Skip to main content

Advertisement

SpringerLink
Log in

18-Des-hydroxy Cytochalasin: an antiparasitic compound of Diaporthe phaseolorum-92C, an endophytic fungus isolated from Combretum lanceolatum Pohl ex Eichler

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

Abstract

Chemical investigation of the ethyl acetate extract from the endophytic fungus Diaporthe phaseolorum-92C (92C) isolated from the roots of Combretum lanceolatum led to the isolation of 18-des-hydroxy Cytochalasin H (compound 1). The trypanocidal and schistosomicidal activity and cytotoxicity of the extract from 92C were evaluated. The schistosomicidal, leishmanicidal, antimicrobial, and antioxidant actions, as well as the antitumor activity against the breast cancer cells MDA-MB-231 and MCF-7, and the cytotoxicity towards normal human lung fibroblasts GM07492A of compound 1 was tested. The extract from 92C (20 μg/mL) exerted potent trypanocidal activity, reducing 82% of the number of amastigotes and trypomastigotes of Trypanosoma cruzi. Compound 1 at 50 μg/mL killed 50% of Schistosoma mansoni adult worms. Compound 1 reduced the viability of Leishmania amazonenses promastigotes (IC50 = 9.2 μg/mL) and of the cancer cells MDA-MB-231 and MCF-7 (IC50 = 17.5 and 8.88 μg/mL, respectively), presented moderate antioxidant activity, and gave IC50 of 2049.7 ± 39.9 μg/mL for the cytotoxicity towards normal cells GM07492A. This knowledge is highly relevant to the search for new promising compounds for therapeutic purposes.

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
Fig. 2

Similar content being viewed by others

References

  • Bale JS, Van Lenteren JC, Bigler F (2008) Biological control and sustainable food production. Philos Trans R Soc Lond Ser B Biol Sci 363:761–776

    Article  CAS  Google Scholar 

  • Biasetto CR (2011) Chemical and biological evaluation of the endophytic fungus Schizophyllum commune isolated from Alchornea glandulosa. Dissertation, São Paulo State University

  • Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. Lebensm-Wiss Technol 28:25–30

    Article  CAS  Google Scholar 

  • Buckner FS, Verlinde CL, Flamme AC, Van Voorhis WC (1996) Efficient technique for screening drugs for activity against Trypanosoma cruzi using parasites expressing beta-galactosidase. Antimicrob Agents Chemother 40:2592–2597

    CAS  PubMed  PubMed Central  Google Scholar 

  • Callejon DR, Riul TB, Feitosa LGP, Guaratini T, Silva DB, Adhikari A, Shrestha RL, Marques LMM, Baruffi MD, Lopes JLC, Lopes NP (2014) Leishmanicidal evaluation of tetrahydroprotoberberine and spirocyclic erythrina-alkaloids. Molecules 1:5692–5703

    Article  Google Scholar 

  • Chandra S (2012) Endophytic fungi: novel sources of anticancer lead molecules. Appl Microbiol Biotechnol 95:47–59

    Article  CAS  PubMed  Google Scholar 

  • Chapla VM, Zeraik ML, Zanardi LM, Lopes MN, Cavalheiro AJ, Young MCM, Fonseca LM, Bolzani V, Araújo AR (2014) Bioactive secondary metabolites from Phomopsis sp., an endophytic fungus from Senna spectabilis. Molecules 19:6597–6608

    Article  PubMed  Google Scholar 

  • Cox RH, Cutler HG, Hurd RE, Cole RJ (1983) Proton and carbon-13 nuclear magnetic resonance studies of the conformation of cytochalasin H derivatives and plant growth regulating effects of cytochalasins. J Agric Food Chem 31:405–408

    Article  CAS  Google Scholar 

  • De Siqueira KA, Brissow ER, Dos Santos JL, White JF, Santos FR, De Almeida EG, Soares MA (2016) Endophytism and bioactivity of endophytic fungi isolated from Combretum lanceolatum Pohl ex Eichler. Symbiosis 71:211–222

    Article  Google Scholar 

  • Finkel T, Holbrook NJ (2000) Oxidants, oxidative stress and the biology of ageing. Nature 408:239–247

    Article  CAS  PubMed  Google Scholar 

  • James KH, Atta MA, Eugene JF, Gary AS, John AP, David PT, Kim LO, Elizabeth MH, David MG (2003) Pestacin: a isobenzofuran 1,3-dihidro Pestalotiopsis microspora. Tetrahedron 59:2471–2476

