RESUMO
Oleracimine and oleracimine A were isolated from Portulaca oleracea L. and described in the J. Agric. Food Chem, but the alternative structures of the two compounds are proposed on the basis of NMR analyses.
Assuntos
Alcaloides/química , Anti-Inflamatórios/química , Extratos Vegetais/química , Portulaca/química , Alcaloides/farmacologia , Anti-Inflamatórios/farmacologia , Estrutura Molecular , Extratos Vegetais/farmacologiaRESUMO
Three novel carbon skeleton alkaloids, named oleracimine (1), oleracimine A (2), and oleracone A (3), with one novel azulene carbon skeleton compound, oleracone B (4), and one known compound, ß-carboline (5), were first isolated from Portulaca oleracea L. The structures were determined using spectroscopic methods, including one- and two-dimensional nuclear magnetic resonance and high-resolution electrospray ionization time-of-flight mass spectrometry techniques. In addition, oleracimine (1) was used to investigate the anti-inflammatory effects on lipopolysaccharide-stimulated macrophages. The results of enzyme-linked immunosorbent assay, western blot, and real-time polymerase chain reaction showed that oleracimine (1) remarkably inhibited nitric oxide production and could dose-dependently decrease the secretions of interleukin 6, tumor necrosis factor α, nitric oxide, and prostaglandin E2 in cell culture supernatants as well as the mRNA of cyclooxygenase-2 and inducible nitric oxide synthase.
Assuntos
Alcaloides/química , Alcaloides/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Portulaca/química , Alcaloides/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Ciclo-Oxigenase 2/imunologia , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Camundongos , Estrutura Molecular , Óxido Nítrico/imunologia , Extratos Vegetais/isolamento & purificação , Células RAW 264.7RESUMO
Bioassay-guided phytochemical studies on Stellera chamaejasme led to the isolation of two new biflavones, chamaejasmenin E (1) and chamaejasmin D (2), together with ten known compounds. The structures of new compounds were elucidated by extensive spectroscopic analyses and their absolute configurations on 2, 3, 2â³ and 3â³ were confirmed by TDDFT quantum chemical calculated ECD spectra combined with experimental ECD spectra. All isolated biflavones were evaluated for their cytotoxic activities against Bel-7402 and A549 tumor cell lines, and sikokianin D (3) was found to possess the most potential cytotoxic activities against both the two cell lines with IC50 values of 1.29 ± 0.21 and 0.75 ± 0.25 µM, respectively. Moreover, some structure-function relationships of these bioflavones for cytotoxic activities were explored and summarized.
Assuntos
Flavonas/química , Thymelaeaceae/química , Biflavonoides/química , Biflavonoides/isolamento & purificação , Linhagem Celular Tumoral , Flavonas/isolamento & purificação , Humanos , Estrutura Molecular , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
A new diterpenoid, 15(S)-isopimar-7-en-1-oxo-15,16-diol (1), was isolated from the stems of mangrove plant Rhizophora apiculata. The structure of the new compound was elucidated by MS, IR, 1D, and 2D NMR techniques, including HMQC, HMBC, and NOESY correlations. In addition, seven known constituents were isolated from this plant for the first time.
