Evaluation of Several Minor Alkaloid Levels in Tobacco with Separation of R- and S-Nornicotine

1. Saunders, J.A. and D.E. Blume: Quantitation of Major Tobacco Alkaloids by High-Performance Liquid Chro-matography; J. Chromatogr. 205 (1981) 147–154.Search in Google Scholar

2. Wu, W., D.L. Ashley, and C.H. Watson: Determination of Nicotine and Other Minor Alkaloids in International Cigarettes by Solid-Phase Microextraction and Gas Chromatography/Mass Spectrometry; Anal. Chem. 74 (2002) 4878–4884.Search in Google Scholar

3. Pakhale, S.S. and G.B. Maru: Distribution of Major and Minor Alkaloids in Tobacco, Mainstream and Sidestream Smoke of Popular Indian Smoking Products; Food Chem. Toxicol. 36 (1998) 1131–1138.Search in Google Scholar

4. Yang, S.S. and I. Smetena: Evaluation of Capillary Electrophoresis for the Analysis of Nicotine and Se-lected Minor Alkaloids from Tobacco; Chromato-graphia 40 (1995) 375–378.Search in Google Scholar

5. Sheng, L.Q., L. Ding, H.W. Tong, G.P. Yong, X.Z. Zhou, and S.M. Liu: Determination of Nicotine-Re-lated Alkaloids in Tobacco and Cigarette Smoke by GC-FID; Chromatographia 62 (2005) 63–68.Search in Google Scholar

6. Chen, P.X., N. Qian, H.R. Burton, and S.C. Moldoveanu: Analysis of Minor Alkaloids in Tobacco: A Collaborative Study; Beitr. Tabakforsch. Int. 21 (2005) 369–379.Search in Google Scholar

7. Gorrod, J.W. and P. Jacob III (Eds.): Analytical De-termination of Nicotine and Related Compounds and Their Metabolites; Elsevier, Amsterdam, Nether-lands,1999.Search in Google Scholar

8. Seeman, J.I.: “The Nicotine Analogue Program” - A 13. Review; Revision (January 16, 1995) of original report (June 13, 1994); available at: http://legacy.library. ucsf.edu/documentStore/n/c/t/nct13e00/Snct13e00.pdf, (accessed September 04, 2013). 14.Search in Google Scholar

9. Hoffmann, D., K.D. Brunnemann, B. Prokopczyk, and M.V. Djordjevic: Tobacco-Specific N-Nitrosamines and Areca-Derived N-Nitrosamines: Chemistry, Bio- chemistry, Carcinogenicity, and Relevance to Hu-15. mans; J. Toxicol. Environ. Health 41 (1994) 1–52.Search in Google Scholar

10. Jacob, P. III, L. Yu, G. Liang, A.T. Shulgin, and N.L. Benowitz: Gas Chromatographic-Mass Spectrometric 16. Method for Determination of Anabasine, Anatabine and Other Tobacco Alkaloids in Urine of Smokers and Smokeless Tobacco Users; J. Chromatogr. 619 (1993) 49–61. 17.Search in Google Scholar

11. Zhang, Y., P. Jacob III, and N.L. Benowitz: Determi-nation of Nornicotine in Smoker's Urine by Gas Chro-matography Following Reductive Alkylation to N’-Propylnornicotine; J. Chromatogr. 525 (1990) 349–357.Search in Google Scholar

12. Siminszky, B., L. Gavilano, S.W. Bowen, and R.E. Dewey: Conversion of Nicotine to Nornicotine in Nicotiana tabacum is Mediated by CYP82E4, a Cyto-chrome P450 Monooxygenase; Proc. Natl. Acad. Sci. USA 102 (2005) 14919–14924.Search in Google Scholar

13. Gorrod, J.W. and J. Wahren (Eds.): Nicotine and Re-lated Alkaloids: Absorption, Distribution, Metabolism and Excretion; Chapman & Hall Ltd., London, UK, 1993.10.1007/978-94-011-2110-1Search in Google Scholar

