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Structural and Biological Diversity of Cyclic Octadecanoids, Jasmonates, and Mimetics

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Abstract

The jasmonate family of plant signaling compounds comprises biologically highly active cyclopentenones (for example, 12-oxo-phytodienoic acid) (12-OPDA) and cyclopentanones (for example, jasmonic acid) (JA) of related origin via the octadecanoid pathway, and structure. Among others, their biological activities include a broad range of defense-related reactions. Several lines of evidence indicate both common and different biological responses mediated by 12-OPDA and/or JA, suggesting the existence of at least two separate structure-activity groups. Based on the structure of a bacterial phytotoxin, coronatine, with similar biological activities compared with jasmonates, indanoyl isoleucine conjugates have been designed as functional synthetic mimics of octadecanoid-derived signals. The structural diversity of naturally occurring jasmonate-related compounds and synthetic mimics is discussed with respect to their corresponding biological activities. Novel strategies for the synthesis of various indanoyl isoleucine conjugates will be presented.

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Authors and Affiliations

  1. Bioorganische Chemie, Beutenberg Campus, Max-Planck-Institut für Chemische Ökologie, Hans-Knöll-Str. 8, D-07745, Jena, Germany

    Axel Mithöfer, Mathias Maitrejean & Wilhelm Boland

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  1. Axel Mithöfer
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  2. Mathias Maitrejean
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  3. Wilhelm Boland
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Correspondence to Wilhelm Boland.

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Mithöfer, A., Maitrejean, M. & Boland, W. Structural and Biological Diversity of Cyclic Octadecanoids, Jasmonates, and Mimetics. J Plant Growth Regul 23, 170–178 (2004). https://doi.org/10.1007/s00344-004-0034-2

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  • DOI: https://doi.org/10.1007/s00344-004-0034-2

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