1. 7,7-Dimethylaporphine alkaloids from the stem of Guatteriopsis friesiana
- Author
-
Francisco A Marques, Marta Cristina Teixeira Duarte, Emmanoel V. Costa, Raquel Marques Braga, Maria Lúcia B. Pinheiro, Camila Delarmelina, Beatriz Helena L. N. Sales Maia, and Nelissa P. Vaz
- Subjects
Circular dichroism ,Aporphines ,Stereochemistry ,Pharmaceutical Science ,Annonaceae ,Microbial Sensitivity Tests ,Pharmacognosy ,Analytical Chemistry ,Alkaloids ,Rhodococcus equi ,Drug Discovery ,Nuclear Magnetic Resonance, Biomolecular ,Pharmacology ,biology ,Molecular Structure ,Plant Stems ,Alkaloid ,Organic Chemistry ,Absolute configuration ,Liriodenine ,biology.organism_classification ,Anti-Bacterial Agents ,Complementary and alternative medicine ,Phytochemical ,Chemotaxonomy ,Molecular Medicine ,Brazil - Abstract
Phytochemical investigation of a methanolic extract of the stem of Guatteriopsis friesiana afforded two new 7,7-dimethylaporphine alkaloids, 6,6a-dihydrodemethoxyguadiscine (1) and guatteriopsiscine (3), together with demethoxyguadiscine (2), liriodenine (4), corypalmine (5), and coreximine (6). Their structures were elucidated on the basis of spectroscopic methods (UV, IR, EIMS, HRESIMS, 1D/2D NMR). The absolute configurations of 1 and 3 were determined from the circular dichroism curves. The presence of 7,7-dimethylaporphine alkaloids in this species is important for the chemotaxonomy of Guatteriopsis. Antimicrobial activity of compounds 1-5 was investigated, and 4 showed activity against Rhodococcus equi, with a MIC value of 10 microg x mL(-1).
- Published
- 2009