RESUMEN
Hyperacmotone A, a polycyclic polyprenylated acylphloroglucinol (PPAP) with an unprecedented skeleton, along with five undescribed congeners and eleven reported ones, was isolated from Hypericum acmosepalum. Hyperacmotone A possesses a unique monocyclic ring skeleton based on a cyclopent-4-ene-1,3-dione acylphloroglucinol core. Their structures were elucidated by extensive analysis of HRESIMS, NMR, biogenetic pathway, and quantum-chemical calculations. In addition, hypercohone G exhibited significant protective effects on high-glucose-injured HUVECs.
Asunto(s)
Hypericum , Humanos , Células Endoteliales , GlucosaRESUMEN
Melodicochinines A - D (1-4), four new monoterpene indole alkaloids (MIAs), along with 21 known ones, were isolated from the stems and twigs of Melodinus cochinchinensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. A ubiquitin-rhodamine 110 assay showed that 11-methyloxytabersonine had potential inhibitory effect against ubiquitin-specific protease 7 (USP7).
Asunto(s)
Apocynaceae/química , Extractos Vegetales/química , Alcaloides de Triptamina Secologanina/aislamiento & purificación , China , Cromatografía Líquida de Alta Presión , Espectroscopía de Resonancia Magnética , Rotación Óptica , Extractos Vegetales/aislamiento & purificación , Tallos de la Planta/química , Alcaloides de Triptamina Secologanina/química , Espectrofotometría InfrarrojaRESUMEN
Acmoxanthones A-E (1-5), five new lavandulylated xanthones, were isolated from the aerial parts of Hypericum acmosepalum, together with four known xanthones. Their structures with absolute configurations were elucidated on the basis of analysis of MS, NMR and chiroptical properties. A bioassay against high glucose-induced damage on human umbilical vein endothelial cells (HUVECs) showed ananixanthone (6) and osajaxanthone (7) had potential antioxidative damage activity with EC50 values of 10.5 µg/mL and 7.6 µg/mL, respectively, while 3-hydroxy-2,4-dimethoxyxanthone (8) exhibited cytotoxic effect on the damaged cells with IC50 values of 7.1 µg/mL.
Asunto(s)
Hypericum/química , Xantonas/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Células Endoteliales de la Vena Umbilical Humana/efectos de los fármacos , Humanos , Isoflavonas , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/química , Xantonas/aislamiento & purificaciónRESUMEN
Uralins A - D, four undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) featuring an unprecedented fused hexacyclic architecture, a unique monocyclic tetra-seco-tetranor-b-PPAP, an oxidative b-PPAP and a rare norspiroindane-type m-PPAP, respectively, were isolated from the aerial parts of Hypericum uralum, along with ten known PPAPs. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques (MS, NMR, [α]D, CD), conceivable biogenetic pathways and time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Biological assays showed three b-PPAPs had moderate antioxidative damage activities, while spiroindanes exhibited moderate cytotoxic effects.
Asunto(s)
Hypericum , Dicroismo Circular , Espectroscopía de Resonancia Magnética , Estructura Molecular , Floroglucinol/farmacologíaRESUMEN
Hookerianones A - E (1-5), five new polyprenylated acylphloroglucinols (PPAPs), along with six known ones, were isolated from the aerial parts of Hypericum hookerianum. Their structures were elucidated by analyses of MS, NMR, chiroptical properties, biogenetic pathway, and/or single crystal X-ray diffraction. A ubiquitin-rhodamine 110 assay showed that furohyperforin and hypercalin C, two representative PPAPs in this plant, inhibited more than 90% USP7 at the concentration of 10 µM.
Asunto(s)
Hypericum/química , Floroglucinol/farmacología , Inhibidores de Proteasas/farmacología , Peptidasa Específica de Ubiquitina 7/antagonistas & inhibidores , China , Estructura Molecular , Floroglucinol/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/química , Inhibidores de Proteasas/aislamiento & purificaciónRESUMEN
Alopecines A-E (1-5), five unusual matrine-type alkaloids featuring with an additional dichlorocyclopropane (1-3) or a di/tri-chloromethyl (4/5) attached on the D ring, were isolated from the seeds of Sophora alopecuroides. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques, and X-ray diffraction analyses or time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Alkaloid 4 exhibited potent inhibitory effects on the proliferation of ConA-induced T lymphocytes or LPS-induced B cells with IC50 value of 3.98 or 3.74 µM, respectively.
Asunto(s)
Alcaloides/farmacología , Inmunosupresores/farmacología , Extractos Vegetales/farmacología , Sophora/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Animales , Linfocitos B/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Concanavalina A/antagonistas & inhibidores , Concanavalina A/farmacología , Relación Dosis-Respuesta a Droga , Femenino , Inmunosupresores/química , Inmunosupresores/aislamiento & purificación , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Ratones , Ratones Endogámicos BALB C , Conformación Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Semillas/química , Estereoisomerismo , Relación Estructura-Actividad , Linfocitos T/efectos de los fármacosRESUMEN
A phytochemical investigation on the twigs and leaves of Flueggea virosa (Euphorbiaceae) led to the isolation of flueggenoids A - E (1-5), five new 13-methyl-ent-podocarpanes, together with eleven known compounds (6-16). Their structures and absolute configurations were elucidated on the basis of extensive MS and NMR data analysis, and/or single-crystal X-ray diffraction, time-dependent density functional theory (TDDFT)-based electronic circular dichroism (ECD) calculations, and chemical transformation. All isolates were evaluated for anti-HCV activity, the results showed that terpenoids of F. virosa had nonnegligible contribution for the anti-HCV activity.