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Phenolic Compound Biotransformation by Trametes versicolor ATCC 200801 and Molecular Docking Studies

  • João Carlos Silva Conceição
  • Herbert Júnior Dias
  • Clarissa Maria Souza Peralva
  • Antônio Eduardo Miller Crotti
  • Samuel Silva da Rocha Pita
  • Eliane de Oliveira SilvaEmail author
Article
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Abstract

The filamentous fungus Trametes versicolor is a rich source of laccase (Tvlac). Laccases catalyze reactions that convert substituted phenol substrates into diverse derivatives through aromatic oxidation. We investigated methyl p-coumarate, methyl ferulate, and methyl caffeate biotransformation by Trametes versicolor ATCC 200801. Despite substrate similarity, the biotransformation reactions varied widely. Only methyl p-coumarate was converted into three derivatives. We isolated and identified the chemical structures of such derivatives by NMR and IR analysis. Hydroxylation, methylation, and hydrolysis were the main reactions resulting from the studied biotransformation. We also analyzed the interactions between Tvlac (PDB ID: 1GYC) and the three phenolic substrates by molecular docking simulations. The substituents in the phenol ring influenced substrate conformation and orientation in the Tvlac site. The biotransformation reaction selectivity correlated with the different binding energies to the Tvlac site. Our results demonstrated that docking studies successfully predict the biotransformation of cinnamic acid analogs by T. versicolor.

Keywords

Biotransformation Laccase Molecular docking Phenolic compounds Trametes versicolor 
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Notes

Acknowledgments

JCSC thanks FAPESB for his scholarship.

Funding Information

This work was supported by the Brazilian National Council for Scientific and Technological Development (CNPq), Brazilian Coordination for Improvement of Personnel Higher Education (CAPES), and Bahia Research Foundation (FAPESB, grant numbers JCB-0039/2013 and RED-008/2013).

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.

Supplementary material

12010_2019_3191_MOESM1_ESM.docx (528 kb)
ESM 1 (DOCX 527 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • João Carlos Silva Conceição
    • 1
  • Herbert Júnior Dias
    • 2
  • Clarissa Maria Souza Peralva
    • 3
  • Antônio Eduardo Miller Crotti
    • 2
  • Samuel Silva da Rocha Pita
    • 3
  • Eliane de Oliveira Silva
    • 1
    Email author
  1. 1.Departamento de Química Orgânica, Instituto de QuímicaUniversidade Federal da BahiaSalvadorBrazil
  2. 2.Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão PretoUniversidade de São PauloRibeirão PretoBrazil
  3. 3.Laboratório de Bioinformática e Modelagem Molecular (LaBiMM), Departamento do Medicamento, Faculdade de FarmáciaUniversidade Federal da BahiaSalvadorBrazil

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