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    
Abstract/OtherAbstract:
(+)-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.
Authors:
Heitor A De Abreu; Izandina Aparecida Dos S Lago; Gilmar P Souza; Dorila Piló-Veloso; Hélio A Duarte; Antônio Flávio de C Alcântara
Related Documents :
11799109 - Formation of peroxynitrite from reaction of nitroxyl anion with molecular oxygen.
3076429 - The mechanism of adenosylcobalamin-dependent rearrangements.
20714669 - Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer: generati...
12612429 - Characterization of hydrazine derivative: proposed decomposition mechanism and structur...
15350099 - Electrochemical oxidation of aliphatic amines and their attachment to carbon and metal ...
16534759 - Nmr spectroscopy and maldi-tof ms characterisation of end-functionalised pvp oligomers ...
1403689 - Vanadium and copper in clinical solutions of albumin and their potential to damage prot...
21579969 - Bis[μ-2-(2,4-difluoro-phen-yl)-1,3-bis-(1,2,4-triazol-1-yl)propan-2-olato-κn,o:o,n]bi...
17361969 - High-density storage of h2 in microporous crystalline silica at ambient conditions.
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    
Affiliation:
Departamento de Química, ICEx-Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil. haabreu@qui.dout.ufmg.br
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
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
Picrates
Plant Bark / chemistry*
Plant Extracts / pharmacology*
Plants, Medicinal
South America
Spectrophotometry, Infrared
Stereoisomerism
beta Carotene / chemistry
Chemical
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


Previous Document:  Layer-by-layer deposition of molecular oligoelectrolytes-investigation of assembling and degradation...
Next Document:  Inhibitors of the kinase IspE: structure-activity relationships and co-crystal structure analysis.