Electrochemical and spectroscopic study of l‑dopa interaction with avarol

Abstract

The electrochemistry of catecholamine neurotransmitters and their precursor l-dopa has been widely studied due to their relevance as biologically important compounds. The detection of these compounds from aqueous solution is hindered by the coexistence of quinone or hydroquinone. However, it was suggested that quinones adsorbed on the electrode surface can enhance catechol detection. In order to estimate the degree of interaction between quinones and l-dopa, cyclic voltammetry and UV-Vis spectroscopic study was performed. A sesquiterpenoid hydroquinone, isolated from the marine sponge Dysidea avara (avarol), has been used in this study. The change of apparent heterogeneous rate constant with different avarol/l-dopa ratio indicated that charge transfer could be enhanced at some extent. In addition to this, the obtained results for avarol and hydroquinone (its structural element) were compared. UV-Vis spectroscopic analysis confirmed interaction between l-dopa and avarol or hydroquinone. Taken all together, the interaction of l-dopa was stronger with hydroquinone than with avarol, presumably reflecting the conformational restrains of avarol caused by its terpenoid moiety.