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    Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides
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    † Instituto de Biologı́a Molecular y Celular de Rosario (IBR), CONICET, Facultad de Ciencias Bioquı́micas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina
    ‡ AgroField Consulting, Gruenstadter Strasse 82, 67283 Obrigheim, Germany
    ⊥ Investigaciones Biológicas en Agroquímicos Rosario S.A. (INBIOAR S.A.), Cordoba 1437, Fifth Floor—Office 2, 2000 Rosario, Argentina
    § Natural Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, P.O. Box 1848, University, Mississippi 38677, United States
    *(M.L.T) E-mail: [email protected]
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2016, 64, 50, 9475–9487
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    https://doi.org/10.1021/acs.jafc.6b02462
    Published November 28, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    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.

    Copyright © 2016 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.6b02462.

    • Additional data as cited in the manuscript. Phytotoxicity of commercial standards of khellin and visnagin as well as five structural analogues (Table ST1). Pictures of Ammi visnaga (L.) Lam. (Figure S1). 1H NMR data of fractions XIV (khellin) (Figure S2), XV (Figure S4), XVI (Figure S5), and XVII (visnagin) (Figure S6). 13C NMR data of fractions XIV (khellin) (Figure S3) and XVII (visnagin) (Figure S7). Dose–response curves of khellin and visnagin on duckweed (Figure S8), lettuce (Figure S10), and ryegrass (Figure S11). Effect of khellin and visnagin on the tissue of duckweed (Figure S9) and cucumber cotyledon disks under different conditions of illumination (Figure S13). Comparison of germination and growth of lettuce and ryegrass in water and solvent control (Figure S12). Detection and quantification of ROS in cucumber cotyledon disks in darkness (Figure S14). Effect of khellin and visnagin on root meristem cell division of A. cepa (Figure S15) (PDF)

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    Cite this: J. Agric. Food Chem. 2016, 64, 50, 9475–9487
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jafc.6b02462
    Published November 28, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

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