RESUMEN
Eleven new furostanol saponins, typaspidosides B-L (1-11), one new spirostanol saponin, typaspidoside M (12), and five known spirostanol saponins, 25S-atropuroside (13), neoaspidistrin (14), (25S)-pratioside D1 (15), 25S-aspidistrin (16) and 25S-neosibiricoside (17) were isolated from the rhizomes of Aspidistra typica Baill. The structures of the new compounds were established using 1D and 2D NMR (1H-1H COSY, HMQC, HMBC and ROESY) spectroscopy, high resolution mass spectrometry, and chemical methods. The aglycones of 1-3 (unusual furostanol saponins with opened E ring type), 9 and 10 (the methoxyl substituent at C-23 position) were found, identified from natural products for the first time. Moreover, the anti-HIV activities of the isolated steroidal glycosides were assessed, and compounds 13, 14, 16 and 17 exhibited high active against HIV-1.
Asunto(s)
Fármacos Anti-VIH/farmacología , VIH-1/efectos de los fármacos , Liliaceae/química , Virus Reordenados/efectos de los fármacos , Rizoma/química , Saponinas/farmacología , Esteroles/farmacología , Fármacos Anti-VIH/aislamiento & purificación , Proteínas de la Cápside/antagonistas & inhibidores , Proteínas de la Cápside/genética , Proteínas de la Cápside/metabolismo , Expresión Génica , Genes Reporteros , Células HEK293 , VIH-1/genética , VIH-1/crecimiento & desarrollo , Humanos , Luciferasas/antagonistas & inhibidores , Luciferasas/genética , Luciferasas/metabolismo , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Virus Reordenados/genética , Virus Reordenados/crecimiento & desarrollo , Saponinas/aislamiento & purificación , Espirostanos/aislamiento & purificación , Espirostanos/farmacología , Esteroides/aislamiento & purificación , Esteroides/farmacología , Esteroles/aislamiento & purificación , Relación Estructura-Actividad , Vesiculovirus/genética , Replicación Viral/efectos de los fármacosRESUMEN
Two new furostanol saponins (1 and 2), along with one known saponin (3), were obtained from the rhizomes of Aspidistra typica Baill. Their structures were elucidated as (25R)-26-O-ß-d-glucopyranosyl-furost-5-ene-12-one-3ß,22α,26-triol-3-O-ß-d-glucopyranosyl-(1 â 2)-[ß-d-xylopyranosyl-(1 â 3)]-ß-d-glucopyranosyl-(1 â 4)-ß-d-galactopyranoside (1, typaspidoside A), (25S)-26-O-ß-d-glucopyranosyl-furost-5-ene-12-one-3ß,22α,26-triol-3-O-ß-d-glucopyranosyl-(1 â 2)-[ß-d-xylopyranosyl-(1 â 3)]-ß-d-glucopyranosyl-(1 â 4)-ß-d-galactopyranoside (2, 25S-typaspidoside A), and timosaponin H1 (3), based on the integrative spectroscopic analysis of 1D- and 2D-NMR experiments, ESI-MS data and chemical evidence. The investigation on the chemical components of this plant is reported for the first time.