Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry.
A fully automated multi-dimensional gas chromatography (MDGC) system with a megabore precolumn and cyclodextrin-based analytical column was developed to analyze the enantiomeric compositions of anatabine, nornicotine and anabasine in commercial tobacco. The enantiomer abundances of anatabine and nornicotine varied among different tobacco. S-(-)-anatabine, as a proportion of total anatabine, was 86.6% for flue-cured, 86.0% for burley and 77.5% for oriental tobacco. S-(-)-nornicotine, as a proportion of total nornicotine, was 90.8% in oriental tobacco and higher than in burley (69.4%) and flue-cured (58.7%) tobacco. S-(-)-anabasine, as a proportion of total anabasine, was relatively constant for flue-cured (60.1%), burley (65.1%) and oriental (61.7%) tobacco. A simple solvent extraction with dichloromethane followed by derivatisation with trifluoroacetic anhydride gave relative standard deviations of less than 1.5% for the determination of the S-(-)-isomers of all three alkaloids. The study also indicated that, a higher proportion of S-(-)-nornicotine is related to the more active nicotine demethylation in the leaf.
Liu
Baizhan
B
Department of Chemistry, University of Science & Technology of China, Jinzai Road 96, Hefei 230026, Anhui Province, China.
Chen
Chaoying
C
Wu
Da
D
Su
Qingde
Q
D000470:Alkaloids / Q000032:analysis*; D000691:Anabasine / Q000032:analysis*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D009538:Nicotine / Q000031:analogs & derivatives* / Q000032:analysis; D011725:Pyridines / Q000032:analysis*; D013237:Stereoisomerism; D014026:Nicotiana / Q000737:chemistry*
D000470:Alkaloids; D011725:Pyridines; C012737:anatabine; D009538:Nicotine; C005311:nornicotine; D000691:Anabasine