Thalictrum dioicum

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). 

The spectral analyses of another new base from Thalictrum dioicum established its structure as a diphenolic isopavine, to which the trivial name (—)-thalidicine was assigned. The nonequivalency of the aromatic protons in the NMR spectrum led to the consideration of the two possible structures, 22 and 23, where 23 was apparently favored for biosynthetic considerations and also by analogy to the NMR aromatic proton chemical shifts of other known isopavine... 

Corydine (25i) was isolated from Thalictrum dioicum (424) and from the bark of Cinnamomum (425), hernangerine (25c) from Hemandia papuana (426), and boldine (24e) and laurolitsine (24b) from Litsea turfosa... 

Roemeria hybrida Thalictrum dioicum T. longipedunculatum T. minus T. polyganum... 

Thalidoxine (208 R = H) is a new aporphine-benzylisoquinoline alkaloid isolated from Thalictrum dioicum. Methylation with diazomethane gave the known thalicarpine (208 R = Me). The site of the phenolic OH was established at C-4" rather than at C-5" by n.m.r. studies of the acetate (208 R = Ac). The... 

Benzylisoquinoline-aporphine dimers have been isolated from Thalictrum dioicum (pennsylvamine), T. revolutum (thalirevoline, thalirevolutine, thalilu-tine, and thalilutidine), and T. minus (thaliadamine). ... 

Berberine, coptisine, and /3-stylopine methohydroxide have been isolated from Papaver rhoeas L., berberine, berberubine, isocorypalmine, and thalifendine from Thalictrum dioicum, berberine from T. sachalinense, corydaline from Corydalis marschalliana, scoulerine, ophiocarpine, isocorypalmine, and cheilanthifoline from C. vaginans, C. gigantea, and C marschalliana, and ophiocarpine, stylopine, cheilanthifoline, isocorypalmine, and the chlorides of berberine, coptisine, and dehydrocheilanthifoline from C. ophiocarpa. The alkaloids of C. ophiocarpa were separated by droplet counter-current chromatography. ... 

Pallidine has been isolated from Thalictrum dioicum f bound morphine and codeine in the polysaccharide fraction from Papaver somniferum capsule has been... 

Thalictrum dioicum produces the known (+ )-thalicarpine and (-i-)-pennsyl-vanine, but not (+ )-thalidoxine. The structure of (-f-)-pennsylvanine was further confirmed by its oxidation into O-desmethylhernahdaline by permanganate. 

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