^Brenneman DE, Petkanas D, Ippolito M, Ward SJ (2025)."Effect of Fatty Acyl Composition for Lysophosphatidylinositol on Neuroinflammatory Responses in Primary Neuronal Cultures".Journal of Molecular Neuroscience.75 (1) 35.doi:10.1007/s12031-025-02326-7.PMC 11760249.PMID 39866868.
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