3-Oxyanthranilic acid derivatives from Actinomadura sp BCC27169

Eight new compounds including 9'-(2-amino-3-(4 ''-O-methyl-alpha-rhamnopyranosyloxy) phenyl]nonanoic acid (1), 9'[2-amino-3-(4 ''-O-methyl-m-ribopyranosyloxy)phenyl] nonanoic acid (2), 11'-[2-amino-3-(4 ''-O-methyl-alpha-rhamnopyranosyloxy)phenyl]undecanoic acid (3), 11'-[2-amino-3-(4 ''-O-methyl-a-ribopyranosyloxy)phenyl]undecanoic acid (4), 8-(4'-O-methyl-alpha-rhamnopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (5), 8-(4'-O-methyl-a-ribopyranosyloxy)-3,4-dihydroquinolin-2(1H)-one (6), 8-(4'-O-methyl-a-rhamnopyranosyloxy)-2-methyquinoline (7), and 8-(4'-O-methyl-a-ribopyranosyloxy)-2-methylquinoline (8) were isolated from Actinomadura sp. BCC27169. The chemical structures of these compounds were determined based on NMR and high-resolution mass spectroscopy. The absolute configurations of these monosaccharides were revealed by the hydrolysis of compounds 7 and 8. Compounds 3 and 8 exhibited antitubercular activity at MIC 50 mu/mL. Only compound 3 showed cytotoxicity against KB cell at IC50 18.63 mu g/mL, while other isolated compounds were inactive at tested maximum concentration (50 mu g/mL). (C) 2014 Elsevier Ltd. All rights reserved.