title: (-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia tupa with Agonist Activity at Nicotinic Acetylcholine Receptor.
abstract: Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at α3β2/α3β4 nAChR and α7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR.
authors.forename: Cristian
authors.initials: C
authors.lastname: Paz
authors.forename: Jose
authors.initials: J
authors.lastname: Becerra
authors.forename: Mario
authors.initials: M
authors.lastname: Silva
authors.forename: Viviana
authors.initials: V
authors.lastname: Burgosa
authors.forename: Matthias
authors.initials: M
authors.lastname: Heydenreich
authors.forename: Bernd
authors.initials: B
authors.lastname: Schmidt
authors.forename: Thu
authors.initials: T
authors.lastname: Tran
authors.forename: Irina
authors.initials: I
authors.lastname: Vetter
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D006801:Humans; D029746:Lobelia / Q000737:chemistry*; D015394:Molecular Structure; D018733:Nicotinic Antagonists; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry*; D011978:Receptors, Nicotinic / Q000737:chemistry
chemical_list: D000470:Alkaloids; D018733:Nicotinic Antagonists; D010936:Plant Extracts; D011978:Receptors, Nicotinic