Phomalactone as the Active Constituent against Mosquitoes from Nigrospora spherica
Affiliation(s)
1 Natural Products Utilization Research Unit, Agricultural Research Service (ARS), United States Department of Agriculture (USDA), University, MS, USA. 2 Center for Medical, Agricultural and Veterinary Entomology (CMAVE), Agricultural Research Service (ARS), United States Department of Agriculture (USDA), Gainesville, FL, USA. 3 Navy Entomology Center of Excellence, Naval Air Station Jacksonville (NASJAX), Jacksonville, FL, USA.
1 Natural Products Utilization Research Unit, Agricultural Research Service (ARS), United States Department of Agriculture (USDA), University, MS, USA. 2 Center for Medical, Agricultural and Veterinary Entomology (CMAVE), Agricultural Research Service (ARS), United States Department of Agriculture (USDA), Gainesville, FL, USA. 3 Navy Entomology Center of Excellence, Naval Air Station Jacksonville (NASJAX), Jacksonville, FL, USA.
ABSTRACT
The culture filtrate of a plant pathogenic fungus that infected Zinnia elegans and Hydrangea macrophylla was investigated for mosquitocidal constituents by bioassay guided isolation. The fungus responsible for the pathogenic effects on Zinnia elegans and Hydrangea macrophylla plants had been identified as Nigrospora spherica by molecular techniques. The mosquito adulticidal constituent in the culture filtrate was identified as phomalactone by spectroscopic techniques. Laboratory bioassays showed that phomalactone had larvicidal activity against permethrin susceptible and resistant Aedes aegypti larvae and topical adulticide activities on permethrin susceptible and resistant Aedes aegypti and Anopheles quadrimaculatus mosquitoes. Phomalactone was effective as a topical adulticide against the standard Orlando reference strain of Ae. aegypti with an LD50 of 0.64 μg/org. Activity against An. quadrimaculatus was 0.20 μg/org.
The culture filtrate of a plant pathogenic fungus that infected Zinnia elegans and Hydrangea macrophylla was investigated for mosquitocidal constituents by bioassay guided isolation. The fungus responsible for the pathogenic effects on Zinnia elegans and Hydrangea macrophylla plants had been identified as Nigrospora spherica by molecular techniques. The mosquito adulticidal constituent in the culture filtrate was identified as phomalactone by spectroscopic techniques. Laboratory bioassays showed that phomalactone had larvicidal activity against permethrin susceptible and resistant Aedes aegypti larvae and topical adulticide activities on permethrin susceptible and resistant Aedes aegypti and Anopheles quadrimaculatus mosquitoes. Phomalactone was effective as a topical adulticide against the standard Orlando reference strain of Ae. aegypti with an LD50 of 0.64 μg/org. Activity against An. quadrimaculatus was 0.20 μg/org.
KEYWORDS
Nigrospora spherica, Phomalactone, Anopheles quadrimaculatus, Aedes aegypti, Permethrin Resistance, Adulticide, Larvicide
Nigrospora spherica, Phomalactone, Anopheles quadrimaculatus, Aedes aegypti, Permethrin Resistance, Adulticide, Larvicide
Cite this paper
M. Meepagala, K. , J. Becnel, J. and S. Estep, A. (2015) Phomalactone as the Active Constituent against Mosquitoes from Nigrospora spherica. Agricultural Sciences, 6, 1195-1201. doi: 10.4236/as.2015.610114.
M. Meepagala, K. , J. Becnel, J. and S. Estep, A. (2015) Phomalactone as the Active Constituent against Mosquitoes from Nigrospora spherica. Agricultural Sciences, 6, 1195-1201. doi: 10.4236/as.2015.610114.
References
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http://dx.doi.org/10.1039/9781849732901-00266 [3] Tanwar, R.S., Dureja, P. and Rathore, H.S. (2012) Biopesticides. In: Rathore, H.S. and Nollet, L.M.L., Eds., Pesticides: Evaluation of Environmental Pollution, CRC Press, London, 587-603.
http://dx.doi.org/10.1201/b11864-28 [4] Meepagala, K.M., Johnson, R.D., Techen, N. and Duke, S.O. (2015) Phomalactone from a Phytopathogenic Fungus infecting Zinnia elegans (Asteraceae) Leaves. In Press. [5] Pridgeon, J.W., Pereira, R.M., Becnel, J.J., Allan, S.A., Clark, G.G. and Linthicum, K.J. (2008) Susceptibility of Aedes aegypti, Culex quinquefasciatus Say, and Anopheles quadrimaculatus Say to 19 Pesticides with Different Modes of Action. Journal of Medical Entomology, 45, 82-87.
http://dx.doi.org/10.1603/0022-2585(2008)45[82:soaacq]2.0.co;2 [6] Pridgeon, J.W., Becnel, J.J., Clark, G.G. and Linthicum, K.J. (2009) A High-Throughput Screening Method to Identify Potential Pesticides for Mosquito Control. Journal of Medical Entomology, 46, 335-341.
