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, β‐sitosterol ( 16 ), stigmasterol ( 17 ), β‐sitosteryl‐D‐glucoside ( 18 ), stigmasteryl‐D‐glucoside ( 19 ) and 6‐ O ‐palmitoyl‐β‐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.