Electrochemical Behaviour of Rosmanol 9-Ethyl Ether, a Diterpene Lactone Antioxidant Isolated from Sage

Abstract

The electrochemical behaviour and mechanism of the redox process of the natural antioxidant rosmanol 9-ethyl ether, isolated from Saliva officinalis L., were studied. The cyclic voltammograms of rosmanol 9-ethyl ether (R9EE), at characteristic pH values, and the electrochemical parameters for all investigated pH values were measured. Three characteristic pH regions, each with different behaviour of R9EE, were identified. In regions of pH < 4 and pH > 5 only one anodic peak appeared, whereas in the solutions of pH 4-5 two anodic peaks could be noted. The overall oxidation mechanism at pH < 4 is an e.H.e.H. oxidation mechanism, which as a final product gives a quinonic molecule. The influence of pH on the second oxidation peak potential tends towards zero in accordance with the preceding dissociation of the one of phenolic groups, thus suggesting an e.e.H. mechanism at pH > 5. This means that at the pH values expected in plant cells, R9EE has an unexpected structure, making this substance a potent antioxidant. Electrochemical and spectrophotometric measurements enabled us to establish an extremely low pKa value (4.35) for R9EE.