Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid

Ito, Yusuke; Sasaki, Kazunobu; Ogihara, Tsuyoshi; Kitaoka, Naoki; Takahahi, Kosaku; Matsuura, Hideyuki

doi:10.1016/j.bmcl.2021.128284

Cited by 4 publications

(18 citation statements)

References 13 publications

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“…The analyses using the UPLC MS/MS system were performed to evaluate endogenous amounts of JA, 1 , 8 , 10 , and (+)- cis -OPDA according to the reported method …”

Section: Experimental Sectionmentioning

confidence: 99%

“…The analyses using the UPLC MS/MS system were performed to evaluate endogenous amounts of JA, 1, 8, 10, and (+)-cis-OPDA according to the reported method. 9 Wound-Triggered Accumulation of JAs and 1. Seeds of A. thaliana were planted in Jiffy-7 Peat Pellets (ϕ 42 mm, BHGS Ltd., Worcestershire, UK) that had each absorbed 50 mL of water.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Syntheses of (+)-cis-OPDA were performed according to reported methods. 8,9 Syntheses of Compounds 2−6. cis-OPDA-(S)-α-monoglyceride (2) and cis-OPDA-(R)-α-monoglyceride (3).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…9 Syntheses of 9 and 10 and Evaluation of 7 and 8 Using UPLC MS/MS. α-LA-α-monoglyceride-d 5 (9) and cis-OPDA-αmonoglyceride-d 5 (10): Synthesis of 9 and 10 were achieved according to the reported method except for using glycerol-1,1,2,3,3-d 5 (Sigma-Aldrich Japan) instead of glycerol, and measurements of the compounds using UPLC MS/MS system were performed according to the reported method. 9 Analysis of Endogenous Amounts of 1 and JAs.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…α-LA-α-monoglyceride-d 5 (9) and cis-OPDA-αmonoglyceride-d 5 (10): Synthesis of 9 and 10 were achieved according to the reported method except for using glycerol-1,1,2,3,3-d 5 (Sigma-Aldrich Japan) instead of glycerol, and measurements of the compounds using UPLC MS/MS system were performed according to the reported method. 9 Analysis of Endogenous Amounts of 1 and JAs. Plant material (1−3 g) was frozen using liquid nitrogen immediately after harvest and then crushed and soaked for 24 h using a solution of EtOH (10 mL) together with the addition of internal standards (cis-OPDA-α-monoglyceride-d 5 (400 ng/sample), uniform 13 C labeled (+)-cis-OPDA (100 ng/sample), and (±)-JA-d 3 (200 ng/sample)).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Hirota,

Ito,

Inoue

et al. 2024

J. Nat. Prod.

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cis-12-oxo-Phytodieneoic acid-α-monoglyceride (1) was isolated from Arabidopsis thaliana. The chemical structure of 1 was elucidated based on exhaustive 1D and 2D NMR spectroscopic measurements and supported by FDMS and HRFDMS data. The absolute configuration of the cis-OPDA moiety in 1 was determined by comparison of 1 H NMR spectra and ECD measurements. With respect to the absolute configuration of the β-position of the glycerol backbone, the 2:3 ratio of (S) to (R) was determined by making ester-bonded derivatives with (R)-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride and comparing 1 H NMR spectra. Wounding stress did not increase endogenous levels of 1, and it was revealed 1 had an inhibitory effect of A. thaliana post germination growth. Notably, the endogenous amount of 1 was higher than the amounts of (+)-7-iso-jasmonic acid and (+)-cis-OPDA in intact plants. 1 also showed antimicrobial activity against Gram-positive bacteria, but jasmonic acid did not. It was also found that α-linolenic acid-α-monoglyceride was converted into 1 in the A. thaliana plant, which implied α-linolenic acid-α-monoglyceride was a biosynthetic intermediate of 1.O xylipin is the general term for structurally diverse plant metabolites produced through oxidation steps of unsaturated fatty acids, including aldehydes, divinyl ethers, oxo, keto, hydroxy, and hydroperoxy derivatives. These molecules play a pivotal role in plants because they are essential for developmental processes and defense. 1 Among oxylipins, jasmonates are representative examples. The compounds are biosynthesized using (+)-cis-12-oxo-phytodienoic acid ((+)-cis-OPDA) or (+)-dinor-cis-OPDA as common intermediates, in which (+)-7-iso-jasmonic acid ((+)-7-iso-JA) is a representative biologically active compound that is easily epimerized into (−)-JA during the process of isolation. 2 α-Linolenic acid (α-LA) and (13Z, 10Z, 7Z)-hexadeca-13,10,7-trienoic acid (HA) released by the lipase enzyme are oxygenated by 13-and 11-lipoxygenase (13-/11-LOX) enzymes, respectively, to afford 13-and 11-hydroperoxide intermediates, which are then catabolized through coupled dehydration−cyclization reactions catalyzed by allene oxide synthase (AOS) and allene oxide cyclase (AOC) enzymes to give cyclopentenones, (+)-cis-OPDA and (+)-dinor-cis-OPDA.