http://dx.doi.org/10.1603/033.046.0219 [7] Wu, S.-H., Chen, Y.-W., Shao, S.-C., Wang, L.-D., Yu, Y., Li, Z.-Y., Yang, L-Y., Li, S.-L. and Huang, R. (2009) Two New Solanapyrone Analogs from the Endophytic Fungus Nigrospora sp. YB-141 of Azadirachta indica. Chemistry & Biodiversity, 6, 79-85.
http://dx.doi.org/10.1002/cbdv.200700421 [8] Moore, A., Tabashnik, B.E. and Stark, J.D. (1989) Leg Autotomy: A Novel Mechanism of Protection against Insecticide Poisoning in Diamondback Moth (Lepidoptera: Plutellidae). Journal of Economic Entomology, 82, 1295-1298.
http://dx.doi.org/10.1093/jee/82.5.1295 [9] Trisuwan, K., Rukachaisirikul, V., Sukpondma, Y., Preedanon, S., Phongpaichit, S. and Sakayaroj, J. (2009) Pyrone Derivatives from Themarine-Derived Fungus Nigrospora sp. PSU-F18. Phytochemistry, 70, 554-557.
http://dx.doi.org/10.1016/j.phytochem.2009.01.008 [10] Kim, J.-C., Choi, G.J., Park, J.-H., Kim, H.T. and Cho, K.Y. (2001) Activity against Plant Pathogenic Fungi of Phomalactone Isolated from Nigrospora sphaerica. Pest Management Science, 57, 554-559.
http://dx.doi.org/10.1002/ps.318 [11] Fukushima, T., Tanaka, M., Gohbara, M. and Fujimori, T. (1998) Phytotoxicity of Three Lactones from Nigrospora sacchari. Phytochemistry, 48, 625-630.
http://dx.doi.org/10.1016/S0031-9422(97)01023-6 [12] Evans Jr., R.H., Ellestad, G.A. and Kunstmann, M.P. (1969) Two New Metabolites from an Unidentified Nigrospora Species. Tetrahedron Letters, 22, 1791-1794.
http://dx.doi.org/10.1016/S0040-4039(01)88013-8 [13] Yamamoto, I., Suide, H., Hemmi, T. and Yamano, T. (1970) Antimicrobial α, β-Unsaturated δ-Lactones from Molds. Takeda Kenkyusho Ho, 29, 1-10. [14] Yamano, T., Hemmi, S., Yamamoto, I. and Tsubaki, K. (1971) Fermentative Production of Antibiotic Phomalactone. Japanese Kokai Tokkyo Koho, JP 46032800 B4 19710925. [15] Jimenez-Romero, C., Ortega-Barria, E., Arnold, A.E. and Cubilla-Rios, L. (2008) Activity against Plasmodium falciparum of Lactones Isolated from the Endophytic Fugus Xylaria sp. Pharmaceutical Biology, 46, 700-703.
http://dx.doi.org/10.1080/13880200802215859 [16] Krasnoff, S.B. and Gupta, S. (1994) Identification of the Antibiotic Phomalactone from the Entomopathogenic Fungus Hirsutella thompsonii var. synnematosa. Journal of Chemical Ecology, 20, 293-302.
http://dx.doi.org/10.1007/BF02064437 [17] Wu, H.-Y., Wang, Y.-L., Tan, J.-L., Zhu, C.-Y., Li, D.-X., Huang, R., Zhang, K.-Q. and Niu, X.-M. (2012) Regulation of the Growth of Cotton Bollworms by Metabolites from the Entomopathogenic Fungus Paecilomyces cateniobliquus. Journal of Agricultural and Food Chemistry, 60, 5604-5608.
http://dx.doi.org/10.1021/jf302054b [18] Khambay, B.P.S., Bourne, J.M., Cameron, S., Kerry, B.R. and Zaki, M.J. (2000) A Nematicidal Metabolite from Verticillium chlamydosporium. Pest Management Science, 56, 1098-1099.
http://dx.doi.org/10.1002/1526-4998(200012)56:12<1098::AID-PS244>3.0.CO;2-H
[1] Ramírez-Lepe, M. and Ramírez-Suero, M. (2012) Biological Control of Mosquito Larvae by Bacillus thuringiensis subsp. israelensis. In: Perveen, F., Ed., Insecticides—Pest Engineering, InTech, Rijeka, 239-264.
http://dx.doi.org/10.5772/29139 [2] Bravo, A., Rincon-Castro, M.C.D., Ibarra, J.E. and Soberon, M. (2011) CHAPTER 8: Towards a Healthy Control of Insect Pests: Potential Use of Microbial Insecticides. Green Trends in Insect Control, 11, 266-299.
http://dx.doi.org/10.1039/9781849732901-00266 [3] Tanwar, R.S., Dureja, P. and Rathore, H.S. (2012) Biopesticides. In: Rathore, H.S. and Nollet, L.M.L., Eds., Pesticides: Evaluation of Environmental Pollution, CRC Press, London, 587-603.
