Alkaloids Thalictrum polygamum

A continuing investigation of the alkaloids of Thalictrum polygamum Muhl. has resulted in the isolation of members of an interesting and novel isoquinoline group, the aporphine-pavine dimers. Pennsylpavine (59) and pennsylpavoline (60) are weakly basic phenolic alkaloids which are accompanied in the plant by the aporphine-benzylisoquinolines pennsylvanine (46) and pennsylvanamine (47). It therefore seems likely that (46) and (47) are biogenetic precursors for (59) and (60), respectively. ... 

The two dimeric pavine alkaloids (pennsylpavine and pennsylpavoline) were isolated from Thalictrum polygamum (565). 

New benzylisoquinoline alkaloids are (+ )-iV-norprotosinomenine (14), found in Erythrina lithosperma Blume (Leguminosae), and A-methylpalaudinium chloride (15), isolated from Thalictrum polygamum Muhl. (Ranunculaceae). ... 

A strongly levorotatory alkaloid isolated from Thalictrum dioicum by Shamma and co-workers (82) was named (-)-thalidine (21) and assigned an isopavine structure on the basis of mass spectral analysis. The diphenolic nature of the alkaloid was evidenced by H-NMR data and by the bathochromic shift in the UV spectrum on addition of alkali. Diazomethane 0-methylation produced (—)-thalisopavine (30) and (—)-0-methylthalisopavine (26). Of the two probable isomeric structures, 21 and 22, 21 was slightly favored on biosynthetic grounds. Final proof to structure was provided by total synthesis (82). (—)-Thalidine has also been reported from T. polygamum (83). 

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