RESUMO
A bioactive molecular networking strategy has been applied to discovery of bioactive constituents from the fruits of Celastrus orbiculatus Thunb., which showed significant inhibitory effects on the α-MSH-induced melanin production in B16F0 melanoma cells. In the obtained molecular network, the nodes with relatively high bioactive scores were prioritized for isolation; as a result, 12 undescribed dihydro-ß-agarofuran sesquiterpenes together with 15 known compounds were isolated from MeOH extracts of the fruits of C. orbiculatus. Their structures were elucidated based on the interpretation of NMR, HRESIMS, ECD data, and single crystal X-ray diffraction. Among the obtained isolates, celastorbin A and (1R,2S,4R,5S,7S,8S,9R,10S)-1,2,8-triacetoxy-9-cinnamoyloxydihydro-ß-agarofuran, which possessed high bioactive scores in the molecular network, exhibited potent inhibitory effects on the α-MSH-induced melanin production in B16F0 cells with IC50 values of 4.1 and 2.0 µM, respectively.
Assuntos
Celastrus , Sesquiterpenos , Celastrus/química , Frutas/química , Melaninas/análise , Estrutura Molecular , Extratos Vegetais/análise , Sesquiterpenos/química , alfa-MSH/análiseRESUMO
A tropolone (2) and an acorane sesquiterpene (3), along with twenty previously known compounds were isolated from the heartwood of Pterocarpus santalinus. The structure of the isolated compounds was elucidated via 1D and 2D NMR spectroscopy and HRESIMS analysis. The absolute configuration of 3 was determined by comparison of the experimental and calculated ECD data. All compounds were evaluated for their inhibitory effects against nitric oxide production in LPS-stimulated RAW 264.7 macrophages.
Assuntos
Pterocarpus , Sesquiterpenos , Macrófagos , Estrutura Molecular , Óxido Nítrico , Pterocarpus/química , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
Three new guaianolide lactones (1-3) and four new 9-oxonerolidol glucosides (5-8) together with 20 known compounds were isolated from the MeOH extract of the flowers of Chrysanthemum indicum. Their structures were elucidated based on the interpretation of NMR, HRESIMS, and electronic circular dichroism (ECD) data along with acid hydrolysis. Of the isolates, sesquiterpenoids 1-4 and 15 and flavones 17 and 18 exhibited inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide production in RAW 264.7 cells with IC50 values in the range 0.2-27.0 µM.
Assuntos
Anti-Inflamatórios/farmacologia , Chrysanthemum/química , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Flavonas/isolamento & purificação , Flavonas/farmacologia , Flores/química , Glucosídeos/isolamento & purificação , Lactonas/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Plantas Medicinais/química , Células RAW 264.7 , República da Coreia , Sesquiterpenos/isolamento & purificaçãoRESUMO
A new phenolic amide, named cis-terrestriamide (7), together with ten known compounds (1-6, 8-11), were isolated from the methanolic extract of the fruits of Tribulus terrestris. The structure of 7 was elucidated on the basis of extensive analyses of 1D and 2D nuclear magnetic resonance spectroscopic and high resolution mass spectrometry data. Compounds 1, 2, 5, 6, 8, 9, and 11 exhibited inhibitory effects on the lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 cells, with IC50 values of 18.7-49.4 µM.