RESUMEN
Two new guaiane derivatives (1 and 2) along with six known sesquiterpenoids (3-8) were isolated from the gorgonian Menella woodin. Their structures -were elucidated by ID and 2D NMR and HRESIMS data as well as by comparison of their spectra with those in the literature. Relative configurations of asymmetric centers in 1 and 2 were suggested on the basis of NOESY and ID NOE correlations, absolute stereochemistry of these compounds was proposed in result of comparison of calculated (for both enatiomers) and experimental ECD. Some suggestions were made regarding a biosynthesis of guaiane sesquiterpenoids in this species. All the compounds were firstly isolated from M woodin.
Asunto(s)
Antozoos/química , Sesquiterpenos/química , Animales , Estructura MolecularRESUMEN
Using combined chromatographic methods, two asterosaponins (compounds 1 and 2), including a new compound novaeguinoside E (compound 1), and six glycosylated polyhydroxysteroids (compounds 3-8) were isolated from a methanol extract of the starfish Culcita novaeguineae. Their structures were determined on the basis of spectroscopic data ((1)H and (13)C NMR, HSQC, HMBC, (1)H-(1)H COSY, ROESY, and HRESI-MS) and by comparison with the literature values. The new compound 1 represents the third example of asterosaponins containing the 5α-cholesta-9(1l)-en-3ß,6α,20,22-tetraol aglycone. Among isolated compounds, 4-7 exhibited moderate to weak cytotoxic activities against five human cancer cell lines such as Hep-G2 (hepatoma), KB (epidermoid carcinoma), LNCaP (prostate cancer), MCF7 (breast cancer), and SK-Mel2 (melanoma).
Asunto(s)
Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Saponinas/aislamiento & purificación , Saponinas/farmacología , Estrellas de Mar/química , Esteroides/aislamiento & purificación , Esteroides/farmacología , Animales , Antineoplásicos/química , Ensayos de Selección de Medicamentos Antitumorales , Glicosilación , Células Hep G2 , Humanos , Células KB , Masculino , Melanoma , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Saponinas/química , Esteroides/químicaRESUMEN
Nine secondary metabolites, including a new cycloartane glucoside, rhizostyloside (1), were isolated from a methanol extract of Rhizophora stylosa leaves through several chromatographic experiments. The structures of the compounds were determined on the basis of NMR spectroscopic (1H and 13C NMR, HSQC, HMBC, 1H-1H COSY, NOESY) and HR-ESI-MS data and by comparison with literature values. Compound 1 exhibited significant cytotoxicity against three human cancer cell lines: KB (epidermoid carcinoma), LU-1 (lung adenocarcinoma), and SK-Mel-2 (melanoma). In addition, 1 strongly activated caspase-3/7 in LU-1 cells.
Asunto(s)
Glucósidos/química , Extractos Vegetales/química , Rhizophoraceae/química , Triterpenos/química , Caspasa 3/genética , Caspasa 3/metabolismo , Caspasa 7/genética , Caspasa 7/metabolismo , Línea Celular Tumoral , Glucósidos/aislamiento & purificación , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Neoplasias/enzimología , Neoplasias/genética , Extractos Vegetales/aislamiento & purificaciónRESUMEN
Phytochemical study of the methanol extract of Artocarpus altilis resulted in the isolation of a new prenylated aurone, artocarpaurone (1), together with eight known compounds including two prenylated chalcones (2 and 3), three prenylated flavanones (4-6), and three triterpenes (7-9). The structure of 1 was elucidated as 6-hydroxy-2-[8-hydroxy-2-methyl-2-(4-methyl-3-pentenyl)-2H-1-benzopyran-5-ylmethylene]-3(2H)-benzofuranone by spectroscopic methods including 1D and 2D NMR spectra and FT-ICR-MS. Compound 1 showed moderate nitric oxide radical scavenging activity, whereas 2 and 3 had moderate 2,2-diphenyl-1-picrylhydrazyl radical scavenging effect, compared with the positive control (+)-catechin.