<abstract xmlns="http://www.w3.org/1999/xhtml"><p>The chiral separation of minor alkaloids from tobacco is of interest because R and S isomers of these compounds have differences in their physiological activity. This difference is also reflected in the physiological properties of tobaccospecific<italic>N</italic>’-nitrosamines (TSNAs), in particular that of <italic>N</italic>’-nitrosonornicotine. This compound results mainly from nornicotinenitrosation. The previously reported analytical techniques for the enantiomer separation of minor alkaloids have various shortcomings, such as the need for bidimensional chromatography or poor enantiomer separation. A new method for the analysis of nornicotine, anabasine and anatabine has been developed, based on an original derivatization and a simple gas chromatography/ mass spectrometry (GC/MS) analysis. The method allows separate quantitation of S-nornicotine and R-nornicotine, and the analysis of anabasine and anatabine (without isomer separation). It was found that the proportion of S-nornicotine in the total nornicotine present in tobacco varies, depending on the tobacco type, between 52.6% for a flue-cured tobacco to 91.4% for a Burley. Green tobaccos (freeze dried) showed lower levels of minor alkaloids and S-nornicotine accounted for between 31.6% to 43.8% of the total nornicotine (in the analyzed samples).</p></abstract>

The chiral separation of minor alkaloids from tobacco is of interest because R and S isomers of these compounds have differences in their physiological activity. This difference is also reflected in the physiological properties of tobaccospecificN’-nitrosamines (TSNAs), in particular that of N’-nitrosonornicotine. This compound results mainly from nornicotinenitrosation. The previously reported analytical techniques for the enantiomer separation of minor alkaloids have various shortcomings, such as the need for bidimensional chromatography or poor enantiomer separation. A new method for the analysis of nornicotine, anabasine and anatabine has been developed, based on an original derivatization and a simple gas chromatography/ mass spectrometry (GC/MS) analysis. The method allows separate quantitation of S-nornicotine and R-nornicotine, and the analysis of anabasine and anatabine (without isomer separation). It was found that the proportion of S-nornicotine in the total nornicotine present in tobacco varies, depending on the tobacco type, between 52.6% for a flue-cured tobacco to 91.4% for a Burley. Green tobaccos (freeze dried) showed lower levels of minor alkaloids and S-nornicotine accounted for between 31.6% to 43.8% of the total nornicotine (in the analyzed samples).

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

R.J. Reynolds Tobacco Co., 950 Reynolds Blvd., Winston-Salem, NC 27105, USA

Contributions to Tobacco & Nicotine Research

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The chiral separation of minor alkaloids from tobacco is of interest because R and S isomers of these compounds have differences in their physiological...

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

Published Online: Dec 30, 2014

Page range: 649 - 659

Received: Apr 15, 2013

Accepted: Aug 30, 2013

DOI: https://doi.org/10.2478/cttr-2013-0941

© 2013 Beiträge zur Tabakforschung International

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.