RESUMEN
Two new glycosides, cinnacassides F (1) and G (2), with a rare geranylphenylacetate carbon skeleton, were isolated from the barks of Cinnamomum cassia, along with three known analogues, cinnacassides A (3), B (4) and C (5). The structures of the new compounds were elucidated on the basis of extensive NMR spectroscopic analyses and chemical method. Compounds 1-5 were investigated for their immunomodulatory activities, and compounds 1, 3 and 4 showed differential immunosuppressive activities against murine lymphocytes.
Asunto(s)
Cinnamomum aromaticum/química , Glicósidos/química , Inmunosupresores/química , Inmunosupresores/farmacología , Fenilacetatos/química , Animales , Evaluación Preclínica de Medicamentos/métodos , Glicósidos/farmacología , Linfocitos/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Fenilacetatos/farmacologíaRESUMEN
Seven filicinic acid-based meroterpenoids (1-7), possessing 6/6/11, 6/6/7/5, or 6/6/10 ring systems, were isolated from Hypericum japonicum. All of them have novel skeletons with the incorporation of sesquiterpenoid moieties to an acylated filicinic acid. Compounds 2a and 4 exhibited significant efficacy on anti-Epstein-Barr virus, with EC50 values of 0.57 and 0.49 µM, respectively. Furthermore, compounds 2a and 4 were well accommodated to the binding pocket of 2GV9 predicted by the molecular docking.
Asunto(s)
Antivirales/farmacología , Ciclohexenos/farmacología , Herpesvirus Humano 4/efectos de los fármacos , Hypericum/química , Terpenos/farmacología , Animales , Antivirales/química , Antivirales/aislamiento & purificación , Línea Celular Tumoral , Ciclohexenos/química , Ciclohexenos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Simulación del Acoplamiento Molecular , Relación Estructura-Actividad , Terpenos/química , Terpenos/aislamiento & purificaciónRESUMEN
Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-ß-D-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5-10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1-4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.