Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius
Ano de defesa: | 2019 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/16735 |
Resumo: | Basidiomycete fungi are important living organisms that present several bioactive compounds, which have antimicrobial, antitumor, antioxidant, and anti-inflammatory potential. Several compounds and potentialities of this class of fungi are still unknown. Therefore, the objective of this work was to prepare fractions of Phellinotus piptadeniae and Pisolithus tinctorius, isolate and identify the secondary metabolites, and evaluate the antimicrobial activities of the fractions and compounds obtained. The antioxidant activity was just assessed for the fractions from P. piptadeniae species. The chemical investigation of P. piptadeniae led to the isolation of five compounds, two triterpenes (ergosterol peroxide (D1) and ergosterol (D2)), two long chain esters (pentadecanoic acid-2-hydroxy, ethyl ester (D6) and tetracosanoic-2-hydroxy, methyl ester (D11)), and a phenolic compound (derived from hispidin (D9)), which was not yet described. The ergosterol acetate (D2a) was obtained from an structural modification through the acetylation reaction of triterpene D2. The study of the Pisolithus tinctorius species drive to the isolation of two lanostane triterpenes (pisolactone (P180) and lanostane, 7,22-dien-3-ol, 24-methyl (P65)), where, P65 compound was identified as a novel metabolite in the literature. In addition, a long chain acid (5-hexadecenoic acid (P1)) and ceramide (P56), it was not in this species, were also identified. All fractions obtained from the species P. piptadeniae and P. tinctorius had antibacterial and antifungal actions. Whereas, against mycobacteria, only the hexanic and methanolic fractions of P. piptadeniae and the ethyl acetate fraction of P. tinctorius were effective at the concentrations tested. The triterpenes, acid derivatives and phenolic compound were active against bacteria (Gram-positive and Gram-negative), fungi and mycobacteria. The ethyl acetate and methanolic fractions of the P. piptadeniae species, when tested against their antioxidant capacity, showed promising results with IC50 because their values were close to the BHT standard. |
id |
UFSM-20_d17d2aec11c1edce823d454815012d26 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/16735 |
network_acronym_str |
UFSM-20 |
network_name_str |
Manancial - Repositório Digital da UFSM |
repository_id_str |
|
spelling |
2019-06-04T14:17:58Z2019-06-04T14:17:58Z2019-01-29http://repositorio.ufsm.br/handle/1/16735Basidiomycete fungi are important living organisms that present several bioactive compounds, which have antimicrobial, antitumor, antioxidant, and anti-inflammatory potential. Several compounds and potentialities of this class of fungi are still unknown. Therefore, the objective of this work was to prepare fractions of Phellinotus piptadeniae and Pisolithus tinctorius, isolate and identify the secondary metabolites, and evaluate the antimicrobial activities of the fractions and compounds obtained. The antioxidant activity was just assessed for the fractions from P. piptadeniae species. The chemical investigation of P. piptadeniae led to the isolation of five compounds, two triterpenes (ergosterol peroxide (D1) and ergosterol (D2)), two long chain esters (pentadecanoic acid-2-hydroxy, ethyl ester (D6) and tetracosanoic-2-hydroxy, methyl ester (D11)), and a phenolic compound (derived from hispidin (D9)), which was not yet described. The ergosterol acetate (D2a) was obtained from an structural modification through the acetylation reaction of triterpene D2. The study of the Pisolithus tinctorius species drive to the isolation of two lanostane triterpenes (pisolactone (P180) and lanostane, 7,22-dien-3-ol, 24-methyl (P65)), where, P65 compound was identified as a novel metabolite in the literature. In addition, a long chain acid (5-hexadecenoic acid (P1)) and ceramide (P56), it was not in this species, were also identified. All fractions obtained from the species P. piptadeniae and P. tinctorius had antibacterial and antifungal actions. Whereas, against mycobacteria, only the hexanic and methanolic fractions of P. piptadeniae and the ethyl acetate fraction of P. tinctorius were effective at the concentrations tested. The triterpenes, acid derivatives and