Determination of hydrogen peroxide scavenging activity of cinnamic and benzoic acids employing a highly sensitive peroxyoxalate chemiluminescence-based assay: structure-activity relationships.
A series of cinnamic acids along with their corresponding benzoate analogues were tested for their ability to scavenge hydrogen peroxide (H(2)O(2)), by using a highly sensitive, peroxyoxalate chemiluminescence assay. Among benzoic acid derivatives, vanillic acid (3-hydroxy-4-methoxybenzoic acid) was found to be the most efficient H(2)O(2) scavenger with its hydrogen peroxide scavenging activity (SA(HP)) being 170.20 microM(-1), whereas protocatechuic acid (3,4-dihydroxybenzoic acid) exhibited the weakest activity (5.90 microM(-1)). Caffeic acid (3,4-dihydroxycinnamic acid) was the strongest antioxidant amongst cinnamate derivatives with a SA(HP) = 8.2 microM(-1), as opposed to m-coumaric acid (2-hydroxycinnamic acid), which was found to be a poor hydrogen peroxide scavenger (SA(HP) = 0.18 microM(-1)). Comparison between the two groups revealed that benzoate derivatives are much stronger hydrogen peroxide quenchers in relation with their cinnamate analogues, and this finding was discussed on a basis of structure-activity relationships and comparative assessment of other antioxidant characteristics.
Mansouri
Abdelhak
A
Department of Food Quality Management & Chemistry of Natural Products, Mediterranean Agronomic Institute of Chania (MAICh), Greece.
Makris
Dimitris P
DP
Kefalas
Panagiotis
P
D001565:Benzoates / Q000737:chemistry / Q000494:pharmacology*; D002934:Cinnamates / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D008163:Luminescent Measurements; D010070:Oxalates / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013329:Structure-Activity Relationship
D001565:Benzoates; D002934:Cinnamates; D016166:Free Radical Scavengers; D010070:Oxalates; C029010:cinnamic acid; C044622:peroxyoxalate; D006861:Hydrogen Peroxide