Isolamento, determinação estrutural e atividades biológicas de metabólitos dos fungos Phellinotus piptadeniae E Pisolithus tinctorius

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Carmo, Gabriele do lattes
Orientador(a): Morel, Ademir Farias lattes
Banca de defesa: Maldaner, Graciela lattes, Moura, Neusa Fernandes de lattes, von Laer, Ana Eucares lattes, Dornelles, Luciano lattes
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.
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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; 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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
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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
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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
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