{{short description|Chemical compound}} {{Chembox | ImageFile = Taspine.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt = | IUPACName = 1-[2-(Dimethylamino)ethyl]-3,8-dimethoxy[1]benzopyrano[5,4,3-''cde''][1]benzopyran-5,10-dione | OtherNames = Thaspine | Section1 = {{Chembox Identifiers | CASNo = 602-07-3 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = V53XN9L07O | PubChem = 215159 | ChemSpiderID = 186530 | 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 | InChIKey =MTAWKURMWOXCEO-UHFFFAOYSA-N | SMILES = CN(C)CCC1=CC(=C2C3=C1C(=O)OC4=C(C=CC(=C34)C(=O)O2)OC)OC}} | Section2 = {{Chembox Properties | Formula = C<sub>20</sub>H<sub>19</sub>NO<sub>6</sub> | MolarMass = 369.4 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = }} }}
'''Taspine''' is an alkaloid which acts as a potent acetylcholinesterase inhibitor and cicatrizant. It is found in various plants including ''Magnolia x soulangeana''<ref>{{cite journal | journal = Journal of Natural Products | year = 2006 | volume = 69 | pages = 1341–1346 | doi = 10.1021/np060268p | pmid = 16989531 | last1 = Rollinger | first1 = JM | last2 = Schuster | first2 = D | last3 = Baier | first3 = E | last4 = Ellmerer | first4 = EP | last5 = Langer | first5 = T | last6 = Stuppner | first6 = H | title = Taspine: Bioactivity-guided isolation and molecular ligand-target insight of a potent acetylcholinesterase inhibitor from ''Magnolia'' x ''soulangiana'' | issue = 9 | pmc=3526713}}</ref> and ''Croton lechleri''.<ref>{{Cite journal | last1 = Vaisberg | first1 = A. | last2 = Milla | first2 = M. | last3 = Planas | first3 = M. | last4 = Cordova | first4 = J. | last5 = De Agusti | first5 = E. | last6 = Ferreyra | first6 = R. | last7 = Mustiga | first7 = M. | last8 = Carlin | first8 = L. | last9 = Hammond | first9 = G. | doi = 10.1055/s-2006-961907 | title = Taspine is the Cicatrizant Principle in Sangre de Grado Extracted from ''Croton lechleri'' | journal = Planta Medica | volume = 55 | issue = 2 | pages = 140–143 | year = 2007 | pmid = 2748730 | pmc = | s2cid = 260251205 }}</ref>
The first total synthesis was reported by T. Ross Kelly and Roger L. Xie in 1998.<ref>{{cite journal|last1=Kelly|first1=T. Ross|last2=Xie|first2=Roger L.|title=Total Synthesis of Taspine|journal=The Journal of Organic Chemistry|date=October 1998|volume=63|issue=22|pages=8045–8048|doi=10.1021/jo981099j}}</ref>
== References == {{reflist}}
{{Acetylcholine metabolism and transport modulators}}
Category:Acetylcholinesterase inhibitors Category:Neurotoxins Category:Alkaloids found in Euphorbiaceae Category:Phenethylamine alkaloids Category:Lactones Category:Dimethylamino compounds Category:Heterocyclic compounds with 4 rings Category:Phenol ethers Category:Methoxy compounds Category:Total synthesis
{{Alkaloid-stub}}