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Org Biomol Chem ; 13(48): 11663-73, 2015 Dec 28.
Article in English | MEDLINE | ID: mdl-26478440

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.


Subject(s)
Allelopathy , Fabaceae/chemistry , Flavones/biosynthesis , Flavones/chemistry , Plant Roots/chemistry , Glycosylation , Molecular Structure , Spectrometry, Mass, Electrospray Ionization
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