Synthesis and biological activity of amino acid conjugates of abscisic acid

Bioorg Med Chem. 2011 Mar 1;19(5):1743-50. doi: 10.1016/j.bmc.2011.01.019. Epub 2011 Jan 18.

Abstract

We prepared 19 amino acid conjugates of the plant hormone abscisic acid (ABA) and investigated their biological activity, enzymatic hydrolysis by a recombinant Arabidopsis amidohydrolases GST-ILR1 and GST-IAR3, and metabolic fate in rice seedlings. Different sets of ABA-amino acids induced ABA-like responses in different plants. Some ABA-amino acids, including some that were active in bioassays, were hydrolyzed by recombinant Arabidopsis GST-IAR3, although GST-ILR1 did not show hydrolysis activity for any of the ABA-amino acids. ABA-L-Ala, which was active in all the bioassays, an Arabidopsis seed germination, spinach seed germination, and rice seedling elongation assays, except in a lettuce seed germination assay and was hydrolyzed by GST-IAR3, was hydrolyzed to free ABA in rice seedlings. These findings suggest that some plant amidohydrolases hydrolyze some ABA-amino acid conjugates. Because our study indicates the possibility that different plants have hydrolyzing activity toward different ABA-amino acids, an ABA-amino acid may function as a species-selective pro-hormone of ABA.

MeSH terms

  • Abscisic Acid* / chemical synthesis
  • Abscisic Acid* / chemistry
  • Abscisic Acid* / metabolism
  • Abscisic Acid* / pharmacology
  • Amino Acids* / chemical synthesis
  • Amino Acids* / chemistry
  • Amino Acids* / metabolism
  • Amino Acids* / pharmacology
  • Arabidopsis Proteins / metabolism
  • Germination
  • Inhibitory Concentration 50
  • Molecular Structure
  • Oryza / metabolism
  • Plant Growth Regulators / chemistry
  • Plant Growth Regulators / metabolism
  • Seeds / growth & development
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Amino Acids
  • Arabidopsis Proteins
  • Plant Growth Regulators
  • Abscisic Acid