Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins

A - Papers appearing in refereed journals

Hao, B., Caulfield, J. C., Hamilton, M. L., Pickett, J. A., Midega, C. A. O., Khan, Z. R., Wang, J. and Hooper, A. M. 2016. Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins. Phytochemistry. 125 (May 2016), pp. 73-87.

AuthorsHao, B., Caulfield, J. C., Hamilton, M. L., Pickett, J. A., Midega, C. A. O., Khan, Z. R., Wang, J. and Hooper, A. M.
Abstract

The rice C-glycosyltransferase (OsCGT) is one of only a small number of characterised plant C-glycosyltransferases (CGT) known. The enzyme C-glucosylates a 2-hydroxyflavanone substrate with UDP-glucose as the sugar donor to produce C-glucosyl-2-hydroxyflavanones. We tested substrate specificity of the enzyme, using synthetic 2-hydroxyflavanones, and showed it has the potential to generate known natural CGFs that have been isolated from rice and also other plants. In addition, we synthesised novel, unnatural 2-hydroxyflavanone substrates to test the B-ring chemical space of substrate accepted by the OsCGT and demonstrated the OsCGT capacity as a synthetic reagent to generate significant quantities of known and novel CGFs. Many B-ring analogues are tolerated within a confined steric limit. Finally the OsCGT was used to generate novel mono-C-glucosyl-2-hydroxyflavanones as putative biosynthetic intermediates to examine the potential of Desmodium incanum biosynthetic CGTs to produce novel di-C-glycosylflavones, compounds implicated in the allelopathic biological activity of Desmodium against parasitic weeds from the Striga genus.

KeywordsOryza sativa; Poaceae; C-Glycosyltransferase; OsCGT; 2-Hydroxyflavanone; C-Glucosylflavone; Di-C-glycosylflavone; Biotechnological synthesis; Substrate specificity; Chemical space
Year of Publication2016
JournalPhytochemistry
Journal citation125 (May 2016), pp. 73-87
Digital Object Identifier (DOI)doi:10.1016/j.phytochem.2016.02.013
Open accessPublished as ‘gold’ (paid) open access
FunderBill and Melinda Gates Foundation
European Union
Funder project or codeDelivering Sustainable Systems (SS) [ISPG]
Adapting Push Pull Technology for Climate Change
Integrated Striga Management for Africa
Project: 5447
Publisher's version
Copyright license
CC BY
Output statusPublished
Publication dates
Online26 Feb 2016
Publication process dates
Accepted19 Feb 2016
PublisherElsevier
ISSN0031-9422

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