RESUMO
Four new jatropholane-type diterpenes (1-4), named sikkimenoids A-D, were isolated from the aerial parts of Euphorbia sikkimensis. The structural elucidations of 1-4 were accomplished by extensive NMR analyses, and their absolute configurations were established by ECD calculations. Compound 2 exhibited weak antiangiogenic activity with an IC(50) value of 43.0 µM when evaluated using a zebrafish model.
Assuntos
Inibidores da Angiogênese/isolamento & purificação , Diterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Euphorbia/química , Algoritmos , Inibidores da Angiogênese/química , Inibidores da Angiogênese/farmacologia , Animais , Modelos Animais de Doenças , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Peixe-ZebraRESUMO
OBJECTIVE: To study the chemical constituents of Gastrodia elata. METHODS: The compounds were isolated by silica gel column chromatography and recrystallization and their structures were elucidated by spectral analysis. RESULTS: The structures of 14 compounds were identified as: p-hydroxybenzyl alcohol (1), p-hydroxybenzaldehyde (2), 3, 4-dihydroxybenzaldehyde (3), 4, 4'-dihydroxy, dibenzyl ether (4), 4-hydroxymethyl benzyl-4'-hydroxy-3'-(4"-hydroxy benzl) benzyl ether (5), 4-ethoxybenzyl alcohol (6), anisic alcohol (7), bis(3, 4-dihydroxyphenyl) methane (8), 4, 4'-dihydroxydiphenyl methane (9), 2, 4-bis(4'-hydroxy-benzyl)-phenol (10), 4-( methoxymenthyl) benzene-1, 2-diol (11), p-methylphenyl-1 -O-beta-D-glucopyranoside (12), N6-(4'-hydroxybenzl) -adenosine (13) and beta-sitosterol (14). CONCLUSION: Compounds 6 - 8 and 11 are isolated from this plant for the first time.
Assuntos
Gastrodia/química , Extratos Vegetais/isolamento & purificação , Plantas Medicinais/química , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Álcoois Benzílicos/química , Álcoois Benzílicos/isolamento & purificação , Etanol/química , Cromatografia Gasosa-Espectrometria de Massas , Estrutura Molecular , Extratos Vegetais/química , Raízes de Plantas/químicaRESUMO
One rare flavonoid-diterpene heterodimer, denticulatain C (1), one modified geranyl-type side chain substituted flavonoid, denticulatain D (2) and one geranylated flavonoid, denticulatain E (3), as well as 11 known compounds (4-14) were isolated from the fronds of Macaranga denticulata. Their structures were elucidated on the basis of extensive spectroscopic interpretation. Compounds 4 and 8 inhibited the proliferation of A-549 cell line with IC50 values of 48.6 and 20.2 µg/mL, respectively. Compounds 3, 6, and 8 exhibited significant antiangiogenic activity on a zebrafish model with IC50 values of 9.78, 0.34, and 2.55 µg/mL, respectively.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Euphorbiaceae/química , Flavonoides/farmacologia , Inibidores da Angiogênese/farmacologia , Animais , Linhagem Celular Tumoral , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Prenilação , Peixe-ZebraRESUMO
Three new diterpenoids, stracheyioids A-C (1-3), as well as 36 known compounds (4-39) were isolated from the whole plants of Euphorbia stracheyi. Compound 1 was a rare 13-deoxy tigliane diterpenoid and compound 2 was an ingenol diterpenoid characterized by an unique 2Z,4Z-decadienoyl acidic moieties. All the known compounds were isolated from E. stracheyi for the first time. Their structures were elucidated on the basis of extensive spectroscopic interpretation. Compounds 1-39 were tested for their cytotoxicity against five cancer cell lines (A-549, MCF-7, Hep G2, Hela and P388) and showed IC50 values in the range 6.64-42.86 µM. The antiangiogenic activities of the isolated compounds were also evaluated using a zebrafish model.