Produção de haloalcaloides por fungos de ambiente terrestre
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/10667 |
Resumo: | The production of secondary metabolites by microorganisms is a tool to find new substances with potential pharmacological activities of human interest. Thus, the search for more extreme environments or even exposure of isolated in extreme conditions lead to the production of new natural products. The fungus Penicillium chrysogenum was able to produce the containing bromine atom alkaloid derived from the biosynthetic pathway of dicetopiperazinic alkaloids. Under natural conditions, the fungus produces roquefortine C, when the culture medium was added ammonium bromide, the microorganism produced 11-bromoroquefortine D, 11-bromoroquertine C and 17-oxy-11-C bromoroquefortine. These metabolites have biosynthetic origin by condensation of tryptophan with histidine and trimethyalil group. There are reports in the literature that the first biosynthetic step of halogenated alkaloid derivatives of tryptophan would be halogenation of this amino acid. The synthesis of bromotryptophan was performed and the formation of three regioisomers were detected. The extract containing the isomers was added to the culture medium during the growth of the fungus and analysis of LCHRMS/MS observed the formation of 11-bromoroquefortine C. Synthesis of roquefortine C with sodium hypobromite has also led to the formation of 11-bromoroquefortine C. During the search of the gene responsible for the expression of halogenase in Penicillium chrysogenum a gene fragment compatible with halogenases deposited in databases was detected and isolated. In Talaromyces wortmannii, fungus isolated from Mallus domestica, producer of some halogenated alkaloid known as rugulovasins, a gene fragment compatible with fungal halogenases was also detected and isolated. Strains belonging to Penicillium and Aspergillus isolated and deposited in mycology collection of LaBioMMi were grown on solid medium and analyzed by MALDI-TOF to build a database. All the microorganisms were separated by gender and grouped into dendrograms for checking the similarity between species. It was also found that the modification of the culture medium does not influence directly the profile obtained from microorganisms. |
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Silva, José Vinicius daRodrigues Filho, Edsonhttp://lattes.cnpq.br/3667941735597178http://lattes.cnpq.br/24344746474547292018-11-12T23:07:48Z2018-11-12T23:07:48Z2016-09-02SILVA, José Vinicius da. Produção de haloalcaloides por fungos de ambiente terrestre. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10667.https://repositorio.ufscar.br/handle/ufscar/10667The production of secondary metabolites by microorganisms is a tool to find new substances with potential pharmacological activities of human interest. Thus, the search for more extreme environments or even exposure of isolated in extreme conditions lead to the production of new natural products. The fungus Penicillium chrysogenum was able to produce the containing bromine atom alkaloid derived from the biosynthetic pathway of dicetopiperazinic alkaloids. Under natural conditions, the fungus produces roquefortine C, when the culture medium was added ammonium bromide, the microorganism produced 11-bromoroquefortine D, 11-bromoroquertine C and 17-oxy-11-C bromoroquefortine. These metabolites have biosynthetic origin by condensation of tryptophan with histidine and trimethyalil group. There are reports in the literature that the first biosynthetic step of halogenated alkaloid derivatives of tryptophan would be halogenation of this amino acid. The synthesis of bromotryptophan was performed and the formation of three regioisomers were detected. The extract containing the isomers was added to the culture medium during the growth of the fungus and analysis of LCHRMS/MS observed the formation of 11-bromoroquefortine C. Synthesis of roquefortine C with sodium hypobromite has also led to the formation of 11-bromoroquefortine C. During the search of the gene responsible for the expression of halogenase in Penicillium chrysogenum a gene fragment compatible with halogenases deposited in databases was detected and isolated. In Talaromyces wortmannii, fungus isolated from Mallus domestica, producer of some halogenated alkaloid known as rugulovasins, a gene fragment compatible with fungal halogenases was also detected and isolated. Strains belonging to Penicillium and Aspergillus isolated and deposited in mycology collection of LaBioMMi were grown on solid medium and