Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress

• Type: Article in International Scientific Journal
• Date: 2012

Authors

Jorge Garrido (Author) Other; Alexandra Gaspar (Author) Other; Manuela Garrido, EM (Author) Other; Ramin Miri (Author) Other; Marjan Tavakkoli (Author) Other; Samaneh Pourali (Author) Other; Luciano Saso (Author) Other; Fernanda Borges (Author) FCUP; Omidreza Firuzi (Author) Other

Journal

Title: Biochimie

Vol. 94

ISSN: 0300-9084

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 101 Citations

Scopus - 103 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

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

Other information

Authenticus ID: P-002-BKA

Abstract (EN): Hydroxycinnamic acids (HCAs) are phenolic compounds present in dietary plants, which possess considerable antioxidant activity. In order to increase the lipophilicity of HCAs, with the aim of improving their cellular absorption and expansion of their use in lipophilic media, methyl, ethyl, propyl and butyl esters of caffeic acid and ferulic acid have been synthesized. All caffeate esters had a slightly lower DPPH IC50 (13.5-14.5 mu M) and higher ferric reducing antioxidant power (FRAP) values (1490-1588 mM quercetin/mole [mMQ/mole]) compared to caffeic acid (16.6 mu M and 1398 mMQ/mole, respectively) in antioxidant assays. In contrast, ferulate esters were less active in DPPH (56.3-74.7 mu M) and FRAP assays (193-262 mMQ/mole) compared to ferulic acid (44.6 mu M and 324 mMQ/mole, respectively). Redox properties of HCAs were in line with their antioxidant capacities, so that compounds with higher antioxidant activities had lower oxidation potentials. Measurement of partition coefficients disclosed the higher lipophilicity of the esters compared to parent compounds. All esters of caffeic acid significantly inhibited hydrogen peroxide-induced neuronal PC12 cell death assessed by MTT assay at 5 and 25 mu M. However, caffeic acid, ferulic acid and ferulate esters were not able to protect the cells. In conclusion, these findings suggest that alkyl esterification of some HCAs augments their antioxidant properties as well as their lipophilicity and as a consequence, improves their cell protective activity against oxidative stress. These compounds could have useful applications in conditions where oxidative stress plays a pathogenic role. (C) 2011 Elsevier Masson SAS. All rights reserved.

Language: English

Type (Professor's evaluation): Scientific