ArticleNature chemical biology2009
(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate.
Article in Nature chemical biology, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 439 papers.
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Who cites it
439 citing papers in PubMed, 989 citations in OpenAlex.
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- Investigation of the Jasmonate ZIM-Domain Family RevealsBiomolecules · 2025Article
- The KH-domain genes FLK and HOS5 integrate flowering and stress responses in Arabidopsis thaliana.Journal of experimental botany · 2025Article
- JA-responsive R2R3-type MYB transcription factor OsMYB4P confers broad-spectrum antiviral immunity in rice.Plant biotechnology journal · 2025Article
- Glycosylated sterols enhance cold tolerance in tomato via membrane stabilization and jasmonate signaling.Plant physiology · 2025Article
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379 more citing papers are in PubMed but not listed here.
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Authors and funding
9 authors at 3 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.