RESUMEN
Five new spirocyclic polycyclic polyprenylated acylphloroglucinols, Hyperpatulones C-G (1-5), were obtained from the leaves of Hypericum patulum. Their structures were characterized by the comprehensive analysis of their IR, NMR, CD spectra and HRESIMS data. All the new compounds were evaluated for the α-glycosidase inhibitory activities. Among them, compounds 3-5 showed α-glucosidase inhibitory activities, with IC50 values of 14.06-37.69 µM.
Asunto(s)
Inhibidores de Glicósido Hidrolasas/farmacología , Hypericum/química , Floroglucinol/farmacología , China , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Estructura Molecular , Floroglucinol/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Hojas de la Planta/química , alfa-GlucosidasasRESUMEN
Nine new spirocyclic acylphloroglucinol derivatives, hyperpatulols A-I (1-9), were characterized from the flowers of Hypericum patulum. Their structures were elucidated by the basic analysis of the obtained spectroscopic data, and their absolute configurations were assigned by both the electronic circular dichroism (ECD) exciton chirality method and ECD calculation. The evaluation of their anti-migration effects on U2-OS human osteosarcoma cells showed that compound 4 exhibited moderate inhibitory activity in a dose-dependent manner. Further pharmacological studies revealed that 4 could regulate the expression of the proteins Vimentin and E-cadherin.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Flores/química , Hypericum/química , Floroglucinol/farmacología , Compuestos de Espiro/farmacología , Antígenos CD/genética , Antígenos CD/metabolismo , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Cadherinas/genética , Cadherinas/metabolismo , Línea Celular Tumoral , Movimiento Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Floroglucinol/análogos & derivados , Floroglucinol/química , Compuestos de Espiro/química , Compuestos de Espiro/aislamiento & purificación , Relación Estructura-Actividad , Vimentina/genética , Vimentina/metabolismoRESUMEN
Hypatulone A (1), an acylphloroglucinol possessing an unprecedented homoadamantane architecture based on a tricyclo-[4.3.1.13,8]-undecane core and a unique 5/5/7/6/6 pentacyclic ring system, together with its biogenetic precursor hyperbeanol B (2), was isolated from Hypericum patulum. The structure of 1 was elucidated by extensive spectroscopic analysis and electronic circular dichroism calculation. Its plausible biosynthetic pathway via Wagner-Meerwein rearrangement was proposed. 1 exhibited nitric oxide inhibitory effect on LPS-induced RAW264.7 cell line (IC50 18.8 ± 1.75 µM).