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

• Published in: Phytochemistry (Oxford) Vol. 65; no. 8; pp. 1047 - 1055
• Main Authors: Frey, Monika, Spiteller, Dieter, Boland, Wilhelm, Gierl, Alfons
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.04.2004; Elsevier
• Subjects: 1-aminocyclopropane-1-carboxylic acid; Acetates - metabolism; Allene oxide cyclase; Allene oxide synthase; alpha-Linolenic Acid - analogs & derivatives; alpha-Linolenic Acid - chemistry; alpha-Linolenic Acid - physiology; Amino Acids, Cyclic - pharmacology; Animals; Aristolochic Acids - pharmacology; Aspirin - pharmacology; Biological and medical sciences; biosynthesis; carboxy-lyases; chemical structure; corn; Cyclooxygenase Inhibitors - pharmacology; Cyclopentanes - metabolism; fatty acid-amino acid conjugates; fatty acids; General pharmacology; Genes, Plant; glutamine; Glutamine - analogs & derivatives; Glutamine - chemistry; Glutamine - physiology; grain crops; Indole-3-glycerol phosphate lyase; Indole-3-Glycerol-Phosphate Synthase - biosynthesis; Indole-3-Glycerol-Phosphate Synthase - genetics; indoles; Indoles - metabolism; Intramolecular Oxidoreductases - biosynthesis; Intramolecular Oxidoreductases - genetics; Jasmonate, Induced defense; jasmonic acid; Lepidoptera - metabolism; Linolenic Acids - chemistry; Linolenic Acids - physiology; Medical sciences; messenger RNA; molecular sequence data; N-Acyl glutamines; nucleotide sequences; Oxylipins; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytophagous insects; Pyrazoles - pharmacology; salicylic acid; signal transduction; Stereoisomerism; Structure-Activity Relationship; structure-activity relationships; transcriptional activation; Transcriptional Activation - drug effects; volatile organic compounds; Volicitin; Zea mays; Zea mays - enzymology; Zea mays - genetics; ACC; AOS; EST; Gln; FAC; MeJa; Indole-3-glycerol phosphate lyase; Volicitin; Allene oxide synthase; AcSA; Allene oxide cyclase; Jasmonate, Induced defense; Glu; AOC; JA; N-Acyl glutamines; GAP C; PCR; Phosphates; Monocotyledones; Herbivorous; Molecular structure; Transcription; Indole; Activation; Biosynthesis; Elicitor; Isomer; N-Acyl glutamines; Volicitin; Indole-3-glycerol phosphate lyase; Allene oxide synthase; Allene oxide cyclase; Jasmonate; Induced defense; Gene; Gramineae; Angiospermae; Elicitation; Zea mays; Interaction; Glycerol; Fatty acids; Biological activity; Aminoacid; Spermatophyta; Kinetics; Glutamine
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2003.11.021

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 (17 S)-( 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. The structural requirements of fatty acid–amino acid conjugates for induction of Igl transcription were investigated. A link to jasmonate signaling is described.