Location: Natural Products Utilization Research
2016 Annual Report
Accomplishments
1. Potent pytotoxins from toothpickweed identified. Plants constitute a rich source of novel and structurally diverse phytotoxic compounds to be explored in searching for effective and environmentally safe herbicides. ARS scientists at USDA-ARS-Natural Products Utilization Research Unit (NPURU) selected toothpickweed (Ammi visnaga) for further study from screening nearly 2400 plant extracts extract. Phytotoxicity-guided fractionation of the extract yielded two compounds: khellin and visnagin, whose herbicidal activity had not been described before. In laboratory assays, khellin and visnagin inhibited the growth of lettuce and duckweed. Also, both compounds reduced the growth and germination of weeds: ryegrass, morningglory, foxtail and millet. The inhibitory activities of these compounds were similar to those of the commercial herbicides acetochlor and glyphosate in the lab bioassays. During greenhouse studies visnagin was more active, with significant contact post-emergence herbicidal activity on velvetleaf and crabgrass 2 kg ai ha-1. Moreover, its effect on velvetleaf, crabgrass and barnyardgrass (Echinochloa crus-galli) at 4 kg ai ha-1 was comparable to the bioherbicide pelargonic acid at the same rate. These results support the potential of visnagin, and possibly khellin, as bioherbicides or lead molecules for the development of new herbicides.
Review Publications
Zheljazkov, V.D., Gawde, A., Cantrell, C.L., Astatkie, T., Schlegel, V. 2015. Distillation time as tool for improved antimalarial activity and differential oil composition of cumin seed oil. PLoS One. doi:10.1371/journal.pone.0144120.
Meepagala, K.M., Johnson, R.D., Duke, S.O. 2016. Curvularin and dehydrocurvularin as phytotoxic constituents from curvularia intermedia infecting pandanus amaryllifolius. Journal of Agricultural and Food Chemistry. 5:12-22.
Dhar, S., Kumar, A., Zhang, L., Rimando, A.M., Lage, J.M., Lewin, J.R., Atfi, A., Zhang, X., Levenson, A.S. 2016. Dietary Pterostilbene is a novel MTA1-targeted chemopreventive and therapeutic agent in prostate cancer. Oncotarget. doi: 10.18632/oncotarget.7841.
Trivella, A., Stawinoga, M., Dayan, F.E., Cantrell, C.L., Mazellier, P., Richard, C. 2015. Photolysis of natural B-triketonic herbicides in water. Water Research. 78:28-36.
Meepagala, K.M., Estep, A.S., Becnel, J.J. 2016. Larvicidal and adulticidal activity chroman and chromene analogues against susceptible and permethrin-resistant mosquito strains. Journal of Agricultural and Food Chemistry. 64(24):4914-4920.
Xie, Q., Li, S.-X., Liao, D.-F., Wang, W., Tekwani, B., Huang, H.-Y., Ali, A., ur Rehman, J., Schrader, K.K, Duke, S.O., Cantrell, C.L., Wedge, D.E. 2015. Bio-pesticidal and antimicrobial coumarins from Angelica dahurica (Fisch. Ex Hoffm). Natural Product Communications. 2016;10(3):294-306.
Meepagala, K.M., Johnson, R.D., Techen, N., Wedge, D.E., Duke, S.O. 2015. Phomalactone from a phytopathogenic fungus infecting Zinnia elegans (Asteraceae) leaves. Journal of Chemical Ecology. 41:602-612.
Kaymakcioglu, B.K., Beyhan, N., Tabanca, N., Ali, A., Wedge, D.E., Duke, S.O., Bernier, U.R., Khan, I.A. 2015. Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective. Medicinal Chemistry Research. 24:3632-3644.
Correa, E.A., Dayan, F.E., Owens, D.K., Rimando, A.M., Duke, S.O. 2016. Glyphosate-resistant and conventional canola (Brassica napus L.) responses to glyphosate and Aminomethylphosphonic Acid (AMPA) treatment. Journal of Agricultural and Food Chemistry. 64:3508-3513.
Carvalho, C.R., Wedge, D.E., Cantrell, C.L., Silva-Hughes, A.F., Pan, Z., Moraes, R.M., Madoxx, V.L., Rosa, L.H. 2016. Molecular phylogeny, diversity and bioprospecting of endophytic fungi associated with wild ethnomedicinal North American plant Echinacea purpurea (Asteraceae). Chemistry and Biodiversity. 13:918-930 DOI: 10.1002/cbdv.201500299.
