Skip to main content
SpringerLink
Log in

In vitro leishmanicidal, antibacterial and antitumour potential of anhydrocochlioquinone A obtained from the fungus Cochliobolus sp.

  • Published:
Journal of Biosciences Aims and scope Submit manuscript

Abstract

The bioassay-guided fractionation of the ethyl acetate extract of the fungus Cochliobolus sp. highlighted leishmanicidal activity and allowed for anhydrocochlioquinone A (ANDC-A) isolation. MS, 1D and 2D NMR spectra of this compound were in agreement with those published in the literature. ANDC-A exhibited leishmanicidal activity with EC50 value of 22.4 µg/mL (44 μM) and, when submitted to the microdilution assay against Gram-positive and Gram-negative bacteria, showed a minimal inhibitory concentration against Staphylococcus aureus ATCC 25295 of 128 μg/mL (248.7 μM). It was also active against five human cancer cell lines, showing IC50 values from 5.4 to 20.3 μM. ANDC-A demonstrated a differential selectivity for HL-60 (SI 5.5) and THP-1 (SI 4.3) cell lines in comparison with Vero cells and was more selective than cisplatin and doxorubicin against MCF-7 cell line in comparison with human peripheral blood mononuclear cells. ANDC-A was able to eradicate clonogenic tumour cells at concentrations of 20 and 50 μM and induced apoptosis in all tumour cell lines at 20 μM. These results suggest that ANDC-A might be used as a biochemical tool in the study of tumour cells biochemistry as well as an anticancer agent with durable effects on tumours.

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

Figure 1
Figure 2
Figure 3

Similar content being viewed by others

References

  • Badisa RB, Darling-Reed SF, Joseph P, Cooperwood JS, Latinwo LM and Goodman CB 2009 Selective cytotoxic activities of two novel synthetic drugs on human breast carcinoma MCF-7 cells. Anticancer Res. 29 2993–2996

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bicalho B, Goncalves RAC, Zibordi APM, Manfio GP and Marsaioli AJ 2013 Antimicrobial compounds of fungi vectored by Clusia spp (Clusiaceae) pollinating bees Z Naturforsch C. J. Biosc. 58 746–751

    Google Scholar 

  • Callahan HL, Portal AC, Devereaux R and Grogl M 1997 An axenic amastigote system for drug screening HL. Antimicrob. Agents Chemother. 41 818–822

    CAS  PubMed  PubMed Central  Google Scholar 

  • Campos FF, Rosa LH, Cota BB, Caligiorne RB, Rabello AL, Alvez TM, Rosa CA and Zani CL 2008 Leishmanicidal metabolites from Cochliobolus sp., an endophytic fungus isolated from Piptadenia adiantoides (Fabaceae). PLoS Negl. Trop. Dis. 3 e348.

    Article  Google Scholar 

  • Ehrenberg J and Ault S 2005 Neglected diseases of neglected populations: Thinking to reshape the determinants of health in Latin America and the Caribbean. BMC Public Health 5 119

    Article  PubMed  PubMed Central  Google Scholar 

  • Farmer P, Frenk J, Knaul FM, Shulman L, Alleyne G, Armstrong L, Atun R, Blayney D, et al. 2010 Expansion of cancer care and control in countries of low and middle income: a call to action. Lancet 376 1186–1193

    Article  PubMed  Google Scholar 

  • Fesik SW 2005 Promoting apoptosis as a strategy for cancer drug discovery. Nat. Rev. Cancer 5 876–885

    Article  CAS  PubMed  Google Scholar 

  • Gazzinelli G, Katz N, Rocha RS and Colley DG 1983 Immune response during human schistosomiasis mansoni X. Production and standardization of an antigen-induced mitogenic activity by peripheral blood mononuclear cells from treated but not active cases of schistosomiasis. J. Immunol. 130 2891–2895

    CAS  PubMed  Google Scholar 

  • Gould IM and Bal AM 2013 New antibiotic agents in the pipeline and how they can overcome microbial resistance. Virulence 4 185–191

    Article  PubMed  PubMed Central  Google Scholar 

  • Housman G, Byler S, Heerboth S, Lapinska K, Longacre M, Snyder N and Sarkar S 2014 Drug resistance in cancer: an overview. Cancers (Basel) 6 1769–1792

    Article  CAS  Google Scholar 

  • Jiang J and Xu Q 2003 Immunomodulatory activity of the aqueous extract from rhizome of Smilax glabra in the later phase of adjuvant-induced arthritis in rats. J. Ethnopharmacol. 85 53–59

    Article  PubMed  Google Scholar 

  • Bartlett JG, Gilbert DN and Spellberg B 2013 Seven ways to preserve the miracle of antibiotics. Clin. Infect. Dis. 56 1445–1450

    Article  CAS  PubMed  Google Scholar 

  • Kale SP, Bhatnagar D and Bennett JW 1994 Isolation and characterization of morphological variants of Aspergillus parasiticus deficient in secondary metabolite production. Mycol. Res. 98 645–652

    Article  CAS  Google Scholar 

  • Mirzayans R, Andrais B, Scott A, Tessier A and Murray D 2007 A sensitive assay for the evaluation of cytotoxicity and its pharmacologic modulation in human solid tumor-derived cell lines exposed to cancer therapeutic agents. J. Pharm. Sci. 10 298–311

    Google Scholar 

  • Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Langley J, Cronise P, et al. 1991 Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor-cell lines. J. Nat. Cancer Inst. 83 757–766

