Molecular cloning and biochemical characterization of three Concord grape (Vitis labrusca) flavonol 7-O-glucosyltransferases

Hall, D. H.; Kim, Kyung Hee; Luca, Vincenzo De

doi:10.1007/s00425-011-1474-0

Cited by 16 publications

(8 citation statements)

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“…Of the enzymes in this cluster, C12RT1 and Cs1,6Rhat showed in vitro rhamnosyl transferring activities toward flavonoid-7- O -glucoside ( Frydman et al, 2004 , 2013 ; Ohashi et al, 2016 ), UGT78G1 catalyzes the glucosylation of flavonoids at the 3- O - hydroxyl site ( Modolo et al, 2007 , 2009 ), and BpUGAT may function as an anthocyanin glucuronosyltransferase to transfer glucuronate onto cyanidin 3- O -glucoside ( Sawada et al, 2005 ; Osmani et al, 2008 ). Such incongruence between the phylogenetic position and substrate specificities has been found in other UGTs, including grape VLOGT2 and onion UGT73G1 and onion UGT73J1 ( Kramer et al, 2003 ; Hall et al, 2011 ). These results support the proposition that the functions and specificities of UGTs is perhaps not accurately determined based on their protein sequences alone ( Dhaubhadel et al, 2008 ).…”

Section: Discussionmentioning

confidence: 73%

Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis)

Liu

Lin

et al. 2018

Front. Plant Sci.

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Fruits of sweet orange (Citrus sinensis), a popular commercial Citrus species, contain high concentrations of flavonoids beneficial to human health. These fruits predominantly accumulate O-glycosylated flavonoids, in which the disaccharides [neohesperidose (rhamnosyl-α-1,2-glucose) or rutinose (rhamnosyl-α-1,6-glucose)] are linked to the flavonoid aglycones through the 3- or 7-hydroxyl sites. The biotransformation of the flavonoid aglycones into O-rutinosides or O-neohesperidosides in the Citrus plants usually consists of two glycosylation reactions involving a series of uridine diphosphate-sugar dependent glycosyltransferases (UGTs). Although several genes encoding flavonoid UGTs have been functionally characterized in the Citrus plants, full elucidation of the flavonoid glycosylation process remains elusive. Based on the available genomic and transcriptome data, we isolated a UGT with a high expression level in the sweet orange fruits that possibly encodes a flavonoid glucosyltransferase and/or rhamnosyltransferase. Biochemical analyses revealed that a broad range of flavonoid substrates could be glucosylated at their 3- and/or 7-hydrogen sites by the recombinant enzyme, including hesperetin, naringenin, diosmetin, quercetin, and kaempferol. Furthermore, overexpression of the gene could significantly increase the accumulations of quercetin 7-O-rhamnoside, quercetin 7-O-glucoside, and kaempferol 7-O-glucoside, implying that the enzyme has flavonoid 7-O-glucosyltransferase and 7-O-rhamnosyltransferase activities in vivo.

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Section: Discussionmentioning

confidence: 73%

Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis)

Liu

Lin

et al. 2018

Front. Plant Sci.

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“…For example, Fh3GT1 showed highest activity toward quercetin, whereas IhAn3GT used malvidin as its best substrate ( Yoshihara et al, 2005 ). The lack of congruence between substrate specificities and phylogenetic position has been observed in other UFGTs like VLOGT2 from grape ( Vitis labrusca ) and two UFGTs from onion ( Kramer et al, 2003 ; Hall et al, 2011 ). These results are in agreement with the past suggestions that function and specificity of UFGT can not predict based on the primary sequence alone ( Dhaubhadel et al, 2008 ).…”

Section: Discussionmentioning

confidence: 92%

Biochemical and Molecular Characterization of a Flavonoid 3-O-glycosyltransferase Responsible for Anthocyanins and Flavonols Biosynthesis in Freesia hybrida

et al. 2016

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The glycosylation of flavonoids increases their solubility and stability in plants. Flowers accumulate anthocyanidin and flavonol glycosides which are synthesized by UDP-sugar flavonoid glycosyltransferases (UFGTs). In our previous study, a cDNA clone (Fh3GT1) encoding UFGT was isolated from Freesia hybrida, which was preliminarily proved to be invovled in cyanidin 3-O-glucoside biosynthesis. Here, a variety of anthocyanin and flavonol glycosides were detected in flowers and other tissues of F. hybrida, implying the versatile roles of Fh3GT1 in flavonoids biosynthesis. To further unravel its multi-functional roles, integrative analysis between gene expression and metabolites was investigated. The results showed expression of Fh3GT1 was positively related to the accumulation of anthocyanins and flavonol glycosides, suggesting its potential roles in the biosynthesis of both flavonoid glycosides. Subsequently, biochemical analysis results revealed that a broad range of flavonoid substrates including flavonoid not naturally occurred in F. hybrida could be recognized by the recombinant Fh3GT1. Both UDP-glucose and UDP-galactose could be used as sugar donors by recombinant Fh3GT1, although UDP-galactose was transferred with relatively low activity. Furthermore, regiospecificity analysis demonstrated that Fh3GT1 was able to glycosylate delphinidin at the 3-, 4-′, and 7- positions in a sugar-dependent manner. And the introduction of Fh3GT1 into Arabidopsis UGT78D2 mutant successfully restored the anthocyanins and flavonols phenotypes caused by lost-of-function of the 3GT, indicating that Fh3GT1 functions as a flavonoid 3-O-glucosyltransferase in vivo. In summary, these results demonstrate that Fh3GT1 is a flavonoid 3-O-glycosyltransferase using UDP-glucose as the preferred sugar donor and may involve in flavonoid glycosylation in F. hybrida.

