Biotransformation of methyleugenol by rat hepatic microsomes

甲基丁香酚的大鼠肝微粒体生物转化(英文)

Methyleugenol （1）, one of the main bioactive constituents of the seeds of Myristicafragrans Houtt. （family： Myristicaceae）, was incubated with rat hepatic microsomes from rats pretreated with sodium phenobarbital. Eight biotransformation products named （R）-l＇-methoxymethyleugenol （2）, 3-（3,4-dimethoxyphenyl）-l-methoxyprop-2-ene （3）, cis-3,4-dimethoxycinnamyl acetate （4）, trans-3,4-dimethoxycinnamyl acetate （5）, （R）-I hydroxymethyleugenol （6）, trans-3,4-dimethoxycinnamyl alcohol （7）, cis-3,4-dimethoxycinnamyl alcohol （8）, and （R）-3-（3,4-dimethoxyphenyl）-propane-l,2-diol （9） were obtained and their structures were elucidated by NMR and MS data analysis and by comparison with the previously reported data. The biotransformation of 1 may provide valuable information for the use of methyleugenol. The NMR data of compounds 4 and 6 were reported for the first time.

甲基丁香酚(1)是中药肉豆蔻的主要成分之一,将其与大鼠肝微粒体共温孵,从温孵物中通过色谱方法得到原形化合物1和8个转化产物(2–9),根据谱学数据并与文献报道数据比较,确定它们分别为(R)-1'-甲氧基甲基丁香酚(2)、3-(3,4-二甲氧基苯基)-l-甲氧基-2-丙烯(3)、顺式-3,4-二甲氧基桂皮酰乙酯(4)、反式-3,4-二甲氧基桂皮酰乙酯(5)、(R)-1′-羟基甲基丁香酚(6)、反式-3,4-二甲氧基桂皮醇(7)、顺式-3,4-二甲氧基桂皮醇(8)、(R)-3-(3,4-二甲氧基苯基)-丙烷-1,2-二醇(9)。化合物7和8的13C NMR数据为首次报道。本文结果为甲基丁香酚的应用提供了有用的信息。