Use este identificador para citar ou linkar para este item: https://repositorio.inpa.gov.br/handle/1/18545
Título: Antioxidant activity of (+)-bergenin-a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae)
Autor: Abreu, Heitor Avelino de
Aparecida Dos, Izandina
Souza, Gilmar P.
Piló?-Veloso, Dorila
Duarte, Hélio Anderson
Alcântara, Antônio Flávio de C.
Palavras-chave: Nuclear Magnetic Resonance
Amazon Region
Anti-oxidant Activities
Bergenin
Fenton System
Theoretical Calculations
Health
Antioxidant
Benzopyran Derivative
Bergenin
Beta Carotene
Biphenyl Derivative
Diphenyl-p-picrylhydrazyl
Diphenyl-p-picrylhydrazyl
Hydrazine Derivative
Hydroxyl Radical
Plant Extract
Bark
Chemical Structure
Chemistry
Computer Simulation
Spectrophotometry, Infrared
Malpighiaceae
Mass Fragmentography
Medicinal Plant
Nuclear Magnetic Resonance Spectroscopy
South America
Stereoisomerism
Antioxidants
Benzopyrans
Beta Carotene
Biphenyl Compounds
Computer Simulation
Gas Chromatography-mass Spectrometry
Hydrazines
Hydroxyl Radical
Magnetic Resonance Spectroscopy
Malpighiaceae
Molecular Structure
Plant Bark
Plant Extracts
Plants, Medicinal
South America
Spectrophotometry, Infrared
Stereoisomerism
Sacoglottis
Data do documento: 2008
Revista: Organic and Biomolecular Chemistry
É parte de: Volume 6, Número 15, Pags. 2713-2718
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.
DOI: 10.1039/b804385j
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