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Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Biol. Chem
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: ACS Chem. Biol doi: 10.1021/cb900269u
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: J Gen Plant Pathol
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Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Comprehensive Natural Products II
Autor Nach Häufigkeit alphabetisch sortiert: Elleuch, A.
Autor Nach Häufigkeit alphabetisch sortiert: Wasternack, C.
Journal / Buchreihe / Preprint-Server Nach Häufigkeit alphabetisch sortiert: Nat. Chem. Biol.
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Fonseca, S.; Chini, A.; Hamberg, M.; Adie, B.; Porzel, A.; Kramell, R.; Miersch, O.; Wasternack, C.; Solano, R.; (+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate Nat. Chem. Biol. 5, 344-350, (2009) DOI: 10.1038/nchembio.161
Hormone-triggered activation of the jasmonate signaling pathway in Arabidopsis thaliana requires SCFCOI1-mediated proteasome degradation of JAZ repressors. (−)-JA-L-Ile is the proposed bioactive hormone, and SCFCOI1 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.