Role of catechol structure in the adsorption and transformation reactions of L-DOPA in soils

Akihiro Furubayashi, Syuntaro Hiradate, Yoshiharu Fujii

Research output: Contribution to journalArticle

32 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)239-250
Number of pages12
JournalJournal of Chemical Ecology
Volume33
Issue number2
DOIs
Publication statusPublished - Feb 1 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Ecology

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