Chemical constituents from Annona glabra III

Twenty compounds including a dioxoaporphine, annobraine (1); two oxoaporphines, liriodenine (2) and lysicamine (3); five aporphines, (-)-nornuciferine (4), (-)-anonaine (5), (-)-N-formylanonaine (6), (-)-asimilobine (7) and (+)-nordomesticine (8); one proaporphine, (+)-stepharine (9); two protoberberines, (-)-kikemanine (10) and dehydrocorydalmine (11); one azaanthraquinone, 1-aza-4-methyl-2-oxo-1,2-dihydro-9, 10-anthracenedione (12); two amides, N-trans-feruloyltyramine (13) and N-p-coumaroyltyramine (14); one ionone, blumenol A (15); and five steroids, beta -sitosterol (16), stigmasterol (17), beta -sitosteryl-D-glucoside (18), stigmasteryl-D-glucoside (19) and 6-O-palmitoyl-beta -sitosteryl-D-glucoside (20), were isolated from the fruits and stems of Annona glabra. Among them, 1 is a novel dioxoaporphine alkaloid and 12 was obtained for the first time from natural sources. These compounds were characterized and identified by physical and spectral evidence.