| Alkyl esters of hydroxycinnamic acids with improved antioxidant activity and lipophilicity protect PC12 cells against oxidative stress. | |
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MedLine Citation:
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PMID: 22210493 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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 IC(50) (13.5-14.5 μM) and higher ferric reducing antioxidant power (FRAP) values (1490-1588 mM quercetin/mole [mMQ/mole]) compared to caffeic acid (16.6 μM and 1398 mMQ/mole, respectively) in antioxidant assays. In contrast, ferulate esters were less active in DPPH (56.3-74.7 μM) and FRAP assays (193-262 mMQ/mole) compared to ferulic acid (44.6 μM 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 μM. 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. |
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Authors:
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Jorge Garrido; Alexandra Gaspar; E Manuela Garrido; Ramin Miri; Marjan Tavakkoli; Samaneh Pourali; Luciano Saso; Fernanda Borges; Omidreza Firuzi |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-12-23 |
Journal Detail:
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Title: Biochimie Volume: - ISSN: 1638-6183 ISO Abbreviation: - Publication Date: 2011 Dec |
Date Detail:
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Created Date: 2012-1-2 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 1264604 Medline TA: Biochimie Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011. Published by Elsevier Masson SAS. |
Affiliation:
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CIQ/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal; Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic Institute of Porto, 4200-072 Porto, Portugal. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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