Formation of 4-(methylnitrosamino)-4-(3-pyridyl)butyric acid in vitro and in mainstream cigarette smoke

Djordjevic, Mirjana V.; Sigountos, Claire W.; Brunnemann, Klaus D.; Hoffmann, Dietrich

doi:10.1021/jf00001a043

Cited by 17 publications

(2 citation statements)

References 19 publications

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“…We identified 14 published studies that met the data inclusion criteria (Adams et al, 1987;Brunnemann and Hoffmann, 1991;Brunnemann et al, 1996;Counts et al, 2005Counts et al, , 2006Djordjevic et al, 1991;Hecht et al, 1979;Hoffmann et al, 1979Hoffmann et al, , 1982Patskan et al, 2008;Roemer et al, 2004;Stepanov et al, 2012;Swauger et al, 2002). Table 1 presents cigarette product identifications, levels of MS smoke tar (mg/cigarette), NNK (ng/cigarette), and NNN (ng/cigarette), and sources of the data presented in this review.…”

Section: Tsna Levels In Ms Smoke: 35 Years Of Datamentioning

confidence: 99%

TSNA levels in machine-generated mainstream cigarette smoke: 35years of data

Appleton

Olegario

Lipowicz

2013

Regulatory Toxicology and Pharmacology

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This paper characterizes historical and current tobacco specific nitrosamine (TSNA) levels in mainstream (MS) cigarette smoke of US commercial cigarettes. To conduct this analysis, we gathered 35 years of published data of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and N-nitrosonornicotine (NNN) levels in MS cigarette smoke. We also assessed internal data of MS smoke NNK and NNN levels generated from various market monitoring initiatives and from control cigarettes used in a multi-year program for testing cigarette ingredients. In all, we analyzed machine smoking data from 401 cigarette samples representing a wide range of products and design characteristics from multiple manufacturers and market leaders. There was no indication that TSNA levels systematically increased in cigarette MS smoke over the 35-year analysis period. In particular, TSNA levels expressed as either per cigarette or normalized for tar suggest a downward trend in MS smoke over the past 10 years. The apparent downward trend in TSNA levels in MS smoke may reflect industry and agricultural community efforts to reduce levels of TSNAs in tobacco and cigarette smoke.

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Section: Tsna Levels In Ms Smoke: 35 Years Of Datamentioning

confidence: 99%

TSNA levels in machine-generated mainstream cigarette smoke: 35years of data

Appleton

Olegario

Lipowicz

2013

Regulatory Toxicology and Pharmacology

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“…TSNAs are generated through the nitrosation of pyridine alkaloids during the curing, processing, and storage of cured tobacco. They may also be produced during pyrolysis, although the relative importance of this route of formation is unclear. − N -Nitrosonornicotine (NNN), N -nitrosoanatabine (NAT), and N -nitrosoanabasine (NAB) are derived directly from nitrosation of nornicotine, anatabine, and anabasine, respectively. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) is likely derived from nicotine via a nitrosation reaction involving an intermediate, possibly pseudo-oxynicotine…”

Section: Introductionmentioning

confidence: 99%

Impact of Alleles at the Yellow Burley (Yb) Loci and Nitrogen Fertilization Rate on Nitrogen Utilization Efficiency and Tobacco-Specific Nitrosamine (TSNA) Formation in Air-Cured Tobacco

Lewis

Parker

Danehower

et al. 2012

J. Agric. Food Chem.

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Tobacco-specific nitrosamine (TSNA) formation in tobacco is influenced by alkaloid levels and the availability of nitrosating agents. Tobacco types differ in their potential for TSNA accumulation due to genetic, agronomic, and curing factors. Highest TSNA concentrations are typically measured in burley tobaccos. One of the main genetic differences between burley and all other tobacco types is that this tobacco type is homozygous for recessive mutant alleles at the Yellow Burley 1 (Yb(1)) and Yellow Burley 2 (Yb(2)) loci. In addition, burley tobacco is typically fertilized at higher nitrogen (N) rates than most other tobacco types. This study utilized nearly isogenic lines (NILs) differing for the presence of dominant or recessive alleles at the Yb(1) and Yb(2) loci to investigate the potential influence of genes at these loci on TSNA accumulation. Three pairs of NILs were evaluated at three different nitrogen fertilization rates for alkaloid levels, nitrogen physiology measures, and TSNA accumulation after air-curing. As previously observed by others, positive correlations were observed between N application rates and TSNA accumulation. Recessive alleles at Yb(1) and Yb(2) were associated with increased alkaloid levels, reduced nitrogen use efficiency, reduced nitrogen utilization efficiency, and increased leaf nitrate nitrogen (NO(3)-N). Acting together, these factors contributed to significantly greater TSNA levels in genotypes possessing the recessive alleles at these two loci relative to those carrying the dominant alleles. The chlorophyll-deficient phenotype conferred by the recessive yb(1) and yb(2) alleles probably contributes in a substantial way to increase available NO(3)-N during curing and, consequently, increased potential for TSNA formation.

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