Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi
- Autores
- dos Santos, Neidy S. S.; Fonseca, Sávio; Almeida, Franco F.; Belo, Ezequiel; Siqueira, Marcelo; dos Santos Niculau, Edenilson; Silva, Sebastião; Santos, Darlisson A.; Provasi, Patricio Federico; Andrade Filho, Tarciso; da Cunha, Antônio R.; Gester, Rodrigo M.
- Año de publicación
- 2023
- Idioma
- inglés
- Tipo de recurso
- documento de conferencia
- Estado
- versión publicada
- Descripción
- INTRODUCTION: The ability of natural products to provide new compounds with applications in various fields, including biology, pharmacology, and materials science, has attracted much attention in recent years. In this study, we explored the extraction of the 1-nitro-2-phenylethane (NPE) compound from Aniba canelilla and its biotransformation to 2- phenylethanol (PE) by fungi species from the Brazilian Amazon. In addition, we performed computational analyzes to track changes in molecular properties. METHODS: The nitrogenous compound was obtained from the essential oil of Aniba canelilla. The biotransformation reactions were carried out using four species of fungi: Aspergillus flavus, Colletotrichum sp., Lasiodiplodia caatinguensis, and Rigidoporus lineatus. After an incubation period of 7 days at 32 °C on an orbital shaker (130 rpm), 50 mg of 1-nitro-2-phenylethane diluted in 100 mL of dimethylsulfoxide (DMSO) was added to the reaction vessels. Aliquots (2 mL) were taken and analyzed by GC-MS (pulverized silicon capillary column, RTX-5MS 30 m 0.25 mm 0.25 m). FTIR spectra of 1-nitro-2-phenylethane and 2- phenylethanol were obtained using total attenuated reflection (ATR). The NPE and PE FTIR spectra were obtained using an Agilent CARY 630 spectrometer in the spectral region between 400 and 650 cm-1 . Calculations were performed in the Gaussian 092 program while the DICE3 code was used to perform the s-MC-QM sequence and generate the liquid environment using default parameters. The interactions were described by coupling the Lennard-Jones and Coulomb potentials using the All-Atom Optimized for Liquid-State Simulations (AA-OPLS) force field. All reactive parameters and electrical excitations were calculated using Density Functional Theory, M06-2X/6-311++G(d,p). 4,5 RESULTS: The finds show that the biotransformation of NPE into PE using the four tested fungal species was successful, as evidenced by an improvement in the nonlinear optical response of PE in comparison to N2PE. We also note that interactions with solvents affect the vibrational spectra of the donor and acceptor groups of compounds and that bioconversion affects the molecular reactivity of the compound. CONCLUSIONS: This study showed that using fungal species to biotransform NPE into PE is a promising technique. In addition, Monte Carlo simulations and vibrational analyses help us understand changes to the molecular properties that occur throughout the biotransformation.
Fil: dos Santos, Neidy S. S.. Universidade Federal do Sul e Sudeste do Pará; Brasil
Fil: Fonseca, Sávio. Universidade Federal do Sul e Sudeste do Pará; Brasil
Fil: Almeida, Franco F.. Universidade Federal do Sul e Sudeste do Pará; Brasil
Fil: Belo, Ezequiel. Universidade Federal do Pará; Brasil
Fil: Siqueira, Marcelo. Universidade Federal Do Amapá.; Brasil
Fil: dos Santos Niculau, Edenilson. Universidade Federal Do Tocantins (ufdt);
Fil: Silva, Sebastião. Universidade Federal do Sul e Sudeste do Pará; Brasil
Fil: Santos, Darlisson A.. Universidade Federal de Pernambuco; Brasil
Fil: Provasi, Patricio Federico. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Modelado e Innovación Tecnológica. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Modelado e Innovación Tecnológica; Argentina
Fil: Andrade Filho, Tarciso. Universidade Federal do Sul e Sudeste do Pará; Brasil
Fil: da Cunha, Antônio R.. Universidade Federal do Maranhao; Brasil
Fil: Gester, Rodrigo M.. Instituto de Fisica (ifspu) ; Universidade Do Sao Paulo;
XXII Simposio Brasilero de Qimica Teorica
Rio de Janeiro
Brasil
Universidade Federal Fluminense - Materia
-
SOLVENT EFFECTS
NLO
DFT
AMAZONIAN BIOME
BIOTRANSFORMATION - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/236371
Ver los metadatos del registro completo
id |
CONICETDig_79832430f8da9ec4f14fa249cbc27547 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/236371 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
network_name_str |
CONICET Digital (CONICET) |
