Radical Scavenger Activity of Three Flavonoid Metabolites Studied by Inhibition of Chemiluminescence in Human PMNs¹

Abstract

3,4-Dihydroxyphenylacetic acid, 3-hydroxyphenylacetic acid, and 3-(4-hydroxyphenyl)-propionic acid, metabolites which arise from quercetin glycosides, respectively, from flavones and probably from procyanidins by the human intestinal microflora, have been tested for their effects on oxygen radical production by human PMNs stimulated with FMLP or opsonized zymosan. Oxygen radicals were detected by luminol-augmented chemiluminescence measurements. Furthermore free radical scavenging activity of these metabolites was investigated in a cell-free system in which oxygen radicals were generated by horseradish peroxidase with H₂O₂ as substrate. 3,4-Dihydroxyphenylacetic acid reduced considerably chemiluminescence in PMNs in an amount which was much more pronounced than those of the other two metabolites. Concentrations of 1 µmol/l showed an inhibition by 84 % with FMLP as stimulant and by 15 % with opsonized zymosan, indicating that different signal transduction pathways are influenced in PMNs. Using the same conditions the unmetabolized quercetin showed an inhibition of chemiluminescence by 74% (FMLP), resp. 20% (opsonized zymosan). In the cell free system 3,4-dihydroxyphenylacetic acid suppressed much more effectively chemiluminescence than 3-hydroxyphenylacetic acid. In contrast, 3-(4-hydroxyphenyl)-propionic acid led to an increase of chemiluminescence generated in the cell-free system (FMLP and zymosan), i.e. by 30% and by 25%, at the highest concentration of 4 µmol/l. In conclusion, flavonoid metabolites differ in their effects on free radical production of PMNs and their radical scavenging potencies.

Key words

Flavonoid metabolites - radical scavenger activity - chemiluminescence - horseradish peroxidase

1 Part of the thesis of J. Heilmann