Cargando…

Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.

Biotransformations are reactions mediated by microorganisms, such as fungi. These bioreactions have high chemo- and stereoselectivity on organic substrates and can be applied in the search for new bioactive compounds. In this study, acanthoic acid (AA) was biotransformed using the fungus Xylaria sp....

Descripción completa

Detalles Bibliográficos
Autores principales: Marinho, Andrey Moacir do Rosario, de Oliveira, Claudia Maria S. C., Silva-Silva, João Victor, de Jesus, Samara C. Anchieta, Siqueira, José Edson S., de Oliveira, Luana C., Auzier, Jéssica Fernandes, Soares, Liviane N., Pinheiro, Maria Lúcia Belém, Silva, Sebastião C., Medeiros, Lívia S., Costa, Emmanoel V., Marinho, Patrícia S. Barbosa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10451833/
https://www.ncbi.nlm.nih.gov/pubmed/37627751
http://dx.doi.org/10.3390/antibiotics12081331
_version_ 1785095514611515392
author Marinho, Andrey Moacir do Rosario
de Oliveira, Claudia Maria S. C.
Silva-Silva, João Victor
de Jesus, Samara C. Anchieta
Siqueira, José Edson S.
de Oliveira, Luana C.
Auzier, Jéssica Fernandes
Soares, Liviane N.
Pinheiro, Maria Lúcia Belém
Silva, Sebastião C.
Medeiros, Lívia S.
Costa, Emmanoel V.
Marinho, Patrícia S. Barbosa
author_facet Marinho, Andrey Moacir do Rosario
de Oliveira, Claudia Maria S. C.
Silva-Silva, João Victor
de Jesus, Samara C. Anchieta
Siqueira, José Edson S.
de Oliveira, Luana C.
Auzier, Jéssica Fernandes
Soares, Liviane N.
Pinheiro, Maria Lúcia Belém
Silva, Sebastião C.
Medeiros, Lívia S.
Costa, Emmanoel V.
Marinho, Patrícia S. Barbosa
author_sort Marinho, Andrey Moacir do Rosario
collection PubMed
description Biotransformations are reactions mediated by microorganisms, such as fungi. These bioreactions have high chemo- and stereoselectivity on organic substrates and can be applied in the search for new bioactive compounds. In this study, acanthoic acid (AA) was biotransformed using the fungus Xylaria sp., giving the novel compound 3β,7β-dihydroxyacanthoic acid (S1). Both the AA and the product S1 were tested against Gram-positive and Gram-negative bacteria. To identify and validate possible biological targets as enzymes or proteins involved in the activity observed in vitro, we used the molecular docking method. Hydroxylation at the C-3 and C-7 positions of the biotransformation product enhanced its activity against Escherichia coli as well as its binding affinity and interactions with superoxide dismutase 1 (SOD1; PDB ID 4A7G). Based on our results, the SOD1 enzyme was suggested to be a possible target for the antioxidant activity of product S1.
format Online
Article
Text
id pubmed-10451833
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-104518332023-08-26 Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp. Marinho, Andrey Moacir do Rosario de Oliveira, Claudia Maria S. C. Silva-Silva, João Victor de Jesus, Samara C. Anchieta Siqueira, José Edson S. de Oliveira, Luana C. Auzier, Jéssica Fernandes Soares, Liviane N. Pinheiro, Maria Lúcia Belém Silva, Sebastião C. Medeiros, Lívia S. Costa, Emmanoel V. Marinho, Patrícia S. Barbosa Antibiotics (Basel) Article Biotransformations are reactions mediated by microorganisms, such as fungi. These bioreactions have high chemo- and stereoselectivity on organic substrates and can be applied in the search for new bioactive compounds. In this study, acanthoic acid (AA) was biotransformed using the fungus Xylaria sp., giving the novel compound 3β,7β-dihydroxyacanthoic acid (S1). Both the AA and the product S1 were tested against Gram-positive and Gram-negative bacteria. To identify and validate possible biological targets as enzymes or proteins involved in the activity observed in vitro, we used the molecular docking method. Hydroxylation at the C-3 and C-7 positions of the biotransformation product enhanced its activity against Escherichia coli as well as its binding affinity and interactions with superoxide dismutase 1 (SOD1; PDB ID 4A7G). Based on our results, the SOD1 enzyme was suggested to be a possible target for the antioxidant activity of product S1. MDPI 2023-08-18 /pmc/articles/PMC10451833/ /pubmed/37627751 http://dx.doi.org/10.3390/antibiotics12081331 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Marinho, Andrey Moacir do Rosario
de Oliveira, Claudia Maria S. C.
Silva-Silva, João Victor
de Jesus, Samara C. Anchieta
Siqueira, José Edson S.
de Oliveira, Luana C.
Auzier, Jéssica Fernandes
Soares, Liviane N.
Pinheiro, Maria Lúcia Belém
Silva, Sebastião C.
Medeiros, Lívia S.
Costa, Emmanoel V.
Marinho, Patrícia S. Barbosa
Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title_full Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title_fullStr Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title_full_unstemmed Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title_short Antimicrobial Activity and Molecular Docking Studies of the Biotransformation of Diterpene Acanthoic Acid Using the Fungus Xylaria sp.
title_sort antimicrobial activity and molecular docking studies of the biotransformation of diterpene acanthoic acid using the fungus xylaria sp.
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10451833/
https://www.ncbi.nlm.nih.gov/pubmed/37627751
http://dx.doi.org/10.3390/antibiotics12081331
work_keys_str_mv AT marinhoandreymoacirdorosario antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT deoliveiraclaudiamariasc antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT silvasilvajoaovictor antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT dejesussamaracanchieta antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT siqueirajoseedsons antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT deoliveiraluanac antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT auzierjessicafernandes antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT soareslivianen antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT pinheiromarialuciabelem antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT silvasebastiaoc antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT medeiroslivias antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT costaemmanoelv antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp
AT marinhopatriciasbarbosa antimicrobialactivityandmoleculardockingstudiesofthebiotransformationofditerpeneacanthoicacidusingthefungusxylariasp