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Structural Factors of Annonaceous Acetogenins and Their Semisynthetic Analogues Related with the Toxicity on Spodoptera frugiperda

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DOI: 10.4236/jacen.2015.42006    3,285 Downloads   3,757 Views   Citations


Toxic and nutritional effects of annonaceous acetogenins and their semisynthetic analogues on Spodoptera frugiperda were evaluated. Structural modification of the natural ACG, blocking the OH flanking THF with MOM, allowed us to suggest the mode of action of ACG in the membrane. Our study emphasizes the role of the flanking OH and acetyl groups of THF with the membrane hydrophilic polar head groups. They are essential structural factors in the ACG that facilitate the intermolecular interaction that dehydrates the membrane and makes it potentially toxic against Spodoptera frugiperda.

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The authors declare no conflicts of interest.

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Di Toto Blessing, L. , Budeguer, F. , Ramos, J. , Bardón, A. , Diaz, S. , Brovetto, M. , Seoane, G. and Neske, A. (2015) Structural Factors of Annonaceous Acetogenins and Their Semisynthetic Analogues Related with the Toxicity on Spodoptera frugiperda. Journal of Agricultural Chemistry and Environment, 4, 56-61. doi: 10.4236/jacen.2015.42006.


[1] Ramos, J.C., Brovetto, M. and Seoane, G. (2013) Chemoenzymatic Synthesisof Trans-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene. Organic Letters, 15, 1982-1985.
[2] Brown, R.C.D. and Suprr, I.B. (2010) Total Synthesis of Annonaceous Acetogenins Belonging to the Non-Adjacent Bis-THF and Non-Adjacent THF-THP Sub-Classes. Molecules, 15, 460-501.
[3] Barrachina, I., Neske, A., Granell, S., Bermejo, A., Chahaboune, N., El Aouad, N., álvarez Colom, O., Bardón, A. and Zafra-Polo, M.C. (2004) Tucumanin, a β-Hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, Is a Potent Inhibitor of Mitochondrial Complex I. Planta Medica, 70, 866-868.
[4] álvarez Colom, O., Neske, A., Chahaboune, N., Zafra-Polo, M.C. and Bardón, A. (2009) Tucupentol, a Novel Mono- Tetrahydrofuranic Acetogenin from Annona montana, as a Potent Inhibitor of Mitochondrial Complex I. Chemistry and Biodiversity, 6, 335-340.
[5] Guadaño, A., Gutiérrez, C., de La Peña, E., Cortes, D. and González-Coloma, A. (2000) Insecticidal and Mutagenic Evaluation of Two Annonaceous Acetogenins. Journal of Natural Products, 63, 773-776.
[6] Marenco, R.J., Foster, R.E. and Sanchez, C.A. (1992) Sweet Corn Response to Fall Armyworm (Lepidoptera: Noctuidae) Damage during Vegetative Growth. Journal of Economic Entomology, 85, 1285-1292.
[7] Kumar, H. and Mihn, J.A. (2002) Fall Armyworm (Lepidoptera: Noctuidae), Southwestern Corn Borer (Lepidoptera: Pyralidae) and Sugarcane Borer (Lepidoptera: Pyralidae) Damage and Grain Yield of Four Maize Hybrids in Relation to Four Tillage Systems. Crop Protection, 21, 121-128.
[8] Clavijo, S. and Pérez Greiner, G. (2000) Insectos plagas del maíz (sección 2). In: Fontana Nieves, H. and González Narváez, C., Eds., Protección y sanidad vegetal (capítulo 6), Fundación Polar, Caracas, 345-361.
