RESUMO
Two new glucosides, salviadigitoside A (1) and salviatalin A-19-O-ß-glucoside (2), belonging to the salviatalin type diterpenoids, and a new cyclopenta[c]pyridine, salviadiginine A (3), were isolated from the roots of Salvia digitaloids. Structures of these compounds were determined on the basis of spectroscopic analysis. In addition, compounds 1-3 were evaluated for their anti-inflammatory activity, but the results showed a weak anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/química , Diterpenos/química , Glucosídeos/química , Extratos Vegetais/química , Salvia/química , Adulto , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Glucosídeos/farmacologia , Humanos , Neutrófilos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Raízes de Plantas/químicaRESUMO
Phytochemical investigation of the roots and stems of Illigera luzonensis afforded two new aporphine alkaloids (1) and (2), one new bisdehydroaporphine alkaloid (3), and one new benzenoid (4), along with 28 known structures. The structures of new compounds were elucidated by spectral and MS analysis. Among the isolated compounds, (1) and (4-13) were subjected into the examination for their inhibitory effects on the aggregation of washed rabbit platelets.
Assuntos
Hernandiaceae/química , Extratos Vegetais/farmacologia , Agregação Plaquetária/efeitos dos fármacos , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Aporfinas/química , Hernandiaceae/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Extratos Vegetais/química , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Caules de Planta/química , Caules de Planta/metabolismo , Inibidores da Agregação Plaquetária/farmacologia , CoelhosRESUMO
A new and efficient synthetic pathway employed the aldol condensation between the acetophenone (3) and vanillin derivative (4) resulted in the precursor chalcone intermediate (14). The target compound viscolin (1) could be afforded through the hydrogenation of the chalcone and followed by deprotection. The present strategy described the development of a more efficient procedure that allowed large-scale production of viscolin for the further research of biological activity both in vitro and in vivo.
Assuntos
Anti-Inflamatórios/síntese química , Compostos de Bifenilo/química , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Propano/análogos & derivados , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Compostos de Bifenilo/síntese química , Compostos de Bifenilo/farmacologia , Linhagem Celular Tumoral , Chalcona/química , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/metabolismo , Propano/síntese química , Propano/química , Propano/farmacologiaRESUMO
Prostate cancer is the most prevalent type of cancer in the United States. The most common site of prostate cancer metastasis is bone. CXCL12 is preferentially expressed in bone and is targeted by prostate cancer cells, which over-express the receptor for CXCL12, CXCR4. In response to CXCL12 stimulation, Rac1, a GTPase, along with its effectors, regulates actin polymerization to form lamellipodia, which is a critical event for cell migration. Cortactin, an actin-binding protein, is recruited to the lamellipodia and is phosphorylated at tyrosine residues. The phosphorylated cortactin is also involved in cell migration. The inhibition of Rac1 activity using a dominant negative Rac1 impairs lamellipodial protrusion as well as cortactin translocation and cortactin phosphorylation. Denbinobin, a substance extracted from Dendrobium nobile, has anticancer effects in many cancer cell lines. Whether denbinobin can inhibit prostate cancer cell migration is not clear. Here, we report that denbinobin inhibited Rac1 activity. The inhibition of Rac1 activity prevented lamellipodial formation. Cortactin phosphorylation and translocation to the lamellipodia were also impaired, and PC3 cells were unable to migrate. These results indicate that denbinobin prevents CXCL12-induced PC3 cell migration by inhibiting Rac1 activity.
Assuntos
Antraquinonas/farmacologia , Antineoplásicos Fitogênicos , Movimento Celular/efeitos dos fármacos , Dendrobium/química , Fenantrenos/farmacologia , Neoplasias da Próstata/patologia , Proteínas rac1 de Ligação ao GTP/antagonistas & inibidores , Actinas/metabolismo , Antraquinonas/uso terapêutico , Quimiocina CXCL12/fisiologia , Cortactina/metabolismo , Humanos , Masculino , Fenantrenos/uso terapêutico , Fosforilação , Polimerização/efeitos dos fármacos , Neoplasias da Próstata/metabolismo , Pseudópodes/metabolismo , Células Tumorais Cultivadas , Proteínas rac1 de Ligação ao GTP/fisiologiaRESUMO
In the present report, a concise synthesis of viscolin (1) has been achieved. The anti-inflammatory effect of viscolin was investigated in vitro and in vivo. Viscolin blocked the expression of iNOS and COX-2, and it also inhibited the ERK for the activation of NF-κB in LPS-stimulated RAW 264.7 macrophages. Western blotting and immunohistochemical analysis revealed that viscolin decreased Carr-induced iNOS and COX-2 expressions. These results could help to deduce the anti-inflammatory mechanisms.
Assuntos
Anti-Inflamatórios/síntese química , Compostos de Bifenilo/síntese química , Compostos de Bifenilo/farmacologia , Propano/análogos & derivados , Animais , Anti-Inflamatórios/farmacologia , Western Blotting , Linhagem Celular , Ciclo-Oxigenase 2/metabolismo , Dinoprostona/antagonistas & inibidores , Dinoprostona/metabolismo , Edema/tratamento farmacológico , MAP Quinases Reguladas por Sinal Extracelular/antagonistas & inibidores , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Imuno-Histoquímica , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Óxido Nítrico Sintase Tipo II/metabolismo , Propano/síntese química , Propano/farmacologia , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/metabolismoRESUMO
Three new [n-pentyl beta-carboline-1-propionate (1), 5-hydroxymethyl-9-methoxycanthin-6-one (2), and 1-hydroxy-9-methoxycanthin-6-one (3)] and 19 known beta-carboline alkaloids were isolated from the roots of Eurycoma longifolia. The new structures were determined by comprehensive analyses of their 1D and 2D NMR and mass spectral data and by chemical transformation. These compounds were screened for in vitro cytotoxic and antimalarial activities, and 9-methoxycanthin-6-one (4) and canthin-6-one (5) demonstrated significant cytotoxicity against human lung cancer (A-549) and human breast cancer (MCF-7) cell lines.