Indirect and direct routes to C-glycosylated flavones in Saccharomyces cerevisiae 

Research output: Contribution to journalJournal article – Annual report year: 2018Researchpeer-review

Documents

DOI

View graph of relations

Background: C-glycosylated flavones have recently attracted increased attention due to their possible benefits in human health. These biologically active compounds are part of the human diet, and the C-linkage makes them more resistant to hydrolysis and degradation than O-glycosides. In contrast to O-glycosyltransferases, few C-glycosyltransferases (CGTs) have so far been characterized. Two different biosynthetic routes for C-glycosylated flavones have been identified in plants. Depending on the type of C-glycosyltransferase, flavones can be glycosylated either directly or indirectly via C-glycosylation of a 2-hydroxyflavanone intermediate formed by a flavanone 2-hydroxylase (F2H).
Results: In this study, we reconstructed the pathways in the yeast Saccharomyces cerevisiae, to produce some relevant CGT substrates, either the flavanones naringenin and eriodictyol or the flavones apigenin and luteolin. We then demonstrated two-step indirect glycosylation using combinations of F2H and CGT, to convert 2-hydroxyflavanone intermediates into the 6C-glucoside flavones isovitexin and isoorientin, and the 8C-glucoside flavones vitexin and orientin. Furthermore, we established direct glycosylation of flavones using the recently identified GtUF6CGT1 from Gentiana triflora. The ratio between 6C and 8C glycosylation depended on the CGT used. The indirect route resulted in mixtures, similar to what has been reported for in vitro experiments. In this case, hydroxylation at the flavonoid 3′-position shifted the ratio towards the 8C-glucosylated orientin. The direct flavone glycosylation by GtUF6CGT1, on the other hand, resulted exclusively in 6C-glucosides.
Conclusions: The current study features yeast as a promising host for production of flavone C-glycosides, and it provides a set of tools and strains for identifying and studying CGTs and their mechanisms of C-glycosylation.
Original languageEnglish
Article number107
JournalMicrobial Cell Factories
Volume17
Number of pages10
ISSN1475-2859
DOIs
Publication statusPublished - 2018

Bibliographical note

Open Access: This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/)

CitationsWeb of Science® Times Cited: No match on DOI

    Research areas

  • Vitexin , Isovitexin, Orientin, Isoorientin , Glycosyl C-transferase , Flavanone 2-hydroxylase
Download as:
Download as PDF
Select render style:
APAAuthorCBE/CSEHarvardMLAStandardVancouverShortLong
PDF
Download as HTML
Select render style:
APAAuthorCBE/CSEHarvardMLAStandardVancouverShortLong
HTML
Download as Word
Select render style:
APAAuthorCBE/CSEHarvardMLAStandardVancouverShortLong
Word

Download statistics

No data available

ID: 153554882