Chemical structure-dependent differential effects of flavonoids on the catalase activity as evaluated by a chemiluminescent method

Abstract

The antioxidative activity of flavonoids depends upon a combination of many factors, such as the concentration and chemical structure of the flavonoids and the arrangement of functional groups in their structure. In the present study, to evaluate the antioxidative effect of several types of flavonoids on catalase activity at a physiological H2O2 concentration, a chemiluminescent (CL) method was used. The H2O2/luminol- dependent CL intensity in a system containing 3.7 nM catalase and low concentrations (10 - 100 nM) of green tea flavanols (epigallocatechin gallate; EGCG and epicatechin gallate; EG) was enhanced in comparison with that of a system without catalase, suggesting that EGCG and EG partially suppressed catalase activity. On the other hand, flavone and flavonols such as rutin (a 3-glycosidic flavone), quercitrin (a 3-glycosidic flavonol), myricetin, and kaempferol (flavonols), respectively, lowered the CL intensity to a greater extent at low concentrations (<0.1 μM) when catalase was present than when catalase was absent, indicating that these flavonoids activate catalase. In addition, isoflavone and flavanone such as daidzein and naringenin, respectively, exhibited weak antioxidative activities against H 2O2 without any effect on the catalase activity over a wide range of flavonoid concentrations (0.04 - 0.4 μM). From these results, it was for the first time suggested that the binding of flavonoids to the heme moiety or a protein region of catalase contributes to the enhancement of catalase activity. © 2007 Pharmaceutical Society of Japan.