Stephalagine, an alkaloid with pancreatic lipase inhibitory activity isolated from the fruit peel of Annona crassiflora Mart
| Autor: | Thaise Lara Teixeira, Mário Machado Martins, Claudio Vieira da Silva, Danielle Diniz Vilela, Foued Salmen Espindola, Leonardo Gomes Peixoto, Allisson Benatti Justino, Luiz Ricardo Goulart, Mariana Nunes Pereira, Paula de Souza Santos, Marcos Pivatto |
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| Rok vydání: | 2017 |
| Předmět: |
Chromatography
biology 010405 organic chemistry Alkaloid Metabolite Triacylglycerol lipase Annona crassiflora biology.organism_classification 01 natural sciences 0104 chemical sciences 010404 medicinal & biomolecular chemistry chemistry.chemical_compound chemistry Annonaceae Organic chemistry Aporphine Isoquinoline Agronomy and Crop Science Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Industrial Crops and Products. 97:324-329 |
| ISSN: | 0926-6690 |
| Popis: | Annona crassiflora Mart., a member of the Annonaceae family found in the Brazilian Savannah, is acknowledged as a plant rich in a variety of isoquinoline alkaloids. The isoquinoline skeleton-derivative alkaloids have been reported as pancreatic lipase (PL) inhibitors. However, the presence of these bioactive compounds in the fruit peel of A. crassiflora remains unclear. This study was conducted to find a bioactive alkaloid not yet described in the fruit peel of A. crassiflora and evaluate its capacity to inhibit the PL activity through in vitro kinetic assay using p -nitrophenyl palmitate as substrate. The ethanolic extract (EtOH) of the peels of A. crassiflora fruits was subjected to liquid−liquid extraction, which yielded an alkaloidal fraction. After a high performance liquid chromatography (HPLC) separation, the purified alkaloid was subjected to structural characterization by high-resolution mass spectrometry with electrospray ionization and electron impact, and nuclear magnetic resonance (NMR) spectroscopy using 1 H, 13 C, correlation spectroscopy (COSY), heteronuclear single-quantum correlation spectroscopy (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC) and HMBC-N analyses. The metabolite stephalagine (1,2-methylenedioxy-3-methoxyaporphine), an aporphine alkaloid, was identified. The purified stephalagine was further evaluated as a PL inhibitor. Stephalagine showed high PL inhibitory activity (IC 50 of 8.35 μg mL −1 ) with low cytotoxicity, suggesting a potential anti-obesity agent. This is the first report of the isolation of stephalagine in Annonaceae and its inhibitory effect on pancreatic lipase activity. |
| Databáze: | OpenAIRE |
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