Identification and characterization of three flavonoid 3-O-glycosyltransferases from Epimedium koreanum Nakai

Lyu, Yunbin; Liu, Shike; Gao, Song; Zhou, Jingwen

doi:10.1016/j.bej.2020.107759

Cited by 20 publications

(11 citation statements)

References 34 publications

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“…Furthermore, EpGT60 could not catalyze the addition of glycosyl groups to kaempferol, suggesting that EpGT60 was different from the previously reported EpPF3RT from E. pseudowushanense or EkF3URhaT from E . koreanum [ 16 , 18 ]. These two recombinant enzymes have a similar function as EpGT60.…”

Section: Discussionmentioning

confidence: 99%

“…Glycosylation directly or indirectly affects the medicinal activity by optimizing the properties of pharmaceutical compounds [ 5 ]. To date, a few UGTs have been proven to be involved in the biosynthesis of icariin, one of the most important active ingredients of flavonol glycosides in Epimedium [ [16] , [17] , [18] , [19] ]. However, the function of hundreds of UGT gene members remains unclear.…”

Section: Introductionmentioning

confidence: 99%

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Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Luo

et al. 2022

Synthetic and Systems Biotechnology

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Luo

et al. 2022

Synthetic and Systems Biotechnology

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“…However, 22.1 mg/L anthocyanins (19.6 mg/L C3G and 2.5 mg/L D3G) were obtained when MdGSTF6 was co-expressed in the aforementioned strain, which was greater than that of AtTT12 and AtGFS9. Meanwhile, ANS belonging to the 2oxoglutarate-dependent dioxygenase (2ODD), has properties of another 2ODD flavanol synthase (FLS) that catalyzes the conversion of dihydroflavonols into flavonols (Wilmouth et al, 2002); then, it can be glycosylated by 3GT (Lyu et al, 2020). Therefore, quercetin-3-O-glucoside (Q3G) and myricetin-3-O-glucoside (M3G) were detected in this study.…”

Section: Introduction Of An Anthocyanin Vacuolar Transportermentioning

confidence: 79%

“…EXG1 was found to be the main anthocyanin-degrading enzyme in this study. EXG1 was reported to be the flavonoid glycoside hydrolase with significant hydrolysis of anthocyanidins (Schmidt et al, 2011) and C-7 flavonoid glycosides (Lyu et al, 2020). Through the knockout of EXG1, the titer of anthocyanins was approximately increased by 100% in the case of co-expressing MdGSTF6.…”

Section: Figurementioning

confidence: 99%

Efficient production of anthocyanins in Saccharomyces cerevisiae by introducing anthocyanin transporter and knocking out endogenous degrading enzymes

Zhou

et al. 2022

Front. Bioeng. Biotechnol.

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Anthocyanins are natural pigments found in various plants. As multifunctional natural compounds, anthocyanins are widely used in food, pharmaceuticals, health products, and cosmetics. At present, the anthocyanins are heterologously biosynthesized in prokaryotes from flavan-3-ols, which is rather expensive. This study aimed to metabolically engineer Saccharomyces cerevisiae for anthocyanin production. Anthocyanin production has been extensively studied to understand the metabolic pathway enzymes in their natural hosts, including CHS (chalcone synthase); FLS (flavonol synthase); CHI (chalcone isomerase); F3H (flavanone 3-hydroxylase); F3′H (flavonoid 3′-hydroxylase); F3′5′H (flavonoid 3′,5′-hydroxylase); DFR (dihydroflavonol 4-reductase); ANS (anthocyanidin synthase); LAR (leucoanthocyanidin reductase); and UFGT (flavonoid 3-O-glucosyltransferase). The anthocyanin transporter MdGSTF6 was first introduced and proven to be indispensable for the biosynthesis of anthocyanins. By expressing MdGSTF6, FaDFR, PhANS0, and Dc3GT and disrupting EXG1 (the main anthocyanin-degrading enzyme), the BA-22 strain produced 261.6 mg/L (254.5 mg/L cyanidin-3-O-glucoside and 7.1 mg/L delphinidin-3-O-glucoside) anthocyanins from 2.0 g/L dihydroflavonols, which was known to be the highest titer in eukaryotes. Finally, 15.1 mg/L anthocyanins was obtained from glucose by expressing the de novo biosynthesis pathway in S. cerevisiae, which is known to be the highest de novo production. It is the first study to show that through the introduction of a plant anthocyanin transporter and knockout of a yeast endogenous anthocyanin degrading enzyme, the anthocyanin titer has been increased by more than 100 times.

