Antioxidant activity of (+)-bergenin-a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae)

Abstract

(+)-Bergenin (1) was isolated from Sacoglottis uchi, a species of vegetable found in the Amazon region and popularly used for the treatment of several hepatic problems. The structure of 1 was fully characterized using IR, GC-MS and NMR (1D and 2D) analyses. This phytoconstituent has been used as an oriental folk medicine for the treatment of many diseases and shows antihepatotoxic properties. Tests with β-carotene, DPPH and a heterogeneous Fenton system were carried out, confirming the antioxidant activity of 1. Theoretical calculations were performed to investigate the formation of the radical derivatives of 1 using ̇H, ̇OH, ̇CH3, and ̇CCl 3 as initiator radicals. DFT thermodynamic calculations showed that the methoxyl group (O-6-CH3) is the most favorable site for radical attack. Frontier molecular orbital analysis showed that nucleophilic radical attack is favored on the aromatic ring of 1 where the LUMO is localized, with antibonding character with respect to the O-6-CH3 bond. The possibilities of attack at other sites on 1 were investigated in detail in order to understand the regiospecificity of this reaction. © The Royal Society of Chemistry.