(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate
| Autor: | Otto Miersch, Andrea Chini, Sandra Fonseca, Mats Hamberg, Roberto Solano, Claus Wasternack, Bruce Adie, Robert Kramell, Andrea Porzel |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Hormone activity
Esterification biology Stereochemistry Arabidopsis Repressor Coronatine Biological activity Cyclopentanes Cell Biology biology.organism_classification chemistry.chemical_compound Biochemistry chemistry Two-Hybrid System Techniques Arabidopsis thaliana Epimer Jasmonate Isoleucine Receptor Molecular Biology Chromatography High Pressure Liquid Signal Transduction |
| Zdroj: | Nature Chemical Biology. 5:344-350 |
| ISSN: | 1552-4469 1552-4450 |
| DOI: | 10.1038/nchembio.161 |
| Popis: | Hormone-triggered activation of the jasmonate signaling pathway in Arabidopsis thaliana requires SCF(COI1)-mediated proteasome degradation of JAZ repressors. (-)-JA-L-Ile is the proposed bioactive hormone, and SCF(COI1) is its likely receptor. We found that the biological activity of (-)-JA-L-Ile is unexpectedly low compared to coronatine and the synthetic isomer (+)-JA-L-Ile, which suggests that the stereochemical orientation of the cyclopentanone-ring side chains greatly affects receptor binding. Detailed GC-MS and HPLC analyses showed that the (-)-JA-L-Ile preparations currently used in ligand binding studies contain small amounts of the C7 epimer (+)-7-iso-JA-L-Ile. Purification of each of these molecules demonstrated that pure (-)-JA-L-Ile is inactive and that the active hormone is (+)-7-iso-JA-L-Ile, which is also structurally more similar to coronatine. In addition, we show that pH changes promote conversion of (+)-7-iso-JA-L-Ile to the inactive (-)-JA-L-Ile form, thus providing a simple mechanism that can regulate hormone activity through epimerization. |
| Databáze: | OpenAIRE |
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