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Structural requirements for biologically active jasmonates: Induction of protease inhibitors and cotyledon senescence

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Abstract

Methyl jasmonate and jasmonate isomers were resolved for studies in stereoselectivity of biological action. Chemical modifications included fluorination at the chiral C7 carbon, trifluorination at the C12 of the pentenyl sidechain, shortening of this pentenyl to a butenyl moiety, and synthesis of the (+) and (–)-epi-methyl jasmonates. The effects of these modifications and stereospecificity were monitored using three assays: proteinase inhibitor II promoter driving the reporter β-glucuronidase; endogenous trypsin proteinase inhibitor induction; and sunflower cotyledon senescence induction. The methyl esters were more active than the corresponding acids, the R absolute configuration at C3 was most effective in all assays, fluorination at C7 abolished activity in the proteinase inhibitor assays, and the trifluorination at C12 or shortening to a butenyl did not alter activity relative to the active (–)- methyl jasmonate, but both of these latter modifications revealed a delayed response in the senescence conductivity measures.

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Author notes

  1. P. Tung

    Present address: K. Ward, Agriculture and Agri-food Canada, Cereal Research Station, 195 Dafoe Road, Winnipeg, Manitoba, Canada, R3T 2M9; P. Tung, Dept. of Medicine, University of Calgary, Health Sciences, 3330 Hospital Dr., NW, Calgary, Alberta, Canada T2N 4N1

Authors and Affiliations

  1. Dept. of Biological Sciences, University of Calgary, 2500 University Dr., NW, Calgary, AB, Canada, T2N 1N4

    K.A. Ward, P. Tung, D.M. Reid & M.M. Moloney

  2. Dept. of Chemistry, University of Saskatchewan, Saskatoon, SK, Canada, S7N 5C9

    N. Lamb

  3. Plant Biotechnology Institute, National Research Council of Canada, Saskatoon, SK, Canada, S7N 0W9

    S.R. Abrams

  4. SemBioSys Genetics Inc., University of Calgary, 2500 University Dr., NW, Calgary, AB, Canada, T2N 1N4

    L.A. Holbrook

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  1. K.A. Ward
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Ward, K., Tung, P., Lamb, N. et al. Structural requirements for biologically active jasmonates: Induction of protease inhibitors and cotyledon senescence. Plant Growth Regulation 27, 49–56 (1999). https://doi.org/10.1023/A:1006188418523

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