phenolic compound were active against bacteria (Gram-positive and Gram-negative), fungi and mycobacteria. The ethyl acetate and methanolic fractions of the P. piptadeniae species, when tested against their antioxidant capacity, showed promising results with IC50 because their values were close to the BHT standard.Fungos Basidiomicetos são importantes organismos vivos que apresentam diversos compostos bioativos, os quais conferem potencial antimicrobiano, antitumoral, antioxidante e anti-inflamatório. Inúmeros compostos e potencialidades desta classe de fungos ainda são desconhecidos. Neste sentido, este trabalho teve por objetivo preparar frações de Phellinotus. piptadeniae e Pisolithus tinctorius, isolar e identificar os metabólitos secundários e avaliar as atividades antimicrobianas das frações e compostos obtidos. A atividade antioxidante também foi avaliada para as frações da espécie P. piptadeniae. A investigação química de Phellinotus piptadeniae levou ao isolamento de cinco compostos, sendo dois triterpenos (peróxido do ergosterol (D1) e ergosterol (D2)), dois ésteres de cadeia longa (2-hidróxi-pentadecanoato de etila (D6) e 2-hidróxi-tetracosanoato de metila (D11)) e um composto fenólico (derivado da hispidina (D9)) ao qual ainda não foi descrito na literatura. O acetato de ergosterol (D2a) foi obtido de uma modificação estrutural através da reação de acetilação do triterpeno D2. O estudo da espécie Pisolithus tinctorius levou ao isolamento de dois triterpenos do tipo lanostanos (pisolactona (P180) e lanostano, 7,22-dien-3-ol, 24-metil (P65)), onde, o composto P65 foi identificado como ainda não descrito na literatura. Além disso, um ácido de cadeia longa (ácido hexadec-5-enóico (P1)) e uma ceramida (P56), não encontrada anteriormente na espécie, também foram identificados. Todas as frações obtidas das espécies P. piptadeniae e P. tinctorius apresentaram ações antibacterianos e antifúngicos. Enquanto que, frente a micobactérias, apenas as frações hexânica e metanólica de P. piptadeniae e a fração acetato de etila de P. tinctorius foram efetivas nas concentrações testadas. Os triterpenos, derivados ácidos e composto fenólico foram ativos frente a bactérias (Gram-positivas e Gram-negativas), fungos e micobactérias. As frações acetato de etila e metanólica da espécie P. piptadeniae, quando testada a sua capacidade antioxidante, apresentaram resultados promissores, com valores de CI50, próximos ao padrão BHT.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessMetabólitos secundáriosAtividade antimicrobianaAtividade antioxidanteSecondary metabolitesAntioxidant activityAntimicrobial activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIsolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctoriusIsolation, structural determination and biological activities of metabolites from Phellinotus piptadeniae AND Pisolithus tinctorius FUNGIinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMorel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Maldaner, Gracielahttp://lattes.cnpq.br/6500796131690728Moura, Neusa Fernandes dehttp://lattes.cnpq.br/0820396530673217von Laer, Ana Eucareshttp://lattes.cnpq.br/4357761673325700Dornelles, Lucianohttp://lattes.cnpq.br/7629319262073140http://lattes.cnpq.br/9377630611329980Carmo, Gabriele do1006000000006006008c99befa-f1b3-4afb-98b8-7fab46c3d49349525a2a-c511-4cb0-9f1b-8995544ac4beb0db7504-a42c-44d0-b7f0-992c14108c1a24bb05e9-ab5c-4992-b51a-839d83a489339b8d56c9-b078-4956-921c-e8a6482493ff6f6ca89d-dfdf-41bb-9190-ea786a030c67reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdfTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdfTese de Doutoradoapplication/pdf6418478http://repositorio.ufsm.br/bitstream/1/16735/1/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf6cc36d0d31a3a3e4b15bd2dff159d826MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/16735/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/16735/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53TEXTTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.txtTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.txtExtracted texttext/plain242577http://repositorio.ufsm.br/bitstream/1/16735/4/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.txt78cfd0363b55ba4224b8392c8134874fMD54THUMBNAILTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.jpgTES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.jpgIM