Structure-Activity Relationships of Synthetic Analogs of Jasmonic Acid and Coronatine on Induction of Benzophenanthridine Alkaloid Accumulation in Eschscholzia californica Cell Cultures
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G. Haider
Abstract
A facile test system based on the accumulation of benzo[c]phenanthridine alkaloids in Eschscholzia californica cell suspension culture (an indicator of defense gene activation) has been used to analyze a series of synthetic compounds for elicitor-like activity. Of the 200 jasmonic acid and coronatine analogs tested with this system, representative results obtained with 49 of them are presented here. The following can be summarized concerning structure-activity relationships: there is a large degree of plasticity allowed at the C-3 of jasmonic acid in the activation of defense genes. The carbonyl moiety is not strictly required, but exocyclic double bond character appears necessary. The pentenyl side chain at C-2 cannot tolerate bulky groups at the terminal carbon and still be biologically active. Substitutions to the C-1′ position are tolerated if they can potentially undergo β-oxidation. Either an alkanoic acid or methyl ester is required at C-1, or a side chain that can be shortened by β-oxidation or by peptidase hydrolysis. Coronatine and various derivatives thereof are not as effective as jasmonic acid, and derivatives in inducing benzo[c]phenanthridine alkaloid accumulation. Jasmonic acid rather than the octadecanoic precursors is therefore considered to be a likely signal transducer of defense gene activation in planta.
Copyright © 2000 by Walter de Gruyter GmbH & Co. KG
Articles in the same Issue
- To Our Authors, Readers and Subscribers
- Highlight: Plant Biological Chemistry
- The Structural Properties of Plant Peroxisomes and Their Metabolic Significance
- Active Oxygen Species as Mediators of Plant Immunity: Three Case Studies
- Post-Transcriptional Regulation of Phenylalanine Ammonia-Lyase Expression in Tobacco Following Recovery from Gene Silencing
- Two Differentially Regulated Class II Chitinases from Parsley
- IAA-Synthase, an Enzyme Complex from Arabidopsis thaliana Catalyzing the Formation of Indole-3-Acetic Acid from (S)-Tryptophan
- Topology Studies of the Chloroplast Protein Import Channel Toc75
- Plant Methionine Synthase: New Insights into Properties and Expression
- The Hepta-? -Glucoside Elicitor-Binding Proteins from Legumes Represent a Putative Receptor Family
- Octadecanoid and Jasmonate Signaling in Tomato (Lycopersicon esculentum Mill.) Leaves: Endogenous Jasmonates Do Not Induce Jasmonate Biosynthesis
- Metabolic Activity Decreases as an Adaptive Response to Low Internal Oxygen in Growing Potato Tubers
- Structure-Activity Relationships of Synthetic Analogs of Jasmonic Acid and Coronatine on Induction of Benzophenanthridine Alkaloid Accumulation in Eschscholzia californica Cell Cultures
- Identification of the Arabidopsis thaliana Flavonoid 3'-Hydroxylase Gene and Functional Expression of the Encoded P450 Enzyme
- Gut Bacteria May Be Involved in Interactions between Plants, Herbivores and Their Predators: Microbial Biosynthesis of N-Acylglutamine Surfactants as Elicitors of Plant Volatiles
- Different Signaling Pathways Are Involved in CCKB Receptor-Mediated MAP Kinase Activation in COS-7 Cells
- Non-Specific Depurination Activity of Saporin-S6, a Ribosome-Inactivating Protein, under Acidic Conditions
- Molecular Evolution in the Hypervariable Regions of Fetuin: Comparison between Human and African Green Monkey Fetuin
Articles in the same Issue
- To Our Authors, Readers and Subscribers
- Highlight: Plant Biological Chemistry
- The Structural Properties of Plant Peroxisomes and Their Metabolic Significance
- Active Oxygen Species as Mediators of Plant Immunity: Three Case Studies
- Post-Transcriptional Regulation of Phenylalanine Ammonia-Lyase Expression in Tobacco Following Recovery from Gene Silencing
- Two Differentially Regulated Class II Chitinases from Parsley
- IAA-Synthase, an Enzyme Complex from Arabidopsis thaliana Catalyzing the Formation of Indole-3-Acetic Acid from (S)-Tryptophan
- Topology Studies of the Chloroplast Protein Import Channel Toc75
- Plant Methionine Synthase: New Insights into Properties and Expression
- The Hepta-? -Glucoside Elicitor-Binding Proteins from Legumes Represent a Putative Receptor Family
- Octadecanoid and Jasmonate Signaling in Tomato (Lycopersicon esculentum Mill.) Leaves: Endogenous Jasmonates Do Not Induce Jasmonate Biosynthesis
- Metabolic Activity Decreases as an Adaptive Response to Low Internal Oxygen in Growing Potato Tubers
- Structure-Activity Relationships of Synthetic Analogs of Jasmonic Acid and Coronatine on Induction of Benzophenanthridine Alkaloid Accumulation in Eschscholzia californica Cell Cultures
- Identification of the Arabidopsis thaliana Flavonoid 3'-Hydroxylase Gene and Functional Expression of the Encoded P450 Enzyme
- Gut Bacteria May Be Involved in Interactions between Plants, Herbivores and Their Predators: Microbial Biosynthesis of N-Acylglutamine Surfactants as Elicitors of Plant Volatiles
- Different Signaling Pathways Are Involved in CCKB Receptor-Mediated MAP Kinase Activation in COS-7 Cells
- Non-Specific Depurination Activity of Saporin-S6, a Ribosome-Inactivating Protein, under Acidic Conditions
- Molecular Evolution in the Hypervariable Regions of Fetuin: Comparison between Human and African Green Monkey Fetuin
