Nitrosation of dietary myosmine as risk factor of human cancer

Wilp, J; Zwickenpflug, Wolfgang; Richter, Elmar

doi:10.1016/s0278-6915(02)00039-x

Cited by 30 publications

(24 citation statements)

References 29 publications

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“…The increased hepatic CAT activity may be a compensatory mechanism to get rid of excess peroxides due to low GPx activity. The third is that the activation of myosmine by peroxidative or n i t r o s a t i v e m e c h a n i s m s c o u l d l e a d t o pyridyloxobutylation of proteins, DNA, and RNA (6,8,30) and could compromise their functioning.…”

Section: Discussionmentioning

confidence: 99%

“…After nitrosation and/or peroxidation, myosmine bioactivates to 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) and can form pyridyloxobutylated DNA adducts (6) or N'-nitrosonornicotine (NNN), which is an oesophageal carcinogen (7). In vitro experiments with calf thymus DNA have shown that myosmine is rapidly nitrosated at pH 2 to pH 4 and forms DNA adducts (8). Using the comet assay in human lymphocytes and upper aerodigestive tract epithelial cells, Kleinsasser et al (9) have demonstrated dose-and time-dependent genotoxic effects of myosmine.…”

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confidence: 99%

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Effects of Myosmine on Antioxidative Defence in Rat Liver

Simeonova

Vitcheva

Gorneva

et al. 2012

Archives of Industrial Hygiene and Toxicology

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Myosmine [3-(1-pyrrolin-2-yl) pyridine] is an alkaloid structurally similar to nicotine, which is known to induce oxidative stress. In this study we investigated the effects of myosmine on enzymatic and nonenzymatic antioxidative defence in rat liver. Wistar rats received a single i.p. injection of 19 mg kg -1 of myosmine and an oral dose of 190 mg kg -1 by gavage. Nicotine was used as a positive control. Through either route of administration, myosmine altered the hepatic function by decreasing the levels of reduced glutathione, superoxide dismutase, and glutathione peroxidase activities on one hand and by increasing malondialdehyde, catalase, and glutathione reductase activity on the other. Compared to control, both routes caused signifi cant lipid peroxidation in the liver and altered hepatic enzymatic and non-enzymatic antioxidative defences. The pro-oxidant effects of myosmine were comparable with those of nicotine.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Effects of Myosmine on Antioxidative Defence in Rat Liver

Simeonova

Vitcheva

Gorneva

et al. 2012

Archives of Industrial Hygiene and Toxicology

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“…Therefore, the composition and content of alkaloids in leaves are critical to tobacco quality (Lewis, 2006). However, some types of alkaloids including nornicotine and myosmine, have adverse effects on human health (Dickerson and Janda, 2002;Wilp et al, 2002;Hecht, 2003;Brogan et al, 2005). Nornicotine is a biochemical precursor of N′-nitrosonornicotine, a tobacco-specific nitrosamine that has been shown to exhibit carcinogenic properties in laboratory animals (Hecht, 2003).…”

Section: Introductionmentioning

confidence: 99%

“…Nornicotine is a biochemical precursor of N′-nitrosonornicotine, a tobacco-specific nitrosamine that has been shown to exhibit carcinogenic properties in laboratory animals (Hecht, 2003). In addition, upon nitrosation, myosmine can yield 4-hydroxy-1-(3-pyridyl)-1-butanone and N′-nitrosonornicotine, which are strong carcinogens (Wilp et al, 2002). Currently, there is no efficient approach for selectively reducing the amount of harmful alkaloids in tobacco leaves.…”

Section: Introductionmentioning

confidence: 99%

Genetic variation in alkaloid accumulation in leaves of Nicotiana

Sun

Zhang

Guang-hong

et al. 2013

J. Zhejiang Univ. Sci. B

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Alkaloids are plant secondary metabolites that are widely distributed in Nicotiana species and contribute greatly to the quality of tobacco leaves. Some alkaloids, such as nornicotine and myosmine, have adverse effects on human health. To reduce the content of harmful alkaloids in tobacco leaves through conventional breeding, a genetic study of the alkaloid variation among different genotypes is required. In this study, alkaloid profiles in leaves of five Nicotiana tabacum cultivars and Nicotiana tomentosiformis were investigated. Six alkaloids were identified from all six genotypes via gas chromatograph-mass spectrometry (GC-MS). Significant differences in alkaloid content were observed both among different leaf positions and among cultivars. The contents of nornicotine and myosmine were positively and significantly correlated (R 2 =0.881), and were also separated from those of other alkaloids by clustering. Thus, the genotype plays a major role in alkaloid accumulation, indicating a high potential for manipulation of alkaloid content through traditional breeding.

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“…4 After nitrosation and/or peroxidation, myosmine gives rise to reactive pyridyloxobutylating species which are capable of forming pyridyloxobutylated DNA adducts. [5][6][7][8] Nitrosation of myosmine also leads to the formation of the esophageal carcinogen N '-nitrosonornicotine. 5 Originally, nitrosonornicotine and 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasing adducts were thought to be highly tobacco-specific.…”

Section: Introductionmentioning

confidence: 99%

Flow Cytometric Analysis of the Influence of Myosmine on the Cell Cycle

Boteva¹,

Mateva²,

Илиев³

et al. 2011

Croat. Chem. Acta

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Abstract. Myosmine (3-(1-pyrrolin-2-yl)pyridine) is an alkaloid found in tobacco as well as various staple foods, fruits and vegetables. Myosmine has recently been suspected to be a tobacco-independent carcinogenic source. Using cell flow cytometry, we have examined the influence of myosmine on the cell cycle of murine erythroleukemia (MEL) cells in vitro and have compared this with its effects on murine bone marrow cells in vivo. Myosmine at low concentrations inhibited cell proliferation dose dependently; while at concentrations close to 300 µmol dm

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Nitrosation of dietary myosmine as risk factor of human cancer

Cited by 30 publications

References 29 publications

Effects of Myosmine on Antioxidative Defence in Rat Liver

Effects of Myosmine on Antioxidative Defence in Rat Liver

Genetic variation in alkaloid accumulation in leaves of Nicotiana

Flow Cytometric Analysis of the Influence of Myosmine on the Cell Cycle

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