RESUMO
Together with twelve known compounds (2-13), melodamide A (1), a new phenolic amide possessing p-quinol moiety, was purified and characterized from the methanolic extracts of the leaves of Melodorum fruticosum. The structure of melodamide A (1) was established with a combination of 2D NMR experiments, HR-ESI-MS and X-ray analyses. The other known compounds were identified by comparison of their spectroscopic and physical data with those reported in the literature. Moreover, some isolated compounds were examined for their inhibitory activity towards superoxide anion generation and elastase release in human neutrophils. Among the tested compounds, 1, 3, and 5 exhibited strong inhibition of superoxide anion generation with IC50 values ranging from 5.25 to 8.65 µM. Furthermore, synthesis and biological evaluation of melodamide A (1) and its analogs (14a-p) were described.
Assuntos
Annonaceae/química , Anti-Inflamatórios não Esteroides/farmacologia , Cinamatos/síntese química , Cinamatos/isolamento & purificação , Cicloexanonas/síntese química , Cicloexanonas/isolamento & purificação , Adulto , Amidas/química , Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/química , Técnicas de Química Sintética , Cinamatos/farmacologia , Cristalografia por Raios X , Cicloexanonas/farmacologia , Inibidores Enzimáticos/farmacologia , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Neutrófilos/efeitos dos fármacos , Neutrófilos/enzimologia , Elastase Pancreática/antagonistas & inibidores , Fenóis/química , Folhas de Planta/química , Superóxidos/antagonistas & inibidores , Adulto JovemRESUMO
In this study, the biomass of Phragmites australis was chemically modified using NaOH and subsequently citric acid to produce an effective adsorbent named SA-RPB. The absorbent was characterized using XRD, SEM, BET, and FT-IR methods. The study's findings indicated that the adsorbent existed mainly as cellulose crystals, contained micropores with an average diameter of 15.97 nm, and had a large number of hydroxyl and carboxyl groups on the surface. The adsorption process of SA-RPB was evaluated through the adsorption of methylene blue (MB) dye in aqueous solution. Adsorption kinetics showed that the pseudo-second-order model well described the adsorption process. The adsorption isotherm process satisfactorily fitted with the Langmuir model with the maximum adsorption capacity of 191.49 mg/g at 303 K. These findings show that MB may be efficiently removed from aqueous solutions using the adsorbent made from the raw biomass of Phragmites australis treated with NaOH and then citric acid.
Assuntos
Azul de Metileno , Poluentes Químicos da Água , Adsorção , Celulose , Ácido Cítrico/química , Concentração de Íons de Hidrogênio , Cinética , Azul de Metileno/química , Hidróxido de Sódio , Espectroscopia de Infravermelho com Transformada de Fourier , ÁguaRESUMO
For past three decades, numerous studies have elucidated the antiproliferative effects of acetogenins in hopes of developing a new class of clinical anticancer agents. However, clear and definitive action mechanisms of acetogenins were less clarified. In the present study, three tetrahydrofuran (THF)-containing acetogenins were found to have potent and selective antiproliferative activity against human nasopharyngeal carcinoma (NPC) cell lines and their methotrexate-resistant counterparts. The THF-containing acetogenins induced G2/M phase arrest, mitochondrial damage and apoptosis, and increased cytosolic and mitochondrial Ca2+ in NPCs. Microarray analysis of NPC-TW01 cells treated with squamostatin A, a non-adjacent bis-THF acetogenin, demonstrated an increased endoplasmic reticulum (ER)-stress response (ESR). Enhanced ESR in squamostatin A-treated cells was confirmed by real-time PCR, Western blot and shRNA gene knockdown experiments. Although our results showed that squamostatin A-induced ESR was independent of extracellular Ca2+, the presence of extracellular Ca2+ enhanced the antiproliferative effect of acetogenins. In vivo analyses demonstrated that squamostatin A showed good pharmacokinetic properties and significantly retarded NPC tumor growth in the xenograft mouse model. Conclusively, our work demonstrates that acetogenins are effective and selective inducers of the ESR that can block NPC proliferation, and illustrate a previously unappreciated antitumor mechanism of acetogenins that is effective against nasopharyngeal malignancies.