Structure-DPPH* scavenging activity relationships: parallel study of catechol and guaiacol acid derivatives.
The scavenging behavior of a series of catechol and guaiacol acid derivatives toward DPPH(*) was examined having as a starting point the order of activity derived on the basis of theoretically calculated BDE values. The studied compounds were protocatechuic, homoprotocatechuic, dihydrocaffeic, and caffeic acids and also vanillic, homovanillic, dihydroferulic, and ferulic acids. Catechol and guaiacol were used as reference compounds. Observations from the parallel study were made with regard to structural features (number and position of hydroxyl groups and the side-carbon chain characteristics) that regulated the behavior of the compounds experimentally. The exceptional DPPH(*) scavenging behavior observed for homoprotocatechuic acid in ethanol and for caffeic acid in acetonitrile could not be supported by the respective BDE values. Ferulic was the most active among guaiacolic acids, whereas dihydroferulic exhibited the highest stoichiometry. Ionizable carboxylic groups seem to affect considerably the relative order of activity as was also evidenced using the ORAC assay. Questions raised about the validity of widely accepted views on criteria for SARs are discussed with regard to literature findings.
Ordoudi
Stella A
SA
Laboratory of Food Chemistry and Technology and Laboratory of Applied Quantum Chemistry, School of Chemistry, Aristotle University of Thessaloniki, Greece.
Tsimidou
Maria Z
MZ
Vafiadis
Anastasios P
AP
Bakalbassis
Evangelos G
EG
D015102:3,4-Dihydroxyphenylacetic Acid / Q000737:chemistry; D001713:Biphenyl Compounds; D002109:Caffeic Acids / Q000737:chemistry; D002396:Catechols / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry*; D006139:Guaiacol / Q000737:chemistry*; D010851:Picrates; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D001713:Biphenyl Compounds; D002109:Caffeic Acids; D002396:Catechols; D003373:Coumaric Acids; D016166:Free Radical Scavengers; D010851:Picrates; D015102:3,4-Dihydroxyphenylacetic Acid; D006139:Guaiacol; C004999:ferulic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; C040048:caffeic acid