Skip to main content
SpringerLink
Log in

Toxic effects of annonaceous acetogenins on Oncopeltus fasciatus

  • Original Paper
  • Published:
Journal of Pest Science Aims and scope Submit manuscript

Abstract

From an Argentine collection of Annona cherimolia and a Bolivian collection of Annona montana (Annonaceae), the acetogenins, squamocin, molvizarin, itrabin, almuñequin, cherimolin-1, annonacin, annonacin-A, densicomacin-1, cis-annonacin-10-one and murihexocin-A, were obtained to study their toxicity against the cotton pest Oncopeltus fasciatus (Hemiptera: Lygaeidae). Topical ventral application of O. fasciatus nymphs with solutions of the mentioned acetogenins produced acute and delayed mortality.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

References

  • Alali F, Liu X, McLaughlin JL (1999) Annonaceous acetogenins: recent progress. J Nat Prod 62:504–540

    Article  PubMed  CAS  Google Scholar 

  • Alkofahi A, Rupprecht JK, Anderson JE, McLaughlin JL, Mikolajczak K, Scott B (1989) Search for new pesticides from higher plants. In: Arnason JT, Philogene B, Morand A (eds) Insecticides of plant origin. American Chemical Society, Washington, pp 25–43

    Google Scholar 

  • 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

    Article  Google Scholar 

  • Barrachina I, Neske A, Granell S, Bermejo A, Chahboune N, El Aoued N, Álvarez O, Bardón A, Zafra Polo MC (2004) Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I. Planta Med 70:866–868

    Article  PubMed  CAS  Google Scholar 

  • Cole MD (1994) Key antifungal, antibacterial and anti-insect assays-a critical review. Biochem Syst Ecol 22:837–856

    Article  CAS  Google Scholar 

  • Cortes D, Myint S, Dupont B, Davoust D (1993) Bioactive acetogenins from seeds of Annona cherimolia. Phytochemistry 32:1475–1482

    Article  CAS  Google Scholar 

  • Finney DJ (1971) Probit analysis. Cambridge University Press, Cambridge

    Google Scholar 

  • Folker Lieb MN, Wachendorff-Neumann U, Detlef W (1990) Annonacins and annonastatin from Annona squamosa. Planta Med 56:317–319

    Article  PubMed  Google Scholar 

  • Gallardo T, Zafra-Polo MC, Tormo JR, González MC, Franck X, Estornell E, Cortes D (2000) Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I. J Med Chem 43:4793–4800

    Article  PubMed  CAS  Google Scholar 

  • 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

    Article  PubMed  Google Scholar 

  • He K, Zeng L, Ye Q, Shi G, Oberlies N, Zhao G, Njoku C, Mc Laughlin J (1997) Comparative SAR evaluations of annonaceous acetogenins for pesticidal activity. Pestic Sci 49:372–378

    Article  CAS  Google Scholar 

  • Kawasu K, Alcántara J, Kobayashi A (1989) Isolation and structure of neoannonin, a novel insecticidal compound from the seeds of Annona squamosa. Agric Biol Chem 53:2719–2722

    Google Scholar 

  • Leatemia JA, Isman MB (2004) Toxicity and antifeedant activity of crude seed extracts of Annona squamosa (Annonaceae) against lepidopteran pests and natural enemies. Int J Trop Insect Sci 24:150–158

    Article  Google Scholar 

  • McCloud TG, Smith DL, Chang CJ, Cassady JM (1987) Annonacin, a novel, biologically active polyketide from Annona densicoma. Experientia 43:947–949

    Article  PubMed  CAS  Google Scholar 

  • McLaughlin JL, Chang ChJ, Smith DL (1993) Simple bench-top bioassays (Brine shrimp and potato discs) for the discovery of plant antitumor compounds. In: Kinghorn D, Balandrin MF (eds) Human medicinal agents from plants. Amer Chem Soc Symp Series 534, Washington, pp 112–137

    Google Scholar 

  • Rieser M, Gu Z, Fang XP, Zeng L, Word KV, McLaughlin JL (1996) Five novel monotetrahydrofuran ring acetogenins from the seeds of Annona muricata. J Nat Prod 59:100–108

    Article  PubMed  CAS  Google Scholar 

  • Yu GL, Ho DK, Cassady JM (1992) Cytotoxic 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by grants from Consejo de Investigaciones de la Universidad de Tucumán (CIUNT), and Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Argentina.

Author information

Authors and Affiliations

  1. Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000, Tucuman, Argentina

    Olga Alvarez Colom, Adriana Neske & Alicia Bardon

  2. Departamento de Farmacología, Facultad de Farmacia, Universidad de Valencia, Burjassot, Spain

    Isabel Barrachina

  3. Centro de Ecología Química Agrícola (CEQA), Universidad Politécnica de Valencia, Campus de Vera s/n. Edificio 9B, Laboratorio 111, 46022, Valencia, Spain

    Ildefonso Ayala Mingol, M. Carmen Gonzalez Mas & Pilar Moya Sanz

Authors
  1. Olga Alvarez Colom
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Isabel Barrachina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ildefonso Ayala Mingol
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Carmen Gonzalez Mas
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pilar Moya Sanz
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Adriana Neske
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Alicia Bardon
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alicia Bardon.

Additional information

Communicated by M. Traugott.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Colom, O.A., Barrachina, I., Mingol, I.A. et al. Toxic effects of annonaceous acetogenins on Oncopeltus fasciatus . J Pest Sci 81, 85–89 (2008). https://doi.org/10.1007/s10340-007-0189-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10340-007-0189-2

Keywords

Search

Navigation