title: Accumulation of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone in alkaloid genotypes of burley tobacco during postharvest processing: comparisons with N'-nitrosonornicotine and probable nitrosamine precursors.
abstract: Recent work showed that 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK) was present in some cured tobacco and was more carcinogenic than N'-nitrosonornicotine (NNN). In the present investigation, the concentration relationships of NNK, NNN, and their probable precursors, i.e., nitrite, nitrate, and alkaloids, were determined: (a) after the growth of Ky 14 burley tobacco under different shade conditions followed by air curing; and (b) during preparation of air-cured and homogenized-leaf-cured (HLC) burley tobaccos from conventionally grown tobaccos of different alkaloid genotypes. A capillary gas chromatography-nitrogen-phosphorus detector procedure was developed and utilized for quantitative determinations of NNK and NNN. NNK contents ranged from 0.2 to 0.5 micrograms/g in air-cured Ky 14 tobacco lamina from leaves grown under 0 to 65% shade (100, 65, and 35% of natural daylight). The highest NNK concentrations were from 45% shade-grown lamina from lower leaf positions on stalks. Concentrations of NNK did not correlate significantly with those of either nitrate or total alkaloids calculated over all shade treatments and stalk positions. During HLC tobacco processing, the following significant correlations of NNK with precursor content changes were found for each of four burley alkaloid genotypes calculated over the four successive stages of processing: NNN (r = 1.0); and nitrate (r = -0.9). NNK also correlated negatively with nicotine concentration changes (r = -0.9) in the low-alkaloid and high-alkaloid isolines during processing. After a 20-h incubation period under aerobic conditions followed by a 1-h standing period without aeration, substantial increases of NNK were observed in each burley line. The increased NNK contents ranged from 9-fold for the low-alkaloid isoline to 99-fold for the nornicotine-converter line. Increases in NNK content (27 to 69%) also occurred during the air drying stage; further increases occurred during a 15-month storage period at ambient conditions. After the HLC process and prolonged storage, maximal NNK contents were observed in each tobacco genotype in the following order of increasing NNK content: Ky 14 cultivar, 79 micrograms/g; low-alkaloid line, 80 micrograms/g; nornicotine converter line, 102 micrograms/g; and high-alkaloid line, 177 micrograms/g. At the beginning of a controlled environmental storage period used for high-alkaloid and low-alkaloid isoline air-cured and HLC tobaccos, NNK contents correlated with nitrite (r = 1.0) and nitrate (r = -0.9) calculated over the two curing regimens.(ABSTRACT TRUNCATED AT 400 WORDS)
mesh_terms: D000470:Alkaloids / Q000032:analysis*; D002273:Carcinogens / Q000032:analysis*; D009538:Nicotine / Q000031:analogs & derivatives / Q000032:analysis; D009602:Nitrosamines / Q000032:analysis*; D010947:Plants, Toxic; D013997:Time Factors; D014026:Nicotiana / Q000032:analysis*
chemical_list: D000470:Alkaloids; D002273:Carcinogens; D009602:Nitrosamines; D009538:Nicotine; C016583:4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone; C005311:nornicotine; C008655:N'-nitrosonornicotine