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

• Published in: Biochemical systematics and ecology Vol. 97; p. 104297
• Main Authors: Nogueira da Silva Avelino Oliveira Rocha, Giovanna, Dutra, Lívia Macedo, Pinheiro Paz, Weider Henrique, Araujo da Silva, Felipe Moura, Costa, Emmanoel Vilaça, Guedes da Silva Almeida, Jackson Roberto
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.08.2021
• Subjects: 3,4,5-Trimethoxyphenol; Annona coriacea; Chemophenetics relationships; Isoquinoline-derived alkaloids; Loliolide; Isoquinoline-derived alkaloids; Annona coriacea; 3,4,5-Trimethoxyphenol; Loliolide; Chemophenetics relationships
• ISSN: 0305-1978; 1873-2925
• DOI: 10.1016/j.bse.2021.104297

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. [Display omitted] •The compounds identified are described for the first time in Annona coriacea.•Compounds suggest close chemophenetics relationships with other Annona species.•Obovanine and pukateine are reported for the first time in the Annona genus.•3,4,5-Trimethoxyphenol described for the first time in the Annonaceae family.•NMR spectroscopic data for pukateine and obovanine were reviewed.