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.
References
Nov 1, 1987·Chemistry and Physics of Lipids·K Yagi
Feb 1, 1987·Journal of Chemical Information and Computer Sciences·A K Ghose, G M Crippen
Jan 1, 1984·Methods in Enzymology·R P Bird, H H Draper
Jan 1, 1996·Free Radical Biology & Medicine·J A Berliner, J W Heinecke
Aug 19, 1996·FEBS Letters·N J MillerC Rice-Evans
May 23, 1998·The Biochemical Journal·J E BrownC A Rice-Evans
Apr 8, 1999·Free Radical Research·R P Patel, V M Darley-Usmar
Nov 24, 1999·Journal of Agricultural and Food Chemistry·F NatellaC Scaccini
Nov 26, 1999·Bioorganic & Medicinal Chemistry Letters·R LargetM Largeron
Dec 10, 1999·Journal of Medicinal Chemistry·M LargeronM B Fleury
Oct 14, 2000·Journal of Agricultural and Food Chemistry·M F AndreasenA Hansen
Apr 21, 2001·Journal of Agricultural and Food Chemistry·J H GrabberR D Hatfield
Jul 20, 2001·Free Radical Biology & Medicine·M F AndreasenM T Garcia-Conesa
Sep 22, 2001·Archives of Biochemistry and Biophysics·M J Burkitt
Jul 11, 2002·Free Radical Biology & Medicine·Andreas R RechnerCatherine A Rice-Evans
Feb 20, 2003·Journal of Agricultural and Food Chemistry·Jane M MaritaRonald D Hatfield
Feb 20, 2003·Journal of Agricultural and Food Chemistry·Mirko BunzelHans Steinhart
Mar 20, 2003·Journal of Agricultural and Food Chemistry·Charlotte C ParkerKeith W Waldron
Mar 26, 2003·Free Radical Biology & Medicine·Cécile Cren-OlivéChristian Rolando
May 2, 2003·Journal of Agricultural and Food Chemistry·Rebecca J Robbins
Aug 16, 2003·Arteriosclerosis, Thrombosis, and Vascular Biology·Anatol KontushM John Chapman
Aug 21, 2003·Free Radical Biology & Medicine·K Indira PriyadarsiniHari Mohan
Sep 1, 1955·The Journal of Clinical Investigation·R J HAVELJ H BRAGDON
Nov 13, 2003·Journal of Agricultural and Food Chemistry·Raffaella BrianteRoberto Nucci
Jan 28, 2004·Free Radical Biology & Medicine·Andreas R RechnerCatherine A Rice-Evans
Apr 1, 2004·Journal of Agricultural and Food Chemistry·Anne NeudörfferMartine Largeron
Oct 14, 2004·Journal of Agricultural and Food Chemistry·Mirko BunzelHans Steinhart
Feb 18, 2005·Journal of Medicinal Chemistry·Estelle BlattesMartine Largeron
Mar 24, 2005·Annals of Botany·John W Finley
Aug 2, 2005·Nutrition, Metabolism, and Cardiovascular Diseases : NMCD·Daniele Del RioNicoletta Pellegrini
Citations
Aug 1, 2012·Journal of Agricultural and Food Chemistry·Fachuang LuJohn Ralph
Sep 2, 2009·Biological & Pharmaceutical Bulletin·Phuong Thien ThuongKeon Wook Kang
Mar 8, 2016·Food Chemistry·Adriana Skendi, Costas G Biliaderis
Jan 13, 2011·Angewandte Chemie·Stéphane QuideauLaurent Pouységu
Aug 22, 2006·Bioorganic & Medicinal Chemistry·Ming-Zhe XuHo-Yong Park
May 24, 2008·Chemistry and Physics of Lipids·Antonella RosaM Assunta Dessì
Jan 26, 2020·Biomolecules·Ying HeFachuang Lu
Jul 30, 2019·Journal of Food Biochemistry·Adeola M AlashiRotimi E Aluko
Mar 21, 2019·Antioxidants·Ruizhi HuJianhua He
Jun 6, 2009·Chemico-biological Interactions·Antonella RosaM Assunta Dessì
Oct 12, 2010·Chemistry and Physics of Lipids·Antonella RosaM Assunta Dessì