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  • Title: Protective effects of 4-hydroxycinnamic ethyl ester derivatives and related dehydrodimers against oxidation of LDL: radical scavengers or metal chelators?
    Author: Neudörffer A, Desvergne JP, Bonnefont-Rousselot D, Legrand A, Fleury MB, Largeron M.
    Journal: J Agric Food Chem; 2006 Mar 08; 54(5):1898-905. PubMed ID: 16506851.
    Abstract:
    4-Hydroxycinnamate derivatives are known to be potent protectors against oxidation of low-density lipoproteins (LDL), via a combination of free radical scavenging and transition metal chelation. Through a series of 4-hydroxycinnamic ethyl ester derivatives and related 8-8 dehydrodimers, we have tried to bring out the structural requirements for radical scavenging and cupric ion chelation. We found that the monomeric compounds, except for highly lipophilic tert-butyl derivative 3, exhibited rather low radical scavenging properties. Furthermore, they did not chelate copper but, in contrast, reduced cupric ion to cuprous ion, affording the related 8-8 dehydrodimers, for which they could be considered as precursors in vitro. In the copper-dependent human LDL oxidation in vitro, the cyclic 8-8 dehydrodimer forms behaved essentially as efficient copper chelators, while related noncyclic 8-8 forms, which were found to be the best protectors, mainly acted as radical scavengers.
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