analyzed by MALDI-TOF to build a database. All the microorganisms were separated by gender and grouped into dendrograms for checking the similarity between species. It was also found that the modification of the culture medium does not influence directly the profile obtained from microorganisms.A produção de metabólitos secundários por microrganismos é uma ferramenta para encontrar novas substâncias com possíveis atividades farmacológicas de interesse humano. Desta forma, a busca por ambientes mais extremos ou até mesmo a exposição dos isolados em condições extremas levam à produção de novos produtos naturais. O fungo Penicillium chrysogenum foi capaz de produzir alcaloides contendo átomo de bromo derivados da rota biossintética dos alcaloides dicetopiperazínicos. Em condições naturais, o fungo produz a roquefortina C e quando ao meio de cultura foi adicionado brometo de amônio, o microrganismo produziu a 11- bromoroquefortina D, 11-bromoroquertina C e 17-oxi-11-bromoroquefortina C. Estes metabólitos tem origem biossintética através da condensação do triptofano com a histidina e o grupo trimetilalil. Há relatos na literatura que a primeira etapa biossintética de alcaloides halogenados derivados do triptofano seria a halogenação deste aminoácido. A síntese do bromotriptofano foi realizada e foi verificada a formação de três regioisômeros. O extrato contendo os isômeros foi adicionado ao meio de cultura durante o crescimento do fungo e por análises de LC-HRMS/MS observou-se a formação da 11- bromoroquefortina C. A síntese da roquefortina C com hipobromito de sódio também levou à formação da 11-bromoroquefortina C. Na busca do gene responsável pela expressão da halogenase em Penicillium chrysogenum foi obtido um fragmento do gene compatível com halogenases depositadas em bancos de dados. De Talaromyces wortmannii, fungo isolado de Mallus domestica, produtor de alguns alcaloides halogenados conhecidos como rugulovasinas, isolou-se um fragmento de gene compatível com halogenases fúngicas. Linhagens pertencentes aos gêneros Penicillium e Aspergillus isoladas e depositadas na micoteca do LaBioMMi foram cultivadas em meio sólido e analisadas por MALDI-TOF para construção de um banco de dados a partir do perfil obtido. Todos os organismos foram separados por gênero e agrupados em dendrogramas para a verificação da similaridade entre as espécies. Constatou-se também que a modificação do meio de cultura não influencia diretamente no perfil obtido dos microrganismos.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarTalaromyces wortmanniiBromoroquefortinaHaloalcaloidesMicrorganismos endofíticosOsmacPenicillium chrysogenumCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAISProdução de haloalcaloides por fungos de ambiente terrestreHaloalkaloids production by terrestrial fungiinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisOnlineinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALTese_JoseViniciusSilva_Set2016_FINAL.pdfTese_JoseViniciusSilva_Set2016_FINAL.pdfapplication/pdf3881253https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/10667/1/Tese_JoseViniciusSilva_Set2016_FINAL.pdf155b369adadd2576a79abfa4ee31a130MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81957https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/10667/3/license.txtae0398b6f8b235e40ad82cba6c50031dMD53TEXTTese_JoseViniciusSilva_Set2016_FINAL.pdf.txtTese_JoseViniciusSilva_Set2016_FINAL.pdf.txtExtracted texttext/plain180447https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/10667/4/Tese_JoseViniciusSilva_Set2016_FINAL.pdf.txt688c8f59575f11d6479144acc2ced453MD54THUMBNAILTese_JoseViniciusSilva_Set2016_FINAL.pdf.jpgTese_JoseViniciusSilva_Set2016_FINAL.pdf.jpgIM Thumbnailimage/jpeg4051https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/10667/5/Tese_JoseViniciusSilva_Set2016_FINAL.pdf.jpgfde05dbdf153820f67e1119fbeaff971MD55ufscar/106672019-09-11 03:27:00.965oai:repositorio.ufscar.br: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Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222019-09-11T03:27Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Produção de haloalcaloides por fungos de ambiente terrestre |
dc.title.alternative.eng.fl_str_mv |
Haloalkaloids production by terrestrial fungi |
title |
Produção de haloalcaloides por fungos de ambiente terrestre |
spellingShingle |
Produção de haloalcaloides por fungos de ambiente terrestre Silva, José Vinicius da Talaromyces wortmannii Bromoroquefortina Haloalcaloides Microrganismos endofíticos Osmac Penicillium chrysogenum CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS |
