Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase

Background: Hydroxycinnamic acids and some of their derivatives are molecules with interesting biological activities; for instance, hydroxylated hydroxycinnamic esters have proved to have antifungal properties, and thus the generation of these molecules is of industrial importance. In this study, th...

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Autores principales:	Ana Daniela Vega-Rodríguez, Mariana Antonieta Armendáriz-Ruiz, Daniel Alberto Grajales-Hernández, Jorge Alberto Rodríguez-González, Ali Asaff-Torres, Juan Carlos Mateos-Díaz
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Antifungal Aspergillus terreus Esterases Esterification Feruloyl esterase Fusarium Biotechnology TP248.13-248.65 Biology (General) QH301-705.5
Acceso en línea:	https://doaj.org/article/5e2f1de5a0834cfda032a94f6cc3f0f2
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spelling	oai:doaj.org-article:5e2f1de5a0834cfda032a94f6cc3f0f22021-11-06T04:20:11ZImproved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase0717-345810.1016/j.ejbt.2021.08.001https://doaj.org/article/5e2f1de5a0834cfda032a94f6cc3f0f22021-11-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S0717345821000403https://doaj.org/toc/0717-3458Background: Hydroxycinnamic acids and some of their derivatives are molecules with interesting biological activities; for instance, hydroxylated hydroxycinnamic esters have proved to have antifungal properties, and thus the generation of these molecules is of industrial importance. In this study, the direct esterification capacity of the pure recombinant type B feruloyl esterase from Aspergillus terreus (AtFAE B) was evaluated by its ability to catalyze the synthesis of isobutyl o-coumarate, an interesting antifungal molecule. A ternary solvent system (isooctane/isobutanol/water) was employed to improve the synthesis of isobutyl o-coumarate, assessing different substrate concentrations, enzyme load, water percentages and pH and temperature values. Results: AtFAE B showed the highest initial rate at 18% (v/v) isobutanol and 50 mM o-coumaric acid, 0.04 mg/ml of enzyme, 4% (v/v) water without buffer and 40°C. AtFAE B half-lives at 30°C, 40°C and 50°C were 16.5 h, 1.75 h and 3.5 min, respectively. Thus, we decided to evaluate the bioconversion yield at 30°C, where the enzyme showed the highest operational stability. At this temperature, we obtained a yield of ~80% after only 8 h of reaction, using a 78:18:4 isooctane:isobutanol:water ternary solvent system, with 50 mM of o-coumaric acid. Conclusions: Under these improved conditions, the productivity was 1.06 g isobutyl o-coumarate/L*h with a biocatalyst yield of 209.6 kg isobutyl o-coumarate/kg free AtFAE B, demonstrating the promising potential of AtFAE B to accept the non-canonical o-coumaric acid as the substrate and to achieve the synthesis of isobutyl o-coumarate.How to cite: Vega-Rodríguez AD, Armendáriz-Ruiz MA, Grajales-Hernández DA, et al. Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase. Electron J Biotechnol 2021;54. https://doi.org/10.1016/j.ejbt.2021.08.001Ana Daniela Vega-RodríguezMariana Antonieta Armendáriz-RuizDaniel Alberto Grajales-HernándezJorge Alberto Rodríguez-GonzálezAli Asaff-TorresJuan Carlos Mateos-DíazElsevierarticleAntifungalAspergillus terreusEsterasesEsterificationFeruloyl esteraseFusariumBiotechnologyTP248.13-248.65Biology (General)QH301-705.5ENElectronic Journal of Biotechnology, Vol 54, Iss , Pp 17-25 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Antifungal Aspergillus terreus Esterases Esterification Feruloyl esterase Fusarium Biotechnology TP248.13-248.65 Biology (General) QH301-705.5
spellingShingle	Antifungal Aspergillus terreus Esterases Esterification Feruloyl esterase Fusarium Biotechnology TP248.13-248.65 Biology (General) QH301-705.5 Ana Daniela Vega-Rodríguez Mariana Antonieta Armendáriz-Ruiz Daniel Alberto Grajales-Hernández Jorge Alberto Rodríguez-González Ali Asaff-Torres Juan Carlos Mateos-Díaz Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
description	Background: Hydroxycinnamic acids and some of their derivatives are molecules with interesting biological activities; for instance, hydroxylated hydroxycinnamic esters have proved to have antifungal properties, and thus the generation of these molecules is of industrial importance. In this study, the direct esterification capacity of the pure recombinant type B feruloyl esterase from Aspergillus terreus (AtFAE B) was evaluated by its ability to catalyze the synthesis of isobutyl o-coumarate, an interesting antifungal molecule. A ternary solvent system (isooctane/isobutanol/water) was employed to improve the synthesis of isobutyl o-coumarate, assessing different substrate concentrations, enzyme load, water percentages and pH and temperature values. Results: AtFAE B showed the highest initial rate at 18% (v/v) isobutanol and 50 mM o-coumaric acid, 0.04 mg/ml of enzyme, 4% (v/v) water without buffer and 40°C. AtFAE B half-lives at 30°C, 40°C and 50°C were 16.5 h, 1.75 h and 3.5 min, respectively. Thus, we decided to evaluate the bioconversion yield at 30°C, where the enzyme showed the highest operational stability. At this temperature, we obtained a yield of ~80% after only 8 h of reaction, using a 78:18:4 isooctane:isobutanol:water ternary solvent system, with 50 mM of o-coumaric acid. Conclusions: Under these improved conditions, the productivity was 1.06 g isobutyl o-coumarate/L*h with a biocatalyst yield of 209.6 kg isobutyl o-coumarate/kg free AtFAE B, demonstrating the promising potential of AtFAE B to accept the non-canonical o-coumaric acid as the substrate and to achieve the synthesis of isobutyl o-coumarate.How to cite: Vega-Rodríguez AD, Armendáriz-Ruiz MA, Grajales-Hernández DA, et al. Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase. Electron J Biotechnol 2021;54. https://doi.org/10.1016/j.ejbt.2021.08.001
format	article
author	Ana Daniela Vega-Rodríguez Mariana Antonieta Armendáriz-Ruiz Daniel Alberto Grajales-Hernández Jorge Alberto Rodríguez-González Ali Asaff-Torres Juan Carlos Mateos-Díaz
author_facet	Ana Daniela Vega-Rodríguez Mariana Antonieta Armendáriz-Ruiz Daniel Alberto Grajales-Hernández Jorge Alberto Rodríguez-González Ali Asaff-Torres Juan Carlos Mateos-Díaz
author_sort	Ana Daniela Vega-Rodríguez
title	Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
title_short	Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
title_full	Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
title_fullStr	Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
title_full_unstemmed	Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase
title_sort	improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the aspergillus terreus type b feruloyl esterase
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/5e2f1de5a0834cfda032a94f6cc3f0f2
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Improved synthesis of the antifungal isobutyl o-coumarate catalyzed by the Aspergillus terreus type B feruloyl esterase

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