Biosynthesis and in vitro enzymatic synthesis of the isoleucine conjugate of 12-oxo-phytodienoic acid from the isoleucine conjugate of α-linolenic acid

Uchiyama, Akira; Yaguchi, Takaomi; Nakagawa, Hiroyuki; Sasaki, Kazunobu; Kuwata, Naoshige; Matsuura, Hideyuki; Takahashi, Kosaku

doi:10.1016/j.bmcl.2018.02.030

Cited by 9 publications

(2 citation statements)

References 23 publications

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“…Even the conjugate of OPDA with isoleucine has been found in flowering A. thaliana [ 30 ] and showed biological activity [ 31 ]. Its formation from the Ile conjugate of α-LeA was shown recently by in vitro enzymatic methods [ 32 ].…”

Section: Occurrence Of Jasmonic Acid (Ja) Compoundsmentioning

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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Section: Occurrence Of Jasmonic Acid (Ja) Compoundsmentioning

confidence: 99%

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

Wasternack

Strnad

2018

IJMS

185

147

View full text Add to dashboard Cite

show abstract

“…Recently, OPDA conjugated with isoleucine (OPDA-Ile) was described in A. thaliana (Floková et al 2016) and its ability to induce OPDA-specific gene expression was confirmed (Arnold et al 2016). In vitro studies recently showed that an isoleucine conjugate of LA can be used as a substrate for OPDA-Ile formation (Uchiyama et al 2018); however, the mechanisms behind the perception of this molecule have not been determined.…”

Section: Indirect Functions Of Esterified Oxylipinsmentioning

confidence: 99%

New insights into the biosynthesis of esterified oxylipins and their involvement in plant defense and developmental mechanisms

et al. 2018

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Plant oxylipins produced following oxidation of unsaturated fatty acids are structurally diverse metabolites that play crucial developmental and defensive roles. Whereas free oxylipins are well studied, oxylipins esterified in complex lipids such as galacto-and phospholipids are thought to be rare and have unclear roles. In the last few years, new analytical methods have been developed, leading to the discovery of many esterified oxylipins in a variety of plant species. This suggests that these molecules may be ubiquitous plant metabolites. While their precise functions are unclear, esterified oxylipins seem to play important roles in plant development and defense. This review focuses on new insights regarding diversity, biosynthesis and function of those interesting and understudied molecules. Keywords Arabidopsides Á Jasmonates Á Lipoxygenase Á Oxylipins Á Plant defense Abbreviations (dn)OPDA OPDA and dnOPDA A. thaliana Arabidopsis thaliana (L.) Heynh ACX1 Acyl-coenzyme A oxidase 1 ADH Alcohol dehydrogenase AGAP1 Acylated galactolipid associated phospholipase 1 AOC Allene oxide cyclase AOS Allene oxide synthase DES Divinyl ether synthase 4,5-ddhJA 4,5-Didehydro-jasmonic acid DGDG Digalactosyldiacylglycerol DGMG Digalactosylmonoacylglycerol dnOPDA 12-Dinor-oxo-phytodienoic acid DOX a-Dioxygenase DW Dry weight EAS Epoxy alcohol synthase EPB Epibrassinolide FW Fresh weight GC Gas chromatography

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Jasmonate: A Versatile Messenger in Plants

Singh

Arif

Siddiqui

et al. 2021

Jasmonates and Salicylates Signaling in Plants

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Biosynthesis and in vitro enzymatic synthesis of the isoleucine conjugate of 12-oxo-phytodienoic acid from the isoleucine conjugate of α-linolenic acid

Cited by 9 publications

References 23 publications

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

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

New insights into the biosynthesis of esterified oxylipins and their involvement in plant defense and developmental mechanisms

Jasmonate: A Versatile Messenger in Plants

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