RESUMEN
The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.
Asunto(s)
Antimaláricos/aislamiento & purificación , Alcaloides Indólicos/aislamiento & purificación , Plantas Medicinales/química , Polyalthia/química , Sesquiterpenos/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/farmacología , Camerún , Cloroquina/farmacología , Alcaloides Indólicos/química , Alcaloides Indólicos/farmacología , Masculino , Estructura Molecular , Mioblastos Esqueléticos/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Pruebas de Sensibilidad Parasitaria , Corteza de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Hidrocarburos Policíclicos Aromáticos/aislamiento & purificación , Ratas , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
Investigation of the crude extract obtained from the aerial parts of Canthium multiflorum led to the isolation of a new iridoid (1) together with twelve known compounds. The structures of these compounds were elucidated by interpretation of 1D and 2D NMR spectroscopic data, accurate mass measurements and comparison with analytical data of previously known analogues. Most of the isolated compounds have been reported for the first time from C. multiflorium. The antimicrobial activities of the isolated compounds were evaluated on five different bacterial strains using agar diffusion technique. The Gram-positive bacterium Staphylococcus aureus subsp. aureus (DSM 799), and the Gram-negative bacteria Actinobacter calco-aceticus (DSM 30006), Serratia plymuthica (DSM 4540), Pseudomonas stutzeri (DSM 4166) and Escherichia coli (DSM 1116) were employed for this purpose. The new iridoid, named 6-oxo-genipin (1), demonstrated significant inhibitory activity against all microbial strains tested, especially the pathogen Staphylococcus aureus. In addition, the compounds 3, 4 and 9 exhibited antiplasmodial activity against Plasmodium falciparum strain K1 and weak cytotoxicity against L6 cell lines.