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Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides

Travaini Maria L., Sosa Gustavo M., Ceccarelli Eduardo A., Walter Helmut, Cantrell Charles L., Carrillo Nestor J., Dayan Franck E., Meepagala Kumudini M., Duke Stephen O.
Journal of agricultural and food chemistry 2016 v.64 no.50 pp. 9475-9487
Abutilon theophrasti, Ammi visnaga, Digitaria sanguinalis, Echinochloa crus-galli, Lactuca sativa, Lemna aequinoctialis, Lolium multiflorum, Panicum, Setaria italica, active ingredients, biopesticides, cell death, cell division, fractionation, germination, grasses, greenhouse experimentation, growth retardation, herbicidal properties, inhibitory concentration 50, lettuce, mechanism of action, methylene chloride, millets, pelargonic acid, photosynthesis, phytotoxicity, plant extracts, psoralens, screening, weeds
Plants constitute a source of novel phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. From a previous screening of plant extracts for their phytotoxicity, a dichloromethane extract of Ammi visnaga (L.) Lam. was selected for further study. Phytotoxicity-guided fractionation of this extract yielded two furanochromones, khellin and visnagin, for which herbicidal activity had not been described before. Khellin and visnagin were phytotoxic to model species lettuce (Lactuca sativa) and duckweed (Lemna paucicostata), with IC₅₀ values ranging from 110 to 175 μM. These compounds also inhibited the growth and germination of a diverse group of weeds at 0.5 and 1 mM. These weeds included five grasses [ryegrass (Lolium multiflorum), barnyardgrass (Echinocloa crus-galli), crabgrass (Digitaria sanguinalis), foxtail (Setaria italica), and millet (Panicum sp.)] and two broadleaf species [morningglory (Ipomea sp.) and velvetleaf (Abutilon theophrasti)]. During greenhouse studies visnagin was the most active and showed significant contact postemergence herbicidal activity on velvetleaf and crabgrass at 2 kg active ingredient (ai) ha–¹. Moreover, its effect at 4 kg ai ha–¹ was comparable to the bioherbicide pelargonic acid at the same rate. The mode of action of khellin and visnagin was not a light-dependent process. Both compounds caused membrane destabilization, photosynthetic efficiency reduction, inhibition of cell division, and cell death. These results support the potential of visnagin and, possibly, khellin as bioherbicides or lead molecules for the development of new herbicides.