Zwickenpflug W
Walther Straub-Institut für Pharmakologie und Toxikologie, Ludwig-Maximilians-Universität, Nussbaumstrasse 26, D-80336 München, Germany.
J Agric Food Chem. 2000 Feb;48(2):392-4. doi: 10.1021/jf9903004.
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.
N-亚硝基降烟碱（NNN）由烟草生物碱降烟碱经合成或生物亚硝化作用形成。NNN经代谢活化后会形成DNA和蛋白质加合物，并释放出4-羟基-1-（3-吡啶基）-1-丁酮（HPB），这是一种区分吸烟者和被动吸烟者的实际生物标志物。NNN和HPB可通过对烟碱类化合物麦斯明进行N-亚硝化反应，以一种新的一步反应法制备，麦斯明不仅存在于烟草中，也存在于坚果产品中。该反应也在人体胃液中进行了测试。NNN和HPB的形成速率取决于反应溶液的pH值。从人类从其他生物来源摄取麦斯明并随后进行生物活化的角度来看，这一点很重要。新的反应途径表明，人类接触烟碱类亚硝化产物似乎并不局限于烟草。