    Article  Google Scholar 

  • Kumaran RS, Hur B (2009) Screening of species of the endophytic fungus Phomopsis for the production of the anticancer drug taxol. Biotechnol Appl Biochem 54:21–30

    Article  CAS  PubMed  Google Scholar 

  • Laatsch H (2014) The natural compound identifier Antibase software. John Wiley & Sons, Hoboken

    Google Scholar 

  • Lai HY, Lim YY, Tan SP (2009) Antioxidative, tyrosinase inhibiting and antibacterial activities of leaf extracts from medicinal ferns. Biosci Biotechnol Biochem 73:1362–1366

    Article  CAS  PubMed  Google Scholar 

  • Lin X, Huang Y, Fang M, Wang J, Zheng Z, Su W (2005) Cytotoxic and antimicrobial metabolites from marine lignicolous fungi, Diaporthe sp. FEMS Microbiol Lett 251:53–58

    Article  CAS  PubMed  Google Scholar 

  • Lingham RB, Silverman KC, Bills GF, Dombrowski ANE, Goldman ME, Ondeyka JG (1992) L-696,474, a new cytochalasin as an inhibitor of HIV-1 protease - biological activity. J Antibiot 45:686–691

    Article  CAS  PubMed  Google Scholar 

  • Monks A, Scudiero D, Skehan PR, Paull K, Vistica D, Mangueira CJ, Langley CP, Vaigro-Wolff A, Gray-Goodrich, Campbell H, Mayo JM (1991) Feasibility of a high flow screen anti-cancer drugs using a diverse panel of human tumor cell lines in culture. J Nat Cancer Inst 83:757–766

    Article  CAS  PubMed  Google Scholar 

  • Mosmann T (1983) A rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63

    Article  CAS  PubMed  Google Scholar 

  • Ondeyka J, Hensens OD, Zink D, Ball R, Lingham RB, Bills G, Goetz M (1992) L-696,474, a new cytochalasin as an inhibitor of HIV-1 protease. J Antibiot 45:679–685

    Article  CAS  PubMed  Google Scholar 

  • Padhi S, Tayung K (2013) Antimicrobial activity and molecular characterization of an endophytic fungus, Quambalaria sp. isolated from Ipomoea carnea. Ann Microbiol 63:793–800

    Article  CAS  Google Scholar 

  • Pimenta LP, Kellner Filho LC, Liotti RG, Soares MA, Aguiar DP, Magalhães LG, Oliveira PF, Tavares DC, Andrade Silva ML, Cunha WR, Pauletti PM, Januario AH (2015) In vitro antischistosomal activity and cytotoxicity of 5-methoxylated flavones from Vochysia divergens, a flood-adapted species from Brazilian Pantanal. Adv Pharmacoepidemiol Drug Saf 4:3 (article ID1000182)

    Google Scholar 

  • Rahman S, Salehin F (2011) In vitro antioxidant and anticancer activity of young Zingiber officinale against human breast carcinoma cell lines. BMC Complement Altern Med 11:76–80

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Romanha AJ, Castro SLD, Soeiro MNC, Lannes VJ, Ribeiro I, Talvani A, Andrade ZDA (2010) In vitro and in vivo experimental models for drug screening and development for Chagas disease. Mem Inst Oswaldo Cruz 105:233–238

    Article  CAS  PubMed  Google Scholar 

  • Rosa LH, Tabanca N, Techen N, Wedge DE, Pan Z, Bernier UR, Moraes RM (2012) Antifungal activity of extracts from endophytic fungi associated with Smallanthus maintained in vitro as autotrophic cultures and as pot plants in the greenhouse. Can J Microbiol 58:1202–1211

    Article  CAS  PubMed  Google Scholar 

  • Rufino MP (2011) Chemical and biological evaluation of the endophytic fungus Colletotrichum sp isolated from Senna spectabilis. Dissertation, São Paulo State University

  • Saleem M, Nazir M, Ali MS, Hussain H, Lee YS, Riaz N, Jabbar A (2010) Antimicrobial natural products: an update on future antibiotic drug candidates. Nat Prod Rep 27:238–254

    Article  CAS  PubMed  Google Scholar 

  • Santiago IF (2011) Bioprospecting bioactive metabolites produced by endophytes associated with angiosperms present in Antarctica. 2011. 76f. Dissertation (Masters in Biotechnology.) - Federal University of Ouro Preto, Ouro Preto

  • Schulz B, Boyle C (2005) The endophytic continuum. Mycol Res 109:661–686

    Article  PubMed  Google Scholar 

  • Sepulveda-Boza S, Cassels BK (1996) Pant metabolites active against Trypanosoma cruzi. Planta Med 62:98–105

