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(-)-Pentylsedinine, a New Alkaloid from the Leaves of Lobelia tupa with Agonist Activity at Nicotinic Acetylcholine Receptor

  • 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 alpha 3 beta 2/alpha 3 beta 4 nAChR and alpha 7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR

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Author:Cristian Paz, Jose Becerra, Mario Silva, Viviana Burgos, Matthias Heydenreich, Bernd SchmidtORCiDGND, Thu Tran, Irina Vetter
ISSN:1934-578X (print)
ISSN:1555-9475 (online)
Pubmed Id:http://www.ncbi.nlm.nih.gov/pubmed?term=26434115
Parent Title (English):Natural product communications : an international journal for communications and reviews
Place of publication:Westerville
Document Type:Article
Year of first Publication:2015
Year of Completion:2015
Release Date:2017/03/27
Tag:Lobelia tupa; Pentylsedinine; Piperidine alkaloid; nAChR
First Page:1355
Last Page:1357
Funder:FONDECYT from the Chilean Government [3130378]; Deutscher Akademischer Austauschdienst (DAAD - Germany); Australian Research Council; Universidad de La Frontera
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert