Reaction of the tobacco alkaloid myosmine with hydrogen peroxide

Chemical Research in Toxicology

Volumn 19, Issue 1, 2006, Pages 150-155

  Zwickenpflug, Wolfgang ^a   Tyroller, Stefan ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ANHYDRIDE; ALKALOID; HYDROGEN PEROXIDE; MYOSMINE; UNCLASSIFIED DRUG;

ACETYLATION; ANALYTIC METHOD; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; NITROSATION; NONHUMAN; RAT; REACTION ANALYSIS; SAMPLING; STRUCTURE ANALYSIS; TOBACCO;

ACETIC ANHYDRIDES; ACETYLATION; ALKALOIDS; BUTANONES; HYDROGEN PEROXIDE; HYDROXYBUTYRATES; KETO ACIDS; MUTAGENS; OXIDATION-REDUCTION; PYRIDINES; TIME FACTORS; TOBACCO; ULTRASONICS;

ANIMALIA; NICOTIANA TABACUM; RATTUS NORVEGICUS;

EID: 31844446641     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0502802     Document Type: Article

References (42)

1. D'Asaro, J. A., and Telepchak, M. J. (2004) Determination of tobacco alkaloids using solid-phase extraction. Am. Lab. 36 (22), 13-17.
2. Brunnemann, K. D., Qi, J., and Hoffmann, D. (2002) Chemical profile of two types of oral snuff tobacco. Food Chem. Toxicol. 40, 1699-1703.
3. Sakuma, H., Kusama, M., Yamaguchi, K., Matsuki, T., and Sugawara, S. (1984) The distribution of cigarette smoke components between mainstream and sidestream smoke. II. Bases. Beitr. Tabakforsch. Int. 12 (4), 199-209.
4. Baker, R. R. (1999) Smoke chemistry. In Tobbacco Production, Chemistry and Technology (Davis, D. L., and Nielsen, M. T., Eds.) pp 398-439, Blackwell Science Ltd., Oxford, U.K.
5. Siegmund, B., Leitner, E., and Pfannhauser, W. (1999) Determination of the nicotine content of various edible nightshades (Solanaceae) and their products and estimation of the associated dietary nicotine intake. J. Agric. Food Chem. 47 (8), 3113-3120.
6. Luanratana, O., and Griffin, W. J. (1982) Alkaloids of Duboisia hopwoodii. Phytochemistry 21 (2), 449-451.
7. Zwickenpflug, W., Meger, M., and Richter, E. (1998) Occurrence of the tobacco alkaloid myosmine in nuts and nut products of Arachus hvpogaea and Corylus avellana. J. Agric. Food Chem. 46 (7), 2703-2706.
8. Tyroller, S., Zwickenpflug, W., and Richter, E. (2002) New sources of dietary myosmine uptake from cereals, fruits, vegetables and milk. J. Agric. Food Chem. 50 (17), 4909-4915.
9. Ambrose, A. M., and DeEds, F. (1946) Some comparative observations on (-)-nicotine and myosmine. Proc. Soc. Exp. Biol. Med. 63, 423-424.
10. Riebe, M., Westphal, K., and Fortnagel, P. (1982) Mutagenicity testing, in bacterial test systems, of some constituents of tobacco. Mutat. Res. 101, 39-43.
11. Kleinsasser, N. H., Wallner, B. C., Harréus, U. A., Zwickenpflug, W., and Richter, E. (2003) Genotoxic effects of myosmine in human lymphocytes and upper aerodigestive tract epithelial cells. Toxicology 192 (2-3), 171-177.
12. International Agency for Research on Cancer (IARC) (2004) IARC Monographs Programme finds smokeless tobacco is carcinogenic to humans. Press Release No. 154, World Health Organization, Lyon, France.
13. Wilp, J., Zwickenpflug, W., and Richter, E. (2002) Nitrosation of dietary myosmine as risk factor of human cancer. Food Chem. Toxicol. 40 (8), 1223-1228.
14. Zwickenpflug, W. (2000) N-Nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1-butanone) and NNN (N-nitrosonornicotine). J. Agric. Food Chem. 48 (2), 392-394.
15. Zwickenpflug, W., Tyroller, S., and Richter, E. (2005) Metabolism of myosmine in Wistar rats. Drug Metab. Dispos. 33 (11), 1648-1656.
16. Brandänge, S., and Rodriguez, B. (1983) Ring chain tautomerism of myosmine. Acta Chem. Scand,. Ser. B 37 (7), 643-644.
17. Zoltewicz, J. A., Bloom, L. B., and Kem, W. R. (1989) Quantitative determination of the ring-chain hydrolysis equilibrium constant for anabaseine and related tobacco alkaloids. J. Org. Chem. 54, 4462-4468.
18. Ogata, Y., and Sawaki, Y. (1973) Peracid oxidation of imines. Kinetics of oxirane formation from benzyliden-tert-butylamines and perbenzoic acid. J. Am. Chem. Soc. 95 (14), 4687-4692.