spelling |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungidos Santos, Neidy S. S.Fonseca, SávioAlmeida, Franco F.Belo, EzequielSiqueira, Marcelodos Santos Niculau, EdenilsonSilva, SebastiãoSantos, Darlisson A.Provasi, Patricio FedericoAndrade Filho, Tarcisoda Cunha, Antônio R.Gester, Rodrigo M.SOLVENT EFFECTSNLODFTAMAZONIAN BIOMEBIOTRANSFORMATIONhttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/1INTRODUCTION: The ability of natural products to provide new compounds with applications in various fields, including biology, pharmacology, and materials science, has attracted much attention in recent years. In this study, we explored the extraction of the 1-nitro-2-phenylethane (NPE) compound from Aniba canelilla and its biotransformation to 2- phenylethanol (PE) by fungi species from the Brazilian Amazon. In addition, we performed computational analyzes to track changes in molecular properties. METHODS: The nitrogenous compound was obtained from the essential oil of Aniba canelilla. The biotransformation reactions were carried out using four species of fungi: Aspergillus flavus, Colletotrichum sp., Lasiodiplodia caatinguensis, and Rigidoporus lineatus. After an incubation period of 7 days at 32 °C on an orbital shaker (130 rpm), 50 mg of 1-nitro-2-phenylethane diluted in 100 mL of dimethylsulfoxide (DMSO) was added to the reaction vessels. Aliquots (2 mL) were taken and analyzed by GC-MS (pulverized silicon capillary column, RTX-5MS 30 m 0.25 mm 0.25 m). FTIR spectra of 1-nitro-2-phenylethane and 2- phenylethanol were obtained using total attenuated reflection (ATR). The NPE and PE FTIR spectra were obtained using an Agilent CARY 630 spectrometer in the spectral region between 400 and 650 cm-1 . Calculations were performed in the Gaussian 092 program while the DICE3 code was used to perform the s-MC-QM sequence and generate the liquid environment using default parameters. The interactions were described by coupling the Lennard-Jones and Coulomb potentials using the All-Atom Optimized for Liquid-State Simulations (AA-OPLS) force field. All reactive parameters and electrical excitations were calculated using Density Functional Theory, M06-2X/6-311++G(d,p). 4,5 RESULTS: The finds show that the biotransformation of NPE into PE using the four tested fungal species was successful, as evidenced by an improvement in the nonlinear optical response of PE in comparison to N2PE. We also note that interactions with solvents affect the vibrational spectra of the donor and acceptor groups of compounds and that bioconversion affects the molecular reactivity of the compound. CONCLUSIONS: This study showed that using fungal species to biotransform NPE into PE is a promising technique. In addition, Monte Carlo simulations and vibrational analyses help us understand changes to the molecular properties that occur throughout the biotransformation.Fil: dos Santos, Neidy S. S.. Universidade Federal do Sul e Sudeste do Pará; BrasilFil: Fonseca, Sávio. Universidade Federal do Sul e Sudeste do Pará; BrasilFil: Almeida, Franco F.. Universidade Federal do Sul e Sudeste do Pará; BrasilFil: Belo, Ezequiel. Universidade Federal do Pará; BrasilFil: Siqueira, Marcelo. Universidade Federal Do Amapá.; BrasilFil: dos Santos Niculau, Edenilson. Universidade Federal Do Tocantins (ufdt);Fil: Silva, Sebastião. Universidade Federal do Sul e Sudeste do Pará; BrasilFil: Santos, Darlisson A.. Universidade Federal de Pernambuco; BrasilFil: Provasi, Patricio Federico. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Modelado e Innovación Tecnológica. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Modelado e Innovación Tecnológica; ArgentinaFil: Andrade Filho, Tarciso. Universidade Federal do Sul e Sudeste do Pará; BrasilFil: da Cunha, Antônio R.. Universidade Federal do Maranhao; BrasilFil: Gester, Rodrigo M.. Instituto de Fisica (ifspu) ; Universidade Do Sao Paulo;XXII Simposio Brasilero de Qimica TeoricaRio de JaneiroBrasilUniversidade Federal FluminenseSociedad Brasilera de Química Teórica2023info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/conferenceObjectSimposioJournalhttp://purl.org/coar/resource_type/c_5794info:ar-repo/semantics/documentoDeConferenciaapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/236371Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi; XXII Simposio Brasilero de Qimica Teorica; Rio de Janeiro; Brasil; 2023; 1-12965-5900CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://proceedings.science/sbqt/sbqt-2023/trabalhos/experimental-and-theoretical-study-of-nitro-compounds-to-aromatic-alcohol-a-sust?lang=pt-brInternacionalinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:15:55Zoai:ri.conicet.gov.ar:11336/236371instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:15:55.617CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
