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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dc.contributor.authorHaider, Georg
dc.contributor.authorSchrader, Thomas von
dc.contributor.authorFüßlein, Martin
dc.contributor.authorBlechert, Siegfried
dc.contributor.authorKutchan, Toni M.
dc.date.accessioned2018-10-11T13:25:59Z
dc.date.available2018-10-11T13:25:59Z
dc.date.issued2000
dc.descriptionDieser Beitrag ist mit Zustimmung des Rechteinhabers aufgrund einer (DFG geförderten) Allianz- bzw. Nationallizenz frei zugänglich.de
dc.descriptionThis 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.en
dc.description.abstractA 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.en
dc.identifier.eissn1437-4315
dc.identifier.issn1431-6730
dc.identifier.urihttps://depositonce.tu-berlin.de/handle/11303/8334
dc.identifier.urihttp://dx.doi.org/10.14279/depositonce-7486
dc.language.isoen
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subject.ddc540 Chemie und zugeordnete Wissenschaftende
dc.subject.ddc570 Biowissenschaften; Biologiede
dc.subject.otherAlkaloid inductionen
dc.subject.otherCoronatineen
dc.subject.otherEschscholzia californicaen
dc.subject.otherMethyl jasmonateen
dc.subject.otherOctadecanoid analogs.en
dc.titleStructure-Activity Relationships of Synthetic Analogs of Jasmonic Acid and Coronatine on Induction of Benzophenanthridine Alkaloid Accumulation in Eschscholzia californica Cell Culturesen
dc.typeArticleen
dc.type.versionpublishedVersionen
dcterms.bibliographicCitation.doi10.1515/BC.2000.094
dcterms.bibliographicCitation.issue8
dcterms.bibliographicCitation.journaltitleBiological chemistryen
dcterms.bibliographicCitation.originalpublishernameDe Gruyteren
dcterms.bibliographicCitation.originalpublisherplaceBerlinen
dcterms.bibliographicCitation.pageend748
dcterms.bibliographicCitation.pagestart741
dcterms.bibliographicCitation.volume381
tub.accessrights.dnbdomain
tub.affiliationFak. 2 Mathematik und Naturwissenschaften::Inst. Chemiede
tub.affiliation.facultyFak. 2 Mathematik und Naturwissenschaftende
tub.affiliation.instituteInst. Chemiede
tub.publisher.universityorinstitutionTechnische Universität Berlinde

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