RESUMEN
Three new alkaloids, cassiarins C-E (1-3), and a new chromone, 10,11-dihydroanhydrobarakol (4), which showed moderate antiplasmodial activity against Plasmodium falciparum 3D7, were isolated from flowers of Cassia siamea, and the structures of 1-4 were elucidated by 2D NMR analysis and chemical transformation. Cassiarin D (2) was a dimeric compound consisting of 5-acetonyl-7-hydroxy-2-methylchromone and cassiarin C (1), and cassiarin E (3) was a dimer of cassiarins A and C (1).
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Cassia/química , Compuestos Heterocíclicos con 3 Anillos/aislamiento & purificación , Compuestos Heterocíclicos con 3 Anillos/farmacología , Plasmodium falciparum/efectos de los fármacos , Alcaloides/química , Animales , Antimaláricos/química , Flores/química , Compuestos Heterocíclicos con 3 Anillos/química , Indonesia , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Pruebas de Sensibilidad ParasitariaRESUMEN
A new bischromone, chrobisiamone A (1) with an antiplasmodial activity has been isolated from the leaves of Cassia siamea and the structure was elucidated by 2D NMR analysis. Cyclization of 5-acetonyl-7-hydroxy-2-methylchromone (2) in the presence of ammonium acetate resulted in generation of cassiarin A (3) with an unprecedented tricyclic skeleton, supporting a biogenetic pathway proposed for 3.
Asunto(s)
Antimaláricos/farmacología , Cassia/metabolismo , Cromonas/química , Compuestos Heterocíclicos con 3 Anillos/química , Extractos Vegetales/química , Biomimética , Química Farmacéutica/métodos , Cromonas/síntesis química , Cromonas/farmacología , Diseño de Fármacos , Espectroscopía de Resonancia Magnética , Malaria/prevención & control , Modelos Químicos , Modelos Moleculares , Hojas de la Planta/metabolismoRESUMEN
Two novel alkaloids with an unprecedented tricyclic skeleton, cassiarins A (1) and B (2), have been isolated from the leaves of Cassia siamea, and the structures were elucidated on the basis of spectroscopic data. Cassiarin A (1) showed a potent antiplasmodial activity.
Asunto(s)
Antimaláricos/química , Cassia/química , Compuestos Heterocíclicos con 3 Anillos/química , Extractos Vegetales/uso terapéutico , Hojas de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Animales , Antimaláricos/uso terapéutico , Compuestos Heterocíclicos con 3 Anillos/farmacología , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Estructura Molecular , Pruebas de Sensibilidad ParasitariaRESUMEN
A new spiro heterocycle, decarboxyportentol acetate (1) was isolated from the barks of Laumoniera bruceadelpha Nooteboom (Simaroubaceae), together with 3,4-dehydrotheaspirone (2), and their structures were elucidated by 2D NMR analysis. 3,4-Dehydrotheaspirone (2) showed potent antiplasmodial activity against Plasmodium falciparum 3D7.
Asunto(s)
Antimaláricos/farmacología , Simaroubaceae/química , Compuestos de Espiro/farmacología , Antimaláricos/química , Estructura Molecular , Plasmodium falciparum/efectos de los fármacos , Compuestos de Espiro/químicaRESUMEN
A novel alkaloid, cassiarin F (1), which showed potent antiplasmodial activity against Plasmodium falciparum in vitro, was isolated from the flowers of Cassia siamea, and its structure was elucidated on the basis of 2D NMR analyses. A total synthesis of 1 was also achieved by employing the Suzuki coupling constructing biaryl unit, nucleophilic aromatic substitution, and Houben-Hoesch type ring construction as key steps.
Asunto(s)
Alcaloides/síntesis química , Cassia/química , Flores/química , Compuestos Heterocíclicos de 4 o más Anillos/síntesis química , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
New quassinoids, delaumonones A (1) and B (2) have been isolated from the bark of Laumoniera bruceadelpha NOOTEBOOM (Simaroubaceae) and the structures were elucidated by 2D NMR analysis and a chemical correlation. Delaumonones showed an antimalarial activity against Plasmodium falciparum.
Asunto(s)
Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Plasmodium falciparum/efectos de los fármacos , Cuassinas/aislamiento & purificación , Cuassinas/farmacología , Simaroubaceae/química , Animales , Antimaláricos/química , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Espectroscopía de Resonancia Magnética/normas , Modelos Moleculares , Conformación Molecular , Pruebas de Sensibilidad Parasitaria , Corteza de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Cuassinas/química , Estándares de Referencia , EstereoisomerismoRESUMEN
From the fruits of Phaleria macrocarpa, icariside C(3) (1), phalerin (2), and mangiferin (3) were isolated and their structures were identified on the basis of spectroscopic data. Icariside C(3) (1) showed a slow vasorelaxant activity against noradrenaline-induced contraction of isolated rat aorta. The structure of phalerin (2) was revised as 2,4',6-trihydroxy-4-methoxybenzophenone-2-O-beta-D-glucoside.