Chemical constituents from the leaves and branches of Annona coriacea Mart. (Annonaceae)

The phytochemical investigation of the leaves and branches of Annona coriacea Mart. (Annonaceae) led to the isolation and characterization of eight compounds: five isoquinoline-derived alkaloids, including pukateine (1), liriodenine (4), anonaine (5), obovanine (6), and norisocorydine (7); one terpene lactone known as loliolide (3); one benzoic acid derivative, 2-methoxybenzoic acid (2), and 3,4,5-trimethoxyphenol (8). All compounds, except liriodenine, are being described for the first time in the species A. coriacea, and their chemophenetics relationships were discussed. The structures were elucidated by extensive analyses of 1D and 2D NMR (COSY, HSQC, and HMBC) spectroscopy in combination with MS, and the data were compared with literature values. The NMR dataset of pukateine and obovanine was reviewed. Our results showed that A. coriacea is a typical species of the Annonaceae family and an important source of aporphine alkaloids with chemophenetic relationships with Xylopia, Duguetia, Guatteria, Artabotrys, and Goniothalamus genera.