Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups.

We studied antioxidant activity of five natural flavonoids in canola oil, an emulsion, and rat red blood cell membrane. In the canola oil heated at 105 degrees C, myricetin most effectively attenuated lipid oxidation, followed by quercetin, morin and kaempferol in a decreasing order. When the emulsion containing canola oil was incubated at 54 degrees C, quercetin was most protective against lipid oxidation, followed by kaempferol, myricetin and morin in a decreasing rank. Apigenin demonstrated no antioxidant activity in either the canola oil or the emulsion. Of the flavonoids tested, quercetin was the best in quenching free radical chain reaction in rat red blood cell membrane. The antioxidative characteristics of these flavonoids was determined by multiple factors including the system used, the hydrophobicity, and the total number and the location of aromatic hydroxyl groups. We conclude that myricetin is an effective antioxidant in canola oil, while quercetin is an effective protector against lipid oxidation in the cell membrane.