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“…The analyses using the UPLC MS/MS system were performed to evaluate endogenous amounts of JA, 1 , 8 , 10 , and (+)- cis -OPDA according to the reported method …”

Section: Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Syntheses of (+)-cis-OPDA were performed according to reported methods. 8,9 Syntheses of Compounds 2−6. cis-OPDA-(S)-α-monoglyceride (2) and cis-OPDA-(R)-α-monoglyceride (3).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

See 3 more Smart Citations

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Hirota,

Ito,

Inoue

et al. 2024

J. Nat. Prod.

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Aminoacylase efficiently hydrolyses fatty acid amino acid conjugates of Helicoverpa armigera potentially to increase the pool of glutamine

Kallure,

Sahoo,

Kale

et al. 2024

Insect Biochemistry and Molecular Biology

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A Light-Powered In Vitro Synthetic Enzymatic Biosystem for the Synthesis of 3-Hydroxypropionic Acid via CO₂ Fixation

Ning,

Li,

Wei

et al. 2024

ACS Synth. Biol.

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3-Hydroxypropionic acid (3-HP) is a highly sought-after platform chemical serving as a precursor to a variety of high value-added chemical products. In this study, we designed and constructed a novel light-powered in vitro synthetic enzymatic biosystem comprising acetyl-CoA ligase, acetyl-CoA carboxylase, malonyl-CoA reductase, and phosphotransferase to efficiently produce 3-HP through CO 2 fixation from acetate, a costeffective and readily available substrate. The system employed natural thylakoid membranes (TMs) for the regeneration of adenosine triphosphate and nicotinamide adenine dinucleotide phosphate. Comprehensive investigations were conducted on the effects of buffer solutions, substrate concentrations, enzyme loading levels, and TMs loading levels to optimize the yield of 3-HP. Following optimization, a production of 0.46 mM 3-HP was achieved within 6 h from an initial 0.5 mM acetate, with a yield nearing 92%. This work underscores the simplicity of 3-HP production via an in vitro biomanufacturing platform and highlights the potential for incorporating TMs as a sustainable and environmentally friendly approach in biomanufacturing processes.

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Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid

Cited by 4 publications

References 13 publications

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Aminoacylase efficiently hydrolyses fatty acid amino acid conjugates of Helicoverpa armigera potentially to increase the pool of glutamine

A Light-Powered In Vitro Synthetic Enzymatic Biosystem for the Synthesis of 3-Hydroxypropionic Acid via CO₂ Fixation

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Verification of the versatility of the in vitro enzymatic reaction giving (+)-cis-12-Oxo-phytodienoic acid

Cited by 4 publications

References 13 publications

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana

Aminoacylase efficiently hydrolyses fatty acid amino acid conjugates of Helicoverpa armigera potentially to increase the pool of glutamine

A Light-Powered In Vitro Synthetic Enzymatic Biosystem for the Synthesis of 3-Hydroxypropionic Acid via CO2 Fixation

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Product

Resources

About

A Light-Powered In Vitro Synthetic Enzymatic Biosystem for the Synthesis of 3-Hydroxypropionic Acid via CO₂ Fixation