title |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
spellingShingle |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi dos Santos, Neidy S. S. SOLVENT EFFECTS NLO DFT AMAZONIAN BIOME BIOTRANSFORMATION |
title_short |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
title_full |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
title_fullStr |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
title_full_unstemmed |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
title_sort |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi |
dc.creator.none.fl_str_mv |
dos Santos, Neidy S. S. Fonseca, Sávio Almeida, Franco F. Belo, Ezequiel Siqueira, Marcelo dos Santos Niculau, Edenilson Silva, Sebastião Santos, Darlisson A. Provasi, Patricio Federico Andrade Filho, Tarciso da Cunha, Antônio R. Gester, Rodrigo M. |
author |
dos Santos, Neidy S. S. |
author_facet |
dos Santos, Neidy S. S. Fonseca, Sávio Almeida, Franco F. Belo, Ezequiel Siqueira, Marcelo dos Santos Niculau, Edenilson Silva, Sebastião Santos, Darlisson A. Provasi, Patricio Federico Andrade Filho, Tarciso da Cunha, Antônio R. Gester, Rodrigo M. |
author_role |
author |
author2 |
Fonseca, Sávio Almeida, Franco F. Belo, Ezequiel Siqueira, Marcelo dos Santos Niculau, Edenilson Silva, Sebastião Santos, Darlisson A. Provasi, Patricio Federico Andrade Filho, Tarciso da Cunha, Antônio R. Gester, Rodrigo M. |
author2_role |
author author author author author author author author author author author |
dc.subject.none.fl_str_mv |
SOLVENT EFFECTS NLO DFT AMAZONIAN BIOME BIOTRANSFORMATION |
topic |
SOLVENT EFFECTS NLO DFT AMAZONIAN BIOME BIOTRANSFORMATION |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.3 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
INTRODUCTION: The ability of natural products to provide new compounds with applications in various fields, including biology, pharmacology, and materials science, has attracted much attention in recent years. In this study, we explored the extraction of the 1-nitro-2-phenylethane (NPE) compound from Aniba canelilla and its biotransformation to 2- phenylethanol (PE) by fungi species from the Brazilian Amazon. In addition, we performed computational analyzes to track changes in molecular properties. METHODS: The nitrogenous compound was obtained from the essential oil of Aniba canelilla. The biotransformation reactions were carried out using four species of fungi: Aspergillus flavus, Colletotrichum sp., Lasiodiplodia caatinguensis, and Rigidoporus lineatus. After an incubation period of 7 days at 32 °C on an orbital shaker (130 rpm), 50 mg of 1-nitro-2-phenylethane diluted in 100 mL of dimethylsulfoxide (DMSO) was added to the reaction vessels. Aliquots (2 mL) were taken and analyzed by GC-MS (pulverized silicon capillary column, RTX-5MS 30 m 0.25 mm 0.25 m). FTIR spectra of 1-nitro-2-phenylethane and 2- phenylethanol were obtained using total attenuated reflection (ATR). The NPE and PE FTIR spectra were obtained using an Agilent CARY 630 spectrometer in the spectral region between 400 and 650 cm-1 . Calculations were performed in the Gaussian 092 program while the DICE3 code was used to perform the s-MC-QM sequence and generate the liquid environment using default parameters. The interactions were described by coupling the Lennard-Jones and Coulomb potentials using the All-Atom Optimized for Liquid-State Simulations (AA-OPLS) force field. All reactive parameters and electrical excitations were calculated using Density Functional Theory, M06-2X/6-311++G(d,p). 4,5 RESULTS: The finds show that the biotransformation of NPE into PE using the four tested fungal species was successful, as evidenced by an improvement in the nonlinear optical response of PE in comparison to N2PE. We also note that interactions with solvents affect the vibrational spectra of the donor and acceptor groups of compounds and that bioconversion affects the molecular reactivity of the compound. CONCLUSIONS: This study showed that using fungal species to biotransform NPE into PE is a promising technique. In addition, Monte Carlo simulations and vibrational analyses help us understand changes to the molecular properties that occur throughout the biotransformation. Fil: dos Santos, Neidy S. S.. Universidade Federal do Sul e Sudeste do Pará; Brasil Fil: Fonseca, Sávio. Universidade Federal do Sul e Sudeste do Pará; Brasil Fil: Almeida, Franco F.. Universidade Federal do Sul e Sudeste do Pará; Brasil Fil: Belo, Ezequiel. Universidade Federal do Pará; Brasil Fil: Siqueira, Marcelo. Universidade Federal Do Amapá.; Brasil Fil: dos Santos Niculau, Edenilson. Universidade Federal Do Tocantins (ufdt); Fil: Silva, Sebastião. Universidade Federal do Sul e Sudeste do Pará; Brasil Fil: Santos, Darlisson A.. Universidade Federal de Pernambuco; Brasil Fil: Provasi, Patricio Federico. