PMID: 10691645Feb 26, 2000

N-Nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1-butanone) and NNN (N-nitrosonornicotine)

Journal of Agricultural and Food Chemistry
W Zwickenpflug

Abstract

N-Nitrosonornicotine (NNN) is formed by synthetic or biological N-nitrosation of the tobacco alkaloid nornicotine. Following metabolic activation of NNN, DNA and protein adducts are formed releasing 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB), an actual biomarker to differentiate between tobacco smokers and passive smokers. NNN and HPB can be prepared in a new one-step reaction by N-nitrosation of the nicotinoid myosmine which has been found not only in tobacco but also in nut products. The reaction was tested also in human gastric juice. The formation rate of NNN and HPB depends on the pH value in the reaction solutions. This is important under the aspect of myosmine uptake by humans from other biological sources and subsequent biological activation. The new reaction pathway indicates that human exposure to nicotinoid nitrosation products seems to be not restricted exclusively to tobacco.

Citations

Jun 18, 2002·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·J WilpE Richter
Feb 13, 2007·Chemical Research in Toxicology·S S HechtPramod Upadhyaya
Mar 28, 2012·Arhiv za higijenu rada i toksikologiju·Rumyana SimeonovaMitka Mitcheva
Mar 10, 2010·Critical Reviews in Toxicology·Kumar A Shah, H Thomas Karnes
May 30, 2009·Biomarkers : Biochemical Indicators of Exposure, Response, and Susceptibility to Chemicals·Katharina Schütte-BorkovecElmar Richter
Dec 18, 2015·Journal of Agricultural and Food Chemistry·W ZwickenpflugThomas Gudermann
Mar 9, 2011·Regulatory Toxicology and Pharmacology : RTP·Robert Nilsson
Dec 2, 2008·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·J B HavlaE Richter
Aug 5, 2005·Drug Metabolism and Disposition : the Biological Fate of Chemicals·W ZwickenpflugE Richter

Related Concepts

Myosmine
N'-nitrosonornicotine, (+-)-isomer
4-hydoxy-1-(3-pyridyl)-1-butanone
Plant alkaloid
Butanones
High Pressure Liquid Chromatography Procedure
Gastric Juice
Nitrogen
Nitrosamines
Pyridines

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