    Article  CAS  PubMed  Google Scholar 

  • Smithers SR, Terry RJ (1965) Infection of laboratory hosts with cercariae of Schistosoma mansoni and recovery of adult worms. Parasitology 55:695–700

    Article  CAS  PubMed  Google Scholar 

  • Strobel GA, Ford E, Worapong J, Harper JK, Arif AM, Grant DM, Fung PC, Chan K (2002) Isopestacin, an isobenzofuranone from Pestalotiopsis microspora, possessing antifungal and antioxidant activities. Phytochemistry 60:179–183

    Article  CAS  PubMed  Google Scholar 

  • Teixeira MC, Santos RJ, Sampaio RB, Pontes-de-Carvalho L, dos Santos WL (2002) A simple and reproducible method to obtain large numbers of axenic amastigotes of different Leishmania species. Parasitol Res 88:963–968

    Article  PubMed  Google Scholar 

  • Tejesvi MV, Nalini MS, Mahesh B, Prakash HS, Kr K, Shetty HS, Subbiah V (2007) New hopes from endophytic fungal secondary metabolites. Bol Soc Quím Méx 1:19–26

    Google Scholar 

  • Weber D, Sterner O, Anke T, Gorzalczancy S, Martino V, Acevedo C (2005) Phomol, a new antiinflammatory metabolite from an endophyte of the medicinal plant Erythrina crista-galli. J Antibiot 57:559–563

    Article  Google Scholar 

Download references

Acknowledgements

The authors thank the National Council for Scientific and Technological Development (CNPq), Coordination for the Improvement of Higher Education Personnel (CAPES), and National Institute of Science and Technology in Wetlands (INAU) for institutional and financial support.

Author information

Authors and Affiliations

  1. Chemistry Graduate Program, UFMT, Federal University of Mato Grosso, Cuiabá, MT, 14800-900, Brazil

    Elson Rudimar Brissow & Igor Pereira da Silva

  2. Institute of Biosciences, UFMT, Federal University of Mato Grosso, Cuiabá, MT, 14800-900, Brazil

    Kátia Aparecida de Siqueira, Jaqueline Alves Senabio & Marcos Antônio Soares

  3. Research Nucleus in Exact and Technological Sciences Center, Natural Products Research Group, UNIFRAN, University of Franca, Franca, SP, 14404-600, Brazil

    Leticia Pereira Pimenta, Ana Helena Januário, Lizandra Guidi Magalhães, Ricardo Andrade Furtado & Denise Crispim Tavares

  4. Research Center René Rachou, FIOCRUZ, Oswaldo Cruz Foundation, Belo Horizonte, MG, 30190-002, Brazil

    Policarpo Ademar Sales Junior

  5. Department of Biological Sciences, UESC, State University of Santa Cruz, Ilhéus, BA, 45650-000, Brazil

    Jane Lima Santos

Authors
  1. Elson Rudimar Brissow
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Igor Pereira da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kátia Aparecida de Siqueira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jaqueline Alves Senabio
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Leticia Pereira Pimenta
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ana Helena Januário
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Lizandra Guidi Magalhães
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ricardo Andrade Furtado
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Denise Crispim Tavares
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Policarpo Ademar Sales Junior
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Jane Lima Santos
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Marcos Antônio Soares
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Contributions to the study design and preparation of the manuscript: ERB, MAS, AHJ, and PASJ. Phytochemical screening: IPS and LPP. Biological experiments: schistosomicidal, LGM; trypanocidal, PASJ; leishmanicidal, KAS and JLS; antioxidant, ERB; antitumor, JAS and JLS; antimicrobial, ERB; cytotoxicity, DCT and RAF. Analysis of the experimental data: MAS, AHJ, DCT, and LGM. All authors drafted the paper and approved the final version.

Corresponding author

Correspondence to Marcos Antônio Soares.

Ethics declarations

The maintenance of S. mansoni life cycle was authorized by the Ethical Committee for Animal Care of the University of Franca and were in accordance with the nationally and internationally accepted principles for laboratory animal handling and care (Protocol 028/12 - September 13, 2012)

Conflict of interest

The authors declare that they have no conflicts of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Brissow, E.R., da Silva, I.P., de Siqueira, K.A. et al. 18-Des-hydroxy Cytochalasin: an antiparasitic compound of Diaporthe phaseolorum-92C, an endophytic fungus isolated from Combretum lanceolatum Pohl ex Eichler. Parasitol Res 116, 1823–1830 (2017). https://doi.org/10.1007/s00436-017-5451-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00436-017-5451-9

Keywords

Search

Navigation