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The biosynthesis of allelopathic di-C-glycosylflavones from the roots of Desmodium incanum (G. Mey.) DC

Hao, Bing, Caulfield, John C., Hamilton, Mary L., Pickett, John A., Midega, Charles A. O., Khan, Zeyaur R., Wang, Junru R. and Hooper, Antony M. 2015. The biosynthesis of allelopathic di-C-glycosylflavones from the roots of Desmodium incanum (G. Mey.) DC. Organic and Biomolecular Chemistry 13 (48) , pp. 11663-11673. 10.1039/C5OB01926E

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Abstract

The allelopathic root exudate of the drought-tolerant subsistence cereal intercrop D. incanum, protecting against the parasitic weed Striga hermonthica, comprises a number of di-C-glycosylflavones specifically containing C-glucosyl, C-galactosyl and C-arabinosyl moieties. Here we demonstrate that the biosynthesis of all compounds containing a C-glucose involves C-glucosylation of 2-hydroxynaringenin with subsequent C-galactosylation, C-glucosylation or C-arabinosylation. In addition, the crude soluble enzyme extract converts two fluorinated 2-hydroxyflavanone analogues to corresponding mono- and di-C-glycosylflavones demonstrating that some differences in C-ring substitution can be tolerated by the plant enzymes. Elucidating the biosynthesis of these C-glycosylflavones (CGFs) has the potential to open up opportunities for transferring the enzymic and genetic basis for the S. hermonthica inhibiting allelopathic trait to food crop plants.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 13 October 2015
Last Modified: 23 Nov 2017 16:28
URI: http://orca.cf.ac.uk/id/eprint/106836

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