Enantioseparation of nornicotine in tobacco by ultraperformance convergence chromatography with tandem mass spectrometry

Abstract

Nornicotine, an alkaloid constituent of tobacco, is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. Accumulating evidence reveals that nornicotine enantiomers have different neurochemical and behavioral effects. In the present study, an accurate and rapid method was developed for the enantioseparation of (R)-(+)-nornicotine and (S)-(-)-nornicotine enantiomers in tobacco by ultra-performance convergence chromatography with tandem mass spectrometry. Chromatographic conditions were investigated to achieve the optimal resolution of two enantiomers. Results indicated that (R)-(+)-nornicotine and (S)-(-)-nornicotine could be separated within 5 min when ammonium hydroxide was added into the cosolvent, and the best resolution (R = 4.76) was achieved on a immobilized cellulose tris-(3,5-dichlorophenylcarbamate) chiral stationary phase. The proposed method was validated and was finally applied to analyze the compositions of (R)-(+)-nornicotine and (S)-(-)-nornicotine in three typical types of tobaccos (flue-cured, burley, and oriental). It was found that, enantiomer fraction of nornicotine (the proportion of (S)-(-)-nornicotine in the nornicotine pool) in burley tobacco samples was relatively high and constant compared with flue-cured and oriental tobaccos. The effective and rapid enantioseparation of nornicotine may help the understanding of alkaloid metabolites in different tobacco varieties and may also benefit pharmacological studies of alkaloid enantiomers.

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

“…Among many different chiral stationary phases that are commercially available today, polysaccharide (derivatized cellulose or amylose)-based CSPs have a dominant position. They are used successfully in HPLC, CEC and SFC [9][10][11][12][13][14][15].…”

Qualitative and Quantitative Analysis of Nicotine, Nicotine Derivatives, and Nicotine-Related Alkaloid Optical Isomers: A Review

“…Nornicotine, a well-documented minor alkaloid constituent of tobacco, is a known precursor to the carcinogen N-nitrosonornicotine, NNN (9,10). NNN is produced during the curing and processing of tobacco (37). Recent evidence has revealed that nornicotine enantiomers have different pharmacological properties.…”

Solvent-Free Synthesis of High-Purity Sucrose Fatty Acid Monoesters and a Comparison of Their Properties with Those of Their Commercial Counterparts

“…While these methods can effectively quantify SE content, they are time-consuming and require high concentrations of analytes. In recent years, UPC 2 -MS has emerged as a highly effective tool for the accurate quantitation of various components in complex mixtures − and was thus used in the study presented here…”

“…The pH of the GITBM system was regulated using a 902 Titrando automated titrator (Metrohm) and maintained at 7 via the addition of an aqueous solution of NaOH (0.1 mM). The proportion of released free fatty acids (FFA) was calculated as follows: where V NaOH and C NaOH are the volume and concentration of added NaOH, respectively, and M lipid (824 g/mol) and W lipid are the molar mass and weight, respectively, of the digestible lipids in the simulated small intestine.…”