Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus

Ogata, Jun; Itoh, Yoshio; Ishida, Masao; Yoshida, Hiroyuki; Ozeki, Yoshihiro

doi:10.5511/plantbiotechnology.21.367

Cited by 61 publications

(40 citation statements)

References 25 publications

(18 reference statements)

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“…Additional mutation of the DFR gene confers better yellow coloration in carnation (Itoh et al, 2002). The existence of several genes encoding THC 2¢GT activity from carnation ( Figure S1; Ogata et al, 2004;Okuhara et al, 2004) indicates that several non-specific enzymes may catalyze the reaction in vivo, unlike the case of anthocyanin GTs. In snapdragon, THC 4¢-glucoside is synthesized by the action of THC 4¢GT, presumably in the cytosol (Ono et al, 2006), transported to the vacuoles, and further converted to aureusidin 6-glucoside by aureusidin synthase [AS, a polyphenol oxidase (PPO)] in the vacuoles (Nakayama et al, 2000).…”

Section: Modification Of Anthocyanidinsmentioning

confidence: 99%

Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids

2008

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SummaryPlant compounds that are perceived by humans to have color are generally referred to as 'pigments'. Their varied structures and colors have long fascinated chemists and biologists, who have examined their chemical and physical properties, their mode of synthesis, and their physiological and ecological roles. Plant pigments also have a long history of use by humans. The major classes of plant pigments, with the exception of the chlorophylls, are reviewed here. Anthocyanins, a class of flavonoids derived ultimately from phenylalanine, are water-soluble, synthesized in the cytosol, and localized in vacuoles. They provide a wide range of colors ranging from orange/red to violet/blue. In addition to various modifications to their structures, their specific color also depends on co-pigments, metal ions and pH. They are widely distributed in the plant kingdom. The lipid-soluble, yellow-to-red carotenoids, a subclass of terpenoids, are also distributed ubiquitously in plants. They are synthesized in chloroplasts and are essential to the integrity of the photosynthetic apparatus. Betalains, also conferring yellow-to-red colors, are nitrogen-containing water-soluble compounds derived from tyrosine that are found only in a limited number of plant lineages. In contrast to anthocyanins and carotenoids, the biosynthetic pathway of betalains is only partially understood. All three classes of pigments act as visible signals to attract insects, birds and animals for pollination and seed dispersal. They also protect plants from damage caused by UV and visible light.

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Section: Modification Of Anthocyanidinsmentioning

confidence: 99%

Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids

2008

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“…The major anthocyanin in the typical pink petals of carnations is 3,5-di-O-glucopyranosyl pelargonidin 699-O-4,6999-O-1-cyclic malate (Pg3,5cyclicmalyldG) (Nakayama et al, 2000). The enzyme UA3GT is active in carnation petals during the biosynthesis of this anthocyanin; a candidate cDNA encoding the enzyme has been isolated, but the 5-Oglucosylation reaction has not yet been identified in the crude extract prepared from carnation petals (Ogata et al, 2004). The 7-O-glucosylation reaction for anthocyanins in petals of delphinium (Delphinium grandiflorum), cineraria (Senecio hybrida), Himalayan blue poppy (Meconopsis grandis), and anemone (Anemone coronaria) flowers remains similarly uncertain (Davies, 2009;Yonekura-Sakakibara et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

A Novel Glucosylation Reaction on Anthocyanins Catalyzed by Acyl-Glucose–Dependent Glucosyltransferase in the Petals of Carnation and Delphinium

et al. 2010

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Glucosylation of anthocyanin in carnations (Dianthus caryophyllus) and delphiniums (Delphinium grandiflorum) involves novel sugar donors, aromatic acyl-glucoses, in a reaction catalyzed by the enzymes acyl-glucose-dependent anthocyanin 5 (7)-O-glucosyltransferase (AA5GT and AA7GT). The AA5GT enzyme was purified from carnation petals, and cDNAs encoding carnation Dc AA5GT and the delphinium homolog Dg AA7GT were isolated. Recombinant Dc AA5GT and Dg AA7GT proteins showed AA5GT and AA7GT activities in vitro. Although expression of Dc AA5GT in developing carnation petals was highest at early stages, AA5GT activity and anthocyanin accumulation continued to increase during later stages. Neither Dc AA5GT expression nor AA5GT activity was observed in the petals of mutant carnations; these petals accumulated anthocyanin lacking the glucosyl moiety at the 5 position. Transient expression of Dc AA5GT in petal cells of mutant carnations is expected to result in the transfer of a glucose moiety to the 5 position of anthocyanin. The amino acid sequences of Dc AA5GT and Dg AA7GT showed high similarity to glycoside hydrolase family 1 proteins, which typically act as b-glycosidases. A phylogenetic analysis of the amino acid sequences suggested that other plant species are likely to have similar acylglucose-dependent glucosyltransferases.

