Chemical and Antiviral Study on Alkaloids from Papaver pseudocanescens M. Pop.

Abstract

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-dihydrofl avinantine, and fl avinantine 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 fi rst time in the species. All structures were established by physical and spectral analysis. As a fi rst 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 signifi cant 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 of Papaver libanoticum and their Cytotoxic Activity

“…The 1 H-NMR spectrum indicated the presence of three -OCH3 groups correlated to C-1, C-10, and C-11, respectively. According to all correlations (NOSY, COSY, and HMBC), the chemical structure of alkaloid 4 was confirmed to be alborine [13]. Alkaloid 6 was isolated in the form of yellow crystals.…”

“…It also showed significant antiplasmodial activities with a good selectivity index [20]. Alborine demonstrated a significant and selective dose-dependent activity against the replication of poliovirus type 1 [13]. Again, berberine was reported to have therapeutic effects on the diseases of the endocrine system, digestive system, circulation system, respiratory system, and other systems [21].…”

Phytocompounds as a source for the development of new drugs to treat respiratory viral infections

“…Different efficacy and safety profiles have also been reported for alkaloids isolated from Papaver pseudocanescens [ 58 ]. Among them, only 8,14-dihydroflavinantine and (−)-flavinantine were considered active against HRV ( Table 7.5 ).…”