Please use this identifier to cite or link to this item: http://dx.doi.org/10.14279/depositonce-7486
Main Title: Structure-Activity Relationships of Synthetic Analogs of Jasmonic Acid and Coronatine on Induction of Benzophenanthridine Alkaloid Accumulation in Eschscholzia californica Cell Cultures
Author(s): Haider, Georg
Schrader, Thomas von
Füßlein, Martin
Blechert, Siegfried
Kutchan, Toni M.
Type: Article
Language Code: en
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.
URI: https://depositonce.tu-berlin.de//handle/11303/8334
http://dx.doi.org/10.14279/depositonce-7486
Issue Date: 2000
Date Available: 11-Oct-2018
DDC Class: 540 Chemie und zugeordnete Wissenschaften
570 Biowissenschaften; Biologie
Subject(s): Alkaloid induction
Coronatine
Eschscholzia californica
Methyl jasmonate
Octadecanoid analogs.
License: http://rightsstatements.org/vocab/InC/1.0/
Journal Title: Biological chemistry
Publisher: De Gruyter
Publisher Place: Berlin
Volume: 381
Issue: 8
Publisher DOI: 10.1515/BC.2000.094
Page Start: 741
Page End: 748
EISSN: 1437-4315
ISSN: 1431-6730
Notes: Dieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG geförderten) Allianz- bzw. Nationallizenz frei zugänglich.
This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.
Appears in Collections:Inst. Chemie » Publications

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