19. Ogata, Y., and Sawaki, Y. (1973) Peracid oxidation of imines. Kinetics and mechanism of competitive formation of nitrones and oxaziranes from cyclic and acyclic imines. J. Am. Chem. Soc. 95 (14), 4692-4698.
20. Emmons, W. D. (1956) The synthesis of oxaziranes. J. Am. Chem. Soc. 78, 6208-6209.
21. Rayburn, C. H., Harlan, W. R., and Hanmer, H. R. (1950) Rearrangement of nicotine oxide. J. Am. Chem. Soc. 72, 1721-1723.
22. Quin, L. D., and Roof, G. L. (1962) Rearrangement of 1-methyl-2- arylpyrrolidine N-oxides to tetrahydro-2-methyl-6-aryl-2H-1,2-oxazines. J. Org. Chem. 27, 4451-4454.
23. Dinizo, A. E., and Watt, D. S. (1975) Oxidative deamination of amines to ketones via oxaziridines. J. Am. Chem. Soc. 97, 6900-6901.
24. Pinner, A. (1893) Über Nicotin. Arch. Pharm. 231, 378-448.
25. Taylor, E. C., and Boyer, N. E. (1959) Pyridine-1-oxides. IV. Nicotine-1-oxide, nicotine-1′-oxide, and nicotine-1,1′-dioxide. J. Org. Chem. 24, 275-277.
26. Frankenburg, W. G., Gottscho, A. M., Woolever Mayaud, E., and Tso, T.-C. (1952) The chemistry of tobacco fermentation. I. Conversion of the alkaloids. A. The formation of 3-pyridyl methyl ketone and of 2,3′-dipyridyl. J. Am. Chem. Soc. 74, 4309-4314.
27. Wada, E., and Yamasaki, K. (1954) Degradation of nicotine by soil bacteria. J. Am. Chem. Soc. 76, 155-157.
28. Aislaitner, G., Li, Y., and Gorrod, J. W. (1992) In vitro metabolic studies on levo-(S)-nornicotine. Med. Sci. Res. 20 (23), 897-899.
29. Hecht, S. S. (1998) Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol. 11 (6), 559-603.
30. Hecht, S. S., Chen, C.-H., and Hoffmann, D. (1980) Metabolic β-hydroxylation and N-oxidation of N′-nitrosonornicotine. J. Med. Chem. 23, 1175-1178.
31. Hecht, S. S., Young, R., and Chen, C. B. (1980) Metabolism in the F344 rat of 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific carcinogen. Cancer Res. 40, 4144-4150.
32. Castonguay, A., Tjälve, H., Trushin, N., and Hecht, S. S. (1984) Perinatal metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanone in C57BL mice. J. Natl. Cancer Inst. 72, 1117-1126.
33. Brandänge, S., and Lindblom, L. (1976) N-Vinyl as N-H protection group. A convenient synthesis of myosmine. Acta Chem. Scand. 30, 39.
34. McKennis, H., Schwartz, S. L., Turnbull, L. B., Tamaki, E., and Bowman, E. R. (1964) The metabolic formation of γ-(3-pyridyl)-γ- hydroxybutyric acid and its possible intermediary role in the mammalian metabolism of nicotine. J Biol. Chem. 239 (11), 3981-3989.
35. Hecht, S. S., Chen, C. B., Dong, M., Ornaf, R. M., Hoffmann, D., and Tso, T. C. (1977) Chemical studies on tobacco smoke LI: studies on non-volatile nitrosamines in tobacco. Beitr. Tabakforsch. 9 (1), 1-6.
36. Ghabrial, S. S., Thomsen, I., and Torssell, K. B. G. (1987) Synthesis of biheteroaromatic compounds via the isoxazoline route. Acta Chem. Scand., Ser. B 41, 426-434.
37. Kisaki, T., Ihida, M., and Tamaki, E. (1960) Chemistry of the N′-oxides of nicotine and myosmine. Bull. Agr. Chem. Soc. Jpn. 24, 719-728.
38. Craig, J. C., Mary, N. Y., Goldman, N. L., and Wolf, L. (1964) Tertiary amine oxide rearrangements. III. The mechanism of the demethylation of nicotine. J. Am. Chem. Soc. 86, 3866-3869.
39. Denton, T. T., Zhang, X., and Cashman, J. R. (2004) Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem. Pharmacol. 67 (4), 751-756.
40. Cosgrove, J. P., Borish, E. T., Church, D. F., and Pryor, W. A. (1985) The metal-mediated formation of hydroxyl radical by aqueous extracts of cigarette tar. Biochem. Biophys. Res. Commun. 132 (1), 390-396.
41. Pryor, W. A., Stone, K., Zang, L.-Y., and Bermúdez, E. (1998) Fractionation of aqueous cigarette tar extracts: fractions that contain the tar radical cause DNA damage. Chem. Res. Toxicol. 11 (5), 441-448.
42. Szatrowski, T. P., and Nathan, C. F. (1991) Production of large amounts of hydrogen peroxide by human tumor cells. Cancer Res. 51 (3), 794-798.