Glycyrrhetinic acid interaction with solvated and free electrons studied by the CIDNP and dissociative electron attachment techniques

Abstract

Electron transfer plays a crucial role in living systems, including the generation of reactive oxygen species (ROS). Oxygen acts as the terminal electron acceptor in the respiratory chains of aerobic organisms as well as in some photoinduced processes followed by the formation of ROS. This is why the participation of exogenous antioxidants in electron transfer processes in living systems is of particular interest. In the present study, using chemically induced dynamic nuclear polarization (CIDNP) and dissociative electron attachment (DEA) techniques, we have elucidated the affinity of solvated and free electrons to glycyrrhetinic acid (GA)—the aglicon of glycyrrhizin (the main active component of Licorice root). CIDNP is a powerful instrument to study the mechanisms of electron transfer reactions in solution, but the DEA technique shows its effectiveness in gas phase processes. For CIDNP experiments, the photoionization of the dianion of 5-sulfosalicylic acid (HSSA2−) was used as a model reaction of solvated electron generation. DEA experiments testify that GA molecules are even better electron acceptors than molecular oxygen, at least under gas-phase conditions. In addition, the effect of the solvent on the energetics of the reactants is discussed.