Caffeine-derived N-nitroso compounds--I: Nitrosatable precursors from caffeine and their potential relevance in the etiology of oesophageal and gastric cancers in Kashmir, India.
Salted tea prepared in Kashmir by adding sodium bicarbonate shows high methylating activity (equivalent to 3 p.p.m. N-methylnitrosourea) upon in vitro nitrosation. Pure caffeine treated under conditions of the tea preparation formed caffeidine and caffeidine acid. We report here the formation of two new compounds, mononitrosocaffeidine, an asymmetric nitrosamine, and dinitrosocaffeidine, a N-nitrosamide, on in vitro nitrosation of caffeidine. Mononitrosocaffeidine is also found after nitrosation of the typical Kashmir tea. The nitrosation of caffeidine acid produced N,N'-dimethyl-parabanic acid, mononitrosocaffeidine and N,N'-dimethyl-N-nitrosourea. In view of the well-known structure-activity relationships of these N-nitroso compounds, their possible endogenous formation due to high consumption of salted tea may be a critical risk factor for the high occurrence of oesophageal and gastric cancers in Kashmir.
Kumar
R
R
Department of Pharmaceutical Sciences, University of Kashmir, Srinagar, India.
Mende
P
P
Wacker
C D
CD
Spiegelhalder
B
B
Preussmann
R
R
Siddiqi
M
M
D001639:Bicarbonates / Q000737:chemistry; D002110:Caffeine / Q000737:chemistry*; D004938:Esophageal Neoplasms / Q000139:chemically induced* / Q000453:epidemiology; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007194:India / Q000453:epidemiology; D008745:Methylation; D009603:Nitroso Compounds / Q000737:chemistry* / Q000633:toxicity; D012307:Risk Factors; D012964:Sodium / Q000737:chemistry; D017693:Sodium Bicarbonate; D012965:Sodium Chloride / Q000737:chemistry; D013274:Stomach Neoplasms / Q000139:chemically induced* / Q000453:epidemiology; D013662:Tea / Q000737:chemistry
D001639:Bicarbonates; D009603:Nitroso Compounds; D013662:Tea; D002110:Caffeine; D012965:Sodium Chloride; D017693:Sodium Bicarbonate; D012964:Sodium