Acetylcholinesterase inhibitory activities and bioguided fractionation of the Ocotea percoriacea extracts: HPLC-DAD-MS/MS characterization and molecular modeling of their alkaloids in the active fraction
| Autor: | Jorge Mauricio David, Isabela de Oliveira Estrela, Dayse Santos Almeida Cassiano, Humberto Fonseca de Freitas, Alexsandro Branco, Samuel Silva da Rocha Pita, Isabella Mary Alves Reis |
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| Rok vydání: | 2019 |
| Předmět: |
0301 basic medicine
Models Molecular Electrospray ionization Chemical structure Ethyl acetate Mass spectrometry Biochemistry 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Alkaloids Structural Biology Tandem Mass Spectrometry Animals Chromatography High Pressure Liquid Dichloromethane Chromatography biology Molecular Structure Silica gel Plant Extracts Organic Chemistry Palmatine biology.organism_classification Plant Leaves Computational Mathematics 030104 developmental biology chemistry Ocotea 030220 oncology & carcinogenesis Electrophorus Acetylcholinesterase Cholinesterase Inhibitors |
| Zdroj: | Computational biology and chemistry. 83 |
| ISSN: | 1476-928X |
| Popis: | In vitro acetylcholinesterase activities of the hexane, dichloromethane, ethyl acetate, n-butanol and aqueous extracts of leaves of Ocotea percoriacea Kosterm. (Lauraceae) were evaluated. The bioguided fractionation of the most active extract (dichloromethane) using silica gel open-column chromatography led to an active alkaloidal fraction composed of isocorydine N-oxide, isocorydine N-oxide derivative, palmatine, roemerine and roemerine N-Oxide. The identification of the chemical structure of these compounds was carried out with high-performance liquid chromatography coupled to electrospray ionization multiple-stage mass spectrometry (HPLC-ESI-MS/MS). Aiming to understand their inhibitory activities, these alkaloids were docked into a 3D model of Electrophorus electricus Acetylcholinesterase (EelAChE) built in the Modeller 9.18 employing homology modeling approach. The results suggest that the alkaloids had the same binding mode and, possibly, the inhibition mechanism of classic drugs (ex. tacrine and donepezil). The structural difference of these compounds opens a new opportunity for the optimization of leading compounds. |
| Databáze: | OpenAIRE |
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