nornicotine/carcinogenesis

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Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase.

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Nornicotine is a secondary tobacco alkaloid that is produced by the N-demethylation of nicotine. Nornicotine production and accumulation in tobacco are undesirable because nornicotine serves as the precursor in the synthesis of the well characterized carcinogen N'-nitrosonornicotine during the

A study of tobacco carcinogenesis XLVIII. Carcinogenicity of N'-nitrosonornicotine in mink (Mustela vison).

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During tobacco processing and smoking, nicotine and nornicotine give rise to N'-nitrosonornicotine (NNN), a highly abundant, strong carcinogen. NNN is known to exert carcinogenic activity in mice, rats and hamsters. Major target organs for NNN carcinogenicity in the rat are the esophagus and the

Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco.

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In the species of genus Nicotiana, nicotine to nornicotine conversion is mediated by closely related nicotine N-demethylase (NND) proteins that are encoded by the CYP82E subfamily of cytochrome P450 genes. The diverse number and transcriptional regulation of the NND genes have created large

Development of a nornicotine-reduced flue-cured tobacco line via EMS mutagenesis of nicotine N-demethylase genes.

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Substantial progress had been made in reducing nornicotine accumulation in burley tobacco, as nornicotine is a precursor of the carcinogen N-nitrosonornicotine (NNN). Three members of the CYP82E2 family encoding nicotine N-demethylase (NND) have been reported to be responsible for the

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

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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,

Contribution of Nicotine and Nornicotine toward the Production of N'-Nitrosonornicotine in Air-Cured Tobacco (Nicotiana tabacum).

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N'-Nitrosonornicotine (6) is a potent and organ-specific carcinogen found in tobacco and tobacco smoke in substantial amounts. Nicotine (1) and nornicotine (2) are proposed to be the precursors of 6 in tobacco. Since 1 can be rapidly demethylated to 2 in tobacco, to distinguish between the direct

Formation of carcinogens indoors by surface-mediated reactions of nicotine with nitrous acid, leading to potential thirdhand smoke hazards.

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This study shows that residual nicotine from tobacco smoke sorbed to indoor surfaces reacts with ambient nitrous acid (HONO) to form carcinogenic tobacco-specific nitrosamines (TSNAs). Substantial levels of TSNAs were measured on surfaces inside a smoker's vehicle. Laboratory experiments using

Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene.

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In most tobacco (Nicotiana tabacum L.) plants, nornicotine is a relatively minor alkaloid, comprising about 2-5% of the total pyridine alkaloid pool in the mature leaf. Changes in gene expression at an unstable locus, however, can give rise to plants that produce high levels of nornicotine,

Conversion of nornicotine to 6-hydroxy-nornicotine and 6-hydroxy-myosmine by Shinella sp. strain HZN7.

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Nornicotine is a natural alkaloid produced by plants in the genus Nicotiana and is structurally related to nicotine. Importantly, nornicotine is the direct precursor of tobacco-specific nitrosamine N'-nitrosonornicotine, which is a highly potent human carcinogen. Microbial detoxification and

RNA interference (RNAi)-induced suppression of nicotine demethylase activity reduces levels of a key carcinogen in cured tobacco leaves.

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Technologies for reducing the levels of tobacco product constituents that may contribute to unwanted health effects are desired. Target compounds include tobacco-specific nitrosamines (TSNAs), a class of compounds generated through the nitrosation of pyridine alkaloids during the curing and

Nornicotine nitrosation in saliva and its relation to endogenous synthesis of N'-nitrosonornicotine in humans.

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BACKGROUND We recently reported that certain amounts of the carcinogen N'-nitrosonornicotine (NNN) can be formed endogenously from nicotine and/or nornicotine in some users of oral nicotine replacement therapy products. Although the acidic environment of the stomach creates the most favorable

Presence of the Carcinogen N'-Nitrosonornicotine in Saliva of E-cigarette Users.

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Many harmful constituents are present in e-cigarettes at much lower levels than in cigarette smoke, and the results of analysis of urinary biomarkers in e-cigarette users are consistent with these findings. However, understanding the health effects of chronic exposures to e-cigarette aerosols may

Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6.

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Nicotine is the major addictive agent in tobacco; it is primarily metabolized by 5'-oxidation. 4-(Methylnitrosamine)-1-(3-pyridyl)-1-butanone (NNK), a potent lung carcinogen generated from nicotine during the curing of tobacco, is metabolically activated by P450 enzymes. P450 2A6 is the primary

Genotoxic effects of myosmine in human lymphocytes and upper aerodigestive tract epithelial cells.

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Myosmine, 3-(1-pyrroline-2-yl)pyridine, is an alkaloid found in tobacco plants. Recently, it was also detected in various edibles and staple foods. Whereas other tobacco alkaloids such as nicotine and nornicotine and their nitrosation products, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)

Chemical studies on tobacco smoke. XLII. Nitrosonornicotine: presence in tobacco, formation and carcinogenicity.

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NNN is the first organic carcinogen isolated from unburned tobacco. It has been found in smoking tobaccos, chewing tobaccos and in snuff in concentrations between 0.3 and 90.0 mug. This appears to be an unusually high concentration for a nitrosamine in an environmental agent. We have presented data

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