Abstract
3-(3′,4′-Dihydroxyphenyl)-l-alanine (l-DOPA), which is synthesized in velvet bean (Mucuna pruriens), inhibits plant growth. The concentration of l-DOPA in soil is reduced by adsorption and transformation reactions, which can result in the reduction of its plant-growth-inhibitory activity. To determine which part of the l-DOPA structure is involved in the adsorption and soil transformation reactions, we compared the kinetics of l-DOPA disappearance in a volcanic ash soil with that of l-phenylalanine (3-phenyl-l-alanine) and l-tyrosine (3-(4′-hydroxyphenyl)-l-alanine), compounds that are similar in structure to l-DOPA but do not have a catechol (o-dihydroxybenzene) moiety. l-Phenylalanine and l-tyrosine were not adsorbed and transformed in the soil at equilibrium pH values between 4 and 7. These results suggest that the adsorption and transformation reactions of l-DOPA in the soil involve the catechol moiety and not the amino and carboxylic acid groups, which are common to all three compounds. Like l-DOPA, (+)-catechin, another allelochemical that contains a catechol moiety, underwent adsorption and soil transformation reactions. Thus, we concluded that the concentrations of allelochemicals bearing a catechol moiety in soils will decrease rapidly owing to adsorption and transformation reactions, and this decrease will be faster in soils with a high pH value or high adsorption ability. Owing to this decrease in concentration, allelopathic phenomena may not occur.
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Furubayashi, A., Hiradate, S. & Fujii, Y. Role of Catechol Structure in the Adsorption and Transformation Reactions of l-Dopa in Soils. J Chem Ecol 33, 239–250 (2007). https://doi.org/10.1007/s10886-006-9218-5
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DOI: https://doi.org/10.1007/s10886-006-9218-5