Liver and lung microsomal metabolism of the tobacco alkaloid beta-nicotyrine.
Liver and lung microsomal metabolism of the tobacco alkaloid beta-nicotyrine.
复制标题
烟草生物碱β-烟酪氨酸的肝脏和肺微粒体代谢。
DOI：
10.1021/tx00011a003
复制
发表时间：
1989
影响因子：
4.1
通讯作者：
CastagnoliJr,N
中科院分区：
文献类型：
--
作者：
Shigenaga,MK;Kim,BH;Caldera-Munoz,P;Cairns,T;Jacob3rd,P;Trevor,AJ;CastagnoliJr,N
The in vitro metabolic fate of ß-nicotyrine has been examined in rabbit lung and liver mi-crosomal preparations as part of an effort to characterize theformation of potentially reactive metabolic species that may contribute to the toxic properties of tobacco products. HPLC analysis revealed the formation of an unstable metabolite which displayed HPLC-MS/MS characteristics consistent with the structure l-methyl-5-(3-pyridyl)-3-pyrrolin-2-one. Attempted synthesis of this pyrrolinone, however, resulted in the isolation ofthe isomeric l-methyl-5-(3-pyridyl)-2-pyrrolin-2-one. TheHPLC, diode array UV, and mass spectral characteristics of this A4, 5-isomer proved to be identical with those of the metabolite derived from 8-nicotyrine. Studies in D20 suggest that the 2-and 3-pyrrolinones are in equilibrium in aqueous solution. The metabolite undergoes autoxidation, possibly via radical intermediates, to yield l-methyl-5-(3-pyridyl)-5-hydroxy-3-pyrrolin-2-one.
