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  Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones

Jimenez-Aleman, G. H., Machado, R. A. R., Görls, H., Baldwin, I. T., & Boland, W. (2015). Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones. Organic & Biomolecular Chemistry, 13(21), 5885-5893. doi:10.1039/C5OB00362H.

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 Creators:
Jimenez-Aleman, Guillermo Hugo1, 2, Author              
Machado, Ricardo A. R.2, 3, Author              
Görls, Helmar, Author
Baldwin, Ian Thomas3, Author              
Boland, Wilhelm1, Author              
Affiliations:
1Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society, ou_24028              
2IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society, Jena, DE, ou_421900              
3Department of Molecular Ecology, Prof. I. T. Baldwin, MPI for Chemical Ecology, Max Planck Society, ou_24029              

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 Abstract: Jasmonates are phytohormones involved in a wide range of plant processes, including growth, development, senescence, and defense. Jasmonoyl-L-isoleucine (JA-Ile, 2), an amino acid conjugate of jasmonic acid (JA, 1), has been identified as a bioactive endogenous jasmonate. However, JA-Ile (2) analogues trigger different responses in the plant. ω-Hydroxylation of the pentenyl side chain leads to the inactive 12-OH-JA-Ile (3) acting as a “stop” signal. On the other hand, a lactone derivative of 12-OH-JA (5) (jasmine ketolactone, JKL) occurs in nature, although with no known biological function. Inspired by the chemical structure of JKL (6) and in order to further explore the potential biological activities of 12-modified JA-Ile derivatives, we synthesized two macrolactones (JA-Ile-lactones (4a) and (4b)) derived from 12-OH-JA-Ile (3). The biological activity of (4a) and (4b) was tested for their ability to elicit nicotine production, a well-known jasmonate dependent secondary metabolite. Both macrolactones showed strong biological activity, inducing nicotine accumulation to a similar extent as methyl jasmonate does in Nicotiana attenuata leaves. Surprisingly, the highest nicotine contents were found in plants treated with the JA-Ile-lactone (4b), which has (3S,7S) configuration at the cyclopentanone not known from natural jasmonates. Macrolactone (4a) is a valuable standard to explore for its occurrence in nature.

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 Dates: 2015-03-132015-03-252015-05-19
 Publication Status: Published in print
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 Identifiers: Other: BOL620
DOI: 10.1039/C5OB00362H
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Title: Organic & Biomolecular Chemistry
  Other : Organic and Biomolecular Chemistry
  Abbreviation : Org. Biomol. Chem.
Source Genre: Journal
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Publ. Info: Cambridge : Royal Society of Chemistry
Pages: - Volume / Issue: 13 (21) Sequence Number: - Start / End Page: 5885 - 5893 Identifier: ISSN: 1477-0520
CoNE: https://pure.mpg.de/cone/journals/resource/954925269322