Stereospecific biosynthesis of (9S,13S)-10-oxo-phytoenoic acid in young maize roots

Ogorodnikova, Anna V.; Gorina, Svetlana S.; Mukhtarova, Lucia S.; Мухитова, Ф. К.; Toporkova, Yana Y.; Hámberg, Mats; Grechkin, Alexander N.

doi:10.1016/j.bbalip.2015.05.004

Cited by 11 publications

(20 citation statements)

References 30 publications

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“…S3). Our results are consistent with recently published findings demonstrating that maize synthesis of predominantly (9S,13S)-10-OPEA is enzymatic and is the result of an undiscovered AOC acting on 9-LOX derived allene oxide(s) (34). Curiously, a portion of the 10-OPEA cyclopentenone appears to undergo two β-oxidation-like steps to form DA 0 -4:1 before an OPR-like mediated cyclopentenone reduction to DA 0 -4:0 ( Fig.…”

Section: Resultssupporting

confidence: 82%

“…The most critical immediate question left unanswered is "do maize plants lacking 10-OPEA biosynthesis display altered biotic or abiotic stress responses?" Given the current work and recently published findings, the most elegant way to address this issue will be the identification of the AOC(s) responsible for 10-OPEA biosynthesis and creation of null mutant plants (34). Additional remaining questions involve the occurrence and function of DAs in multiple grain crops, the role of individual DAs as transcriptional mediators, and mechanistic basis for differential activity in gene expression.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Maize death acids, 9-lipoxygenase–derived cyclopente(a)nones, display activity as cytotoxic phytoalexins and transcriptional mediators

Christensen

Huffaker

Kaplan

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

140

125

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Plant damage promotes the interaction of lipoxygenases (LOXs) with fatty acids yielding 9-hydroperoxides, 13-hydroperoxides, and complex arrays of oxylipins. The action of 13-LOX on linolenic acid enables production of 12-oxo-phytodienoic acid (12-OPDA) and its downstream products, termed “jasmonates.” As signals, jasmonates have related yet distinct roles in the regulation of plant resistance against insect and pathogen attack. A similar pathway involving 9-LOX activity on linolenic and linoleic acid leads to the 12-OPDA positional isomer, 10-oxo-11-phytodienoic acid (10-OPDA) and 10-oxo-11-phytoenoic acid (10-OPEA), respectively; however, physiological roles for 9-LOX cyclopentenones have remained unclear. In developing maize (Zea mays) leaves, southern leaf blight (Cochliobolus heterostrophus) infection results in dying necrotic tissue and the localized accumulation of 10-OPEA, 10-OPDA, and a series of related 14- and 12-carbon metabolites, collectively termed “death acids.” 10-OPEA accumulation becomes wound inducible within fungal-infected tissues and at physiologically relevant concentrations acts as a phytoalexin by suppressing the growth of fungi and herbivores including Aspergillus flavus, Fusarium verticillioides, and Helicoverpa zea. Unlike previously established maize phytoalexins, 10-OPEA and 10-OPDA display significant phytotoxicity. Both 12-OPDA and 10-OPEA promote the transcription of defense genes encoding glutathione S transferases, cytochrome P450s, and pathogenesis-related proteins. In contrast, 10-OPEA only weakly promotes the accumulation of multiple protease inhibitor transcripts. Consistent with a role in dying tissue, 10-OPEA application promotes cysteine protease activation and cell death, which is inhibited by overexpression of the cysteine protease inhibitor maize cystatin-9. Unlike jasmonates, functions for 10-OPEA and associated death acids are consistent with specialized roles in local defense reactions.

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Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Maize death acids, 9-lipoxygenase–derived cyclopente(a)nones, display activity as cytotoxic phytoalexins and transcriptional mediators

Christensen

Huffaker

Kaplan

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

140

125

View full text Add to dashboard Cite

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“…19,13 First isolated from potato (Solanum tuberosum), 10-OPEA and 10-OPDA were identified as products of 9-allene oxide synthase enzymes and subsequent nonenzymatic cyclization, resulting in racemic mixtures of low yield stereoisomers. 19,20 In contrast, our empirical findings in maize silks 13 and a concurrent study done in maize roots 21 showed that cis-10-OPEA synthesis in maize is consistent with full enzymatic biosynthesis, yielding predominantly (9S,13S)-10-OPEA as a result of an as-yet unidentified enzyme with novel 9-AOC activity. Together, these results suggest pathway diversity in 9-cyclopentenone formation between dicot and monocot species.…”

contrasting

confidence: 54%

A maize death acid, 10-oxo-11-phytoenoic acid, is the predominant cyclopentenone signal present during multiple stress and developmental conditions

Christensen

Huffaker

Hunter

et al. 2015

Plant Signaling & Behavior

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“…Similar to the dual positional specific LOXs of maize [62] and rice [59], the barley AOS [68], rice AOS2 (Os03g0225900) [73] and recently maize (ZmAOS2b) [74] were reported to possess dual substrate specificity capabilities of catalyzing either 9- or 13-HPOD/T into the corresponding allene oxides. None of the AOS2 clade members (Figure 6) encode predicted CTPs.…”

Section: Allene Oxide Synthasementioning

confidence: 99%

“…The 9-LOX isoforms responsible for their biosynthesis have not been identified yet in maize or any other plant species. In maize, following 9-LOX activity on C18:2, the 9-hydroperoxy fatty acid (9-HPOD) is catalyzed into 9,10-epoxy octadecadienoic acid (9,10-EOD) through the action of ZmAOS2b [74]. The 9,10-EOD is cyclized into 10-OPEA by an, as yet uncharacterized, AOC-like enzyme [74].…”

Section: 9-oxylipin Jasmonate Analogs (10-opea 10-opda and Derivmentioning

confidence: 99%

Synthesis and Functions of Jasmonates in Maize

Borrego

Kolomiets

2016

Plants

109

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Of the over 600 oxylipins present in all plants, the phytohormone jasmonic acid (JA) remains the best understood in terms of its biosynthesis, function and signaling. Much like their eicosanoid analogues in mammalian system, evidence is growing for the role of the other oxylipins in diverse physiological processes. JA serves as the model plant oxylipin species and regulates defense and development. For several decades, the biology of JA has been characterized in a few dicot species, yet the function of JA in monocots has only recently begun to be elucidated. In this work, the synthesis and function of JA in maize is presented from the perspective of oxylipin biology. The maize genes responsible for catalyzing the reactions in the JA biosynthesis are clarified and described. Recent studies into the function of JA in maize defense against insect herbivory, pathogens and its role in growth and development are highlighted. Additionally, a list of JA-responsive genes is presented for use as biological markers for improving future investigations into JA signaling in maize.

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Stereospecific biosynthesis of (9S,13S)-10-oxo-phytoenoic acid in young maize roots

Cited by 11 publications

References 30 publications

Maize death acids, 9-lipoxygenase–derived cyclopente(a)nones, display activity as cytotoxic phytoalexins and transcriptional mediators

Maize death acids, 9-lipoxygenase–derived cyclopente(a)nones, display activity as cytotoxic phytoalexins and transcriptional mediators

A maize death acid, 10-oxo-11-phytoenoic acid, is the predominant cyclopentenone signal present during multiple stress and developmental conditions

Synthesis and Functions of Jasmonates in Maize

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