4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers: Relationship between Oxidation Potential and Protective Effects against Oxidation of Low-Density Lipoproteins
- 3 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Agricultural and Food Chemistry
- Vol. 52 (7), 2084-2091
- https://doi.org/10.1021/jf035068n
Abstract
The electrochemical oxidation potential of a series of monomeric and dimeric 4-hydroxycinnamic ethyl ester derivatives has been compared with their antioxidant activity toward copper-catalyzed human low-density lipoproteins (LDL) oxidation. Within the series of monomeric hydroxycinnamate derivatives, both oxidation potential and IC50 values decreased in the following order: sinapate > ferulate > p-coumarate. Among the 4-hydroxycinnamate dehydrodimer derivatives, noncyclized 8−8 diphenol dehydrodimers followed the same aforementioned sequence order and were found to be better antioxidants than their monomer counterparts. A good correlation between the inhibitory concentration and the oxidation potential was established among all these derivatives. However, a significantly deviating behavior was observed with the 8−5 dihydrobenzofuran and the 8−8 dihydronaphthol cyclic dehydrodimers, which showed lower activities toward copper-catalyzed human LDL, although their oxidation potentials remained very close to those of the noncyclized 8−8 dehydrodimers. Conversely, in the Trolox equivalent antioxidant capacity (TEAC) assay system, the 8−8 dihydronaphthol dehydrodimers were found to be the most efficient free-radical scavengers. Finally, in the series of dehydrodimers studied, it could be concluded that, whatever the in vitro test system used, (a) all dehydrodimer derivatives tested could contribute efficiently to the overall intake of antioxidants in the diet and (b) a low oxidation potential value was in favor of a satisfactory antioxidant activity. Keywords: 4-Hydroxycinnamic ethyl ester derivatives; low-density lipoproteins; dehydrodimers; free radical-scavenging activity; electrochemical oxidation potential−antioxidant activity relationshipThis publication has 25 references indexed in Scilit:
- Phenolic acids in foods: An overview of analytical methodologyJournal of Agricultural and Food Chemistry, 2003
- Structure−Antioxidant Activity Relationship of Ferulic Acid Derivatives: Effect of Carbon Side Chain Characteristic GroupsJournal of Agricultural and Food Chemistry, 2003
- Electrochemical Oxidative Coupling of 4-Hydroxycinnamic Ester Derivatives: A Convenient Methodology for the Biomimetic Synthesis of Lignin PrecursorsCollection of Czechoslovak Chemical Communications, 2003
- Diferulates as structural components in soluble and insoluble cereal dietary fibreJournal of the Science of Food and Agriculture, 2001
- Content of Phenolic Acids and Ferulic Acid Dehydrodimers in 17 Rye (Secale cereale L.) VarietiesJournal of Agricultural and Food Chemistry, 2000
- Benzoic and Cinnamic Acid Derivatives as Antioxidants: Structure−Activity RelationJournal of Agricultural and Food Chemistry, 1999
- The role of oxidized lipoproteins in atherogenesisFree Radical Biology & Medicine, 1996
- Electrochemical Behaviour and Antioxidant Activity of Some Natural PolyphenolsHelvetica Chimica Acta, 1996
- Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivativesFree Radical Biology & Medicine, 1995
- THE DISTRIBUTION AND CHEMICAL COMPOSITION OF ULTRACENTRIFUGALLY SEPARATED LIPOPROTEINS IN HUMAN SERUMJCI Insight, 1955