Nitrogen-containing compounds in tobacco and tobacco smoke

Schmeltz, I.; Hoffmann, Dietrich

doi:10.1021/cr60307a001

Cited by 322 publications

(190 citation statements)

References 49 publications

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“…Methane reagent gas is commonly used in PCI mode. Due to its relatively lower proton affinity, CH 5 ϩ of the CI reagent ions generated by methane reacts rapidly with almost every compound; the use of methane as reagent gas for analysis of the complex tobacco matrix lacks selectivity; ammonia as reagent gas forms NH 4 ϩ adduct with sample molecule in PCI mode, especially the heterocyclics (containing N, O, et al) and the unsaturated compounds [27]. However, ammonia is not facile.…”

Section: Selection Of CI Reagentsmentioning

confidence: 99%

“…Nornicotine and anatabine are the two most abundant minor pyridine alkaloids present in roughly equal amounts, together accounting for ϳ4% to 5% of total alkaloids [4]. Moreover, there are some minor pyridine alkaloids in tobacco, such as anabasine, myosmine, cotinine, and 2, 3=-bipyridyl, etc, which are present at smaller amounts [5]. Thus, data on the contents of total alkaloids and amounts of individual components are important and necessary in evaluating tobacco products for potential biochemical activity and marketing quality.…”

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confidence: 99%

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Selective determination of pyridine alkaloids in tobacco by PFTBA ions/analyte molecule reaction ionization ion trap mass spectrometry

Zhang

Houwei

Sun

et al. 2007

J. Am. Soc. Mass Spectrom.

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The application of perfluorotributylamine (PFTBA) ions/analyte molecule reaction ionization for the selective determination of tobacco pyridine alkaloids by ion trap mass spectrometry (IT-MS) is reported. The main three PFTBA ions (CF 3 ϩ , C 3 F 5 ϩ , and C 5 F 10 N ϩ ) are generated in the external source and then introduced into ion trap for reaction with analytes. Because the existence of the tertiary nitrogen atom in the pyridine makes it possible for PFTBA ions to react smoothly with pyridine and forms adduct ions, pyridine alkaloids in tobacco were selectively ionized and formed quasi-molecular ion [M ϩ H] ϩ and adduct ions, includingϩ , and [M ϩ 264] ϩ , in IT-MS. These ions had distinct abundances and were regarded as the diagnostic ions of each tobacco pyridine alkaloid for quantitative analysis in selected-ion monitoring mode. Results show that the limit of detection is 0.2 g/mL, and the relative standard deviations for the seven alkaloids are in the range of 0.71% to 6.8%, and good recovery of 95.6% and 97.2%. The proposed method provides substantially greater selectivity and sensitivity compared with the conventional approach and offers an alternative approach for analysis of tobacco alkaloids. (J Am Soc Mass Spectrom 2007, 18, 1774 -1782

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Section: Selection Of CI Reagentsmentioning

confidence: 99%

mentioning

confidence: 99%

Selective determination of pyridine alkaloids in tobacco by PFTBA ions/analyte molecule reaction ionization ion trap mass spectrometry

Zhang

Houwei

Sun

et al. 2007

J. Am. Soc. Mass Spectrom.

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“…Such diversity has been exclusively aimed at as an analytical target to know the components elucidating their differences resulting in various tastes and aromas of tobacco products (3,4). For this reason, numerous components such as cembranoid, labdanoid, hydrocarbon, carotenoid, lipid, alkaloid, polyphenol, carbohydrate, organic acid, cation, anion, amino acid and polymers have been qualitatively and quantitative-ly analyzed and reported (1,(3)(4)(5)(6). However, those studies, in other words "target analyses", have focused on a component elucidating the difference between tobacco leaves and have remained partial knowledge within preliminary assumption of target component.…”

Section: Introductionmentioning

confidence: 99%

A Simultaneous Analytical Method to Profile Non-Volatile Components with Low Polarity Elucidating Differences Between Tobacco Leaves Using Atmospheric Pressure Chemical Ionization Mass Spectrometry Detection