[9] Murillo, A. (1991) Distribución, importancia y manejo del complejo Spodoptera en Colombia. In: Zuluaga, J.L. and Muñoz, G., Eds., Memorias Seminario Spodoptera frugiperda (El gusano cogollero) en sorgo, maíz y otros cultivos, Calí, Colombia, 15-23.
[10] Sparks, A.N. (1979) A Review of the Biology of the Fall Armyworm. The Florida Entomologist, 62, 82-87.
[11] Murúa, M.G., Virla, E.G. and Defagó, V. (2003) Evaluación de cuatro dietas artificiales para la cría de Spodoptera frugiperda (Lep.: Noctuidae) destinada a mantener poblaciones experimentales de himenópteros parasitoides. Boletín de Sanidad Vegetal de Plagas, 29, 43-51.
[12] Murúa, M.G. and Virla, E. (2004) Population Parameters of Spodoptera frugiperda (Smith) (Lep.: Noctuidae) Fed on Corn and Two Predominant Grasess in Tucumán (Argentina). Acta Zoológica Mexicana, 20, 199-210.
[13] álvarez Colom, O., Neske, A., Popich, S. and Bardón, A. (2007) Toxic Effects of Annonaceous Acetogenins from Annona cherimolia (Magnoliales: Annonaceae) on Spodoptera frugiperda (Lepidoptera: Noctuidae). Journal of Pest Science, 80, 63-67.
[14] álvarez Colom, O., Barrachina, I., Ayala Mingol, I., González Mas, M.C., Moya Sanz, P., Neske, A. and Bardón, A. (2008) Toxic Effects of Annonaceous Acetogenins on Oncopeltus fasciatus. Journal of Pest Science, 81, 85-89.
[15] álvarez Colom, O., Salvatore, A., Willink, E., Ordóñez, R., Isla, M.I., Neske, A. and Bardón, A. (2010) Insecticidal, Mutagenic and Genotoxic Evaluation of Annonaceous Acetogenins. Natural Product Communications, 5, 391-394.
[16] Di Toto Blessing, L., álvarez Colom, O., Popich, S., Neske, A. and Bardón, A. (2010) Antifeedant and Toxic Effects of Acetogenins from Annona montana on Spodoptera frugiperda. Journal of Pest Science, 83, 307-310.
[17] Tolosa, D., álvarez Colom, O., Bardón, A. and Neske, A. (2012) Insecticidal Effects of Annonaceous Acetogenins from Rollinia occidentalis Seeds Extract on Spodoptera frugiperda. Natural Product Communications, 7, 1645-1646.
[18] Tolosa, D., Ruiz Hidalgo, J., Sal, P.E., Popich, S., Bardón, A. and Neske, A. (2014) Insecticidal Effects of the Annonaceous Acetogenin Squamocin and the Acetogenin Fraction of Seeds of Rollinia occidentalis on Soybean and Corn Pests. Journal of Agricultural Chemistry and Environment, 3, 156-160.
[19] McCloud, T.G., Smith, D.L., Chang, C.J. and Cassady, J.M. (1987) Annonacin, a Novel, Biologically Active Polyketide from Annona densicoma. Experientia, 43, 947-949.
[20] Pettit, G.R., Riensen, R., Leet, J.E., Polonsky, J., Smith, C.R., Schmidt, J.M., Dufresne, C., Schaufelberger, D. and Moretti, C. (1989) Isolation and Structure of Rolliniastatin-2, a New Cell Growth Inhibitory Acetogenin from Rollinia mucosa. Heterocycles, 28, 213-217.
[21] Cortes, D., Myint, S. and Hocquemiller, R. (1991) Molvizarin and Motrilin: Two Novel Cytotoxic Bis-Tetrahydro-Furanic γ-Lactone Acetogenins from Annona cherimolia. Tetrahedron, 47, 8195-8202.
[22] Chahboune, N., Barrachina, I., Royo, I., Romero, V., Sáez, J., Tormo, J.R., De Pedro, N., Estornell, E., Zafra-Polo, M.C., Peláez, F. and Cortes, D. (2006) Guanaconetins, New Antitumoral Acetogenins, Mitochondrial Complex I and Tumor Cell Growth Inhibitors. Bioorganic of Medicinal Chemistry, 14, 1089-1094.

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