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“…DzGT1 has 35.1% amino acids identity to β-solanine/β-chaconine (steroidal glycoalkaloid) rhamnosyltransferase StSGT3 from potato (McCue et al, 2007), 28.2% amino acids identity to soyasaponin III (triterpene saponin) rhamnosyltransferase GmSGT3 from soybean (Shibuya et al, 2010) and 27.2% amino acids identity to 17-hydroxygeranyllinalool (diterpene) rhamnosyltransferase UGT91T1 from Nicotiana attenuata (Heiling et al, 2021). In addition, DzGT1 shows 22.4-36.2% amino acid identity to these flavonoid UDP-rhamnosyltransferases UGT78D1 (Jones et al, 2003), UGT76F1 (Liu et al, 2018), UGT79B2 (Li et al, 2017), UGT91L1 (Casas et al, 2016), UGT89C1 (Zong et al, 2019), and EkF3URhaT (Lyu et al, 2020). These results demonstrated that DzGT1 displays low amino acid sequence identities to other known rhamnosyltransferases.…”

Section: Alignment Resultsmentioning

confidence: 99%

Identification and Characterization of a Trillin Rhamnosyltransferase From Dioscorea zingiberensis

Mosongo

Han

et al. 2021

Front. Plant Sci.

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Dioscorea zingiberensis accumulates abundant steroidal saponins, such as dioscin, which is the principal bioactive ingredient displaying a wide range of pharmacological activities. Diosgenin is the aglycone of dioscin, and recently, genes encoding cytochrome P450 enzymes in the late steps of diosgenin biosynthesis have been isolated. Diosgenin was successfully synthesized in the cholesterol-producing yeasts. From diosgenin to dioscin, one glucose and two rhamnose groups need to be added. Although genes encoding UDP-glucosyltransferases converting diosgenin to trillin were isolated, genes encoding UDP-rhamnosyltransferases involved in dioscin biosynthesis remain unknown. In this study, we isolated the cDNA encoding the trillin rhamnosyltransferase (designated DzGT1) from D. zingiberensis. Heterologous expression of DzGT1 in Escherichia coli cells showed that the gene product exhibits an enzyme activity that glycosylates the trillin to form prosapogenin A of dioscin (PSA). The transcript level of DzGT1 is in accord with PSA accumulation in different organs of D. zingiberensis. Integration of the biochemical, metabolic, and transcriptional data supported the function of DzGT1 in dioscin biosynthesis. The identification and characterization of DzGT1 will help understand the metabolism of steroidal saponins in D. zingiberensis and provide candidate UDP-rhamnosyltransferase for efficient production of PSA, dioscin, and relevant steroidal saponins in microbial hosts.

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Identification and characterization of three flavonoid 3-O-glycosyltransferases from Epimedium koreanum Nakai

Cited by 20 publications

References 34 publications

Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Genome-wide analysis of UGT gene family identified key gene for the biosynthesis of bioactive flavonol glycosides in Epimedium pubescens Maxim.

Efficient production of anthocyanins in Saccharomyces cerevisiae by introducing anthocyanin transporter and knocking out endogenous degrading enzymes

Identification and Characterization of a Trillin Rhamnosyltransferase From Dioscorea zingiberensis

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