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

@article{Kitaoka2014CYP94B3AA,
  title={CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-$\beta$-glucopyranosyl-jasmonoyl-L-isoleucine as an additional metabolite.},
  author={Naoki Kitaoka and Hiroshi Kawaide and Naruki Amano and Takuya Matsubara and Kensuke Nabeta and Kosaku Takahashi and Hideyuki Matsuura},
  journal={Phytochemistry},
  year={2014},
  volume={99},
  pages={
          6-13
        }
}
The hormonal action of jasmonate in plants is controlled by the precise balance between its biosynthesis and inactivation. Oxidation of jasmonoyl-L-isoleucine at the C-12 position, which is catalyzed by cytochrome P450s CYP94B3 and CYP94C1, is thought to be one of the main inactivation pathways. In this study, an additional function of CYP94B3 was elucidated, as well additional jasmonoyl-L-isoleucine metabolites being investigated. It was found that CYP94B3 also catalyzes the hydroxylation of… 
Sequential oxidation of Jasmonoyl-Phenylalanine and Jasmonoyl-Isoleucine by multiple cytochrome P450 of the CYP94 family through newly identified aldehyde intermediates.
TLDR
This work extends the range and complexity of JA-amino acid oxidation by multifunctional CYP94 enzymes in response to environmental cues and suggests conserved roles of its members in JA conjugate homeostasis and possibly in adaptative functions are suggested.
The glycosyltransferase UGT76E1 significantly contributes to 12-O-glucopyranosyl-jasmonic acid formation in wounded Arabidopsis thaliana leaves
TLDR
The findings have elucidated the missing step in the wound-induced synthesis of 12-O-glucopyranosyl-jasmonic acid in A. thaliana.
Functional Characterization of CYP94-Genes and Identification of a Novel Jasmonate Catabolite in Flowers
TLDR
Evaluation of the in vivo function of the different CYP94-enzymes on the JA-sensitivity demonstrated that particularly CyP94B-enz enzymes might play an essential role for JA-response, whereas CYP 94C1 might only be of minor importance.
Endoplasmic Reticulum-associated Inactivation of the Hormone Jasmonoyl-l-Isoleucine by Multiple Members of the Cytochrome P450 94 Family in Arabidopsis*
TLDR
The results provide an integrated view of how multiple ER-localized CYP94 and JA amidohydrolase enzymes attenuate JA signaling during stress responses and report that a third member (CYP94B1) of the CYP 94 family also participates in oxidative turnover of JA-Ile in Arabidopsis.
Synthesis, structural characterization and biological activity of two diastereomeric JA-Ile macrolactones.
TLDR
Two macrolactones showed strong biological activity, inducing nicotine accumulation to a similar extent as methyl jasmonate does in Nicotiana attenuata leaves, and the highest nicotine contents were found in plants treated with the JA-Ile-lactone, which has (3S,7S) configuration at the cyclopentanone not known from natural jAsmonates.
Characterization of Jasmonoyl-Isoleucine (JA-Ile) Hormonal Catabolic Pathways in Rice upon Wounding and Salt Stress
TLDR
Two gene families in rice in which some members were described previously in Arabidopsis to encode enzymes metabolizing JA-Ile hormone are explored, namely cytochrome P450 of the CYP94 subfamily and amidohydrolases (AH, 9 members).
Analyse fonctionnelle de cytochromes P450 de la famille CYP94 et des amidohydrolases IAR3 et ILL6 dans le catabolisme hormonal des jasmonates chez Arabidopsis thaliana
TLDR
This work highlights the dynamic metabolism of jasmonate derivatives in a complex branched network involving the concerted action of two enzyme families.
Optimized Jasmonic Acid Production by Lasiodiplodia theobromae Reveals Formation of Valuable Plant Secondary Metabolites
TLDR
It is shown that jasmonic acid-formation is not associated to fungal growth, which suggests that jAsmonic Acid, despite its enormous amount being produced upon fungal development, serves merely as secondary metabolite.
Omega hydroxylated JA-Ile is an endogenous bioactive jasmonate that signals through the canonical jasmonate signaling pathway.
TLDR
It is proposed that after a strong immune response mediated by JA-Ile, the ω-hydroxylated form modulates JA- Ile activated processes thereby improving plant resilience.
Jasmonates: biosynthesis, perception and signal transduction.
TLDR
Understanding the molecular circuits that control plant responses to pests and pathogens is a necessary pre-requisite to engineering plants with enhanced resilience to biotic challenges for improved agricultural yields.
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Arabidopsis CYP94B3 encodes jasmonyl-L-isoleucine 12-hydroxylase, a key enzyme in the oxidative catabolism of jasmonate.
TLDR
The kinetics of wound-induced accumulation of 12-hydroxyJA-Ile in plants were examined, and its involvement in the plant wound response is described, demonstrating that CYP94B3 plays a major regulatory role in controlling the level of JA-Iel in plants.
Cytochrome P450 CYP94B3 mediates catabolism and inactivation of the plant hormone jasmonoyl-L-isoleucine
TLDR
It is demonstrated that CYP94B3 exerts negative feedback control on JA-Ile levels and performs a key role in attenuation of jasmonate responses, as well as in promoting the formation of COI1-JAZ receptor complexes.
Hydroxylated jasmonates are commonly occurring metabolites of jasmonic acid and contribute to a partial switch-off in jasmonate signaling.
TLDR
It is demonstrated that 12-OH-JA, as well as its sulfated and glucosylated derivatives, are constituents of various organs of many plant species and alters expression pattern of genes including a switch off in JA signaling for a subset of genes.
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TLDR
Hormone-triggered activation of the jasmonate signaling pathway in Arabidopsis thaliana requires SCF(COI1)-mediated proteasome degradation of JAZ repressors and pH changes promote conversion of (+)-7-iso-JA- L-Ile to the inactive (-)-JA-L-Iel form, thus providing a simple mechanism that can regulate hormone activity through epimerization.
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TLDR
It is concluded that NaJIH1 encodes a new homeostatic step in JA metabolism that rapidly attenuates the JA-Ile burst, allowing plants to tailor the expression of direct and indirect defenses against herbivore attack in nature.
Cytochromes P450 CYP94C1 and CYP94B3 Catalyze Two Successive Oxidation Steps of Plant Hormone Jasmonoyl-isoleucine for Catabolic Turnover
TLDR
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A tomato enzyme synthesizes (+)-7-iso-jasmonoyl-l-isoleucine in wounded leaves
TLDR
Results show that SlJAR1 synthesizes the bioactive conjugate (+)-7-iso-JA-Ile and this is the predominant isomer accumulated in wounded tomato leaves.
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TLDR
Functional characterization of the full complement of CYP94 P450s promises to reveal new pathways for jasmonate metabolism and provide insight into the evolution of oxylipin signaling in land plants.
The Oxylipin Signal Jasmonic Acid Is Activated by an Enzyme That Conjugates It to Isoleucine in Arabidopsis
TLDR
JAR1 is a JA-amino synthetase that is required to activate JA for optimal signaling in Arabidopsis and might provide a mechanism to coregulate the availability of JA and ACC for conversion to the active hormones JA-Ile and ethylene, respectively.
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TLDR
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