Issue 48, 2015

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
16 Sep 2015
Accepted
13 Oct 2015
First published
14 Oct 2015

Org. Biomol. Chem., 2015,13, 11663-11673

Author version available

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

B. Hao, J. C. Caulfield, M. L. Hamilton, J. A. Pickett, C. A. O. Midega, Z. R. Khan, J. R. Wang and A. M. Hooper, Org. Biomol. Chem., 2015, 13, 11663 DOI: 10.1039/C5OB01926E

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