Dataset Information

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

ABSTRACT:

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.

SUBMITTER: Vanegas KG

PROVIDER: S-EPMC6036675 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Publications

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

Vanegas Katherina Garcia KG Larsen Arésu Bondrup AB Eichenberger Michael M Fischer David D Mortensen Uffe Hasbro UH Naesby Michael M

Microbial cell factories 20180709 1

<h4>Background</h4>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 ...[more]

PMID: 29986709

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Dataset Information

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

Background

Results

Conclusions

Publications

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

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