2-fluoroabscisic acid analogues: their synthesis and biological activities

J Agric Food Chem. 1999 Jan;47(1):313-7. doi: 10.1021/jf980265l.

Abstract

Fluorine was introduced into the 2-position of the side chain of abscisic acid (ABA) analogues by Wittig reaction of alpha-ionone derivatives with ethyl triethylphosphono-2-fluoroacetate. The effects of the fluorinated analogues were evaluated on inhibition of cress seed germination and inhibition of gibberellin-inducible alpha-amylase induction in embryoless barley half-seeds. (2E, 4E)-2-Fluoro-5-(1'-hydroxy-2',6', 6'-trimethyl-2'-cyclohexen-1'-yl)-3-methyl-2,4-pentadienoic acid (5b) showed potent inhibitory activity at the same level as ABA in the cress seed germination test, and 5b also inhibited gibberellin-inducible alpha-amylase induction at 4 x 10(-)(6), 3 times the concentration of ABA (1 x 10(-)(6)) for 50% inhibition of alpha-amylase production. 5b also showed dehydrin induction activity. These results indicate that fluorinated ABA analogues mimic ABA action and can be a lead for a plant growth regulator which regulates plant growth or protects plants from environmental stresses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abscisic Acid / analogs & derivatives*
  • Abscisic Acid / chemical synthesis
  • Abscisic Acid / pharmacology
  • Enzyme Induction
  • Germination / drug effects
  • Hordeum / embryology
  • Hordeum / enzymology

Substances

  • Abscisic Acid