Structure-property studies on the antioxidant activity of flavonoids present in diet

• Type: Article in International Scientific Journal
• Date: 2005

Authors

Teixeira, S (Author) Other; Christophe Siquet (Author) FEUP; Alves, C (Author) Other; Boal, I (Author) Other; Marques, MP (Author) Other; Borges, F (Author) FFUP; Lima, JLFC (Author) FFUP; Reis, S (Author) FFUP

Journal

Title: Free Radical Biology and Medicine

Vol. 39 No. 8

Pages: 1099-1108

ISSN: 0891-5849

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 138 Citations

ISI Web of Science

Scopus - 157 Citations

Scientific classification

FOS: Medical and Health sciences > Clinical medicine

CORDIS: Health sciences

Other information

Authenticus ID: P-000-0XK

DOI: 10.1016/j.freeadbiomed.2005.05.028

Resumo (PT): The screening of natural flavonoids for their bioactivity as antioxidants is usually carried out by determinination of their profile as chain-breaking antioxidants, by the evaluation of their direct free radical-scavenging activity as hydrogen- or electron-donating compounds. Since this may not be the only mechanism underlying the antioxidant activity it is important to check the ability of these compounds to act as chelators of transition metal ions. Accordingly, in the present study the acidity constants of catechin and taxifolin, as well as the formation constants of the corresponding copper (II) complexes, were investigated by potentiometry and/or spectrophotometry. Moreover, a detailed quantitative examination of the coordination species formed is presented. In addition, the partition coefficients of both catechin and taxifolin in a biomimetic system (micelles) were determined, since these properties may also contribute to the antioxidant behavior of this type of compound. The log P values determined depend on the electrostatic interactions of the compounds with the differently charged micelles (the highest values were obtained for zwitterionic and cationic micelles). The prooxidant behavior of the compounds was assessed through the oxidation of 2′-deoxyguanosine, induced by a Fenton reaction, catalyzed by copper. The data obtained reveal that the flavonoids under study did not present prooxidant activity, in this particular system. The results obtained are evidence of a clear difference among the pKa, the complexation properties, and the lipophilicity of the flavonoids studied, which can partially explain their distinct antioxidant activity. The most stable geometries of the free compounds were determined by theoretical (ab initio) methods, in order to properly account for the electron correlation effects which occur in these systems, thus allowing a better interpretation of the experimental data. <br> <br> Keywords: Flavonoids; Catechin; Taxifolin; Antioxidant activity; Acidity constants; Ab initio calculations; Formation constants; Copper (II); Partition coefficients <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T38-4H6P80F-G&_user=2460038&_coverDate=10%2F15%2F2005&_rdoc=14&_fmt=high&_orig=browse&_srch=doc-info(%23toc%234940%232005%23999609991%23607099%23FLA%23display%23Volume)&_cdi=4940&_sort=d&_docanchor=&_ct=17&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=b8e8d312f9268e1461d40a9169d098c7 "> Texto integral </a> <br> <br>

Abstract (EN): The screening of natural flavonoids for their bioactivity as antioxidants is usually carried out by determinination of their profile as chain-breaking antioxidants, by the evaluation of their direct free radical-scavenging activity as hydrogen- or electron-donating compounds. Since this may not be the only mechanism underlying the antioxidant activity it is important to check the ability of these compounds to act as chelators of transition metal ions. Accordingly, in the present study the acidity constants of catechin and taxifolin, as well as the formation constants of the corresponding copper (II) complexes, were investigated by potentiometry and/or spectrophotometry. Moreover, a detailed quantitative examination of the coordination species formed is presented. In addition, the partition coefficients of both catechin and taxifolin in a biomimetic system (micelles) were determined, since these properties may also contribute to the antioxidant behavior of this type of compound. The log P values determined depend on the electrostatic interactions of the compounds with the differently charged micelles (the highest values were obtained for zwitterionic and cationic micelles). The prooxidant behavior of the compounds was assessed through the oxidation of 2'-deoxyguanosine, induced by a Fenton reaction, catalyzed by copper. The data obtained reveal that the flavonoids under study did not present prooxidant activity, in this particular system. The results obtained are evidence of a clear difference among the pK(a), the complexation properties, and the lipophilicity of the flavonoids studied, which can partially explain their distinct antioxidant activity. The most stable geometries of the free compounds were determined by theoretical (ab initio) methods, in order to properly account for the electron correlation effects which occur in these systems, thus allowing a better interpretation of the experimental data.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10