New sesquiterpene and flavone arabinofuranoside derivative from the leaves of Fissistigma bicolor

Abstract

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-β-D-apiofuranosyl-(1→2)-α-L-arabinofuranoside (2), quercetin 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinofuranoside (3), quercetin 3-O-α-L-arabinofuranoside (4), kaempferol 3-O-β-D-apiofuranosyl-(1→2)-α-L-arabinofuranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-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).

Keywords: Annonaceae; Fissistigma bicolor; flavone arabinofuranoside; muurolane; nitric oxide inhibitor.