Chlorinated alkaloids in Menispermum dauricum DC.: Root culture

被引:34
|
作者
Sugimoto, Y
Babiker, HAA
Saisho, T
Furumoto, T
Inanaga, S
Kato, M
机构
[1] Tottori Univ, Arid Land Res Ctr, Tottori 6800001, Japan
[2] Nara Womens Univ, Grad Sch Human Culture, Div Mat Sci, Nara 6308506, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 10期
关键词
D O I
10.1021/jo001494l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Feeding experiments using Cl-36 showed that Melzispermum,dauricum root culture produces four alkaloids containing chlorine. They included the novel alkaloids dauricumine and dauricumidine as well as the known alkaloids acutumine and acutumidine. The structures of novel alkaloids were established by spectroscopic, crystallographic, and chemical methods. These four alkaloids were labeled with Cl-36, isolated, and fed independently to root cultures. Mutual conversion between acutumine and acutumidine, and between dauricumine and dauricumidine by N-methylation and N-demethylation, was demonstrated. Moreover, dauricumine was converted to acutumine and acutumidine. Epimerization of acutumidine to dauricumidine or vice versa was not observed. These results suggest that dauricumine is the first chlorinated alkaloid formed in cultured M. dauricum roots. Skewed distribution of radioactivity derived from labeled dauricumine is proof that epimerization at C-l proceeds at a lower rate than N-demethylation.
引用
收藏
页码:3299 / 3302
页数:4
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