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“…In this study, we isolated five cDNAs encoding THC2ЈGT activity from carnations; the genes isolated are different from those previously reported DicGT4 and DicGT5 (Ogata et al 2004). We also isolated a cDNA encoding THC2ЈGT activity from both cyclamen and catharanthus.…”

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confidence: 73%

“…THC2ЈGT genes can be alternative and useful molecular tools to produce yellow color by genetic engineering. Ogata et al (2004) isolated 18 types of GT genes from yellow carnations and identified two genes (DicGT4 and DicGT5) encoding THC2ЈGT activity and three genes (DicGT1, DicGT2, and DicGT3) encoding anthocyanidin 3GT.…”

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confidence: 99%

Isolation of cDNAs encoding tetrahydroxychalcone 2′-glucosyltransferase activity from carnation, cyclamen, and catharanthus

Togami

Okuhara

Nakamura

et al. 2011

Plant Biotechnology

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Flavonoids are one of the major secondary metabolites of plants. Flavonoids and their colored class, anthocyanins, are dominant constituents of flower color. Floral flavonoids are usually modified with one or more sugar moieties, and are localized in vacuoles (Tanaka et al. 2008). The glycosylation of flavonoids is catalyzed by family 1 glycosyltransferases of the 91 subfamilies of glycosyltransferases classified on the basis of sequence similarity, catalytic mechanisms, and the presence of conserved sequence motifs (Yonekura-Sakakibara 2009). Family 1 glycosyltransferases utilize specific UDPsugars, such as UDP-glucose, UDP-rhamnose, and UDPgalactose, as sugar donors. Glucosyltransferase (GT) that utilizes UDP-glucose is the most common in this family. Family 1 glycosyltransferases contain a carboxylterminal conserved sequence, the secondary product glycosyltransferase box of plants (Gachon et al. 2005), and are classified into many clusters depending on sequence homology. Glycosyltransferases from different plant species having the same function usually belong to the same clusters in the family.Glycosylation of flavonoids has been extensively studied in terms of its biochemistry and molecular biology. More recently, Arabidopsis flavonoid glycosyltransferases have been comprehensively analyzed (Yonekura-Sakakibara 2009). Flavonoid glycosylation, typically glucosylation, is catalyzed by position-specific glycosyltransferases. GT in the flavonoid biosynthetic pathway includes flavonoid 3-glucosyltransferase (3GT), flavonoid 5-glucosyltransferase (5GT), flavonoid 7-glucosyltransferase (7GT), and flavonoid 3Ј-glucosyltransferase (3ЈGT); 3GT and 5GT form separate clusters, and 7GT and 3ЈGT belong to the same cluster (FukuchiMizutani et al. 2003;Tanaka et al. 2008). Acyl-glucosedependent glycoside hydrolase-like anthocyanin GTs have been recently identified in carnations and delphiniums (Matsuba et al. 2010).Chalcones and aurones are yellow flavonoids. 4,2Ј,4Ј,6Ј-Tetrahydroxy chalcone (THC) imparts pale yellow color but is rapidly isomerized to colorless naringenin by the catalysis of chalcone isomerase (CHI) in vivo (Figure 1) Abstract 4,2Ј,4Ј,6Ј-Tetrahydroxychalcone (THC) 2Ј-glucoside that confers yellow color to the petals of carnation, cyclamen, and catharanthus is biosynthesized by the action of UDP-glucose-dependent THC 2Ј-glucosyltransferase (THC2ЈGT). We isolated 18 types of full-length cDNA encoding GT-like sequences from carnation petals. Expression of these cDNA in Escherichia coli identified five cDNAs encoding THC2ЈGT that were different from the previously isolated THC2ЈGT. We also isolated a cDNA encoding THC2ЈGT from both catharanthus and cyclamen. These THC2ЈGT cDNAs were introduced to petunia. Transgenic petunia that expressed three of the GTs produced THC 2Ј-glucoside, which indicated that they function as THC2ЈGT in vivo. These cDNAs could be useful molecular tools to yield yellow flower color, although the amount accumulated in the transgenic petals was too small to alter the flower color in this...

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Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus

Cited by 61 publications

References 25 publications

Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids

Biosynthesis of plant pigments: anthocyanins, betalains and carotenoids

A Novel Glucosylation Reaction on Anthocyanins Catalyzed by Acyl-Glucose–Dependent Glucosyltransferase in the Petals of Carnation and Delphinium

Isolation of cDNAs encoding tetrahydroxychalcone 2′-glucosyltransferase activity from carnation, cyclamen, and catharanthus

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