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The influence of various phenolic compounds on scavenging activity assessed by an enzymatic method
Author(s) -
de Gaulejac Nathalie SaintCricq,
Vivas Nicolas,
de Freitas Victor,
Bourgeois Guy
Publication year - 1999
Publication title -
journal of the science of food and agriculture
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.782
H-Index - 142
eISSN - 1097-0010
pISSN - 0022-5142
DOI - 10.1002/(sici)1097-0010(199906)79:8<1081::aid-jsfa330>3.0.co;2-g
Subject(s) - chemistry , polyphenol , radical , scavenging , monomer , proanthocyanidin , stereochemistry , phenols , chemical structure , organic chemistry , antioxidant , polymer
The effect of pure monomeric and dimeric procyanidins on superoxide anion radicals (O 2 ° − ) was studied with an enzymatic method and their IC 50 was determined. A comparative study of the results suggested that the antiradical potential of these phenolic compounds closely depends on their stereochemical structure. Modification of the chiral carbon, C 3 involved in the oxidation mechanism induces differences in the scavenging action of (+)‐catechin (2R : 3S) or (−)‐epicatechin (2R : 3R). The stereochemical conformation of the interflavan linkage (axial or pseudo) according to the chemical nature of dimeric procyanidin units also influences the radical oxidation mechanism. The nature of the interflavan linkage between the two units in dimeric procyanidins (C 4 –C 8 or C 4 –C 6 linkage) is an important factor responsible for effectiveness of the behaviour polyphenols towards O 2 ° − . The extraction of oligomeric procyanidins in grape seeds enabled us to study the effect of polymerisation and galloylation on their scavenging activities. The results clearly showed that the molecular scavenging mechanism of these molecules is closely connected with their spatial conformation. © 1999 Society of Chemical Industry