RESUMEN
Two pairs of rare benzofuran glucoside epimers, indicuses A and B and indicuses C and D, three biogenetically related compounds indicuses E-G, and one coumarin indicus H, as well as 11 known compounds, were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of indicuses A-H were elucidated by NMR and MS data, as well as by CD. (S)-Marmesinin exhibited moderate antimicrobial activity in vitro against Bacillus subtilis and Saccharomyces cerevisiae. 7,8-Dihydroxy-3-(3-methyl-2-butenyl) coumarin, umbelliferone, and scopoletin displayed strong cytotoxic activity in vitro against human bladder carcinoma cell line EJ. The structure-activity relationships indicate that hydroxylation at C-7 in the cytotoxic compounds is crucial to their activities.
Asunto(s)
Benzofuranos/química , Cumarinas/química , Glicósidos/química , Moraceae/química , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Bacillus subtilis/efectos de los fármacos , Benzofuranos/aislamiento & purificación , Línea Celular Tumoral , Cumarinas/aislamiento & purificación , Furanos/química , Furanos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Humanos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Corteza de la Planta/química , Extractos Vegetales/química , Saccharomyces cerevisiae/efectos de los fármacos , Escopoletina/química , Escopoletina/aislamiento & purificación , Relación Estructura-Actividad , Umbeliferonas/química , Umbeliferonas/aislamiento & purificaciónRESUMEN
A pair of enantiomers and a pair of 2,3-dihydro-1H-indene epimers, rac-indidene A (rac-1), indidenes B and C (2, 3); four new coumarin glucosides (4-7); and four known coumarin glucosides (8-11) were isolated from the bark of Streblus indicus (Bur.) Corner. The structures of 1-11 were defined by physical data analyses, including MS, NMR, and single-crystal X-ray diffraction. The absolute configurations of the 2,3-dihydro-1H-indene derivatives were defined via experimental and calculated ECD data. rac-Indidene A and indidenes B and C showed inhibitory activity against A549 and MCF-7 tumor cells with IC50 values in the range of 2.2 ± 0.1 to 7.2 ± 0.9 µM.