14. Armstrong, D.W., X. Wang, and N. Ercal: Enantiomeric Composition of Nicotine in Smokeless Tobacco, Medicinal Products, and Commercial Re-agents; Chirality 10 (1998) 587–591.Search in Google Scholar

15. Armstrong, D.W., X. Wang, J.-T. Lee, and Y.-S. Liu: Enantiomeric Composition of Nornicotine, Anatabine, and Anabasine in Tobacco; Chirality 11 (1999) 82–84.Search in Google Scholar

16. Stepanov, I., K. Yershova, S. Carmella, P. Upadhyaya, S.S. Hecht: Levels of (S)-N’-Nitrosonornicotine in U.S. Tobacco Products; Nicotine Tob. Res. 15 (2013) 1305–1310.10.1093/ntr/nts249368284023212437Search in Google Scholar

17. Balbo, S., S. James-Yi, M.G. O'Sullivan, I. Stepanov, M. Wang, S. Zhang, F. Kassie, S. Carmella, C. Wettlaufer, K. Hohol, A. Knezevich, P. Upadhyaya, and S.S. Hecht: (S)-N’-Nitrosonornicotine, a Constitu-ent of Smokeless Tobacco, Is a Potent Oral Tumorigen in Rats; Proc. AACR 103^rd Annual Meeting, March 31–April 4, 2012, Chicago, IL, Abstract LB-63, Cancer Res. 72 (8 Suppl. 1) (2012) LB-63.10.1158/1538-7445.AM2012-LB-63Search in Google Scholar

18. Hoffmann, D. and S.S. Hecht: Nicotine-Derived N-Nitrosamines and Tobacco-Related Cancer; Current Status and Future Directions; Cancer Res. 45 (1985) 935–944.Search in Google Scholar

19. Hecht, S.S. and D. Hoffmann: Tobacco-Specific Nitrosamines, an Important Group of Carcinogens in Tobacco and Tobacco Smoke; Carcinogenesis 9 (1988) 875–884.Search in Google Scholar

20. Cai, B., A. Jack, R.S. Lewis, R.E. Dewey, H. Ji, L. Bush: Accumulation of Nicotine and Nornicotine En-antiomers in Leaves of Nicotine Demethylase Mutants During Growth and Curing; 66^th Tobacco Science Research Conference, Concord, NC, Sept. 9-12, 2012, Poster No. 13.Search in Google Scholar

21. Späth, E. and F. Kesztler: Über das Vorkommen von d, l-Nor-nicotin, d, l-Anatabin und l-Anabasin im Tabak (XII. Mitteil. über Tabakalkaloide) [On the Presence of d, l-Nornicotine, d, l-Anatabine and l-Anabasine in Tobacco (XII^th Report on Tobacco Alkaloids)]; Ber. Dtsch. Chem. Ges. A/B 70 (1937) 704–709.Search in Google Scholar

22. Tang, Y., W.L. Zielinski, and H.M. Bigott: Separation of Nicotine and Nornicotine Enantiomers via Normal Phase HPLC on Derivatized Cellulose Chiral Station-ary Phases; Chirality 10 (1998) 364–369.Search in Google Scholar

23. Perfetti, T.A. and W.M. Coleman III: Chiral-Gas Chromatograpy-Selected Ion Monitoring-Mass Selective Detection Analysis of Secondary Alkaloids in Tobacco and Tobacco Smoke; Beitr. Tabakforsch. Int. 18 (1998) 35–42.Search in Google Scholar

24. Liu, B., C. Chen, D. Wu, and Q. Su: Enantiomeric Analysis of Anatabine, Nornicotine and Anabasine in Commercial Tobacco by Multi-Dimensional Gas Chromatography and Mass Spectrometry; J. Chro-matogr. B 865 (2008) 13–17.Search in Google Scholar

25. Cai, J., B. Liu, P. Lin, and Q. Su: Fast Analysis of Nicotine and Related Alkaloids in Tobacco and Ciga-rette Smoke by Megabore Capillary Gas Chromatogra-phy; J. Chromatogr. A 1017 (2003) 187–193.Search in Google Scholar