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

Life Sciences

Volumn 78, Issue 5, 2005, Pages 495-505

  Wei, Xiaochen ^a   Sumithran, Sangeetha P ^a   Deaciuc, A Gabriela ^a   Burton, Harold R ^b   Bush, Lowell P ^b   Dwoskin, Linda P ^a   Crooks, Peter A ^a  

^a University of Kentucky   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Alkaloids; Neuronal nicotinic acetylcholine receptors; Nicotiana tabacum; Nicotine

Indexed keywords

ALKALOID DERIVATIVE; ANABASINE; ANATABINE; DOPAMINE; NICOTINE; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR BLOCKING AGENT; NORNICOTINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; CONFERENCE PAPER; CONTROLLED STUDY; DOPAMINE RECEPTOR BLOCKING; DOPAMINE RELEASE; DRUG DETERMINATION; DRUG ISOLATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; RAT; RECEPTOR AFFINITY; TOBACCO;

ALKALOIDS; ANIMALS; BINDING, COMPETITIVE; DOPAMINE; HUMANS; NICOTINE; PLANT ROOTS; RECEPTORS, NICOTINIC; TOBACCO;

ANIMALIA; NICOTIANA TABACUM;

EID: 27844477780     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2005.09.009     Document Type: Conference Paper

References (17)

1. K. Bernauer, and F. Gretillat Stereoselectivity in reactions of metal complexes: Part XI. 2,6-Bis(pyrrolidin-2-yl)pyridine: synthesis and resolution of the meso and optically active isomers. Complex formation with copper(II) ion in aqueous solution Helvetica Chimica Acta 72 1989 477 481
2. L. Bush, W.P. Hempflin, and H. Burton Biosynthesis of nicotine and related compounds J.W. Gorrod P. Jacob III. Analytical Determination of Nicotine and Related Compounds and Their Metabolites 1999 Elsevier Science B.V. Amsterdam, The Netherlands 13 44
3. Y.-C. Cheng, and W.H. Prusoff Relation between the inhibition constant K1) and the concentration of inhibitor which causes fifty percent inhibition (I50) of an enzymic reaction Biochemical Pharmacology 22 23 1973 3099 3108
4. P.M. Dewick Medicinal Natural Products: A Biosynthetic Approach 1997 J. Wiley & Sons Chichester Chapter 6
5. Ernest L. Eliel, Richard T. McBride, and St. Kaufmann Abnormal Chichibabin reactions. The condensation of phenylacetaldehyde and homoveratraldehyde with ammonia Journal of the American Chemical Society 75 1953 4291 4296
6. Friedhelm Feth, and Karl G. Wagner Determination of ornithine, putrescine, N-methylputrescine and N-methylpyrroline pools in tobacco tissue by high-performance liquid chromatography Physiologia Plantarum 75 1989 71 74
7. 3H] dopamine overflow from superfused rat striatal slices Journal of Pharmacology and Experimental Therapeutics 306 3 2003 1011 1020
8. E. Leete, S.H. Kim, and J. Rana Chemistry of the tropane alkaloids and related compounds. Part 38. The incorporation of [2-13C, 14C,15N]-1-methyl- Δ1-pyrrolinium chloride into cuscohygrine in Erythroxylum coca Phytochemistry 27 2 1988 401 406
9. N.J. Leonard, and A.G. Cook Unsaturated amines: XIV. The mercuric acetate oxidation of substituted pyrrolidines Journal of the American Chemical Society 81 1959 5627 5631
10. R. Lukes, J. Plesek, and J. Trojanek 1-Methylpyrrole reduction products Collection of Czechoslovak Chemical Communications 24 1959 1987 1992
11. G. Massiot, and C. Delaude Pyrrolidine alkaloids A. Brossi The Alkaloids vol. 27 1986 Academic Press, Inc. Orlando, FL 269 322
12. D.P. Matthews Synthesis of novel N-(1,2,3,7,8,9,9a,9b-octahydro-3- (phenylmethyl)-5H-dipyrrolo[1,2-c:3,2-e]pyrimidine-5-ylidene)benzenamine derivatives Journal of Heterocyclic Chemistry 22 5 1985 1381 1382
13. E. Späth, and H. Bretschneider A new synthesis of nicotine and some remarks on the work of Nagal on ephedrine Chemische Berichte 61B 1928 327 334
14. G.A. Swan, and J.D. Wilcock Reduction of N-alkyl- and N-arylpyrrolidin-2-ones and-piperidin-2-ones by lithium aluminum hydrides Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry 8 1974 885 891
15. Weeks, W.W., 1999. Chapter 8D, Relationship between leaf chemistry and organoleptic properties of tobacco smoke, In: Davis, D.L., Nielsen, M.T. (Ed), Tobacco: Production, Chemistry, and Technology, Iowa State Press. Blackwell Science, Inc., Malden, MA. pp. 304-312.
16. Wei, X., 2000. Studies on the biosynthesis and metabolism of pyridine alkaloids in Nicotiana Species. Dissertation. The University of Kentucky, Lexington, KY.
17. G. Zheng, L.P. Dwoskin, A.G. Deaciuc, J. Zhu, M.D. Jones, and P.A. Crooks Lobeline analogues as novel ligands for the vesicular monoamine transporter-2 Bioorganic and Medicinal Chemistry 13 12 2005 3899 3909