RESUMEN
The two new lignans 3α-O-(ß-D-glucopyranosyl)desoxypodophyllotoxin (1) and 4-O-(ß-D-glucopyranosyl)dehydropodophyllotoxin (2) were isolated from Cleistanthus boivinianus, together with the known lignans deoxypicropodophyllotoxin (3), (±)-ß-apopicropodophyllin (4), (-)-desoxypodophyllotoxin (5), (-)-yatein (6), and ß-peltatin-5-O-ß-D-glucopyranoside (7). The structures of all compounds were characterized by spectroscopic techniques. Compounds 1, 4, and 5 showed potent antiproliferative activities against the A2780 ovarian cancer cell line, with IC50 values of 33.0 ± 3.6, 63.1 ± 6.7, and 230 ± 1 nM, respectively. Compounds 2 and 7 showed only modest A2780 activities, with IC50 values of 2.1 ± 0.3 and 4.9 ± 0.1 µM, respectively, while compounds 3 and 6 had IC50 values of >10 µM. Compound 1 also had potent antiproliferative activity against the HCT-116 human colon carcinoma cell line, with an IC50 value of 20.5 nM, and compound 4 exhibited modest antiproliferative activity against the A2058 human caucasian metastatic melanoma and MES-SA human uterine sarcoma cell lines, with IC50 values of 4.6 and 4.0 µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Lignanos/aislamiento & purificación , Lignanos/farmacología , Malpighiaceae/química , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , Antineoplásicos Fitogénicos/química , Proliferación Celular/efectos de los fármacos , Dioxoles/química , Ensayos de Selección de Medicamentos Antitumorales , Bosques , Células HCT116 , Humanos , Concentración 50 Inhibidora , Lignanos/química , Madagascar , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta/química , Plasmodium falciparum/efectos de los fármacos , EstereoisomerismoRESUMEN
Antiproliferative bioassay-guided fractionation of the ethanol extract of the stems of Anisocycla grandidieri led to the isolation of the known alkaloids stebisimine (1), (+)-1,2-dehydrotelobine (2), (+)-2'-norcocsuline (3) and puetogaline B (4). Herein, we report the full NMR assignments of all compounds and the X-ray crystallography of single crystals of compounds 1 and 3. Compounds 2 and 3 showed moderate antiproliferative activity against the A2780 human ovarian cancer cell line with IC50 values of 4.1 ± 0.3 and 2.7 ± 0.3 µM, respectively, and they also displayed selective activity toward the H460 (large cell lung cancer), MCF-7 (breast ductal carcinoma), and UACC-257 (melanoma) cell lines.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Menispermaceae/química , Árboles/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Células MCF-7 , Madagascar , Espectroscopía de Resonancia Magnética/normas , Modelos Moleculares , Estructura Molecular , Tallos de la Planta/química , Estándares de Referencia , Relación Estructura-ActividadRESUMEN
An ethanol extract of leaves of the plant species Malleastrum sp. collected in northern Madagascar afforded the new clerodane diterpene 18-oxo-cleroda-3,13-dien-16,15-olide (1), together with the three known clerodane diterpenes 16,18-dihydroxykolavenic acid lactone (2), solidagolactone (3) and (-)-kolavenol (4), and the known labdane diterpene 3-oxo-ent-Iabda-8(17),13-dien-15,16-olide (5). Compounds 1, 3, and 4 showed moderate antiproliferative activities against the A2780 ovarian cancer cell line, with the IC50 values of 3.01 ± 0.8, 7.84 ± 0.2, and 17.9 ± 3 µM, respectively. The structure elucidations of all compounds were carried out based on analysis of NMR and mass spectroscopic data. The relative stereochemistry of compound 1 was determined by NOESY NMR spectrum.
Asunto(s)
Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Diterpenos/química , Diterpenos/farmacología , Meliaceae/química , Línea Celular Tumoral , Femenino , Bosques , Humanos , Concentración 50 Inhibidora , Madagascar , Estructura Molecular , Neoplasias Ováricas/tratamiento farmacológicoRESUMEN
Fractionation of an antiplasmodial ethanolic extract from the aerial parts of Vitex cauliflora led to the isolation of the new labdane diterpene 1 together with the known triterpene uvaol. The structure of the new compound 1 was established as 3-oxo,15,17,18-triacetoxy-labda-7,13E-diene on the basis of spectroscopic data (1D and 2D NMR, MS).