Transcriptional activation of Igl, the gene for indole formation in Zea mays: a structure-activity study with elicitor-active N-acyl glutamines from insects

Phytochemistry. 2004 Apr;65(8):1047-55. doi: 10.1016/j.phytochem.2003.11.021.

Abstract

The indole-3-glycerol phosphate lyase Igl is the structural gene of volatile indole biosynthesis in the tritrophic interaction in maize. The gene is activated on transcriptional level with the same kinetics and to the same level by the fatty acid-amino acid conjugates (FAC's) volicitin (17S)-(N-(17-hydroxylinolenoyl)-L-glutamine) and N-linolenoyl-L-glutamine. Both conjugates are present in the regurgitates of herbivorous caterpillars. Modifications of the fatty acid moiety of the FACs greatly reduces the elicitation of Igl and only the L-stereo-isomer of the FACs shows biological activity in the system. Volicitin treatment leads to a fast increase of AOS and AOC transcription levels and methyl jasmonate application induces Igl transcription. Hence, the induction of jasmonate biosynthesis appears to be an integral part of the elicitor mediated increase of Igl gene transcription.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / metabolism
  • Amino Acids, Cyclic / pharmacology
  • Animals
  • Aristolochic Acids / pharmacology
  • Aspirin / pharmacology
  • Cyclooxygenase Inhibitors / pharmacology
  • Cyclopentanes / metabolism
  • Genes, Plant
  • Glutamine / analogs & derivatives*
  • Glutamine / chemistry
  • Glutamine / physiology*
  • Indole-3-Glycerol-Phosphate Synthase / biosynthesis
  • Indole-3-Glycerol-Phosphate Synthase / genetics*
  • Indoles / metabolism*
  • Intramolecular Oxidoreductases / biosynthesis
  • Intramolecular Oxidoreductases / genetics
  • Lepidoptera / metabolism*
  • Linolenic Acids / chemistry
  • Linolenic Acids / physiology*
  • Oxylipins
  • Pyrazoles / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Transcriptional Activation / drug effects
  • Zea mays / enzymology*
  • Zea mays / genetics
  • alpha-Linolenic Acid / analogs & derivatives*
  • alpha-Linolenic Acid / chemistry
  • alpha-Linolenic Acid / physiology*

Substances

  • Acetates
  • Amino Acids, Cyclic
  • Aristolochic Acids
  • Cyclooxygenase Inhibitors
  • Cyclopentanes
  • Indoles
  • Linolenic Acids
  • N-linolenoyl-L-glutamine
  • Oxylipins
  • Pyrazoles
  • volicitin
  • alpha-Linolenic Acid
  • Glutamine
  • 1-aminocyclopropane-1-carboxylic acid
  • indole
  • methyl jasmonate
  • aristolochic acid I
  • Indole-3-Glycerol-Phosphate Synthase
  • Intramolecular Oxidoreductases
  • hydroperoxide isomerase
  • phenidone
  • Aspirin