RESUMO
A bioassay-guided investigation of Gustavia hexapetala led to the isolation of a new cancer cell growth inhibitor designated gustastatin (1) and four previously known cancer cell growth inhibitors that included betulinic acid (2). The structures were assigned on the basis of analyses of HRMS combined with 1D and 2D NMR data. The structure of portentol (5) was confirmed by an X-ray crystal structure determination.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Lecythidaceae/química , Ácido Oleanólico/análogos & derivados , Fenóis/química , Fenóis/isolamento & purificação , Plantas Medicinais/química , Animais , Antineoplásicos Fitogênicos/farmacologia , Brasil , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Leucemia P388 , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Triterpenos Pentacíclicos , Fenóis/farmacologia , Árvores , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Ácido BetulínicoRESUMO
Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines)-guided separation of an extract prepared from the stem bark and twigs of the previously uninvestigated Ruprechtia tangarana led to the isolation of a new isocarbostyril designated ruprechstyril (1), secalonic acid A (2), 2'-O-methylevernic acid (3), 3,3',4-tri-O-methylflavellagic acid (4), lichexanthone (5), methyl asterrate (6), and 3beta,22E,24S-stigmasta-5,22-dien-3-ol (7). Only secalonic acid A exhibited cancer cell and microbial growth inhibition. The structure of ruprechstyril (1) was determined by HRMS and 1D and 2D NMR spectra and confirmed by single-crystal X-ray analysis. The structures and absolute stereochemistry of five of the other compounds were also established by X-ray crystal structure determination.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Hidroxiquinolinas/isolamento & purificação , Plantas Medicinais/química , Polygonaceae/química , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidroxiquinolinas/química , Hidroxiquinolinas/farmacologia , Leucemia P388 , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Peru , EstereoisomerismoRESUMO
Bioassay (P388 lymphocytic leukemia cell line and human cancer cell lines) guided separation of an extract prepared from the leaves of Hymenaea palustris Ducké led to the isolation of six cancer cell growth inhibitory flavonoids (1-6). The structures were elucidated by HRMS and 1D and 2D NMR spectral analysis. The new flavonolignan 1 designated palstatin proved to be a methoxy structural modification of 5'-methoxyhydnocarpin-D (2). Flavones 1-4 inhibited growth of the pathogenic bacteria Enterococcus faecalis and/or Neisseria gonorrhoeae.