Nitration of Flavonoids and Tocopherols as Potential Modulators of Nitrosative Stress—A Study Based on Their Conformational Structures and Energy Content

Abstract

Vitamin E and dietary flavonoids are natural substances with antioxidant and anti-inflammatory activities, showing little or no side effects. Fruit and vegetable diets based on flavonoids and vitamin E provide a benefit to hypertensive subjects by regulating blood pressure. However, the exact mechanism of their anti-inflammatory properties has not been chemically explained. It has been proposed that their anti-oxidant and anti-inflammatory properties may be related to their ability to scavenge free radicals. We here describe the chemical considerations that flavonoids and tocopherols required to act as potential scavengers of the •NO2 radical, a key radical in the cellular oxidative process. Moreover, we provide a theoretical study of the energy content of the nitrated compounds in the different possible positions. With this analysis, it was predicted that five flavonoids from different families (quercetin (flavanol), naringenin (flavanone), luteolin (flavone), catechin (flavanol) and aurantinidin (anthocyanin)) and three tocopherols (β-, γ-, and δ-tocopherol, but not α-tocopherol) could act as potential scavengers of the harmful •NO2 radical. These results may help to explain their beneficial effect on cardiovascular health through its antioxidant role. To validate our theoretical considerations, we also examined uric acid, a well-known •NO2-scavenger. We hope this study could help to elucidate the potential scavenging activity of other dietary antioxidants.

Keywords

• flavonoids
• tocopherols
• antioxidants
• peroxynitrite
• ^•NO₂ radical
• biomolecules