RESUMO
A new muurolane-type sesquiterpene, a new flavone arabinofuranoside derivative, and other five known flavone arabinofuranoside derivatives were isolated from the leaves of Fissistigma bicolor (Annonaceae family). Their chemical structures were determined to be (1S,6R,7S)-muurola-4,10(14)-diene-15-ol (1), quercetin 3-O-ß-D-apiofuranosyl-(1â2)-α-L-arabinofuranoside (2), quercetin 3-O-α-L-rhamnopyranosyl-(1â2)-α-L-arabinofuranoside (3), quercetin 3-O-α-L-arabinofuranoside (4), kaempferol 3-O-ß-D-apiofuranosyl-(1â2)-α-L-arabinofuranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1â2)-α-L-arabinofuranoside (6), and kaempferol 3-O-α-L-arabinofuranoside (7) by analyses of HR-ESI-MS and NMR spectral data. Compounds 4 and 7 containing monosaccharide, arabinofuranoside, potentially inhibited NO productions in LPS activated RAW264.7 cells (IC50 13.4 ± 0.5 and 12.6 ± 0.4 µM) in compared to disaccharide derivatives (IC50 ranging from 58.9 ± 3.3 to 65.6 ± 3.8 µM).
Assuntos
Annonaceae , Flavonas , Quempferóis/análise , Quercetina , Annonaceae/química , Flavonas/farmacologia , Flavonas/análise , Glicosídeos/química , Folhas de Planta/química , Estrutura MolecularRESUMO
Three new muurolane type sesquiterpene glycosides, named balanoindicosides A - C (1 - 3), were isolated from the whole plant of Balanophora fungosa subsp. indica using various chromatographic methods. Their structures were determined by extensive analysis of HR-ESI-MS and NMR spectroscopy. The stereochemistry of muurolane sesquiterpene backbone was demonstrated by NOESY analysis. Configuration of C-12 in compounds 2 and 3 could be distinguished by chemical shift value of C-14. Compounds 1-3 exhibited weak cytotoxic activity towards HepG-2, HL-60, LU-1, and MCF-7 cell lines.