http://dx.doi.org/10.1201/b11864-28 [4] Meepagala, K.M., Johnson, R.D., Techen, N. and Duke, S.O. (2015) Phomalactone from a Phytopathogenic Fungus infecting Zinnia elegans (Asteraceae) Leaves. In Press. [5] Pridgeon, J.W., Pereira, R.M., Becnel, J.J., Allan, S.A., Clark, G.G. and Linthicum, K.J. (2008) Susceptibility of Aedes aegypti, Culex quinquefasciatus Say, and Anopheles quadrimaculatus Say to 19 Pesticides with Different Modes of Action. Journal of Medical Entomology, 45, 82-87.
http://dx.doi.org/10.1603/0022-2585(2008)45[82:soaacq]2.0.co;2 [6] Pridgeon, J.W., Becnel, J.J., Clark, G.G. and Linthicum, K.J. (2009) A High-Throughput Screening Method to Identify Potential Pesticides for Mosquito Control. Journal of Medical Entomology, 46, 335-341.
http://dx.doi.org/10.1603/033.046.0219 [7] Wu, S.-H., Chen, Y.-W., Shao, S.-C., Wang, L.-D., Yu, Y., Li, Z.-Y., Yang, L-Y., Li, S.-L. and Huang, R. (2009) Two New Solanapyrone Analogs from the Endophytic Fungus Nigrospora sp. YB-141 of Azadirachta indica. Chemistry & Biodiversity, 6, 79-85.
http://dx.doi.org/10.1002/cbdv.200700421 [8] Moore, A., Tabashnik, B.E. and Stark, J.D. (1989) Leg Autotomy: A Novel Mechanism of Protection against Insecticide Poisoning in Diamondback Moth (Lepidoptera: Plutellidae). Journal of Economic Entomology, 82, 1295-1298.
http://dx.doi.org/10.1093/jee/82.5.1295 [9] Trisuwan, K., Rukachaisirikul, V., Sukpondma, Y., Preedanon, S., Phongpaichit, S. and Sakayaroj, J. (2009) Pyrone Derivatives from Themarine-Derived Fungus Nigrospora sp. PSU-F18. Phytochemistry, 70, 554-557.
http://dx.doi.org/10.1016/j.phytochem.2009.01.008 [10] Kim, J.-C., Choi, G.J., Park, J.-H., Kim, H.T. and Cho, K.Y. (2001) Activity against Plant Pathogenic Fungi of Phomalactone Isolated from Nigrospora sphaerica. Pest Management Science, 57, 554-559.
http://dx.doi.org/10.1002/ps.318 [11] Fukushima, T., Tanaka, M., Gohbara, M. and Fujimori, T. (1998) Phytotoxicity of Three Lactones from Nigrospora sacchari. Phytochemistry, 48, 625-630.
http://dx.doi.org/10.1016/S0031-9422(97)01023-6 [12] Evans Jr., R.H., Ellestad, G.A. and Kunstmann, M.P. (1969) Two New Metabolites from an Unidentified Nigrospora Species. Tetrahedron Letters, 22, 1791-1794.
http://dx.doi.org/10.1016/S0040-4039(01)88013-8 [13] Yamamoto, I., Suide, H., Hemmi, T. and Yamano, T. (1970) Antimicrobial α, β-Unsaturated δ-Lactones from Molds. Takeda Kenkyusho Ho, 29, 1-10. [14] Yamano, T., Hemmi, S., Yamamoto, I. and Tsubaki, K. (1971) Fermentative Production of Antibiotic Phomalactone. Japanese Kokai Tokkyo Koho, JP 46032800 B4 19710925. [15] Jimenez-Romero, C., Ortega-Barria, E., Arnold, A.E. and Cubilla-Rios, L. (2008) Activity against Plasmodium falciparum of Lactones Isolated from the Endophytic Fugus Xylaria sp. Pharmaceutical Biology, 46, 700-703.
http://dx.doi.org/10.1080/13880200802215859 [16] Krasnoff, S.B. and Gupta, S. (1994) Identification of the Antibiotic Phomalactone from the Entomopathogenic Fungus Hirsutella thompsonii var. synnematosa. Journal of Chemical Ecology, 20, 293-302.
http://dx.doi.org/10.1007/BF02064437 [17] Wu, H.-Y., Wang, Y.-L., Tan, J.-L., Zhu, C.-Y., Li, D.-X., Huang, R., Zhang, K.-Q. and Niu, X.-M. (2012) Regulation of the Growth of Cotton Bollworms by Metabolites from the Entomopathogenic Fungus Paecilomyces cateniobliquus. Journal of Agricultural and Food Chemistry, 60, 5604-5608.
http://dx.doi.org/10.1021/jf302054b [18] Khambay, B.P.S., Bourne, J.M., Cameron, S., Kerry, B.R. and Zaki, M.J. (2000) A Nematicidal Metabolite from Verticillium chlamydosporium. Pest Management Science, 56, 1098-1099.
http://dx.doi.org/10.1002/1526-4998(200012)56:12<1098::AID-PS244>3.0.CO;2-H