Antioxidant properties of carotenoids: QSAR prediction of their redox potentials.
There is a great need to predict the antioxidant properties of molecules such as carotenoids. These compounds are of great interest due to their contribution to various important biological and industrial processes, including toxicity and fate. In our study, redox potentials were compiled from several literature sources. Redox potential values ranged from 537.2 mV for zeaxanthin up to 691.5 mV for beta-carotene; they correspond to the formation of cation radicals, using the standard calomel electrode (SCE). The redox potential values were measured using conventional electrochemical techniques, cyclic voltammetry and Osteryoung square-wave voltammetry. A quantitative structure-activity relationship (QSAR) was developed to model and consequently to predict the values of redox potential. The predicted values of redox potential for four external carotenoids, namely beta-carotene, zeaxanthin, cantaxanthin and astaxanthin, are presented and discussed. They indicate the dependence of redox potential on structure, donor and acceptor groups and polarisability.
Faculty of Chemical and Food Technology, Slovak Technical University, 812 37 Bratislava 1, Slovakia.
M
M
Kleinová
M
M
Hewitt
V
V
Brezová
J C
JC
Madden
M T D
MT
Cronin
M
M
Valko
D000975:Antioxidants / Q000032:analysis / Q000378:metabolism*; D002338:Carotenoids / Q000032:analysis / Q000378:metabolism*; D003625:Data Collection; D001330:Electronic Data Processing; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011237:Predictive Value of Tests; D021281:Quantitative Structure-Activity Relationship; D015203:Reproducibility of Results
D000975:Antioxidants; D005609:Free Radicals; D002338:Carotenoids