RESUMO
Antiradical and cytoprotective activities of several flavanones isolated from Paulownia tomentosa (Thunb.) Steud. (Scrophulariaceae) have been evaluated using different in vitro and in vivo methods. The capacity of flavanones to scavenge radicals was measured in vitro by means of DPPH and ABTS assays, the inhibition of hydroxyl radicals produced in Fenton reactions, FRAP, scavenging superoxide radicals using enzymatic and nonenzymatic assays and the inhibition of peroxynitrite-induced nitration of tyrosine. The in vivo testing involved measuring the cytoprotective effect of chosen flavanones against alloxan-induced diabetes in mice. The activity of tested compounds was expressed either as a Trolox® equivalent or was compared with rutin or morine as known antioxidant compounds. The highest activity in most tests was observed for diplacone and 3´-O-methyl-5´-hydroxydiplacone, and the structure vs. the antioxidant activity relationship of geranyl or prenyl-substituted flavonoids with different substitutions at the B and C ring was discussed.
Assuntos
Citoproteção/efeitos dos fármacos , Flavanonas/farmacologia , Sequestradores de Radicais Livres/farmacologia , Scrophulariaceae/química , Animais , Diabetes Mellitus Experimental/tratamento farmacológico , Flavanonas/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Frutas/química , Camundongos , Relação Estrutura-AtividadeRESUMO
Eight C-6-geranylflavonoids ( 1- 8) were isolated from an ethanol extract of Paulownia tomentosa fruits. Tomentodiplacone ( 1), 3'- O-methyl-5'-hydroxydiplacone ( 2), 3'- O-methyl-5'- O-methyldiplacone ( 3), and tomentodiplacone B ( 4) were obtained as new compounds, and 3'- O-methyldiplacol ( 5) was isolated for the first time from a natural source. The structures of these new compounds were determined by using mass spectrometry (including HRMS) and 1D and 2D NMR spectroscopy, and the absolute configurations of the compounds were determined by circular dichroism. The antibacterial activities of 1- 8 against seven bacteria and yeast were evaluated.
Assuntos
Antibacterianos/isolamento & purificação , Flavonoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Plantas Medicinais/química , Scrophulariaceae/química , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Dicroísmo Circular , República Tcheca , Flavonoides/química , Flavonoides/farmacologia , Frutas/química , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Paulownia tomentosa is a large indecidous tree planted mostly for its fast growing wood and decorative purposes. The tree is also used in traditional Chinese medicine. As a part of our study of natural polyphenols, the fruits of Paulownia tomentosa were extracted by EtOH and than subjected to liquid/liquid extraction. Fractions were analysed by TLC and HPLC to determine presence of phenolic substances. We identified and quantified acteoside (1) and isoacteoside (2) in the EtOAc and n-BuOH extracts; mimulone (3) and diplacone (4) in the MeOH extract. To determine the antiradical activity of extracts we used the anti DPPH and peroxynitrite assays. The activity was expressed as Trolox C equivalents, IC50 for DPPH scavenging and a time dependency course was established. The polyphenols content was determined; results were expressed as gallic acid equivalents. Using these methods we found the fractions of the n-BuOH, EtOAc and MeOH extracts that display antiradical activity, which could be exploited as potential pharmaceuticals.
