Cloning, Functional Identification and Sequence Analysis of Flavonoid 3′-hydroxylase and Flavonoid 3′,5′-hydroxylase cDNAs Reveals Independent Evolution of Flavonoid 3′,5′-hydroxylase in the Asteraceae Family

Seitz, Christian; Eder, Christian; Deiml, Bettina; Kellner, Sandra; Martens, Stefan; Forkmann, G.

doi:10.1007/s11103-006-0012-0

Cited by 144 publications

(144 citation statements)

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“…The majority of known F3959Hs are members of the CYP75A subfamily. Phylogenetic analysis implicated that the divergence of CYP75A and CYP75B (F39H) members predated the speciation of angiosperms (Seitz et al, 2006). However, genome sequences of several dicot plants, such as Arabidopsis, carnation, and a few Rosaceae species, do not harbor any CYP75A homologous sequences, consistent with their absence of 59-modified flavonoids (Tanaka and Brugliera, 2014).…”

Section: Discussionmentioning

confidence: 99%

“…Accordingly, apigenin needs to be first converted to tricetin by a flavonoid 39,59-hydroxylase (F3959H) in a pathway leading to tricin formation. The vast majority of characterized F3959Hs are CYP enzymes belonging to the CYP75A subfamily (Seitz et al, 2006). Interestingly, several F3959Hs in Asteraceae fall into the same subfamily (CYP75B) with canonical flavonoid 39-hydroxylases (F39Hs), suggesting the recruitment of F3959H from F39H members within this plant family (Seitz et al, 2006).…”

mentioning

confidence: 99%

“…The vast majority of characterized F3959Hs are CYP enzymes belonging to the CYP75A subfamily (Seitz et al, 2006). Interestingly, several F3959Hs in Asteraceae fall into the same subfamily (CYP75B) with canonical flavonoid 39-hydroxylases (F39Hs), suggesting the recruitment of F3959H from F39H members within this plant family (Seitz et al, 2006). F3959H activities enable plants to synthesize delphinidin-based anthocyanins, which confer violet/ blue color in flowers and fruits, potentially a selective advantage in angiosperms for attraction of pollinators and seed dispersers (Harborne, 2014).…”

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confidence: 99%

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Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5′-Hydroxylase

2015

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Flavones are ubiquitously accumulated in land plants, but their biosynthesis in monocots remained largely elusive until recent years. Recently, we demonstrated that the rice (Oryza sativa) cytochrome P450 enzymes CYP93G1 and CYP93G2 channel flavanones en route to flavone O-linked conjugates and C-glycosides, respectively. In tricin, the 39,59-dimethoxyflavone nucleus is formed before O-linked conjugations. Previously, flavonoid 39,59-hydroxylases belonging to the CYP75A subfamily were believed to generate tricetin from apigenin for 39,59-O-methylation to form tricin. However, we report here that CYP75B4 a unique flavonoid B-ring hydroxylase indispensable for tricin formation in rice. A CYP75B4 knockout mutant is tricin deficient, with unusual accumulation of chrysoeriol (a 39-methoxylated flavone). CYP75B4 functions as a bona fide flavonoid 39-hydroxylase by restoring the accumulation of 39-hydroxylated flavonoids in Arabidopsis (Arabidopsis thaliana) transparent testa7 mutants and catalyzing in vitro 39-hydroxylation of different flavonoids. In addition, overexpression of both CYP75B4 and CYP93G1 (a flavone synthase II) in Arabidopsis resulted in tricin accumulation. Specific 59-hydroxylation of chrysoeriol to selgin by CYP75B4 was further demonstrated in vitro. The reaction steps leading to tricin biosynthesis are then reconstructed as naringenin → apigenin → luteolin → chrysoeriol → selgin → tricin. Hence, chrysoeriol, instead of tricetin, is an intermediate in tricin biosynthesis. CYP75B4 homologous sequences are highly conserved in Poaceae, and they are phylogenetically distinct from the canonical CYP75B flavonoid 39-hydroxylase sequences. Recruitment of chrysoeriol-specific 59-hydroxylase activity by an ancestral CYP75B sequence may represent a key event leading to the prevalence of tricin-derived metabolites in grasses and other monocots today.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5′-Hydroxylase

2015

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“…The isolation of AOMT genes from more plant species will help to clarify the molecular evolution of AOMT Copyright © 2015 The Japanese Society for Plant Cell and Molecular Biology genes. Gene duplication and the neofunctionalization of flavonoid biosynthetic pathway genes is not uncommon and have been reported previously (Rausher 2006;Seitz et al 2006).…”

