RESUMO
Twelve new diterpenoids based on two rare skeletal types, namely, paralianones A-D (1-4) and pepluanols A-H (5-12), along with five known compounds, were isolated from an acetone extract of Euphorbia peplus. Their structures were proposed based on 1D and 2D NMR spectroscopic data analysis. These diterpenoids were evaluated for potential anti-inflammatory activity in a lipopolysaccharide-stimulated mouse macrophage cellular model. Compounds 3, 4, 11, 13, and 16 displayed moderate inhibitory effects on NO inhibition, with IC50 values ranging from 29.9 to 38.3 µM.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Euphorbia/química , Animais , Anti-Inflamatórios/química , Antineoplásicos Fitogênicos/química , Diterpenos/química , Medicamentos de Ervas Chinesas/química , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Raízes de Plantas/químicaRESUMO
AIM: To study the 9, 19-cycloartane triterpenes from the roots of Cimicifuga foetida. METHOD: Chromatographic separations by silica gel, C18 reversed phase silica gel, and high-performance liquid chromatography (HPLC) were used. All of the structures were elucidated on the basis of spectroscopic analysis and chemical methods. RESULTS: Five 9, 19-cycloartane triterpenes, (3ß, 12ß, 15α, 24R)-12, 2'-diacetoxy-24, 25-epoxy-15-hydroxy-16, 23-dione-3-O-α-L-arabinopyranoside (1), actein (2), 23-epi-26-deoxyactein (3), asiaticoside B (4), and 12ß-hydroxycimigenol (5) were isolated from the roots of Cimicifuga foetida. CONCLUSION: Compound 1 is a new triterpene with two acetoxy groups at C-2' and C-12.
Assuntos
Cimicifuga/química , Medicamentos de Ervas Chinesas/química , Raízes de Plantas/química , Triterpenos/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Estrutura Molecular , Triterpenos/isolamento & purificaçãoRESUMO
Six new cucurbitane-type triterpenoids, karavilagenin F (1), karavilosides XII and XIII (2, 3), momordicines VI, VII, and VIII (4, 5 and 6), along with four known ones, 5ß,19-epoxy-25-methoxycucurbita-6,23-diene-3ß,19-diol (7), 5ß,19-epoxycucurbita-6, 23-diene-3ß,19,25-triol (8), kuguacin R (9), and (19R,23E)-5ß,19-epoxy-19-methoxycucurbita-6,23,25-trien-3ß-ol (10), were isolated from the stems and leaves of Momordica charantia L. Their chemical structures were elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, COSY, and ROESY), MS experiments, and CD spectrum. Compound 6 showed weak cytotoxicity against five human cancer cells lines with IC50 values of 14.3-20.5µmol/L.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Momordica charantia/química , Extratos Vegetais/isolamento & purificação , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Folhas de Planta/química , Caules de Planta/química , Triterpenos/química , Triterpenos/farmacologiaRESUMO
A phytochemical investigation of the flowers of Rhododendron molle has yielded two new grayanane diterpenoids, rhodomolleins F and G (1, 2). Compounds 1 and 2 possessed an oxo-bridge between C-5 and C-9, and their structures were elucidated on the basis of interpretation of spectroscopic data, including 1D and 2D NMR techniques.