title_short |
Produção de haloalcaloides por fungos de ambiente terrestre |
title_full |
Produção de haloalcaloides por fungos de ambiente terrestre |
title_fullStr |
Produção de haloalcaloides por fungos de ambiente terrestre |
title_full_unstemmed |
Produção de haloalcaloides por fungos de ambiente terrestre |
title_sort |
Produção de haloalcaloides por fungos de ambiente terrestre |
author |
Silva, José Vinicius da |
author_facet |
Silva, José Vinicius da |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/2434474647454729 |
dc.contributor.author.fl_str_mv |
Silva, José Vinicius da |
dc.contributor.advisor1.fl_str_mv |
Rodrigues Filho, Edson |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3667941735597178 |
contributor_str_mv |
Rodrigues Filho, Edson |
dc.subject.por.fl_str_mv |
Talaromyces wortmannii Bromoroquefortina Haloalcaloides Microrganismos endofíticos |
topic |
Talaromyces wortmannii Bromoroquefortina Haloalcaloides Microrganismos endofíticos Osmac Penicillium chrysogenum CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS |
dc.subject.eng.fl_str_mv |
Osmac Penicillium chrysogenum |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::QUIMICA DOS PRODUTOS NATURAIS |
description |
The production of secondary metabolites by microorganisms is a tool to find new substances with potential pharmacological activities of human interest. Thus, the search for more extreme environments or even exposure of isolated in extreme conditions lead to the production of new natural products. The fungus Penicillium chrysogenum was able to produce the containing bromine atom alkaloid derived from the biosynthetic pathway of dicetopiperazinic alkaloids. Under natural conditions, the fungus produces roquefortine C, when the culture medium was added ammonium bromide, the microorganism produced 11-bromoroquefortine D, 11-bromoroquertine C and 17-oxy-11-C bromoroquefortine. These metabolites have biosynthetic origin by condensation of tryptophan with histidine and trimethyalil group. There are reports in the literature that the first biosynthetic step of halogenated alkaloid derivatives of tryptophan would be halogenation of this amino acid. The synthesis of bromotryptophan was performed and the formation of three regioisomers were detected. The extract containing the isomers was added to the culture medium during the growth of the fungus and analysis of LCHRMS/MS observed the formation of 11-bromoroquefortine C. Synthesis of roquefortine C with sodium hypobromite has also led to the formation of 11-bromoroquefortine C. During the search of the gene responsible for the expression of halogenase in Penicillium chrysogenum a gene fragment compatible with halogenases deposited in databases was detected and isolated. In Talaromyces wortmannii, fungus isolated from Mallus domestica, producer of some halogenated alkaloid known as rugulovasins, a gene fragment compatible with fungal halogenases was also detected and isolated. Strains belonging to Penicillium and Aspergillus isolated and deposited in mycology collection of LaBioMMi were grown on solid medium and analyzed by MALDI-TOF to build a database. All the microorganisms were separated by gender and grouped into dendrograms for checking the similarity between species. It was also found that the modification of the culture medium does not influence directly the profile obtained from microorganisms. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-09-02 |
dc.date.accessioned.fl_str_mv |
2018-11-12T23:07:48Z |
dc.date.available.fl_str_mv |
2018-11-12T23:07:48Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
SILVA, José Vinicius da. Produção de haloalcaloides por fungos de ambiente terrestre. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10667. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/10667 |
identifier_str_mv |
SILVA, José Vinicius da. Produção de haloalcaloides por fungos de ambiente terrestre. 2016. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2016. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10667. |
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https://repositorio.ufscar.br/handle/ufscar/10667 |
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por |
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por |
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openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química - PPGQ |
dc.publisher.initials.fl_str_mv |
UFSCar |
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Universidade Federal de São Carlos Câmpus São Carlos |
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