Thumbnailimage/jpeg4338http://repositorio.ufsm.br/bitstream/1/16735/5/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.jpg0b6089c4f9434246d09dd1f92afad2d3MD551/167352019-06-05 03:02:38.755oai:repositorio.ufsm.br:1/16735TElDRU7Dh0EgREUgRElTVFJJQlVJw4fDg08gTsODTy1FWENMVVNJVkEKCkNvbSBhIGFwcmVzZW50YcOnw6NvIGRlc3RhIGxpY2Vuw6dhLCB2b2PDqiAobyBhdXRvciAoZXMpIG91IG8gdGl0dWxhciBkb3MgZGlyZWl0b3MgZGUgYXV0b3IpIGNvbmNlZGUgw6AgVW5pdmVyc2lkYWRlCkZlZGVyYWwgZGUgU2FudGEgTWFyaWEgKFVGU00pIG8gZGlyZWl0byBuw6NvLWV4Y2x1c2l2byBkZSByZXByb2R1emlyLCAgdHJhZHV6aXIgKGNvbmZvcm1lIGRlZmluaWRvIGFiYWl4byksIGUvb3UKZGlzdHJpYnVpciBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gKGluY2x1aW5kbyBvIHJlc3VtbykgcG9yIHRvZG8gbyBtdW5kbyBubyBmb3JtYXRvIGltcHJlc3NvIGUgZWxldHLDtG5pY28gZQplbSBxdWFscXVlciBtZWlvLCBpbmNsdWluZG8gb3MgZm9ybWF0b3Mgw6F1ZGlvIG91IHbDrWRlby4KClZvY8OqIGNvbmNvcmRhIHF1ZSBhIFVGU00gcG9kZSwgc2VtIGFsdGVyYXIgbyBjb250ZcO6ZG8sIHRyYW5zcG9yIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbwpwYXJhIHF1YWxxdWVyIG1laW8gb3UgZm9ybWF0byBwYXJhIGZpbnMgZGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIHRhbWLDqW0gY29uY29yZGEgcXVlIGEgVUZTTSBwb2RlIG1hbnRlciBtYWlzIGRlIHVtYSBjw7NwaWEgYSBzdWEgdGVzZSBvdQpkaXNzZXJ0YcOnw6NvIHBhcmEgZmlucyBkZSBzZWd1cmFuw6dhLCBiYWNrLXVwIGUgcHJlc2VydmHDp8Ojby4KClZvY8OqIGRlY2xhcmEgcXVlIGEgc3VhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbyDDqSBvcmlnaW5hbCBlIHF1ZSB2b2PDqiB0ZW0gbyBwb2RlciBkZSBjb25jZWRlciBvcyBkaXJlaXRvcyBjb250aWRvcwpuZXN0YSBsaWNlbsOnYS4gVm9jw6ogdGFtYsOpbSBkZWNsYXJhIHF1ZSBvIGRlcMOzc2l0byBkYSBzdWEgdGVzZSBvdSBkaXNzZXJ0YcOnw6NvIG7Do28sIHF1ZSBzZWphIGRlIHNldQpjb25oZWNpbWVudG8sIGluZnJpbmdlIGRpcmVpdG9zIGF1dG9yYWlzIGRlIG5pbmd1w6ltLgoKQ2FzbyBhIHN1YSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gY29udGVuaGEgbWF0ZXJpYWwgcXVlIHZvY8OqIG7Do28gcG9zc3VpIGEgdGl0dWxhcmlkYWRlIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgdm9jw6oKZGVjbGFyYSBxdWUgb2J0ZXZlIGEgcGVybWlzc8OjbyBpcnJlc3RyaXRhIGRvIGRldGVudG9yIGRvcyBkaXJlaXRvcyBhdXRvcmFpcyBwYXJhIGNvbmNlZGVyIMOgIFVGU00Kb3MgZGlyZWl0b3MgYXByZXNlbnRhZG9zIG5lc3RhIGxpY2Vuw6dhLCBlIHF1ZSBlc3NlIG1hdGVyaWFsIGRlIHByb3ByaWVkYWRlIGRlIHRlcmNlaXJvcyBlc3TDoSBjbGFyYW1lbnRlCmlkZW50aWZpY2FkbyBlIHJlY29uaGVjaWRvIG5vIHRleHRvIG91IG5vIGNvbnRlw7pkbyBkYSB0ZXNlIG91IGRpc3NlcnRhw6fDo28gb3JhIGRlcG9zaXRhZGEuCgpDQVNPIEEgVEVTRSBPVSBESVNTRVJUQcOHw4NPIE9SQSBERVBPU0lUQURBIFRFTkhBIFNJRE8gUkVTVUxUQURPIERFIFVNIFBBVFJPQ8ONTklPIE9VCkFQT0lPIERFIFVNQSBBR8OKTkNJQSBERSBGT01FTlRPIE9VIE9VVFJPIE9SR0FOSVNNTyBRVUUgTsODTyBTRUpBIEEgVUZTTQosIFZPQ8OKIERFQ0xBUkEgUVVFIFJFU1BFSVRPVSBUT0RPUyBFIFFVQUlTUVVFUiBESVJFSVRPUyBERSBSRVZJU8ODTyBDT01PClRBTULDiU0gQVMgREVNQUlTIE9CUklHQcOHw5VFUyBFWElHSURBUyBQT1IgQ09OVFJBVE8gT1UgQUNPUkRPLgoKQSBVRlNNIHNlIGNvbXByb21ldGUgYSBpZGVudGlmaWNhciBjbGFyYW1lbnRlIG8gc2V1IG5vbWUgKHMpIG91IG8ocykgbm9tZShzKSBkbyhzKQpkZXRlbnRvcihlcykgZG9zIGRpcmVpdG9zIGF1dG9yYWlzIGRhIHRlc2Ugb3UgZGlzc2VydGHDp8OjbywgZSBuw6NvIGZhcsOhIHF1YWxxdWVyIGFsdGVyYcOnw6NvLCBhbMOpbSBkYXF1ZWxhcwpjb25jZWRpZGFzIHBvciBlc3RhIGxpY2Vuw6dhLgoKRepositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132019-06-05T06:02:38Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
dc.title.alternative.eng.fl_str_mv |
Isolation, structural determination and biological activities of metabolites from Phellinotus piptadeniae AND Pisolithus tinctorius FUNGI |
title |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
spellingShingle |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius Carmo, Gabriele do Metabólitos secundários Atividade antimicrobiana Atividade antioxidante Secondary metabolites Antioxidant activity Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
title_full |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
title_fullStr |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
title_full_unstemmed |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
title_sort |
Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius |
author |
Carmo, Gabriele do |
author_facet |
Carmo, Gabriele do |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Morel, Ademir Farias |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3554994385525333 |
dc.contributor.referee1.fl_str_mv |
Maldaner, Graciela |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/6500796131690728 |
dc.contributor.referee2.fl_str_mv |
