RESUMEN
Chemical investigation of the stems of Dulacia egleri resulted in the isolation of eglerisine (1: ), a compound with a rare sesquiterpenoid tropolone skeleton. Its structure was determined by analysis of spectrometric and spectroscopic data, including HRESIMS, 1D, and 2D NMR. The antiproliferative effects of eglerisine were tested in human leukemia lineages. In the Kasumi-1 lineage, an acute myeloid leukemia cell line, eglerisine reduced cell metabolism, as determined by the resazurin assay. Eglerisine did not induce cell death by either apoptotic or necrotic mechanisms. However, a reduction of the absolute number of cells was observed. Eglerisine induced cell cycle arrest after 72 h of treatment by phosphorylation of H2AX histone, reducing the S phase and increasing the G2 phase of the cell cycle.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Olacaceae/química , Extractos Vegetales/farmacología , Sesquiterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ciclo Celular/efectos de los fármacos , Línea Celular Tumoral , Histonas/metabolismo , Humanos , Leucemia Mieloide Aguda , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Sesquiterpenos/química , Sesquiterpenos/farmacologíaRESUMEN
The study about Eugenia dysenterica led to the isolation of 3-acetyl-urs-12-en-28-oic (1), 3-acetyl-olean-12-en-28-oic acid (2) and isoquercetin (3) from the stem barks, and of 3-O-ß-glucopyranosyl-ß-sitosterol (4), methyl 3-hydroxy-4-methoxybenzoate (5), methyl 4-hydroxyphenyl propionate (6), E-methyl-4-hydroxycinnamate (7), quercetin-3-O-(6êê-O-galloyl)-ß-d-glucopyranoside (8) and quercetin-3-O-ß-d-galactopyranoside (9) from the leaves. The structures 1-9 were set through the analysis of their NMR spectroscopic data. Compounds 2, 3 and 5-8 were reported for the first time in the Eugenia genus. Compound 8 reduced cell viability and presented IC50 values 40.3 and 36.7 µM, for the CCRF-CEM and the Kasumi-1 cells, respectively.