Isolation and selective glycosylation of antisalmonellal anthraquinones from the stem bark of Morinda lucida Benth. (Rubiaceae)

Abstract

In this work we report the isolation, identification and antibacterial activity of two anthraquinones, 2-hydroxy-1-methoxyanthraquinone (1) and 2,5-dihydroxy-1-methoxy-6-methoxymethylanthraquinone (2), from the stem bark of Morinda lucida. These two natural products were selectively converted into two new glycosylated derivatives, 2-hydroxy-1-methoxyanthraquinone-4′-O-methyl-2-O-β-d-glucopyranoside (3) and 2,5-dihydroxy-1-methoxy-6-methoxymethylanthraquinone-4′-O-methyl-2-O-β-d-glucopyranoside (4) by the filamentous fungus Beauveria bassiana ATCC 7159. Structure elucidation was accomplished based on the 1D and 2D NMR, IR and mass spectra. The glycosylated compounds 3 and 4 showed higher in vitro antibacterial activity against Salmonella enterica subsp. enterica sérovars Typhimurim (MIC of 8 μg/mL each) than the corresponding aglycons 1 and 2 (MIC of 16 μg/mL and 32 μg/mL, respectively). These results indicated that microbial glycosylation is an effective approach to modify natural products for enhanced biological activities.