Advances in plant-derived C-glycosides: Phytochemistry, bioactivities, and biotechnological production

Zhang, Yaqun; Zhang, Meng; Wang, Zilong; Qiao, Xue; Ye, Min

doi:10.1016/j.biotechadv.2022.108030

Cited by 30 publications

(43 citation statements)

References 197 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the kinetic assay of ScCGT1, the reaction was carried out at 30 °C for 15 min. Briefly, an enzymatic assay containing 200 mM MES buffer (pH 6.5), 5 μg of purified ScCGT1, 1 mM UDP-Glc, and various concentrations of phloretin or 2-hydroxynaringenin (5,10,20,50,75,100,150,200, and 300 μM). All the reactions were quenched with an equal volume of methanol.…”

Section: Determination Of Kinetic Parametersmentioning

confidence: 99%

See 1 more Smart Citation

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Zhang

et al. 2022

Microb Cell Fact

View full text Add to dashboard Cite

Background Flavonoid C-glycosides have many beneficial effects and are widely used in food and medicine. However, plants contain a limited number of flavonoid C-glycosides, and it is challenging to create these substances chemically. Results To screen more robust C-glycosyltransferases (CGTs) for the biosynthesis of flavonoid C-glycosides, one CGT enzyme from Stenoloma chusanum (ScCGT1) was characterized. Biochemical analyses revealed that ScCGT1 showed the C-glycosylation activity for phloretin, 2-hydroxynaringenin, and 2-hydroxyeriodictyol. Structure modeling and mutagenesis experiments indicated that the glycosylation of ScCGT1 may be initiated by the synergistic action of conserved residue His26 and Asp14. The P164T mutation increased C-glycosylation activity by forming a hydrogen bond with the sugar donor. Furthermore, when using phloretin as a substrate, the extracellular nothofagin production obtained from the Escherichia coli strain ScCGT1-P164T reached 38 mg/L, which was 2.3-fold higher than that of the wild-type strain. Finally, it is proved that the coupling catalysis of CjFNS I/F2H and ScCGT1-P164T could convert naringenin into vitexin and isovitexin. Conclusion This is the first time that C-glycosyltransferase has been characterized from fern species and provides a candidate gene and strategy for the efficient production of bioactive C-glycosides using enzyme catalysis and metabolic engineering.

show abstract

Section: Determination Of Kinetic Parametersmentioning

confidence: 99%

“…Based on their substrate structures, plant CGTs could be categorized into 2 types: type I and type II (Additional file 1: Fig. S1) [10]. Type I CGTs attach one glucosyl moiety to a 2-hydroxyflavanone aglycone, which is formed by the hydroxylation at the C2 of the C-ring under the catalysis of flavanone 2-hydroxylase (F2H) [7].…”

Section: Introductionmentioning

confidence: 99%

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Zhang

et al. 2022

Microb Cell Fact

View full text Add to dashboard Cite

show abstract

“…C -Glycosides represent an important class of bioactive natural products and are widely distributed in plants. 1 The sugar moieties are connected to aglycones through a C–C glycosidic bond. 2 In plants, the C–C glycosidic bonds are usually synthesized by C -glycosyltransferases (CGTs).…”

mentioning

confidence: 99%

“…4 According to substrate selectivity, CGTs could be divided into two types. 1 Most of them belong to type I, which use 2-hydroxyflavanones, dihydrochalcones, or benzophenones as substrates. Typical type I CGTs include GgCGT from Glycyrrhiza glabra and UGT708D1 from Glycine max .…”

mentioning

confidence: 99%

See 1 more Smart Citation

Functional characterization of a C-glycosyltransferase from Pueraria lobata with dual-substrate selectivity

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

Reaction intensification for biocatalytic production of polyphenolic natural product di‐C‐β‐glucosides

Borg

Krammer

et al. 2023

Biotech & Bioengineering

View full text Add to dashboard Cite

Polyphenolic aglycones featuring two sugars individually attached via C-glycosidic linkage (di-C-glycosides) represent a rare class of plant natural products with unique physicochemical properties and biological activities. Natural scarcity of such di-C-glycosides limits their use-inspired exploration as pharmaceutical ingredients. Here, we show a biocatalytic process technology for reaction-intensified production of the di-C-β-glucosides of two representative phenol substrates, phloretin (a natural flavonoid) and phenyl-trihydroxyacetophenone (a phenolic synthon for synthesis), from sucrose. The synthesis proceeds via an iterative two-fold C-glycosylation of the respective aglycone, supplied as inclusion complex with 2-hydroxypropyl β-cyclodextrin for enhanced water solubility of up to 50 mmol/L, catalyzed by a kumquat di-C-glycosyltransferase (di-CGT), and it uses UDP-Glc provided in situ from sucrose by a soybean sucrose synthase, with catalytic amounts (≤3 mol%) of UDP added. Time course analysis reveals the second C-glycosylation as rate-limiting (0.4-0.5 mmol/L/min) for the di-C-glucoside production. With internal supply from sucrose keeping the UDP-Glc at a constant steady-state concentration (≥50% of the UDP added) during the reaction, the di-C-glycosylation is driven to completion (≥95% yield). Contrary to the mono-C-glucoside intermediate which is stable, the di-C-glucoside requires the addition of reducing agent (10 mmol/L 2-mercaptoethanol) to prevent its decomposition during the synthesis. Both di-C-glucosides are isolated from the reaction mixtures in excellent purity (≥95%), and their expected structures are confirmed by NMR. Collectively, this study demonstrates efficient glycosyltransferase cascade reaction for flexible use in natural product di-C-β-glucoside synthesis from expedient substrates.

show abstract

Advances in plant-derived C-glycosides: Phytochemistry, bioactivities, and biotechnological production

Cited by 30 publications

References 197 publications

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Identification of a flavonoid C-glycosyltransferase from fern species Stenoloma chusanum and the application in synthesizing flavonoid C-glycosides in Escherichia coli

Functional characterization of a C-glycosyltransferase from Pueraria lobata with dual-substrate selectivity

Reaction intensification for biocatalytic production of polyphenolic natural product di‐C‐β‐glucosides

Contact Info

Product

Resources

About