Nicotine demethylation in Nicotiana cell suspension cultures: N′-formylnornicotine is not involved

Phytochemistry

Volumn 66, Issue 20, 2005, Pages 2432-2440

  Bartholomeusz, Trixie Ann ^a   Bhogal, Ramneek K ^a   Molinié, Roland ^b   Felpin, François Xavier ^b   Mathé Allainmat, Monique ^b   Meier, Anna Carolin ^c   Dräger, Birgit ^c   Lebreton, Jacques ^b   Roscher, Albrecht ^a   Robins, Richard J ^b   Mesnard, François ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^b UNIVERSITÉ DE NANTES   (France)

^c MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Demethylation; N Formylnornicotine; Nicotiana plumbaginifolia; Nicotine; Nornicotine; Solanaceae

Indexed keywords

ALKALOID; COTININE; DRUG DERIVATIVE; MYOSMINE; N' FORMYLNORNICOTINE; N'-FORMYLNORNICOTINE; NICOTINE; NITROGEN; NORNICOTINE;

ARTICLE; CELL CULTURE; CULTURE TECHNIQUE; CYTOLOGY; MASS FRAGMENTOGRAPHY; METABOLISM; METHODOLOGY; METHYLATION; TOBACCO;

ALKALOIDS; CELL CULTURE TECHNIQUES; CELLS, CULTURED; COTININE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; METHYLATION; NICOTINE; NITROGEN ISOTOPES; TOBACCO;

MAGNOLIOPHYTA; NICOTIANA; NICOTIANA PLUMBAGINIFOLIA; SOLANACEAE;

EID: 26444567301     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2005.07.005     Document Type: Article

References (29)

1. W. Barz, M. Kettner, and W. Hüsemann On the degradation of nicotine in Nicotiana cell suspension cultures Planta Med 34 1978 73 78
2. B.C. Bose, H.N. De, and S. Mohammed Studies on the biogenesis of nicotine alkaloids in tobacco plants. Part II. Investigation on transmethylation of nicotine and nor-nicotine in Nicotiana tabacum Ind. J. Med. Res. 44 1956 91 97
3. M. Botte, F. Mabon, M. Le Mouillour, and R.J. Robins Biosynthesis of nornicotine in root cultures of Nicotiana alata does not involve oxidation at C-5′ of nicotine Phytochemistry 46 1997 117 122
4. R. Chelvarajan, F. Fannin, and L.P. Bush Study of nicotine demethylation in Nicotiana otophora J. Agric. Food Chem. 41 1993 858 862
5. R.F. Dawson On the biogenesis of nornicotine and anabasine J. Am. Chem. Soc. 67 1945 503 504
6. A.M. Duffield, H. Budzikiewicz, and C. Djerassi Mass spectrometry in structural and stereochemical problems. LXXXII. A study of the fragmentation processes of some tobacco alkaloids J. Am. Chem. Soc. 87 1965 2926 2932
7. J. Dyar Nicotine to nornicotine conversion Plant Physiol. 6 suppl 1975 56
8. Girard, S., 2000. Etude du mécanisme de demethylation de la nicotine chez les plantes. Ph.D. thesis, University of Nantes, Nantes.
9. J.W. Gorrod, and G. Schepers Biotransformation of nicotine in mammalian systems J.W. Gorrod P. Jacob Analytical Determination of Nicotine and Related Compounds and Their Metabolites 1999 Elsevier Amsterdam 45 67
10. A.D. Hanson, D.A. Gage, and Y. Shachar-Hill Plant one-carbon metabolism and its engineering Trends Plant Sci. 5 2000 206 213
11. D.Y. Hao, and M.M. Yeoman Mechanism of nicotine N-demethylation in tobacco cell suspension cultures Phytochemistry 41 1996 477 482
12. D.Y. Hao, and M.M. Yeoman Nicotine N-demethylase in cell-free preparations from tobacco cell cultures Phytochemistry 42 1996 325 329
13. D.Y. Hao, and M.M. Yeoman Evidence in favour of an oxidative N-demethylation of nicotine to nornicotine in tobacco cell cultures J. Plant Physiol. 152 1998 420 426
14. M.C. Hobbs, and M.M. Yeoman Biotransformation of nicotine to nornicotine by cell suspensions of Nicotiana tabacum L. cv. Wisconsin-38 New Phytol. 119 1991 477 482
15. T. Kisaki, and E. Tamaki Phytochemical studies of the tobacco alkaloids. Degradation of the tobacco alkaloids and their optical rotatory changes in tobacco plants Phytochemistry 5 1966 293 300
16. G. Laue, C.A. Preston, and I.T. Baldwin Fast track to the trichome: induction of N-acyl nornicotines precedes nicotine induction in Nicotiana repanda Planta 210 2000 510 514
17. E. Leete Biosynthesis and metabolism of the tobacco alkaloids S. Pelletier Alkaloids: Chemical and Biological Perspectives 1983 John Wiley and Sons Chichester 85 152
18. E. Leete, and V.M. Bell The biogenesis of the Nicotiana alkaloids. VIII. The metabolism of nicotine in N. tabacum J. Am. Chem. Soc. 81 1959 4358 4359
19. E. Leete, and M.R. Chedekel Metabolism of nicotine in Nicotiana glauca Phytochemistry 13 1974 1853 1859
20. F. Manceau, M.-A. Fliniaux, and A. Jacquin-Dubreuil Ability of a Nicotiana plumbaginifolia cell suspension to demethylate nicotine into nornicotine Phytochemistry 28 1989 2671 2674
21. H. Matsushita, Y. Tsujino, D. Yoshida, A. Saito, T. Kisaki, K. Kato, and M. Noguchi New minor alkaloids in flue-cured tobacco leaf (Nicotiana tabacum cv. BY260-9) Agric. Biol. Chem. 43 1979 193 194
22. F. Mesnard, S. Girard, O. Fliniaux, R.K. Bhogal, F. Gillet, J. Lebreton, M.-A. Fliniaux, and R.J. Robins Chiral specificity of the degradation of nicotine by Nicotiana plumbaginifolia cell suspension cultures Plant Sci. 161 2001 1011 1018
23. F. Mesnard, A. Roscher, A. Garlick, S. Girard, E. Baguet, R. Arroo, J. Lebreton, R.J. Robins, and R.G. Ratcliffe Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures Planta 214 2002 911 919
24. Molinié, R., 2005. Effet isotopique cinétique de l'azote au cours de la déméthylation des alcaloÏdes par les plantes et les bactéries. Ph.D. thesis, Université de Nantes, Nantes.
25. T.L. Nguyen, L.D. Gruenke, and N.J. Castagnoli Metabolic oxidation of nicotine to chemically reactive intermediates J. Med. Chem. 22 1979 259 263
26. L.A. Peterson, and N.J. Castagnoli Regio- and stereochemical studies on the α-carbon oxidation of (S)-nicotine by cytochrome P-450 model systems J. Med. Chem. 31 1988 637 640
27. G.M. Strunz, and J.A. Findlay Pyridine and piperidine alkaloids A. Brossi The Alkaloids 1985 Academic Press Orlando, FL 89 183
28. T.C. Tso, and R.N. Jeffery Biochemical studies on tobacco alkaloids IV. The dynamic state of nicotine supplied to N. rustica Arch. Biochem. Biophys. 92 1961 253 256
29. G. Vo-Thanh, F.X. Felpin, G. Nourrisson, M. Trierweiler, R.J. Robins, and J. Lebreton Synthesis of N-15-labelled nornicotine and N-15-labelled nicotine J. Label. Compds. Radiopharm. 4 2001 881 888