ArticleThe Journal of biological chemistry2009
The C-glycosylation of flavonoids in cereals.
Article in The Journal of biological chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 98 papers.
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Who cites it
98 citing papers in PubMed, 300 citations in OpenAlex.
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- Extraction, Purification of C‑Glycosides from Arisaema decipiens for Studying its Anti-Inflammatory and Bioactivities.ACS omega · 2026Article
- Integrated transcriptomic and metabolomic analyses identify OsCGT as essential for C-glycosyl flavone biosynthesis in OsDET1-mutant rice seeds.BMC plant biology · 2026Article
- Advances in UDP-Glycosyltransferases from Medicinal Plants: Discovery, Catalytic Mechanism, Engineering and Biosynthetic Application.Metabolites · 2026Review
- Comprehensive review of biosynthesis, plant function, metabolism and new therapeutic bioactivities of flavonoids.ADMET & DMPK · 2026Review
- Tissue-specific profiles of phenolic metabolites in rice deprived ofFrontiers in plant science · 2026Article
- HalophyticACS omega · 2025Article
- Accumulation of phytoalexins and alteration in plant hormone profiles in rice leaves following sap sucking by the brown planthopper and green rice leafhopper.Journal of pesticide science · 2025Article
- Natural variation of the wheat root exudate metabolome and its influence on biological nitrification inhibition activity.Plant biotechnology journal · 2025Article
- Metabolomic Analysis Reveals the Diversity of Defense Metabolites in Nine Cereal Crops.Plants (Basel, Switzerland) · 2025Article
- Integrative Analyses of Metabolome and Transcriptome Reveal Regulatory Network of Puerarin Biosynthesis inMolecules (Basel, Switzerland) · 2024Article
- UGT708S6 from Dendrobium catenatum, catalyzes the formation of flavonoid C-glycosides.BMC biotechnology · 2024Article
- Unravelling and reconstructing the biosynthetic pathway of bergenin.Nature communications · 2024Article
- Accumulation mechanism of metabolite markers identified by machine learning between Qingyuan and Xiushui counties in Polygonatum cyrtonema Hua.BMC plant biology · 2024Article
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- Comparative Transcriptome Analysis ofBiomolecules · 2023Article
- Multi-omics characterization of the microbial populations and chemical space composition of a water kefir fermentation.Frontiers in molecular biosciences · 2023Article
- Designing plant flavonoids: harnessing transcriptional regulation and enzyme variation to enhance yield and diversity.Frontiers in plant science · 2023Review
- Stressing the importance of plant specialized metabolites: omics-based approaches for discovering specialized metabolism in plant stress responses.Frontiers in plant science · 2023Review
38 more citing papers are in PubMed but not listed here.
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Flavonoids normally accumulate in plants as O-glycosylated derivatives, but several species, including major cereal crops, predominantly synthesize flavone-C-glycosides, which are stable to hydrolysis and are biologically active both in planta and as dietary components. An enzyme (OsCGT) catalyzing the UDP-glucose-dependent C-glucosylation of 2-hydroxyflavanone precursors of flavonoids has been identified and cloned from rice (Oryza sativa ssp. indica), with a similar protein characterized in wheat (Triticum aestivum L.). OsCGT is a 49-kDa family 1 glycosyltransferase related to known O-glucosyltransferases. The recombinant enzyme C-glucosylated 2-hydroxyflavanones but had negligible O-glucosyltransferase activity with flavonoid acceptors. Enzyme chemistry studies suggested that OsCGT preferentially C-glucosylated the dibenzoylmethane tautomers formed in equilibrium with 2-hydroxyflavanones. The resulting 2-hydroxyflavanone-C-glucosides were unstable and spontaneously dehydrated in vitro to yield a mixture of 6C- and 8C-glucosyl derivatives of the respective flavones. In contrast, in planta, only the respective 6C-glucosides accumulated. Consistent with this selectivity in glycosylation product, a dehydratase activity that preferentially converted 2-hydroxyflavanone-C-glucosides to the corresponding flavone-6C-glucosides was identified in both rice and wheat. Our results demonstrate that cereal crops synthesize C-glucosylated flavones through the concerted action of a CGT and dehydratase acting on activated 2-hydroxyflavanones, as an alternative means of generating flavonoid metabolites.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.