Applied Microbiology and Biotechnology

, Volume 103, Issue 7, pp 2985–3000 | Cite as

Synthesis of chitosan biocomposites loaded with pyrrole-2-carboxylic acid and assessment of their antifungal activity against Aspergillus niger

  • Alma Carolina Gálvez-Iriqui
  • Mario Onofre Cortez-Rocha
  • Armando Burgos-Hernández
  • Montserrat Calderón-Santoyo
  • Waldo Manuel Argüelles-Monal
  • Maribel Plascencia-JatomeaEmail author
Biotechnological products and process engineering


A wide variety of chitosan (CS) biomaterials have been loaded with different antimicrobial agents to improve the activity of CS against phytopathogenic fungi. Recently, the antimicrobial activity of 1H-pyrrole-2-carboxylic acid (PCA) has been reported as a secondary metabolite of Streptomyces griseus, which was identified as the main bioactive compound in the biological control. However, it is sensitive to light and its activity against filamentous fungi has not yet been reported. The aim of the present research work was to evaluate the biological activity of CS-PCA biocomposites for the control of Aspergillus niger. CS-PCA biocomposites were obtained through nanoprecipitation. In vitro antifungal activity was determined by viability assay, spore germination, morphometric analysis of spores and hyphae, and the analysis of cellular components by fluorescence microscopy. CS-PCA showed an average size and Z potential of 502 ± 72 nm and + 54.7 ± 15 mV, respectively. Micrographs demonstrated well-distributed biocomposites with an apparently spherical shape. A new signal at 1473 cm−1 in the FT-IR spectrum of the CS-PCA biocomposite was observed, confirming the presence of PCA in the composition of the CS-PCA nanosystem. CS-PCA biocomposites reduced the spores’ viability by up to 58%. Effects on fungi morphometry, observed as an increase in the spores’ average diameter, swelling, distortion, and an increase in the branching of hyphae, were observed. Fluorescence analysis showed oxidative stress and membrane and cell wall damage, mainly at early growth stages. The inhibitory effect against CS-resistant fungi, such as A. niger, opens a door for the control of CS-sensitive fungi.


Antifungal Aspergillus niger Chitosan biocomposites Secondary metabolite Nanoprecipitation 



The study was funded by the Mexican Council for Science and Technology (CONACyT) through the project 219786 at the University of Sonora and for the scholarship to Alma Carolina Gálvez-Iriqui. Special thanks also go to the anonymous referees whose critical analysis of the original manuscript helped to improve the work substantially.


This study was funded by CONACyT (grant number 219786).

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Alma Carolina Gálvez-Iriqui
    • 1
  • Mario Onofre Cortez-Rocha
    • 1
  • Armando Burgos-Hernández
    • 1
  • Montserrat Calderón-Santoyo
    • 2
  • Waldo Manuel Argüelles-Monal
    • 3
  • Maribel Plascencia-Jatomea
    • 1
    Email author
  1. 1.Microbiology and Micotoxins Laboratory, Departamento de Investigación y Posgrado en AlimentosUniversidad de SonoraHermosilloMexico
  2. 2.Integral Laboratory of Food ResearchInstituto Tecnológico de TepicTepicMexico
  3. 3.Biopolymer LaboratoryCentro de Investigación y Desarrollo en Alimentación, A.CHermosilloMexico

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