Skip to main content
Log in

Metabolites from the leaf extract of Serjania yucatanensis with trypanocidal activity against Trypanosoma cruzi

  • Original Paper
  • Published:
Parasitology Research Aims and scope Submit manuscript

Abstract

The bioassay-guided phytochemical investigation of the leaf extract of Serjania yucatanensis, a woody climbing plant endemic to the Yucatan peninsula, led to the identification of a mixture of a triterpene [lup-20(29)-en-3-one] and an oxygenated sesquiterpene (β-caryophyllene oxide), as that responsible for the originally detected trypanocidal activity in the organic crude extract. Results showed that the mixture of lup-20(29)-en-3-one and β-caryophyllene oxide is active against trypomastigotes of Trypanosoma cruzi (IC50 = 80.3 μg/mL) and inhibits the egress of trypomastigotes from infected Vero cells (when tested at 100 μg/mL) without being cytotoxic.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Barrero A, Molina J, Oltra E, Altarejos J, Barragán A, Lara A, Segura M (1995) Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds. Tetrahedron 51:3813–3822

    Article  CAS  Google Scholar 

  • Budzikiewicz H, Djerassi C, Williams D (1964) Structure Elucidation of Natural Products by Mass Spectrometry. Vol II: Steroids, Terpenoids, Sugars and Miscellaneous Classes. Holden-Day, San Francisco USA.

  • Camargo EP (1964) Growth and differentiation in Trypanosoma cruzi. I. Origin of metacyclic trypomastigotes in liquid medium. Rev Inst Med Trop São Paulo 6:93–100

    PubMed  CAS  Google Scholar 

  • Castro JA, Montalvo M (2006) Toxic side effects of drugs used to treat Chagas’ disease (American trypanosomiasis). Hum Exp Toxicol 25:471–479

    Article  PubMed  CAS  Google Scholar 

  • Coll JC, Bowden BF (1986) The application of vacuum liquid chromatography to the separation of terpene mixtures. J Nat Prod 49:934–936

    Article  CAS  Google Scholar 

  • de Diego C, Avendaño C, Alcina A, Carrasco L, Elguero J (1988) Effects of heterocyclic analogues of triphenylmethane dyes against Trypanosoma cruzi. Ann Trop Med Parasitol 82:235–241

    PubMed  Google Scholar 

  • Durán R, Campos G, Trejo JC, Simá P, May F, Juan M (2000) Listado florístico de la Península de Yucatán. Impresiones Profesionales del Sureste, Mérida, Yucatán, México, 99 pp

    Google Scholar 

  • Escobar P, Leal SM, Herrera LV, Martinez JR, Stashenko E (2010) Chemical composition and antiprotozoal activities of Colombian Lippia spp essential oils and their major components. Mem Inst Oswaldo Cruz 105:184–190

    Article  PubMed  CAS  Google Scholar 

  • González J, Sagua H, Araya J, Loyola A, Morales G, Pereira J, Estrada M (1990) In vitro activity of natural products against the trypomastigote form of Trypanosoma cruzi. Phytother Res 4:1–4

    Article  Google Scholar 

  • Harvey A (2000) Strategies for discovery drugs from previously unexplored natural products. Drug Discov Today 5:294–300

    Article  PubMed  Google Scholar 

  • Herrera N, Correa E, Cardona D, Archbold R, Torres F, Quiñones W, Velez I (2007) Estructura y actividad de sapogeninas triterpénicas. Scientia et Technica 13:87–90

    Google Scholar 

  • Kumar S, Misra N, Raj K, Srivastava K, Puri SK (2008) Novel class of hybrid natural products derived from lupeol as antimalarial agents. Nat Prod Res 22:305–319

    Article  PubMed  CAS  Google Scholar 

  • Marín-Solano N, Ordoñez-Calderon S (2008) Determinación de metabolitos secundarios volátiles y semivolátiles, y ácidos aristolóquicos en Aristolochia ringens Vahl. Universidad Industrial de Santander, Bucaramanga, Colombia, Tesis de Licenciatura, 94 pp

    Google Scholar 

  • Newman DJ, Cragg GM (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461–477

    Article  PubMed  CAS  Google Scholar 

  • O’Brien J, Wilson I, Orton T, Pognan F (2002) Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem 267:5421–5426

    Article  Google Scholar 

  • Özek G, Demirci F, Özek T, Tabanca N, Wedge D, Shabana K, Hüsnu K, Duran A, Hamzaoglu E (2010) Gass-chromatographic-mass spectrometric analysis of volatiles obtained by four different techniques from Salvia rosifolia Sm., and evaluation for biological activity. J Chromatogr A 1217:741–748

