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Taspine

Taspine
Names
IUPAC name
1-[2-(Dimethylamino)ethyl]-3,8-dimethoxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione
Other names
Thaspine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C20H19NO6/c1-21(2)8-7-10-9-13(25-4)18-16-14(10)20(23)27-17-12(24-3)6-5-11(15(16)17)19(22)26-18/h5-6,9H,7-8H2,1-4H3
    Key: MTAWKURMWOXCEO-UHFFFAOYSA-N
  • CN(C)CCC1=CC(=C2C3=C1C(=O)OC4=C(C=CC(=C34)C(=O)O2)OC)OC
Properties
C20H19NO6
Molar mass 369.4 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Taspine is an alkaloid which acts as a potent acetylcholinesterase inhibitor and cicatrizant. It is found in various plants including Magnolia x soulangeana[1] and Croton lechleri.[2]

The first total synthesis was reported by T. Ross Kelly and Roger L. Xie in 1998.[3]

References

  1. ^ Rollinger, JM; Schuster, D; Baier, E; Ellmerer, EP; Langer, T; Stuppner, H (2006). "Taspine: Bioactivity-guided isolation and molecular ligand-target insight of a potent acetylcholinesterase inhibitor from Magnolia x soulangiana". Journal of Natural Products. 69 (9): 1341–1346. doi:10.1021/np060268p. PMC 3526713. PMID 16989531.
  2. ^ Vaisberg, A.; Milla, M.; Planas, M.; Cordova, J.; De Agusti, E.; Ferreyra, R.; Mustiga, M.; Carlin, L.; Hammond, G. (2007). "Taspine is the Cicatrizant Principle in Sangre de Grado Extracted from Croton lechleri". Planta Medica. 55 (2): 140–143. doi:10.1055/s-2006-961907. PMID 2748730. S2CID 260251205.
  3. ^ Kelly, T. Ross; Xie, Roger L. (October 1998). "Total Synthesis of Taspine". The Journal of Organic Chemistry. 63 (22): 8045–8048. doi:10.1021/jo981099j.


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