    Article  CAS  PubMed  Google Scholar 

  • Mordant PL, Loriot Y, Leteur C, Calderaro J, Bourhis J, Wislez M, Soria JC and Deutsch E 2010 Dependence on phosphoinositide 3-kinase and RAS-RAF pathways drive the activity of RAF265, a novel RAF/VEGFR2 inhibitor, and RAD001 (Everolimus) in combination. Mol. Cancer Ther. 9 358–368

    Article  CAS  PubMed  Google Scholar 

  • NCCLS (National Committee for Clinical Laboratory Standards) 2003 Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard M7-A6, 6th ed. (Wayne, USA)

  • Nicholson DW 2000 From bench to clinic with apoptosis-based therapeutic agents. Nature 407 810–816

    Article  CAS  PubMed  Google Scholar 

  • Nicoletti I, Migliorati G, Pagliacci MC, Grignani F and Riccardi C 1991 A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry. J. Immunol. Methods 139 271–279

    Article  CAS  PubMed  Google Scholar 

  • PAHO (Pan-American Health Organization) 2016 Leishmaniases: epidemiological reports in the Americas. Washington: PAHO/Leishmaniases. Report n.4.

  • Phuwapraisirisan P, Sawang K, Siripong P and Tip-Pyang S 2007 Anhydrocochlioquinone A, a new antitumor compound from Bipolaris oryzae. Tetrahedron Lett. 48 5193–5195

    Article  CAS  Google Scholar 

  • Pinto MCL, Dias DF, Del Puerto HL, Martins AS, Teixeira-Carvalho A, Martins-Filho OA, Badet B, Durand P, et al. 2011 Discovery of cytotoxic and pro-apoptotic compounds against leukemia cells: Tert-butyl-4-[(3-nitrophenoxy) methyl]-2,2-dimethyloxazolidine-3-carboxylate. Life Sci. 89 786–794

    Article  CAS  PubMed  Google Scholar 

  • Pinto EG, Santos IO, Schmidt TJ, Borborema SET, Ferreira VF, Rocha DR and Tempone AG 2014 Potential of 2-hydroxy-3-phenylsulfanylmethyl-[1,4]-naphthoquinones against Leishmania (L.) infantum: biological activity and structure-activity relationships. PLoS One 9 105–127

    Google Scholar 

  • Qi QY, Huang L, He LW, Han JJ, Chen Q, Cai L and Liu HW 2014 Cochlioquinone derivatives with apoptosis-inducing effects on HCT116 colon cancer cells from the phytopathogenic fungus Bipolaris luttrellii L439. Chem. Biodivers. 11 1892–1899

    Article  CAS  PubMed  Google Scholar 

  • Savoia D 2015 Recent updates and perspectives on leishmaniasis. J. Infect. Dev. Ctries 9 588–596

    Article  PubMed  Google Scholar 

  • Teixeira MC, De Jesus SR, Sampaio RB, Pontes-De-Carvalho L and 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 

  • Ventola CL 2015 The antibiotic resistance crisis: Part 1: Causes and threats. P&T 40 277–283.

    Google Scholar 

  • WHO (World Health Organization) 2010 The control of the leishmaniases. WHO Technical Report Series 949

  • WHO (World Health Organization) 2017 Global health observatory data: Leishmaniasis (https://www.who.int/gho/neglected_diseases/leishmaniasis/en/)

Download references

Acknowledgements

The authors acknowledge Caryne Margotto Bertollo and Daniela Nabak Bueno for technical assistance. This work was supported by the Fundação Oswaldo Cruz (RPT10A), Fundação de Amparo à Pesquisa do Estado de Minas Gerais (CBB - APQ-00145-12-296841) and Conselho Nacional de Desenvolvimento Científico e Tecnológico (472175/2012-2).

Author information

Authors and Affiliations

  1. Faculty of Medicine, Federal University of Vales do Jequitinhonha e Mucuri, Diamantina, Brazil

    Fernanda F Campos

  2. Laboratory of Chemistry of Bioactive Natural Products, Centro de Pesquisas René Rachou, Fundação Oswaldo Cruz, Rio de Janeiro, Brazil

    Fernanda F Campos, Tânia M A Alves, Carlos L Zani & Betania B Cota

  3. Department of Physiology and Biofisics, Federal University of Minas Gerais, Belo Horizonte, Brazil

    Jonas P Ramos & Elaine M De Souza-Fagundes

  4. Department of Chemistry, Southwest Bahia State University, Jequié, Bahia, Brazil

    Djalma M De Oliveira

  5. Department of Pharmacy, Federal University of Vales do Jequitinhonha e Mucuri, Diamantina, Brazil

    Fábio C Sampaio

  6. Department of Civil, Chemical and Environmental Engineering, University of Genova, Genova, Italy

    Attilio Converti

Authors
  1. Fernanda F Campos
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jonas P Ramos
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Djalma M De Oliveira
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tânia M A Alves
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Elaine M De Souza-Fagundes
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Carlos L Zani
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Fábio C Sampaio
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Attilio Converti
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Betania B Cota
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fernanda F Campos.

Additional information

Corresponding editor: Seyed E Hasnain

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Campos, F.F., Ramos, J.P., De Oliveira, D.M. et al. In vitro leishmanicidal, antibacterial and antitumour potential of anhydrocochlioquinone A obtained from the fungus Cochliobolus sp.. J Biosci 42, 657–664 (2017). https://doi.org/10.1007/s12038-017-9718-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12038-017-9718-1

Keywords

Search

Navigation