Skip to main content
SpringerLink
Log in

Acaricidal activity of the hyacinthacine analogues derived from pyrrolizidine alkaloids on Rhipicephalus (Boophilus) microplus

  • Short Communication
  • Published:
Parasitology Research Aims and scope Submit manuscript

Abstract

This study reports the effect of six hyacinthacine analogues derived from pyrrolizidine alkaloids on egg hatchability and mortality rates of newly hatched larvae of the cattle tick Rhipicephalus (Boophilus) microplus. All the compounds were toxic to the larvae of the ticks and inhibited the eggs hatchability in the higher concentration tested (5 μg/ml). Even in the lowest concentration (0.625 μg/ml), some effect in the eggs hatchability was observed.

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

References

  • Asano N, Kuro H, Ikeda K, Kizu H, Kameda Y, Kato A, Adachi I, Watson AA, Nash RJ, Fleet GWJ (2000) New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: structural determination and biological activity. Tetrahedron Asymmetry 11:1–8

    Article  CAS  Google Scholar 

  • Asano N, Ikeda K, Kasahara M, Arai Y, Kizu H (2004) Glycosidase-inhibiting pyrrolidines and pyrrolizidines with a long side chain in Scilla peruviana. J Nat Prod 67:846–850

    Article  PubMed  CAS  Google Scholar 

  • Borges LMF, Ferri PH, Silva WC, Silva WJ, Melo LS, Souza LAD, Soares SF, Faria KA, Gomes NA, Mori A, Silva NF (2005) Ação do extrato hexânico de frutos maduros de Melia azedarach (Meliaceae) sobre Boophilus microplus (Acari: Ixodidae) em bezerros infestados artificialmente. Rev Patol Trop 34:53–59

    Google Scholar 

  • Cardona F, Faggi E, Liguori F, Cacciarini M, Goti A (2003) Total syntheses of hyacinthacine A(2) and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone. Tetrahedron Lett 44:2315–2318

    Article  CAS  Google Scholar 

  • Desvergnes S, Py S, Vallee Y (2005) Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung. J Org Chem 70:1459–1462

    Article  PubMed  CAS  Google Scholar 

  • Duarte MO (2008) Síntese em Fase sólida e em solução de anéis pirrolizidínicos e avalição da atividade carrapaticida contra R.(B.) microplus. Dissertação de mestrado. Programa de Pós-graduação em Ciências Farmacêuticas, Faculdade de Farmácia, UFRGS

  • Duarte MO, Pazinato M, Martinez PD, Stedele GM, Eifler-Lima VL, Oliveira de ER (2007) Studies of a convergent approach towards hyacinthacine A and analogs. In: 12th Brazilian Meeting on Organic Synthesis, Itapema

  • Ducornez S, Barré N, Miller RJ, de Garine-Wichatisky M (2005) Diagnosis of amitraz resistance in Boophilus microplus in New Caledonia with modified larval packet test. Vet Parasitol 130:285–292

    Article  PubMed  CAS  Google Scholar 

  • García-García JC, Gonzalez IL, González DM, Valdés M, Méndez L, Lamberte J, D'Agostino B, Citroni D, Fragoso H, Ortiz M, Rodríguez M, De La Fuente J (1999) Sequence variations in the Boophilus microplus Bm86 locus and implications for immunoprotection in cattle vaccinated with this antigen. Biomed Life Sci 23:883–895

    Google Scholar 

  • Macel M, Bruinsma M, Dijkstra SM, Ooijendijk T, Niemeyer HM, Klinkhamer PGL (2005) Differences in effects of pyrrolizidine alkaloids on five generalist insect herbivore species. J Chem Ecol 31:1493–1508

    Article  PubMed  CAS  Google Scholar 

  • Pietrosiuk A, Kropczyńska D, Furmanowa M, Kawka B, Wiedenfeld H (2003) Life history parameters of the two-spotted spider mite (Tetranychus urticae Koch) feeding on bean leaves treated with pyrrolizidine alkaloids. J Appl Toxicol 23:187–190

    Article  PubMed  CAS  Google Scholar 

  • Ribeiro VLS, Toigo E, Bordignon SAL, Gonçalves K, von Poser GL (2007) Acaricidal properties of extracts from the aerial parts of Hypericum polyanthemum on the cattle tick Boophilus microplus. Vet Parasitol 147:199–203

    Article  PubMed  Google Scholar 

  • Ribeiro VLS, Avancini C, Gonçalves K, Toigo E, von Poser GL (2008) Investigation of the acaricidal activity of Calea serrata (Asteraceae) on Boophilus microplus and Rhipicephalus sanguineus. Vet Parasitol 151:351–354

    Article  PubMed  Google Scholar 

  • Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP (2007) Loline alkaloids: currencies of mutualism. Phytochemistry 68:980–999

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by CNPq and CAPES, Brazil. The authors want to thank Andresa Betti for the statistical analysis.

Author information

Authors and Affiliations

  1. Programa de Pós Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Av. Ipiranga 2752, 90610-000, Porto Alegre, RS, Brazil

    Mônica Oliveira Duarte, Stela Regina Ferrarini, Vera Lucia Eifler-Lima & Gilsane von Poser

  2. Instituto de Química, Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves 9500, 91509-900, Porto Alegre, RS, Brazil

    Mariane Pazinatto & Eduardo Rolim de Oliveira

  3. Faculdade de Veterinária, Universidade Federal do Rio Grande do Sul, Av. Bento Gonçalves 9090, 90540-000, Porto Alegre, RS, Brazil

    Verônica Rolim & Vera Lucia Sardá Ribeiro

Authors
  1. Mônica Oliveira Duarte
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stela Regina Ferrarini
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mariane Pazinatto
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eduardo Rolim de Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Verônica Rolim
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Vera Lucia Eifler-Lima
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Vera Lucia Sardá Ribeiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Gilsane von Poser
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Gilsane von Poser.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Duarte, M.O., Ferrarini, S.R., Pazinatto, M. et al. Acaricidal activity of the hyacinthacine analogues derived from pyrrolizidine alkaloids on Rhipicephalus (Boophilus) microplus . Parasitol Res 103, 723–726 (2008). https://doi.org/10.1007/s00436-008-1022-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-008-1022-4

Keywords

Search

Navigation