Identification and synthesis of novel alkaloids from the root system of Nicotiana tabacum: affinity for neuronal nicotinic acetylcholine receptors.

作者: Xiaochen Wei , Sangeetha P. Sumithran , A. Gabriela Deaciuc , Harold R. Burton , Lowell P. Bush

DOI: 10.1016/J.LFS.2005.09.009

关键词:

摘要: A novel pyridine derivative, 3,5-bis-(1-methyl-pyrrolidin-2-yl)-pyridine, and a pair of diastereomers 1,1'-dimethyl-[2,3']bipyrrolidinyl were isolated from the root Nicotiana tabacum plants identified as alkaloids by GC-MS analysis. The structures these new confirmed total synthesis. affinities alkaloids, other structurally related compounds for alpha4beta2*, alpha7* neuronal nicotinic acetylcholine receptors (nAChRs), nAChRs mediating nicotine-evoked dopamine release rat striatum also assessed. results indicate that do not interact with nAChRs, but inhibit [3H]nicotine binding to alpha4beta2* nAChR subtype. demonstrate act antagonists at striatum.

参考文章(14)
Lowell Bush, Walter P. Hempfling, Harold Burton, Biosynthesis of nicotine and related compounds Analytical Determination of Nicotine and Related Compounds and their Metabolites. pp. 13- 44 ,(1999) , 10.1016/B978-044450095-3/50003-6
R. Lukeš, J. Plešek, J. Trojánek, Über die reduktionsprodukte des 1-methylpyrrols Collection of Czechoslovak Chemical Communications. ,vol. 24, pp. 1987- 1992 ,(1959) , 10.1135/CCCC19591987
T. Cserháti, Analytical Determination of Nicotine and Related Compounds and their Metabolites Journal of Chromatography B: Biomedical Sciences and Applications. ,vol. 752, pp. 187- ,(2001) , 10.1016/S0378-4347(00)00480-1
Paul M. Dewick, Medicinal Natural Products: A Biosynthetic Approach Medicinal natural products: a biosynthetic approach.. ,(1997)
Edward Leete, Sung Hoon Kim, Jatinder Rana, The incorporation of [2-13C,14C,15N]-1-methyl-Δ1-pyrrolinium chloride into cuscohygrine in Erythroxylum coca Phytochemistry. ,vol. 27, pp. 401- 406 ,(1988) , 10.1016/0031-9422(88)83107-8
Guangrong Zheng, Linda P. Dwoskin, Agripina G. Deaciuc, Jun Zhu, Marlon D. Jones, Peter A. Crooks, Lobelane analogues as novel ligands for the vesicular monoamine transporter-2 Bioorganic & Medicinal Chemistry. ,vol. 13, pp. 3899- 3909 ,(2005) , 10.1016/J.BMC.2005.04.013
George A. Swan, John D. Wilcock, Reduction of some N-alkyl- and N-aryl-pyrrolidin-2-ones and -piperidin-2-ones by lithium aluminium hydride Journal of the Chemical Society, Perkin Transactions 1. ,vol. 5, pp. 885- 891 ,(1974) , 10.1039/P19740000885