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Modelado e Innovación Tecnológica. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Modelado e Innovación Tecnológica; Argentina Fil: Andrade Filho, Tarciso. Universidade Federal do Sul e Sudeste do Pará; Brasil Fil: da Cunha, Antônio R.. Universidade Federal do Maranhao; Brasil Fil: Gester, Rodrigo M.. Instituto de Fisica (ifspu) ; Universidade Do Sao Paulo; XXII Simposio Brasilero de Qimica Teorica Rio de Janeiro Brasil Universidade Federal Fluminense |
description |
INTRODUCTION: The ability of natural products to provide new compounds with applications in various fields, including biology, pharmacology, and materials science, has attracted much attention in recent years. In this study, we explored the extraction of the 1-nitro-2-phenylethane (NPE) compound from Aniba canelilla and its biotransformation to 2- phenylethanol (PE) by fungi species from the Brazilian Amazon. In addition, we performed computational analyzes to track changes in molecular properties. METHODS: The nitrogenous compound was obtained from the essential oil of Aniba canelilla. The biotransformation reactions were carried out using four species of fungi: Aspergillus flavus, Colletotrichum sp., Lasiodiplodia caatinguensis, and Rigidoporus lineatus. After an incubation period of 7 days at 32 °C on an orbital shaker (130 rpm), 50 mg of 1-nitro-2-phenylethane diluted in 100 mL of dimethylsulfoxide (DMSO) was added to the reaction vessels. Aliquots (2 mL) were taken and analyzed by GC-MS (pulverized silicon capillary column, RTX-5MS 30 m 0.25 mm 0.25 m). FTIR spectra of 1-nitro-2-phenylethane and 2- phenylethanol were obtained using total attenuated reflection (ATR). The NPE and PE FTIR spectra were obtained using an Agilent CARY 630 spectrometer in the spectral region between 400 and 650 cm-1 . Calculations were performed in the Gaussian 092 program while the DICE3 code was used to perform the s-MC-QM sequence and generate the liquid environment using default parameters. The interactions were described by coupling the Lennard-Jones and Coulomb potentials using the All-Atom Optimized for Liquid-State Simulations (AA-OPLS) force field. All reactive parameters and electrical excitations were calculated using Density Functional Theory, M06-2X/6-311++G(d,p). 4,5 RESULTS: The finds show that the biotransformation of NPE into PE using the four tested fungal species was successful, as evidenced by an improvement in the nonlinear optical response of PE in comparison to N2PE. We also note that interactions with solvents affect the vibrational spectra of the donor and acceptor groups of compounds and that bioconversion affects the molecular reactivity of the compound. CONCLUSIONS: This study showed that using fungal species to biotransform NPE into PE is a promising technique. In addition, Monte Carlo simulations and vibrational analyses help us understand changes to the molecular properties that occur throughout the biotransformation. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/conferenceObject Simposio Journal http://purl.org/coar/resource_type/c_5794 info:ar-repo/semantics/documentoDeConferencia |
status_str |
publishedVersion |
format |
conferenceObject |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/236371 Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi; XXII Simposio Brasilero de Qimica Teorica; Rio de Janeiro; Brasil; 2023; 1-1 2965-5900 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/236371 |
identifier_str_mv |
Experimental and theoretical study of nitro compounds to aromatic alcohol: a sustainable biocatalytic transformation from Amazonian fungi; XXII Simposio Brasilero de Qimica Teorica; Rio de Janeiro; Brasil; 2023; 1-1 2965-5900 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://proceedings.science/sbqt/sbqt-2023/trabalhos/experimental-and-theoretical-study-of-nitro-compounds-to-aromatic-alcohol-a-sust?lang=pt-br |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.coverage.none.fl_str_mv |
Internacional |
dc.publisher.none.fl_str_mv |
Sociedad Brasilera de Química Teórica |
publisher.none.fl_str_mv |
Sociedad Brasilera de Química Teórica |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
_version_ |
1844614098598232064 |
score |
13.070432 |