| 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.