Document Detail

Antioxidant activity of (+)-bergenin: a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae).
MedLine Citation:
PMID:  18633529     Owner:  NLM     Status:  MEDLINE    
(+)-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 beta-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, *CH(3), and *CCl(3) as initiator radicals. DFT thermodynamic calculations showed that the methoxyl group (O-6-CH(3)) 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-CH(3) bond. The possibilities of attack at other sites on 1 were investigated in detail in order to understand the regiospecificity of this reaction.
Heitor A De Abreu; Izandina Aparecida Dos S Lago; Gilmar P Souza; Dorila Piló-Veloso; Hélio A Duarte; Antônio Flávio de C Alcântara
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-06-02
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  6     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2008 Aug 
Date Detail:
Created Date:  2008-07-17     Completed Date:  2008-10-14     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  2713-8     Citation Subset:  IM    
Departamento de Química, ICEx-Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil.
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MeSH Terms
Antioxidants / chemistry*,  pharmacology
Benzopyrans / chemistry*,  pharmacology
Biphenyl Compounds / chemistry
Computer Simulation
Gas Chromatography-Mass Spectrometry
Hydrazines / chemistry
Hydroxyl Radical / chemistry*
Magnetic Resonance Spectroscopy
Malpighiaceae / chemistry*
Molecular Structure
Plant Bark / chemistry*
Plant Extracts / pharmacology*
Plants, Medicinal
South America
Spectrophotometry, Infrared
beta Carotene / chemistry
Reg. No./Substance:
0/Antioxidants; 0/Benzopyrans; 0/Biphenyl Compounds; 0/Hydrazines; 0/Picrates; 0/Plant Extracts; 1898-66-4/2,2-diphenyl-1-picrylhydrazyl; 3352-57-6/Hydroxyl Radical; 477-90-7/bergenin; 7235-40-7/beta Carotene

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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