CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-β-glucopyranosyl-jasmonoyl-l-isoleucine as an additional metabolite

Kitaoka, Naoki; Kawaide, Hiroshi; Amano, Naruki; Matsubara, Takeo; Nabeta, Kensuke; Takahashi, Kosaku; Matsuura, Hideyuki

doi:10.1016/j.phytochem.2013.12.019

Cited by 27 publications

(21 citation statements)

References 25 publications

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“…12OH-JA-Ile is less active than JA-Ile in promoting COI1 binding to JAZ proteins (Koo et al 2011). The fact that 12OH-JA-Ile retains some activity in COI1-JAZ interaction assays, however, suggests that CYP94-mediated oxidation of 12OH-JA-Ile to 12COOH-JA-Ile, or conjugation of 12OH-JA-Ile to other small molecules (Gidda et al 2003; Kitaoka et al 2014), is required for complete inactivation of JA-Ile.…”

Section: Negative Regulation Of Jatimentioning

confidence: 99%

Jasmonate-Triggered Plant Immunity

2014

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The plant hormone jasmonate (JA) exerts direct control over the production of chemical defense compounds that confer resistance to a remarkable spectrum of plant-associated organisms, ranging from microbial pathogens to vertebrate herbivores. The underlying mechanism of JA-triggered immunity (JATI) can be conceptualized as a multi-stage signal transduction cascade involving: i) pattern recognition receptors (PRRs) that couple the perception of danger signals to rapid synthesis of bioactive JA; ii) an evolutionarily conserved JA signaling module that links fluctuating JA levels to changes in the abundance of transcriptional repressor proteins; and iii) activation (de-repression) of transcription factors that orchestrate the expression of myriad chemical and morphological defense traits. Multiple negative feedback loops act in concert to restrain the duration and amplitude of defense responses, presumably to mitigate potential fitness costs of JATI. The convergence of diverse plant- and non-plant-derived signals on the core JA module indicates that JATI is a general response to perceived danger. However, the modular structure of JATI may accommodate attacker-specific defense responses through evolutionary innovation of PRRs (inputs) and defense traits (outputs). The efficacy of JATI as a defense strategy is highlighted by its capacity to shape natural populations of plant attackers, as well as the propensity of plant-associated organisms to subvert or otherwise manipulate JA signaling. As both a cellular hub for integrating informational cues from the environment and a common target of pathogen effectors, the core JA module provides a focal point for understanding immune system networks and the evolution of chemical diversity in the plant kingdom.

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Section: Negative Regulation Of Jatimentioning

confidence: 99%

Jasmonate-Triggered Plant Immunity

2014

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“…In vitro COI1-JAZ pull-down assays were performed as previously described (25). Ligands used in the COI1-JAZ pull-down assays were enantiomeric mixtures of chemically synthesized JA-Ile and 12COOH-JA-Ile (37).…”

Section: Heterologous Expression In Yeast Andmentioning

confidence: 99%

“…One pathway is catalyzed by amidohydrolases that cleave JA-Ile to jasmonic acid and Ile (32)(33)(34). A second pathway involves oxidation of the C12 position JA-Ile to generate 12OH-JA-Ile, which is further oxidized to the carboxyl derivative 12COOH-JA-Ile (35)(36)(37). Elucidation of this pathway was advanced by the discovery that two members (CYP94B3 and CYP94C1) of the CYP94 family of cytochromes P450 in Arabidopsis catalyze the sequential oxidation reactions (38 -40).…”

mentioning

confidence: 99%

Endoplasmic Reticulum-associated Inactivation of the Hormone Jasmonoyl-l-Isoleucine by Multiple Members of the Cytochrome P450 94 Family in Arabidopsis

Koo

Thireault

Zemelis

et al. 2014

Journal of Biological Chemistry

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101

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Background: Accumulation of the plant hormone jasmonoyl-L-isoleucine (JA-Ile) is tightly controlled to prevent overactivation of defense responses. Results: Cytochrome P450 94s (CYP94s) with distinct tissue expression patterns localize to ER and oxidize JA-Ile to a dicarboxy derivative that fails to assemble JA-Ile co-receptor complexes. Conclusion: Sequential CYP94-catalyzed oxidations block receptor activation and signaling. Significance: P450s inactivate fatty acid-derived signals in both plants and animals.

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“…[4b,6] When we tried to obtain the 12 hydroxy derivatives, a mixture of Z/E isomers (ratio 2.5:1) was always obtained, Scheme 1. [5] To the best of our knowledge, only diastereomeric mixtures of 12-COOH JA-Ile have been reported. [5] To the best of our knowledge, only diastereomeric mixtures of 12-COOH JA-Ile have been reported.…”

Section: Resultsmentioning

confidence: 99%

“…[5] The 12hydroxylated derivative was synthesized through Wittig reaction. [5] The 12hydroxylated derivative was synthesized through Wittig reaction.…”

Section: Resultsmentioning

confidence: 99%