RESUMO
Bis(3-indolyl)methanes (BIMs) are known for their important bioactivities, which include anti-cancer, anti-inflammatory, antibacterial, and antioxidant properties. In this study, we are disclosing a metal catalyst-free synthesis of BIMs in high yields via the alkylation reaction of indoles and alcohols in the presence of lithium tert-butoxide base. Notably, oxygen in air played an important role as an oxidant for the facilitation of this transformation. Interestingly, unactivated aliphatic alcohols could be successfully used as alkylating reagents in the alkylation reactions of indole. Especially, several chemical intermediates detected by GC-MS gave important information about the mechanism insights. This method demonstrated cost and environmental advantages for the development of green processes.
RESUMO
A new chalcone named as balanochalcone (1) together with eight known compounds, methyl caffeate (2), ß-hydroxydihydrochalcone (3), methyl gallate (4), dimethyl-6,9,10-trihydroxybenzo[kl]xanthene-1,2-dicarboxylate (5), p-coumaric acid (6), quercetin (7), scopoletin (8) and pinoresinol (9) have been isolated from the ethyl acetate extract of Vietnamese Balanophora laxiflora Hemsl. Their structures were characterised by IR, UV, HR-ESI-MS, 1D and 2D NMR and CD spectroscopies. Compounds 2 and 5 showed moderate cytotoxicity against four cancer cell lines, KB (a human epidermal carcinoma), MCF7 (human breast carcinoma), SK-LU-1 (human lung carcinoma) and HepG2 (hepatocellular carcinoma). In addition, compounds 1 and 5 showed moderate antioxidant activity.
Assuntos
Antineoplásicos Fitogênicos/química , Antioxidantes/farmacologia , Chalconas/química , Santalaceae/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/química , Linhagem Celular Tumoral , Chalconas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais/métodos , Células Hep G2 , Humanos , Células MCF-7 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
One new schiartane-type triterpene, heteroclitalactone N (1), and four known compounds (2-5), seco-coccinic acid F, dihydroguaiaretic acid, schizanrin F, and kadsuralignan B were isolated from the stems of Kadsura heteroclita. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D-, 2D-NMR, and CD spectra as well as by comparing with the NMR data reported in the literature. The cytotoxic activities of all isolated compounds were evaluated on three human cancer cell lines. Compound 3 exhibited moderate to weak cytotoxic activities on three human cancer cell lines, OVCAR, HT-29, and A-549, with IC50 values ranging from 16.2 to 36.4 microM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Kadsura/química , Triterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Células HT29 , Humanos , Estrutura Molecular , Triterpenos/químicaRESUMO
A new ceramide alomacrorrhiza A was isolated from the ethanolic extract of the plant Alocasia macrorrhiza (L.) Schott. Its chemical structure was elucidated as (2S,3S,4R)-2N-[(2'R)-2'-hydroxy-hexacosanoyl]-tetradecane-1,3,4-triol based on extensive 1D, 2D NMR, EI-MS, FAB-MS, HR-FAB-MS spectroscopic data and chemical degradation studies.