RESUMO
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.
Assuntos
Alcaloides/farmacologia , Antivirais/farmacologia , Papaver/química , Alcaloides/isolamento & purificação , Antivirais/química , Linhagem Celular , Efeito Citopatogênico Viral/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria UltravioletaRESUMO
Protopine is an isoquinoline alkaloid contained in plants in northeast Asia. In this study, we investigated whether protopine derived from Hypecoum erectum L could suppress lipopolysaccharide (LPS)-induced inflammatory responses in murine macrophages (Raw 264.7 cells). Protopine was found to reduce nitric oxide (NO), cyclooxygenase-2 (COX-2), and prostaglandin E(2) (PGE(2)) production by LPS-stimulated Raw 264.7 cells, without a cytotoxic effect. Pre-treatment of Raw 264.7 cells with protopine reduced the production of pro-inflammatory cytokines. These inhibitory effects were caused by blocking phosphorylation of mitogen-activated protein kinases (MAP kinases) and also blocking activation of a nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB).
Assuntos
Benzofenantridinas/farmacologia , Alcaloides de Berberina/farmacologia , Inflamação/metabolismo , Animais , Benzofenantridinas/química , Alcaloides de Berberina/química , Linhagem Celular , Ciclo-Oxigenase 2/metabolismo , Citocinas/metabolismo , Dinoprostona/metabolismo , Lipopolissacarídeos/toxicidade , Macrófagos/efeitos dos fármacos , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Papaveraceae/química , FosforilaçãoRESUMO
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.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides de Berberina/isolamento & purificação , Ecossistema , Papaveraceae/química , Alcaloides/química , Benzofenantridinas/química , Benzofenantridinas/isolamento & purificação , Alcaloides de Berberina/química , Estrutura Molecular , MongóliaRESUMO
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.
Assuntos
Alcaloides/isolamento & purificação , Papaver/química , Alcaloides/química , Estrutura Molecular , Morfinanos/isolamento & purificação , Análise EspectralRESUMO
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.