Burkhardt, A., Gawde, A., Cantrell, C.L., Zheljazkov, V.D. 2015. Effect of varying ratios of produced water and municipal water on soil characteristics, plant biomass, and secondary metabolites of Artemisia annua and Panicum virgatum. Industrial Crops and Products. 76:987-994.
Burkhardt, A., Sintim, H., Gawde, A., Cantrell, C.L., Astatkie, T., Zheljazkov, V.D., Schlegel, V. 2015. Method for attaining fennel (Foeniculum vulgare Mill.) seed oil fractions with different composition and antioxidant capacity. Journal of Applied Research on Medicinal and Aromatic Plants. 2:87-91.
Chakraborty, S., Kumar, A., Butt, N.A., Zhang, L., Williams, R., Rimando, A.M., Biswas, P.K., Levenson, A.S. 2016. Molecular insight into the differential anti-androgenic activity of resveratrol and its natural analogs: In Silico approach to understand biological actions. Molecular Biosystems. 12:1702-1709. DOI: 10.1039/C6MB00186F
Dhar, S., Kumar, A., Rimando, A.M., Zhang, X., Levenson, A.S. 2015. Resveratrol and pterostilbene epigenetically restore PTEN expression by targeting OncomiRs of the miR-17 family in prostate cancer. Oncotarget. 6(29):27214-27226.
Gadetskaya, A.V., Tarawneh, A.H., Zhusupova, G.E., Gemejiyeva, N.G., Cantrell, C.L., Cutler, S.J., Ross, S.A. 2015. Sulfated phenolic compounds from Limonium caspium: Isolation, structural elucidation, and biological evaluation. Fitoterapia. 104:80-85.
Nicolau-Goncalves, V., Cantrell, C.L., Wedge, D.E., Ferreira, M.C., Soares, M.A., Jacob, M.R., Oliveira, F., Galante, D., Rodrigues, F., Alves, T., Zani, C., Junior, P., Murta, S., Romanho, A., Barbosa, E., Kroon, E., Oliveira, J., Gomez-Silva, B., Galetovic, A., Rosa, C.A., Rosa, L. 2015. Fungi associated with rocks of the Atacama Desert: taxonomy, distribution, diversity, ecology and bioprospection for bioactive compounds. Environmental Microbiology. 18:232-245.
Goncalves, V.N., Carvalho, C.R., Johann, S., Mendes, G., Alves, T.M., Zani, C.L., Policarpo, Jr, A., Murta, S.M., Romanha, A.J., Cantrell, C.L., Rosa, C.A., Rosa, L.H. 2015. Antibacterial, antifungal and antiprotozoal activities of fungal communities present in different substrates from Antarctica. Polar Biology. 38:1143-1152.
Joyce, B.L., Zheljazkov, V.D., Sykes, R., Cantrell, C.L., Hamilton, C., Mann, D.G., Rodriquez, M., Mielenz, J., Astatkie, T., Stewart, Jr., C. 2015. Ethanol and high-value terpene co-production from lignocellulosic biomass of Cymbopogon flexuosus and Cymbopogon martinii. PLoS One. 10(10):1-17. doi:10.1371/journal.pone.0139195
Kumar, A., Dhar, S., Rimando, A.M., Lage, J.M., Lewin, J.R., Zhang, X., Levenson, A.S. 2015. Epigenetic potential of resveratrol and analogs in preclinical models of prostate cancer. Annals of the New York Academy of Sciences. 1348:1-9.
Poudyal, S., Zheljazkov, V.D., Cantrell, C.L. 2016. Coal-bed methane water effects on dill and essential oils. Journal of Environmental Quality. 45:728-733.
Rimando, A.M., Khan, S.I., Mizuno, C., Ren, G., Mathews, S.T., Kim, H., Yokoyama, W.H. 2015. Evaluation of PPARa activation by known blueberry constituents. Journal of the Science of Food and Agriculture. 96(5):1666-1671. doi: 10.1002/jsfa.7269.
Burkhardt, A., Gawde, A., Cantrell, C.L., Baxter, H.L., Joyce, B.L., Stewart, Jr., C.N., Zheljazkov, V.D. 2015. Effects of produced water on soil characteristics, plant biomass, and secondary metabolites. Journal of Environmental Quality. 44:1938-1947.
Chen, S., Yu, J., Li, Q., Zhao, J., Wedge, D.E., Duke, S.O., Liao, D., Wang, Y., Fronczek, F.R., Khan, I.A., Wang, W. 2016. 7a-hydroxfriedelan-3one-26-OL-29-OIC acid and other constituents from Pileostegia Viburnoids VAR. Glabrescens. Natural Product Communications. 11(7):931-934.
