Adsorption and transformation reactions of L-DOPA in soils

Abstract

3-(3′,4′-Dihydroxyphenyl)-L-alanine (L-DOPA), which is a component of velvetbean (Mucuna pruriens), displays a high inhibitory activity to plant growth. The inhibitory activity is influenced by the presence of soils, because L-DOPA is eliminated in soils. In the present study, the effect of several soil types (volcanic ash, calcareous, and alluvial soils) on the L-DOPA disappearance was investigated at constant equilibrium pH values. In the presence of soils, L-DOPA disappeared with the reaction time, and the disappearance was associated with three reactions: adsorption reaction (characterized by fast and sudden disappearance of L-DOPA within the initial 8 h period), catalytic transformation reaction (constant L-DOPA disappearance throughout the reaction period), and biotransformation caused by microbial activity (accelerated L-DOPA disappearance observed after 72 h of reaction time). The adsorption and transformation reactions consisted of physicochemical reactions mediated by the presence of soils. The amount of L-DOPA adsorbed was largest in the presence of volcanic ash soil among the three soil types. It is likely that the mechanism of L-DOPA adsorption includes a ligand exchange reaction. In the presence of soils, L-DOPA transformation was observed at equilibrium pH values higher than 4 and it increased with increasing equilibrium pH values. In the absence of soil, however, L-DOPA transformation did not occur at an equilibrium pH value lower than 6.0, indicating that L-DOPA transformation was accelerated by the presence of soil. The rate of L-DOPA transformation mediated by soils at constant equilibrium pH value was in the following order: alluvial soil > calcareous soil > volcanic ash soil. The plant-growth-inhibitory activity of L-DOPA was also reduced by the presence of soils, and the reduction in the case of L-DOPA was more obvious than in the case of 2,4-dichlorophenoxyacetic acid (2,4-D). Based on the reduction effect of soils on the plant-growth-inhibitory activity of L-DOPA (without pH-adjustment), calcareous soil ranked first, followed by volcanic ash soil, then alluvial soil. This was because the calcareous soil showed the highest soil pH value (7.8), and thereby the L-DOPA transformation reaction was accelerated. In soils with high pH values, the plant-growth-inhibitory activity of L-DOPA could therefore not be detected.