Isolation, spectral characterization, molecular docking, and cytotoxic activity of alkaloids from Erythroxylum pungens O. E. Shulz.
Gabrielle Macedo Pereira, Letícia Gondim Lambert Moreira, Themístocles da Silva Negreiros Neto, Wamberto Alristenio Moreira de Almeida, Jailma Almeida-Lima, Hugo Alexandre Oliveira Rocha, Euzébio Guimarães Barbosa, José Angelo S Zuanazzi, Mauro Vieira De Almeida, Richard Michael Grazul, Armando Navarro-Vázquez, Fernando Hallwass, Leandro de Santis Ferreira, Matheus de Freitas Fernandes-Pedrosa, Raquel Brandt Giordani
Phytochemistry November 2018 DOI: 10.1016/j.phytochem.2018.07.003 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Phytochemical and in vitro study Peer reviewed |
|---|---|
| Keywords | Cytotoxicity Erythroxylaceae Erythroxylum pungens N,N-Dimethyltryptamine Tropane alkaloids |
| Key points | DMT was isolated and characterized from Erythroxylum pungens roots, which the authors state is the first indole alkaloid reported from Erythroxylaceae. Eleven known tropane alkaloids and two new tropane alkaloid esters were identified, with complete NMR data reported for the first time. The tropane alkaloid aliphatic ester showed discrete cytotoxicity (0.3-1.0 mg/mL), while atropine (0.3 mg/mL) and DMT (0.5 mg/mL) reduced viability by 50% in HeLa, SiHa, PC3, and 786-0 cells. |
Abstract
Stem bark, root bark, and leaf extracts of Erythroxylum pungens were subjected to phytochemical analysis. N,N-dimethyltryptamine (DMT) was isolated and characterized from E. pungens roots. This unprecedented result is remarkable since no indole alkaloid has been previously reported from Erythroxylaceae so far. Eleven known tropane alkaloids were identified by their mass spectra and 3-(2-methylbutyryloxy)tropan-6,7-diol as well as 3-(2-methylbutyryloxy)nortropan-6,7-diol were isolated and characterized based on mass spectrometry, 1H, 13C, COSY, and NOESY NMR analysis. The complete NMR data are reported for the first time. Inverse Structure-based and Ligand-Based virtual screening were carried out to identify possible targets for 3-(2-methylbutyryloxy)tropan-6,7-diol. The level of cytotoxicity of this tropane alkaloid aliphatic ester was discrete with potencies on the order of 0.3-1.0 mg/mL and better results against HeLa (50% cell viability reduction). Otherwise, atropine (0.3 mg/mL), a Solanaceae tropane alkaloid, and DMT (0.5 mg/mL) from E. pungens roots impaired at 50% the cell viability against HeLa, SiHa, PC3, and 786-0. This study stimulates scientific investigation of the impact of edaphoclimatic features in a semi-arid environment on tropane alkaloid biosynthesis.
Citations in the library
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