Anthraquinone derivatives from Heterophyllaea pustulata

From the leaves of Heterophyllaea pustulata two new monomeric anthraquinones, heterophylline ( 1,6-dihydroxy-7-methoxy-2-methylanthraquinone, 1) and pustuline ( 2-hydroxy-3-methoxy-7-methylanthraquinone, 2), and one new bianthraquinone, ( S)-5,5'-bisoranjidiol [( S)-5,5'-bis( 1,6-dihydroxy-2-methylanthraquinone), 3], were isolated. Furthermore, the iridoid glycoside asperuloside and three known flavonoids, quercetin, isoquercitrin, and quercetin-3-O-beta-D-glucosyl-6"-acetate, were obtained. The structures were determined by analysis of their spectroscopic data and chemical evidence.