Resumo Virola venosa, popularmente conhecida como ucuuba-da-mata, ocorre naturalmente na região amazônica e tem potencial para fornecer compostos naturais úteis, como já foi mostrado para outras espécies de Virola. Por isso, o objetivo deste estudo foi determinar a composição química dos extratos do tronco e das folhas de V. venosa e os possíveis potenciais antioxidantes e de inibição contra α-glucosidase de seus compostos. Os extratos polares mostraram-se mais ativos em ambos os testes, portanto, um fracionamento guiado por bioatividade foi realizado para designar os compostos responsáveis pelas atividades registradas. Através da combinação de análise CL-EM/EM e isolamento com identificação por RMN, foram identificados oito compostos fenólicos. Testes com os compostos puros principais das frações mais ativas indicaram o ácido ferúlico como o principal contribuinte das atividades biológicas observadas para os extratos brutos, e, consequentemente, o princípio ativo principal de V. venosa.

ABSTRACT Virola venosa, popularly known in Brazil as ucuuba-da-mata, occurs naturally in the Amazon region and has potential to provide useful natural compounds, as already known for other Virola species. Therefore, the objective of this study was to determine the chemical composition of bark and leaf extracts of V. venosa, and to test the antioxidant capacity and α-glucosidase inhibition potential of their compounds. Polar extracts showed to be more active in both assays, therefore a bioactivity-guided fractionation was performed to identify the compounds that were responsible for the recorded activities. Using a combination of LC-MS/MS analysis and isolation with NMR identification, eight phenolic compounds were identified. Assays with pure compounds of the active fraction revealed that ferulic acid was the main contributor compound to the observed bioactivity in the crude extracts.

The NMR conformational study of 4',7-di-hydroxy-8-prenylflavan 1 was carried out in acetone-d6, DMSO-d6 and CDCl3 which enabled the proposition of three conformations, namely 1a, 1b and 1c, differing in the position of the prenyl group. Geometry optimizations performed using AM1 method showed that 1a (deltaHf = -86.2 kcal/mol) is as stable as 1b (deltaHf = -85.1 kcal/mol) and 1c (deltaHf = -85.4 kcal/mol). When the solvent was included, the calculations showed that the solute-solvent interactions could be explained either in the light of the electronic intermolecular delocalization or the electrostatic character between solute and solvent. Theoretical calculations (HF/6-31G*, deltaFT/BLYP/6-31G*, and deltaFT/B3LYP/6-31G*) showed that the combination of these types of interactions present in each solute-solvent system, dependent on the chemical properties of the solvent, lead to different spatial arrangements of the prenyl group, which in turn determined the conformation of 1.