Produção de haloalcaloides por fungos de ambiente terrestre

Detalhes bibliográficos
Autor(a) principal: Silva, José Vinicius da
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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spelling 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.
url https://repositorio.ufscar.br/handle/ufscar/10667
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language por
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv 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
publisher.none.fl_str_mv Universidade Federal de São Carlos
Câmpus São Carlos
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institution UFSCAR
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