Moura, Neusa Fernandes de |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0820396530673217 |
dc.contributor.referee3.fl_str_mv |
von Laer, Ana Eucares |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/4357761673325700 |
dc.contributor.referee4.fl_str_mv |
Dornelles, Luciano |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/7629319262073140 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9377630611329980 |
dc.contributor.author.fl_str_mv |
Carmo, Gabriele do |
contributor_str_mv |
Morel, Ademir Farias Maldaner, Graciela Moura, Neusa Fernandes de von Laer, Ana Eucares Dornelles, Luciano |
dc.subject.por.fl_str_mv |
Metabólitos secundários Atividade antimicrobiana Atividade antioxidante |
topic |
Metabólitos secundários Atividade antimicrobiana Atividade antioxidante Secondary metabolites Antioxidant activity Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Secondary metabolites Antioxidant activity Antimicrobial activity |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Basidiomycete fungi are important living organisms that present several bioactive compounds, which have antimicrobial, antitumor, antioxidant, and anti-inflammatory potential. Several compounds and potentialities of this class of fungi are still unknown. Therefore, the objective of this work was to prepare fractions of Phellinotus piptadeniae and Pisolithus tinctorius, isolate and identify the secondary metabolites, and evaluate the antimicrobial activities of the fractions and compounds obtained. The antioxidant activity was just assessed for the fractions from P. piptadeniae species. The chemical investigation of P. piptadeniae led to the isolation of five compounds, two triterpenes (ergosterol peroxide (D1) and ergosterol (D2)), two long chain esters (pentadecanoic acid-2-hydroxy, ethyl ester (D6) and tetracosanoic-2-hydroxy, methyl ester (D11)), and a phenolic compound (derived from hispidin (D9)), which was not yet described. The ergosterol acetate (D2a) was obtained from an structural modification through the acetylation reaction of triterpene D2. The study of the Pisolithus tinctorius species drive to the isolation of two lanostane triterpenes (pisolactone (P180) and lanostane, 7,22-dien-3-ol, 24-methyl (P65)), where, P65 compound was identified as a novel metabolite in the literature. In addition, a long chain acid (5-hexadecenoic acid (P1)) and ceramide (P56), it was not in this species, were also identified. All fractions obtained from the species P. piptadeniae and P. tinctorius had antibacterial and antifungal actions. Whereas, against mycobacteria, only the hexanic and methanolic fractions of P. piptadeniae and the ethyl acetate fraction of P. tinctorius were effective at the concentrations tested. The triterpenes, acid derivatives and phenolic compound were active against bacteria (Gram-positive and Gram-negative), fungi and mycobacteria. The ethyl acetate and methanolic fractions of the P. piptadeniae species, when tested against their antioxidant capacity, showed promising results with IC50 because their values were close to the BHT standard. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-06-04T14:17:58Z |
dc.date.available.fl_str_mv |
2019-06-04T14:17:58Z |
dc.date.issued.fl_str_mv |
2019-01-29 |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/16735 |
url |
http://repositorio.ufsm.br/handle/1/16735 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 |
dc.relation.authority.fl_str_mv |
8c99befa-f1b3-4afb-98b8-7fab46c3d493 49525a2a-c511-4cb0-9f1b-8995544ac4be b0db7504-a42c-44d0-b7f0-992c14108c1a 24bb05e9-ab5c-4992-b51a-839d83a48933 9b8d56c9-b078-4956-921c-e8a6482493ff 6f6ca89d-dfdf-41bb-9190-ea786a030c67 |
dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/16735/1/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf http://repositorio.ufsm.br/bitstream/1/16735/2/license_rdf http://repositorio.ufsm.br/bitstream/1/16735/3/license.txt http://repositorio.ufsm.br/bitstream/1/16735/4/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.txt http://repositorio.ufsm.br/bitstream/1/16735/5/TES_PPGQUIMICA_2019_CARMO_GABRIELE.pdf.jpg |
bitstream.checksum.fl_str_mv |
6cc36d0d31a3a3e4b15bd2dff159d826 4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df 78cfd0363b55ba4224b8392c8134874f 0b6089c4f9434246d09dd1f92afad2d3 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
|
_version_ |
1794524398537932800 |