Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley

Ube, Naoki; Katsuyama, Yuhka; Kariya, Keisuke; Tebayashi, Shin ichi; Sue, Masayuki; Tohnooka, Takuji; Ueno, Kotomi; Taketa, Shin; Ishihara, Atsushi

doi:10.1016/j.phytochem.2020.112650

Cited by 10 publications

(5 citation statements)

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“…Meanwhile, genkwanin (7‐ O ‐methylapigenin) displayed antifungal activity in vitro (Förster et al ., 2021 ), and 7‐ O ‐methylated flavonoids were related to rice disease resistance (Chen et al ., 2018 ). It should, however, be noted that complex O ‐methylflavonoid mixtures, rather than the 7‐ O ‐methylflavonoids alone, were elicited by pathogens in other grasses such as maize and barley (Balmer et al ., 2013 ; Ube et al ., 2021 ). Therefore, investigating the F7MT activity may help to unravel the functional involvement of metabolites participating in wheat adverse environmental responses.…”

Section: Discussionmentioning

confidence: 99%

Beyond pathways: Accelerated flavonoids candidate identification and novel exploration of enzymatic properties using combined mapping populations of wheat

Chen,

Zhang,

Wei

et al. 2024

Plant Biotechnology Journal

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SummaryAlthough forward‐genetics‐metabolomics methods such as mGWAS and mQTL have proven effective in providing myriad loci affecting metabolite contents, they are somehow constrained by their respective constitutional flaws such as the hidden population structure for GWAS and insufficient recombinant rate for QTL. Here, the combination of mGWAS and mQTL was performed, conveying an improved statistical power to investigate the flavonoid pathways in common wheat. A total of 941 and 289 loci were, respectively, generated from mGWAS and mQTL, within which 13 of them were co‐mapped using both approaches. Subsequently, the mGWAS or mQTL outputs alone and their combination were, respectively, utilized to delineate the metabolic routes. Using this approach, we identified two MYB transcription factor encoding genes and five structural genes, and the flavonoid pathway in wheat was accordingly updated. Moreover, we have discovered some rare‐activity‐exhibiting flavonoid glycosyl‐ and methyl‐transferases, which may possess unique biological significance, and harnessing these novel catalytic capabilities provides potentially new breeding directions. Collectively, we propose our survey illustrates that the forward‐genetics‐metabolomics approaches including multiple populations with high density markers could be more frequently applied for delineating metabolic pathways in common wheat, which will ultimately contribute to metabolomics‐assisted wheat crop improvement.

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Section: Discussionmentioning

confidence: 99%

Beyond pathways: Accelerated flavonoids candidate identification and novel exploration of enzymatic properties using combined mapping populations of wheat

Chen,

Zhang,

Wei

et al. 2024

Plant Biotechnology Journal

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“…For example, sakuranetin (7- O -methylnaringenin), produced by the FOMT OsNOMT in rice ( Oryza sativa ) leaves upon fungal infection or abiotic stress, inhibits the growth of rice blast fungus ( Pyricularia oryzae ) in vivo and shows antifungal activity in vitro [ 20 , 21 , 22 , 23 , 24 ]. Similarly, pathogen-induced formation of O -methylflavonoids was also detected in other grasses, such as sorghum ( Sorghum bicolor ), maize ( Zea mays ), and barley ( Hordeum vulgare ) [ 25 , 26 , 27 ]. Recently, we characterized four FOMTs from maize, ZmFOMT2 and ZmFOMT3, ZmFOMT4, and ZmFOMT5, that methylate the hydroxyl groups of various flavonoids regiospecifically at positions 5, 7, and 6 of the A ring, respectively, and are involved in the fungus-induced formation of complex O -methylflavonoid mixtures [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Evolution of DIMBOA-Glc O-Methyltransferases from Flavonoid O-Methyltransferases in the Grasses