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“…A neighbor-joining (NJ) tree was constructed using a Poisson model with 1,000 bootstrap replicates. The protein sequences included CCD1, CCD4a, NCED1, NCED2, ALDH12, ALDH14, UGT60, UGT67, UGT86, and UGT89 from this study; AtCCD1, AtCCD4, AtNCED3, AtNCED5, AtNCED6, AtCCD7, AtCCD8, AtALDH2C4, AtALDH2B7 UGT73C6, and UGT73B2 from A. thaliana (Skibbe et al, 2002; Jones et al, 2003; Nair et al, 2004; Auldridge et al, 2006; Kim et al, 2006; Alder et al, 2012; Frey et al, 2012; Gonzalez-Jorge et al, 2013); CsCCD2, CsGT45, and UGTCs2 from C. sativus (Moraga et al, 2004; Frusciante et al, 2014); MtCCD1 and UGT73K1 from Medicago truncatula (Achnine et al, 2005; Floss et al, 2008; Moraga et al, 2009); CmCCD1 from Cucumis melo (Ibdah et al, 2006); CmCCD4a from C. morifolium (Ohmiya et al, 2006); CitCCD4 from C. unshiu (Ma et al, 2013; Rodrigo et al, 2013); CaALDH1 from C. annuum (Kim and Hwang, 2015); AaALDH1 from A. annua (Teoh et al, 2009); BoBADH from B. orellana (Bouvier et al, 2003); REF1 from B. napus (Mittasch et al, 2013); Zmrf2 (ALDH2B2) from Z. mays (Cui et al, 1996); BALDH from A. majus (Long et al, 2009); UGT75L6 and UGT94E5 from G. jasminoides (Nagatoshi et al, 2012); VLOGT1, VLOGT2, and VLOGT3 from Vitis labrusca (Hall et al, 2011); Gt5GT7 from Gentiana triflora (Nakatsuka et al, 2008); UGT1, UGTPg29, and UGTPg45 from P. ginseng (Yan et al, 2014; Wang et al, 2015); CrUGT8 from Catharanthus roseus (Asada et al, 2013); AdGT4 from Actinidia deliciosa (Yauk et al, 2014); GAME2 from Solanum lycopersicum (Itkin et al, 2013); ZOG1 from Phaseolus lunatus (Martin et al, 1999b); and ZOX1 from Phaseolus vulgaris (Martin et al, 1999a). Conserved motifs in CCDs, ALDHs and UGTs were detected using motif based sequence analysis tool MEME (Suite version 4.11.2).…”

Section: Methodsmentioning

confidence: 99%

Transcriptome-Guided Mining of Genes Involved in Crocin Biosynthesis

Jia

et al. 2017

Front. Plant Sci.

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Gardenia jasminoides is used in traditional Chinese medicine and has drawn attention as a rich source of crocin, a compound with reported activity against various cancers, depression and cardiovascular disease. However, genetic information on the crocin biosynthetic pathway of G. jasminoides is scarce. In this study, we performed a transcriptome analysis of the leaves, green fruits, and red fruits of G. jasminoides to identify and predict the genes that encode key enzymes responsible for crocin production, compared with Crocus sativus. Twenty-seven putative pathway genes were specifically expressed in the fruits, consistent with the distribution of crocin in G. jasminoides. Twenty-four of these genes were reported for the first time, and a novel CCD4a gene was predicted that encodes carotenoid cleavage dioxygenase leading to crocin synthesis, in contrast to CCD2 of C. sativus. In addition, 6 other candidate genes (ALDH12, ALDH14, UGT94U1, UGT86D1, UGT71H4, and UGT85K18) were predicted to be involved in crocin biosynthesis following phylogenetic analysis and different gene expression profiles. Identifying the genes that encode key enzymes should help elucidate the crocin biosynthesis pathway.

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Molecular cloning and biochemical characterization of three Concord grape (Vitis labrusca) flavonol 7-O-glucosyltransferases

Cited by 16 publications

References 50 publications

Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis)

Functional Characterization of a Flavonoid Glycosyltransferase in Sweet Orange (Citrus sinensis)

Biochemical and Molecular Characterization of a Flavonoid 3-O-glycosyltransferase Responsible for Anthocyanins and Flavonols Biosynthesis in Freesia hybrida

Transcriptome-Guided Mining of Genes Involved in Crocin Biosynthesis

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