    Article  PubMed  Google Scholar 

  • Polanco-Hernández G, Escalante-Erosa F, García-Sosa K, Acosta K, Chan-Bacab M, Sagua H, Gonzalez J, Osorio L, Peña-Rodríguez LM (2012) In vitro and in vivo trypanocidal activity of native plants from the Yucatan Peninsula. Parasitol Res 110:31–35

    Article  PubMed  Google Scholar 

  • Pulido MT, Serralta L (1993) Lista anotada de las plantas medicinales de uso actual en el Estado de Quintana Roo. México, Centro de Investigaciones de Quintana Roo, 106 pp

    Google Scholar 

  • Rahman K, Nahar K, Khan M, Hasan C (2007) Phytochemical and biological studies of Nephelium longan. Bol Latinoam Caribe Plant Med Aromatica 6:68–72

    Google Scholar 

  • Rodrigues-Coura J, de Castro SL (2002) A critical review on Chagas disease chemotherapy. Mem Inst Oswaldo Cruz 97:3–24

    Article  Google Scholar 

  • Rolón M, Vega C, Escario J, Gómez-Barrio A (2006) Development of resazurin microtiter assay for drug sensibility testing of Trypanosoma cruzi epimastigotes. Parasitol Res 99:103–107

    Article  PubMed  Google Scholar 

  • Rosas LV, Cordeiro MSC, Campos FR, Nascimiento SKR, Januário AH, Franca SC, Nomizo A, Toldo MP, Alburquerque S, Pereira OS (2007) In vitro evaluation of the cytotoxic and trypanocidal activities of Ampelozizyphus amazonicus (Rhamnaceae). Braz J Med Biol Res 40:663–670

    Article  PubMed  CAS  Google Scholar 

  • Sánchez-Medina A (2001) Phytochemical and pharmacological studies on some endemic yucatecan medicinal plants. PhD thesis, Universidad de Greenwich, Londres, 204 pp.

  • Setzer W, Vogler B, Schmidt J, Petty J, Haber W (2005) Isolation of cupanioside, a novel cytotoxic and antibacterial long-chain fatty alcohol glycoside from the bark of Cupania glabra. Planta Med 71:686–688

    Article  PubMed  CAS  Google Scholar 

  • Setzer W, Stokes S, Bansal A, Haber W, Caffrey C, Hansell E, McKerrow J (2007) Chemical composition and cruzain inhibitory activity of Croton draco bark essential oil from Monteverde, Costa Rica. Nat Product Commun 2:685–689

    CAS  Google Scholar 

  • Silva LH, Nussenzweig V (1953) Sobre uma cepa de Trypanosama cruzi altamente virulenta para o camundongo branco. Folia Clin Biol 20:191–208

    Google Scholar 

  • Vera-Ku M (2003) Evaluación de la actividad biológica en plantas nativas de la península de Yucatán. MSc thesis, Centro de Investigación Científica de Yucatán, México, 175 pp

  • Vieira GM, Leite de Souza CM, Chaves MH (2005) Resina de Protium heptaphyllum: isolamento, caracterização estrutural e avaliação das propriedades térmicas. Quim Nova 28:183–187

    Article  Google Scholar 

  • WHO-World Health Organization (2000) Special Programme for Research and Training in Tropical Disease (TDR). Natural products for parasitic diseases. TDR News, 62,4.

  • WHO-World Health Organization (2010) Nota descriptive no.340. At: http://www.who.int/mediacentre/factsheets/fs340/es/. Accessed 15 July 2010.

  • Xiao JB, Chen XQ, Zhang YW, Jiang XY, Xu M (2006) Cytotoxicity of Marchantia convoluta leaf extracts to human liver and lung cancer cells. Braz J Med Biol Res 39:731–738

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

The authors wish to thank Paulino Cimá for technical assistance and the identification of the plant material. GPH acknowledges the support of Consejo Nacional de Ciencia y Tecnología (CONACYT), through its “Becas Mixtas” Program, to carry out a research stay at the University of Antofagasta. This work was supported by Project FOMIX-Yucatán (66262) and Programa de Cooperación Bilateral México-Chile.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Luis M. Peña-Rodríguez.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Polanco-Hernández, G., Escalante-Erosa, F., García-Sosa, K. et al. Metabolites from the leaf extract of Serjania yucatanensis with trypanocidal activity against Trypanosoma cruzi . Parasitol Res 111, 451–455 (2012). https://doi.org/10.1007/s00436-012-2861-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-012-2861-6

Keywords

Navigation