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- Title
Role of Catechol Structure in the Adsorption and Transformation Reactions of <span style="font-variant:small-caps">l</span> -D<span style="font-variant:small-caps">opa</span> in Soils.
- Authors
Akihiro Furubayashi; Syuntaro Hiradate; Yoshiharu Fujii
- Abstract
Abstract??3-(3?,4?-Dihydroxyphenyl)-<span style="font-variant:small-caps">l-alanine (<span style="font-variant:small-caps">l-DOPA), which is synthesized in velvet bean (Mucuna pruriens), inhibits plant growth. The concentration of<span style="font-variant:small-caps">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<span style="font-variant:small-caps">l-DOPA structure is involved in the adsorption and soil transformation reactions, we compared the kinetics of<span style="font-variant:small-caps">l-DOPA disappearance in a volcanic ash soil with that of<span style="font-variant:small-caps">l-phenylalanine (3-phenyl-<span style="font-variant:small-caps">l-alanine) and<span style="font-variant:small-caps">l-tyrosine (3-(4?-hydroxyphenyl)-<span style="font-variant:small-caps">l-alanine), compounds that are similar in structure to<span style="font-variant:small-caps">l-DOPA but do not have a catechol (o-dihydroxybenzene) moiety.<span style="font-variant:small-caps">l-Phenylalanine and<span style="font-variant:small-caps">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<span style="font-variant:small-caps">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<span style="font-variant:small-caps">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.
- Subjects
DOPA; PHENYLALANINE; ADSORPTION (Chemistry); AMINO acids
- Publication
Journal of Chemical Ecology, 2007, Vol 33, Issue 2, p239
- ISSN
0098-0331
- Publication type
Article
- DOI
10.1007/s10886-006-9218-5