Chemical and antiviral study on alkaloids from Papaver pseudocanescens M. Pop.

The phytochemical investigation of the aerial parts of Papaver pseudocanescens M. Pop. of Mongolian origin resulted in the isolation and structural elucidation of 8 alkaloids of the isoquinoline and promorphinane type. 8,14-Dihydroamurine, 8,14-dihydroflavinantine, and flavinantine are promorphinanes. Alborine, mecambridine, and mecambridine methohydroxide are retroprotoberberines. Amurensinine is an isopavine alkaloid and O-methylarmepavine is a benzylisoquinoline alkaloid. O-Methylarmepavine is a new alkaloid for the genus Papaver. Promorphinane-type alkaloids have been found for the first time in the species. All structures were established by physical and spectral analysis. As a first attempt to describe some of the biological activities of these alkaloids, the antiviral effect was tested against the in vitro replication of several viruses which belong to different taxonomic groups and represent significant human pathogens. Based on the results, the conclusion could be drawn that particular alkaloids from P. pseudocanescens possess selective antiviral effects against the replication of poliovirus 1 and human rhinovirus 14, two viruses from the Enterovirus genus of the Picornaviridae family.

Alkaloids from Papaver nudicaule L.

A new promorphinane alkaloid (-)-8,14-dihydroflavinantine was isolated from the aerial parts of Papaver nudicaule L. (Papaveraceae) growing in Mongolia. Six known isoquinoline alkaloids (+)-amuronine, pseudoprotopine, allocryptopine, (-)-dihydroamuronine, (-)-amurensinine N-oxide A and (-)-amurensinine N-oxide B were isolated, too. Pseudoprotopine has been found for the first time in a plant of the family Papaveraceae. (-)-dihydroamuronine, (-)-amurensinine N-oxide A and (-)-amurensinine N-oxide B are new for the genus Papaver. All structures were established using spectral and physical data.

A new 8,14-dihydropromorphinane alkaloid from Papaver nudicaule L.

A racem. 8,14-dihydroamurine is a new promorphinane alkaloid isolated from the aerial parts of Papaver nudicaule L. (Papaveraceae) of Mongolian origin. The known promorphinane and isopavine alkaloids (+)-amurine, (-)-amurensinine, (-)-O-methylthalisopavine, (-)-flavinantine and (-)-amurensine were also described. All structures were established by physical and spectral analysis. Flavinantine has been found for the first time in the species.

Alkaloids from Isopyrum thalictroides L.

Two new aporphine-benzylisoquinoline alkaloids thaliphine and isothaliphine with a new type of ether bridge were isolated from the roots and rhyzomes of Isopyrum thalictroides L. (Ranunculaceae). Their structures were established by physical and spectral analysis. The known alkaloid N-methylglaucine was isolated for the first time from a plant of the family Ranunculaceae.

Alkaloids from Mongolian species Hypecoum lactiflorum Kar. et Kir. Pazij.

A new secoberbine alkaloid (-)-N-methylcorydalisol was isolated from the aerial parts of Hypecoum lactiflorum Kar. et Kir. Pazij. (Papaveraceae) of Mongolian origin and was characterised. The known alkaloids of protopine and protoberberine type protopine, allocryptopine, (-)-N-methylcanadine and (-)-N-methylstylopine were also isolated. (-)-N-methylstylopine is a new alkaloid for the genus, while (-)-N-methylcanadine is new for the species. All structures were established by physical and spectral analysis.