One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid

Maynard, Daniel; Müller, Sara Mareike; Hahmeier, Monika; Löwe, Jana; Feußner, Ivo; Gröger, Harald; Viehhauser, Andrea; Dietz, Karl‐Josef

doi:10.1016/j.bmc.2017.07.061

Cited by 13 publications

(29 citation statements)

References 38 publications

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“…1). This observation is consistent with the affinity of OPR3 for cyclic “enones” such as cyclohexenone (Costa et al 2000), phytoprostanes (Mueller et al 2008) or OCPD (Maynard et al 2018a). The first description of the α-LeA-derived metabolite 12-OPDA as substrate of OPR3 occurred by Vick and Zimmerman in 1986.…”

Section: Discussionsupporting

confidence: 84%

“…Cyclopentenone, cyclopentanone, N-ethyl maleimide and 1,4-benzoquinone were purchased from Sigma-Aldrich (Darmstadt, Germany), traumatic acid from Tokyo Chemical Industry (Japan), MVK and trans-hex-2-enal from Acros-Chemicals (Thermo Fisher Scientific, Geel, Belgium). 12-OPDA was synthesized as described in Maynard et al (2018a). 10 mmol/L and 20 mmol/L malondialdehyde stock solutions were generated from bis-dimethyl-acetal (Sigma Aldrich) in 1% H 2 SO 4 as described in Esterbauer and Cheeseman (1990).…”

Section: Methodsmentioning

confidence: 99%

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12-oxophytodienoic acid reductase 3 (OPR3) functions as NADPH-dependent α,β-ketoalkene reductase in detoxification and monodehydroascorbate reductase in redox homeostasis

Maynard

Kumar

Sproß

et al. 2019

Preprint

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Arabidopsis (Arabidopsis thaliana) 12-oxophytodienoic acid reductase isoform 3 (OPR3) is involved in the synthesis of jasmonic acid by reducing the α,β-unsaturated double bond of the cyclopentenone moiety in 12-oxo-phytodienoic acid. Recent research revealed that jasmonic acid synthesis is not strictly dependent on the peroxisomal OPR3. In addition, OPR3 is able to reduce trinitrotoluene suggesting that the old yellow enzyme homologue OPR3 has additional functions. Here we demonstrate that OPR3 catalyzes the reduction of a wide spectrum of electrophilic species that share a reactivity towards the major redox buffers glutathione (GSH) and ascorbate (ASC). Furthermore, we demonstrate that OPDA reacts with ascorbate to form an ASC-OPDA adduct, but in addition OPR3 has the ability to regenerate ASC from monodehydroascorbate (MDHA). The presented data characterize OPR3 as a bifunctional enzyme with NADPH-dependent α,β-ketoalkene double bond reductase and monodehydroascorbate reductase activities (MDHAR). opr3 mutants exhibited a slightly less reduced ASC pool in leaves in line with the MDHAR activity of OPR3 in vitro. These functions link redox homeostasis as mediated by ASC and GSH with OPR3 activity and metabolism of reactive electrophilic species (RES).

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Section: Discussionsupporting

confidence: 84%

Section: Methodsmentioning

confidence: 99%

12-oxophytodienoic acid reductase 3 (OPR3) functions as NADPH-dependent α,β-ketoalkene reductase in detoxification and monodehydroascorbate reductase in redox homeostasis

Maynard

Kumar

Sproß

et al. 2019

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…Cross talk between OPDA and ABA has been deeply studied and it is suggested that both of the hormones are involved in similar processes [18]. Therefore, we next analyzed the levels of abscisic acid and observed that, at short time points, the ABA levels in uninfected WT plants were higher than those observed in the other plants ( Figure 2E).…”

Section: Siopr3 Plants Accumulate More Opda Upon Infectionmentioning

confidence: 92%

“…Maynard et al recently reviewed current knowledge regarding OPDA crosstalk with other phytohormones [18]. Overall, the authors conclude that the regulation of the oxylipin pathways by salicylic acid (SA) is controversial and it differs among plant species.…”