Ishida

2016

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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SUMMARYA comprehensive analytical method using liquid chromatography atmospheric pressure chemical ionization mass spectrometry detector (LC/APCI-MSD) was developed to determine key non-volatile components with low polarity elucidating holistic difference among tobacco leaves. Nonaqueous reversed-phase chromatography (NARPC) using organic solvent ensured simultaneous separation of various components with low polarity in tobacco resin. Application of full-scan mode to APCI-MSD hyphenated with NARPC enabled simultaneous detection of numerous intense product ions given by APCI interface. Parameters for data processing to filter, feature and align peaks were adjusted in order to strike a balance between comprehensiveness and reproducibility in analysis. 63 types of components such as solanesols, chlorophylls, phytosterols, triacylglycerols, solanachromene and others were determined on total ion chromatograms according to authentic components, wavelength spectrum and mass spectrum. The whole area of identified entities among the ones detected on total ion chromatogram reached to over 60% and major entities among those identified showed favorable linearity of determination coefficient of over 0.99. The developed method and data processing procedure were therefore considered feasible for subsequent multivariate analysis. Data matrix consisting of a number of entities was then subjected to principal component analysis (PCA) and hierarchical clustering analysis. Cultivars of tobacco leaves were distributed far from each cultivar on PCA score plot and each cluster seemed to be characterized by identified non-volatile components with low polarity. While fluecured Virginia (FCV) was loaded by solanachromene, phytosterol esters and triacylglycerols, free phytosterols and chlorophylls loaded Burley (BLY) and Oriental (ORI) respectively. Consequently the whole methodology consisting of comprehensive method and data processing procedure proved useful to determine key-components among cultivars of tobacco leaves, and was expected to additionally expand coverage that metabolomics study has ensured. [Beitr. Tabakforsch. Int. 27 (2016)

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“…It is estimated that more than 4,000 compounds are present in tobacco leaves and tobacco smoke [22]. While the pharmacological activity of the majority of these compounds have not been identified, several commercially available alkaloid components of tobacco smoke have been structurally characterized [22] and their binding affinities to nAChRs established [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Screening of tobacco smoke condensate for nicotinic acetylcholine receptor ligands using cellular membrane affinity chromatography columns and missing peak chromatography

Maciuk

Moaddel

Haginaka

et al. 2008

Journal of Pharmaceutical and Biomedical Analysis

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This manuscript reports an approach to the screening of natural product extracts for compounds which are active at membrane-bound receptors, ion channels and transporters. The technique is based upon cellular membrane affinity chromatography (CMAC) columns created through the immobilization of cellular membrane fragments on liquid chromatography stationary phases. In this study a CMAC (nAChR(+)) column was created out of membranes from a transfected cell line expressing the α 3 β 4 neuronal nicotinic acetylcholine receptor (nAChR) and the column was used to screen tobacco smoke condensates. A strategy involving parallel screening with a CMAC column created from a non-transfected form of the same cell line, CMAC(nAChR(−)) was adopted. The condensate was chromatographed on both columns, timed fractions collected and concentrated. Each fraction was analyzed on a C 18 column in order to establish a chromatographic fingerprint of each fraction and a differential elution profile of each compound. Comparison of the elution profiles from the CMAC (nAChR(+)) and CMAC(nAChR(−)) columns identified patterns that could be associated with high affinity ligands and with low-affinity/non-binding compounds. Known strong ligands ((S)-Nicotine, (R,S)-Anatabine, N'-Nitrosonornicotine), weak ligands ((R,S)-Nornicotine, Anabasine) as well as known non-ligands (N-Methyl-γ-oxo-3-pyridinebutanamide, (1'S,2′S)-Nicotine 1'-oxide) have been identified in the complex extract. The results demonstrate that CMAC-based screens can be used in the identification of compounds within natural product extracts that bind to membrane-based targets.

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Nitrogen-containing compounds in tobacco and tobacco smoke

Cited by 322 publications

References 49 publications

Selective determination of pyridine alkaloids in tobacco by PFTBA ions/analyte molecule reaction ionization ion trap mass spectrometry

Selective determination of pyridine alkaloids in tobacco by PFTBA ions/analyte molecule reaction ionization ion trap mass spectrometry

A Simultaneous Analytical Method to Profile Non-Volatile Components with Low Polarity Elucidating Differences Between Tobacco Leaves Using Atmospheric Pressure Chemical Ionization Mass Spectrometry Detection

Screening of tobacco smoke condensate for nicotinic acetylcholine receptor ligands using cellular membrane affinity chromatography columns and missing peak chromatography

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