2022

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O-Methylated benzoxazinoids (BXs) and flavonoids are widespread defenses against herbivores and pathogens in the grasses (Poaceae). Recently, two flavonoid O-methyltransferases (FOMTs), ZmFOMT2 and ZmFOMT3, have been reported to produce phytoalexins in maize (Zea mays). ZmFOMT2 and ZmFOMT3 are closely related to the BX O-methyltransferases (OMTs) ZmBX10-12 and ZmBX14, suggesting a common evolutionary origin in the Poaceae. Here, we studied the evolution and enzymatic requirements of flavonoid and BX O-methylation activities in more detail. Using BLAST searches and phylogenetic analyses, we identified enzymes homologous to ZmFOMT2 and ZmFOMT3, ZmBX10-12, and ZmBX14 in several grasses, with the most closely related candidates found almost exclusively in species of the Panicoideae subfamily. Biochemical characterization of candidate enzymes from sorghum (Sorghum bicolor), sugar cane (Saccharum spp.), and teosinte (Zea nicaraguensis) revealed either flavonoid 5-O-methylation activity or DIMBOA-Glc 4-O-methylation activity. However, DIMBOA-Glc 4-OMTs from maize and teosinte also accepted flavonols as substrates and converted them to 3-O-methylated derivatives, suggesting an evolutionary relationship between these two activities. Homology modeling, sequence comparisons, and site-directed mutagenesis led to the identification of active site residues crucial for FOMT and BX OMT activity. However, the full conversion of ZmFOMT2 activity into BX OMT activity by switching these residues was not successful. Only trace O-methylation of BXs was observed, indicating that amino acids outside the active site cavity are also involved in determining the different substrate specificities. Altogether, the results of our study suggest that BX OMTs have evolved from the ubiquitous FOMTs in the PACMAD clade of the grasses through a complex series of amino acid changes.

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“…In barley, there is a number of reports of various phytoalexins produced in response to diverse pathogens. These include phenylamides, such as the dimeric hordatine A and B, the indole-derived gramine, benzoxazinones such as 2,4dihydroxy-1,4-benzoxazin-3-one (DIBOA), methoxychalcones as well as tyramine and related amines (5)(6)(7). There is also extensive data on the nature and biosynthesis of a range of terpenoid phytoalexins in other important grass crops.…”

Section: Introductionmentioning

confidence: 99%

Metabolic arms race between a plant and a fungal pathogen

Liu,

Mahdi,

Porzel

et al. 2023

Preprint

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In this work, we uncover a metabolite interaction between barley and the fungal pathogen Bipolaris sorokiniana (Bs), involving hordedanes, a previously undescribed set of labdane-related diterpenoids with antimicrobial properties. Bs infection of barley roots elicits hordedane synthesis from a 600-kb gene cluster. Heterologous reconstruction of the synthesis pathway in yeast produced several hordedanes, including one of the most advanced products 19-β-hydroxy-hordetrienoic acid (19-OH-HTA). Barley mutants in the diterpene synthase genes of the cluster are unable to produce hordedanes but, unexpectedly, show reduced Bs colonization. Accordingly, 19-OH-HTA enhances both germination and growth of Bs, while it inhibits other fungi, and Bs chemically modifies 19-OH-HTA. Thus, plant and pathogen molecular interactions extend beyond protein-protein recognition and the simple detoxification of plant antimicrobial metabolites.

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Identification of methoxylchalcones produced in response to CuCl2 treatment and pathogen infection in barley

Cited by 10 publications

References 50 publications

Beyond pathways: Accelerated flavonoids candidate identification and novel exploration of enzymatic properties using combined mapping populations of wheat

Beyond pathways: Accelerated flavonoids candidate identification and novel exploration of enzymatic properties using combined mapping populations of wheat

Evolution of DIMBOA-Glc O-Methyltransferases from Flavonoid O-Methyltransferases in the Grasses

Metabolic arms race between a plant and a fungal pathogen

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