Abstract
Several species of the large family of tropical plants Annonaceae have been intensely investigated over the last 20 years, mainly because of the discovery of annonaceous acetogenins. These compounds are powerful cytotoxics, with potential applications as insecticides, antiparasitics, acaricides, fungicides, and antitumor drugs. Annona montana Macfad. (Annonaceae) grows in Santa Cruz de la Sierra, Bolivia, where an infusion of leaves is used for the treatment of lice, influenza, and insomnia. The major acetogenins from a Bolivian collection of A. montana, annonacin (1), cis-annonacin-10-one (2), densicomacin-1 (3), gigantetronenin (4), murihexocin-B (5), and tucupentol (6), were evaluated for their antifeedant and toxic effects on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae), a serious pest affecting corn crops in Argentina. All the acetogenins produced 100% mortality during the larval or pupal stages at 100 μg of treatment per gram of diet. In addition, compounds 2, 3, and 4 deterred more than 80% feeding at the same dose. Relative toxicity values of LD50 for the strongest larvicidal compounds 1, 2, and 4 were determined, indicating that the three compounds are effective natural insecticides. This is the first report on the antifeedant and toxic effects produced by the particular type of acetogenins, the mono-THF acetogenins, on the lepidopteran S. frugiperda. No correlation was detected between the toxicity of the mentioned compounds to larvae and the known capacity of the acetogenins 1, 2, and 4 to inhibit the NADH oxidase, indicating that the inhibition of the mitochondrial complex I is not the only cause for larval mortality of S. frugiperda.
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References
Álvarez Colom O, Neske A, Popich S, Bardón A (2007) Toxic effects of annonaceous acetogenins from Annona cherimolia (Magnoliales: Annonaceae) on Spodoptera frugiperda (Lepidoptera: Noctuidae). J Pest Sci 80:63–67
Álvarez Colom O, Barrachina I, Ayala Mingol I, Gonzalez Mas MC, Moya Sanz P, Neske A, Bardon A (2008) Toxic effects of annonaceous acetogenins on Oncopeltus fasciatus. J Pest Sci 81:85–89
Álvarez Colom O, Neske A, Chahboune N, Zafra-Polo MC, Bardon A (2009) Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I. Chem Biodivers 6:335–340
Cole MD (1994) Key antifungal, antibacterial and anti-insect assays—a critical review. Biochem Syst Ecol 22:837–856
Fang XP, Anderson JE, Smith DL, Mc Laughlin JL, Wood KV (1992) Gigantetronenin and gigantrionenin: novel cytotoxic acetogenins from Goniothalamus giganteus. J Nat Prod 55:1655–1663
Finney DJ (1964) Probit analysis: statistical treatment of the sigmoid response curve. Cambridge University Press, London
Gu Z, Fang XP, Zeng L, Word KV, Mc Laughlin JL (1996) Five novel monotetrahydrofuran ring acetogenins from the seeds of Annona muricata. J Nat Prod 59:100–108
Guadaño A, Gutiérrez C, de la Peña E, Cortes D, González-Coloma A (2000) Insecticidal and mutagenic evaluation of two annonaceous acetogenins. J Nat Prod 63:773–776
Jossang A, Dubaele B, Cavé A, Bartoli M, Beriel H (1991) Annomontacine: une nouvelle acétogénine γ-lactone-monotetrahydrofurannique cytotoxique de l` Annona montana. J Nat Prod 54:967–971
Liaw Ch, Chang F, Wu Ch, Chen S, Bastow K, Hayashi K, Nosaki H, Lee K, Wu Y (2004) Nine new cytotoxic monotetrahydrofuranic annonaceous acetogenins from Annona montana. Planta Med 70:948–959
Mc Cloud TG, Smith DL, Chang CJ, Cassady JM (1987) Annonacin, a novel, biologically active polyketide from Annona densicoma. Experientia 43:947–949
Tormo JR, Gallardo T, Gonzalez MC, Bermejo A, Cabedo N, Andreu I, Estornell E (1999a) Annonaceous acetogenins as inhibitors of mitochondrial complex I. Curr Top Phytochem 2:69–90
Tormo JR, Gallardo T, Aragon R, Cortes D, Estornell E (1999b) Specific interactions of monotetrahydrofuranic annonaceous acetogenins as inhibitors of mitochondrial complex I. Chem-Biol Interact 122:171–183
Wang L, Li Y, Min B, Nakamura N, Qin G, Li C, Hattori M (2001) Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana. Planta Med 67:847–852
Yu GL, Ho DK, Cassady JM (1992) Citotoxic polyketides from Annona densicoma (Annonaceae) 10,13-trans-13,14-erythro-densicomacin, 10,13-trans-13,14-threo-densicomacin and 8-hydroxyannonacin. J Org Chem 57:6198–6202
Zeng L, Wu FE, Gu ZM, McLaughlin JL (1995) Murihexocins A and B: two novel mono-THF acetogenins with six hydroxyls, from Annona muricata (Annonaceae). Tetrahedron Lett 36:5291–5294
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This study was supported by grants from Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) and Consejo de Investigaciones de la Universidad Nacional de Tucumán (CIUNT).
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Communicated by J. Gross.
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Di Toto Blessing, L., Álvarez Colom, O., Popich, S. et al. Antifeedant and toxic effects of acetogenins from Annona montana on Spodoptera frugiperda . J Pest Sci 83, 307–310 (2010). https://doi.org/10.1007/s10340-010-0299-0
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DOI: https://doi.org/10.1007/s10340-010-0299-0