Antioxidant profile of dihydroxy- and trihydroxyphenolic acids - A structure-activity relationship study

• Type: Article in International Scientific Journal
• Date: 2006

Authors

Christophe Siquet (Author) FEUP; Paiva Martins, F (Author) FCUP; Lima, JLFC (Author) FFUP; Reis, S (Author) FFUP; Borges, F (Author) FFUP

Journal

Title: Free Radical Research

Vol. 40 No. 4

Pages: 433-442

ISSN: 1071-5762

Publisher: Taylor & Francis

Indexing

ISI Web of Knowledge - 140 Citations

Scopus - 157 Citations

Scientific classification

FOS: Natural sciences > Biological sciences

CORDIS: Health sciences ; Physical sciences > Chemistry > Applied chemistry > Pharmaceutical chemistry

Other information

Authenticus ID: P-004-ME9

DOI: 10.1080/10715760500540442

Resumo (PT): Eight structurally similar dihydroxy and trihydroxyphenolic acids (protocatechuic acid, 3,4-dihydroxyphenylacetic acid, hydrocaffeic acid, caffeic acid, gallic acid, 3,4,5-trihydroxyphenylacetic acid, 3-(3,4,5-trihydroxyphenyl)propanoic acid and 3-(3,4,5-trihydroxyphenyl)propenoic acid) were examined for their total antioxidant capacity (TAC). Furthermore, their ability to scavenge peroxyl radicals, generated by AAPH in liposomes, was determined. The antioxidant/pro-oxidant activity of the compounds was screened using the 20-deoxyguanosine assay. All compounds behave as radical scavengers, with 3,4,5- trihydroxyphenylacetic acid being the most potent. Nevertheless, in the lipid peroxidation assay an inverse ranking order was observed, 3,4-dihydroxyphenylacetic acid being the most effective compound. All the dihydroxylated compounds showed a pro-oxidant behaviour leading to an increase of 50% in 8-OH-dG induction. From the structure–antioxidant activity relationship studies performed it may be concluded that the number of phenolic groups and the type of the alkyl spacer between the carboxylic acid and the aromatic ring strongly influence the antioxidant activity. <br> <br> Keywords: Dihydroxyphenolic acid, trihydroxyphenolic acid, ABTS, DPPH, lipoperoxidation, 20-deoxyguanosine <br> <a target="_blank" href="http://web.ebscohost.com/ehost/detail?vid=4&hid=7&sid=e74f4ef8-6751-438b-b73c-46f6a4e1ac01%40sessionmgr14&bdata=JnNpdGU9ZWhvc3QtbGl2ZQ%3d%3d#db=a9h&AN=19937596#db=a9h&AN=19937596#db=a9h&AN=19937596 "> Texto integral </a> <br> <br>

Abstract (EN): Eight structurally similar dihydroxy and trihydroxyphenolic acids (protocatechuic acid, 3,4-dihydroxyphenylacetic acid, hydrocaffeic acid, caffeic acid, gallic acid, 3,4,5-trihydroxyphenylacetic acid, 3-(3,4,5-trihydroxyphenyl) propanoic acid and 3-(3,4,5-trihydroxyphenyl)propenoic acid) were examined for their total antioxidant capacity (TAC). Furthermore, their ability to scavenge peroxyl radicals, generated by AAPH in liposomes, was determined. The antioxidant/pro-oxidant activity of the compounds was screened using the 2'-deoxyguanosine assay. All compounds behave as radical scavengers, with 3,4,5-trihydroxyphenylacetic acid being the most potent. Nevertheless, in the lipid peroxidation assay an inverse ranking order was observed, 3,4-dihydroxyphenylacetic acid being the most effective compound. All the dihydroxylated compounds showed a pro-oxidant behaviour leading to an increase of 50% in 8-OH-dG induction. From the structure-antioxidant activity relationship studies performed it may be concluded that the number of phenolic groups and the type of the alkyl spacer between the carboxylic acid and the aromatic ring strongly influence the antioxidant activity.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10