Protective effects of 4-hydroxycinnamic ethyl ester derivatives and related dehydrodimers against oxidation of LDL: radical scavengers or metal chelators?

Journal of Agricultural and Food Chemistry
Anne NeudörfferMartine Largeron

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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Citations

Aug 1, 2012·Journal of Agricultural and Food Chemistry·Fachuang LuJohn Ralph
Sep 2, 2009·Biological & Pharmaceutical Bulletin·Phuong Thien ThuongKeon Wook Kang
Jan 13, 2011·Angewandte Chemie·Stéphane QuideauLaurent Pouységu
Aug 22, 2006·Bioorganic & Medicinal Chemistry·Ming-Zhe XuHo-Yong Park
Jul 30, 2019·Journal of Food Biochemistry·Adeola M AlashiRotimi E Aluko
Oct 12, 2010·Chemistry and Physics of Lipids·Antonella RosaM Assunta Dessì

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