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Isolation and evaluation of the antioxidant activity of phenolic constituents of the Garcinia brasiliensis epicarp |
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| Authors: | Vanessa Silva Gontijo Wagner Vilegas |
| Affiliation: | a Laboratório de Fitoquímica e Química Medicinal, Instituto de Química Exatas, Universidade Federal de Alfenas, UNIFAL-MG, Brazil b Laboratório de Plantas Medicinais e Fitoterápicos, Faculdade de Ciências Farmacêuticas, Universidade Federal de Alfenas, UNIFAL-MG, Brazil c Departamento de Química Orgânica, Instituto de Química de Araraquara, UNESP, Araraquara, Brazil |
| Abstract: | A new glycosylated biflavonone, morelloflavone-4′″-O-β-d-glycosyl, and the known compounds 1,3,6,7-tetrahydroxyxanthone, morelloflavone (fukugetin) and morelloflavone-7″-O-β-d-glycosyl (fukugeside) were isolated from the epicarp of Garcinia brasiliensis collected in Brazil. The structures of these compounds were established using 1H and 13C NMR, COSY, gHMQC and gHMBC spectroscopy. The compounds exhibited antioxidant activity. The greatest potency was displayed by morelloflavone (2), with IC50 = 49.5 mM against DPPH and absorbance of 0.583 at 400 μg/mL for the reduction of Fe3+. The weakest potency was displayed by 1,3,6,7-tetrahydroxyxanthone (1), with IC50 = 148 mM against DPPH and absorbance of 0.194 at 400 μg/mL for the reduction of Fe3+. |
| Keywords: | EAEE ethyl acetate epicarp extract BHT butylhydroxytoluene NMR nuclear magnetic resonance gHMQC gradient-assisted heteronuclear multiple quantum coherence detection of short range (1J) correlations between directly connected 1H and 13C nuclei gHMBC gradient-assisted heteronuclear multiple bond coherence detection of long distance (2J and 3J) correlations between 1H and 13C nuclei connected by a series of bonds COSY 1H-1H homonuclear correlation spectroscopy UV ultraviolet IR infrared MS mass spectrometry DPPH 1-diphenyl-2-picrylhydrazyl HSCCC high speed countercurrent chromatography IC50 50% inhibitory concentration CTLC comparative thin-layer chromatography TLC thin-layer chromatography HPLC high performance liquid chromatography β internal measurement equipment |
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