Section: Introductionmentioning

confidence: 99%

Role of Jasmonic Acid Pathway in Tomato Plant-Pseudomonas syringae Interaction

Scalschi

Llorens

García‐Agustín

et al. 2020

Plants

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The jasmonic acid pathway has been considered as the backbone of the response against necrotrophic pathogens. However, a hemi-biotrophic pathogen, such as Pseudomonas syringae, has taken advantage of the crosstalk between the different plant hormones in order to manipulate the responses for its own interest. Despite that, the way in which Pseudomonas syringae releases coronatine to activate jasmonic acid-derived responses and block the activation of salicylic acid-mediated responses is widely known. However, the implication of the jasmonic intermediates in the plant-Pseudomonas interaction is not studied yet. In this work, we analyzed the response of both, plant and bacteria using SiOPR3 tomato plants. Interestingly, SiOPR3 plants are more resistant to infection with Pseudomonas. The gene expression of bacteria showed that, in SiOPR3 plants, the activation of pathogenicity is repressed in comparison to wild type plants, suggesting that the jasmonic acid pathway might play a role in the pathogenicity of the bacteria. Moreover, treatments with JA restore the susceptibility as well as activate the expression of bacterial pathogenicity genes. The observed results suggest that a complete jasmonic acid pathway is necessary for the susceptibility of tomato plants to Pseudomonas syringae.

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“…For research purpose, there is permanent demand for OPDA. Now, OPDA can be synthesized by covalently immobilized recombinant rice AOS-1, together with bound soybean LOX and rice AOC, which are able to form OPDA from α–LeA up to more than 80% yield [ 82 ] or by enzymatic multi-step one-pot synthesis using all three enzymes from A. thaliana and α–LeA as substrate [ 83 ].…”

Section: Biosynthesis Of Jamentioning

confidence: 99%

Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds

Wasternack

Strnad

2018

IJMS

185

147

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Jasmonic acid (JA) and its related derivatives are ubiquitously occurring compounds of land plants acting in numerous stress responses and development. Recent studies on evolution of JA and other oxylipins indicated conserved biosynthesis. JA formation is initiated by oxygenation of α-linolenic acid (α-LeA, 18:3) or 16:3 fatty acid of chloroplast membranes leading to 12-oxo-phytodienoic acid (OPDA) as intermediate compound, but in Marchantia polymorpha and Physcomitrella patens, OPDA and some of its derivatives are final products active in a conserved signaling pathway. JA formation and its metabolic conversion take place in chloroplasts, peroxisomes and cytosol, respectively. Metabolites of JA are formed in 12 different pathways leading to active, inactive and partially active compounds. The isoleucine conjugate of JA (JA-Ile) is the ligand of the receptor component COI1 in vascular plants, whereas in the bryophyte M. polymorpha COI1 perceives an OPDA derivative indicating its functionally conserved activity. JA-induced gene expressions in the numerous biotic and abiotic stress responses and development are initiated in a well-studied complex regulation by homeostasis of transcription factors functioning as repressors and activators.

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One-pot synthesis of bioactive cyclopentenones from α-linolenic acid and docosahexaenoic acid

Cited by 13 publications

References 38 publications

12-oxophytodienoic acid reductase 3 (OPR3) functions as NADPH-dependent α,β-ketoalkene reductase in detoxification and monodehydroascorbate reductase in redox homeostasis

12-oxophytodienoic acid reductase 3 (OPR3) functions as NADPH-dependent α,β-ketoalkene reductase in detoxification and monodehydroascorbate reductase in redox homeostasis

Role of Jasmonic Acid Pathway in Tomato Plant-Pseudomonas syringae Interaction

Jasmonates: News on Occurrence, Biosynthesis, Metabolism and Action of an Ancient Group of Signaling Compounds

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