Section: Isolation Of the Torenia Aomt Homologmentioning

confidence: 92%

Flower color modification in Rosa hybrida by expressing the S-adenosylmethionine: anthocyanin 3′,5′-O-methyltransferase gene from Torenia hybrida

Nakamura

Katsumoto

Brugliera

et al. 2015

Plant Biotechnology

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We isolated a cDNA encoding S-adenosylmethionine: anthocyanin 3′,5′-O-methyltransferase (A3′5′OMT) from a cDNA library derived from Torenia hybrida petals that mainly accumulated malvidin type anthocyanins using the petunia A3′OMT cDNA as a probe. The torenia A3′5′OMT shared 52-72% amino acid sequence identity with previously reported AOMTs and belongs to the Group A1 methyltransferase family that also include caffeoyl CoA O-methyltransferase. The recombinant A3′5′OMT produced by Escherichia coli efficiently catalyzed methylation of the 3-glucoside and 3,5-diglucoside of delphinidin and cyanidin, but it did not catalyze the methylation of anthocyanidins, flavonols, or flavones. The torenia A3′5′OMT gene was expressed in Nierembergia sp., the petals of which naturally accumulate anthocyanins derived from delphinidin. The resultant transgenic petals produced methylated anthocyanins, based on malvidin and petunidin, in addition to delphinidin, which indicated that the torenia A3′5′OMT gene was functional in a heterologous plant. Rose petals rarely contain methylated anthocyanins. Transgenic rose petals expressing both a pansy flavonoid 3′,5′-hydroxylase (F3′5′H) and the torenia A3′5′OMT genes accumulated methylated anthocyanins based upon malvidin, petunidin, and peonidin, which comprised up to 88% of the total anthocyanidins, and their magenta color was more brilliant than that of the petals that accumulated delphinidin type anthocyanins by expressing the F3′5′H gene alone. These results indicate that the torenia A3′5′OMT gene is a useful molecular tool for altering and diversifying flower color.

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“…16) They belong to the same family, CYP75, of the P450 superfamily. In the chrysanthemum family, the F3 0 5 0 H gene evolved from the F3 0 H gene after the speciation of the chrysanthemum 21) and a few amino acid substitutions of F3 0 H resulted in F3 0 5 0 H activity. 22) Dihydroflavonols are also at a branching point of flavonoid biosynthesis, and are the direct precursors of flavonols.…”

Section: Recent Progress In the Biosynthesis Of Flavonoids Relevant Tmentioning

confidence: 99%

Flower Color Modification by Engineering of the Flavonoid Biosynthetic Pathway: Practical Perspectives

Tanaka¹,

Brugliera²,

Kalc³

et al. 2010

Bioscience, Biotechnology, and Biochemistry

151

113

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The status quo of flavonoid biosynthesis as it relates to flower color is reviewed together with a success in modifying flower color by genetic engineering. Flavonoids and their colored class compounds, anthocyanins, are major contributors to flower color. Many plant species synthesize limited kinds of flavonoids, and thus exhibit a limited range of flower color. Since genes regulating flavonoid biosynthesis are available, it is possible to alter flower color by overexpressing heterologous genes and/or down regulating endogenous genes. Transgenic carnations and a transgenic rose that accumulate delphinidin as a result of expressing a flavonoid 3 0 ,5 0 -hydroxylase gene and have novel blue hued flowers have been commercialized. Transgenic Nierembergia accumulating pelargonidin, with novel pink flowers, has also been developed. Although it is possible to generate white, yellow, and pink-flowered torenia plants from blue cultivars by genetic engineering, field trial observations indicate difficulty in obtaining stable phenotypes.

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Cloning, Functional Identification and Sequence Analysis of Flavonoid 3′-hydroxylase and Flavonoid 3′,5′-hydroxylase cDNAs Reveals Independent Evolution of Flavonoid 3′,5′-hydroxylase in the Asteraceae Family

Cited by 144 publications

References 61 publications

Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5′-Hydroxylase

Completion of Tricin Biosynthesis Pathway in Rice: Cytochrome P450 75B4 Is a Unique Chrysoeriol 5′-Hydroxylase

Flower color modification in <i>Rosa hybrida</i> by expressing the <i>S</i>-adenosylmethionine: anthocyanin 3′,5′-<i>O</i>-methyltransferase gene from <i>Torenia hybrida</i>

Flower Color Modification by Engineering of the Flavonoid Biosynthetic Pathway: Practical Perspectives

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