Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis

Detalhes bibliográficos
Ano de defesa: 2016
Autor(a) principal: Costa, Luis Paulo de Sousa [UNESP]
Orientador(a): Silva, Dulce Helena Siqueira [UNESP]
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Estadual Paulista (Unesp)
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Palavras-chave em Português:
Palavras-chave em Inglês:
Palavras-chave em Espanhol:
Link de acesso: http://hdl.handle.net/11449/143765
Resumo: This work dealt with the study of fungal strains Sarocladium strictum (Ps-02) e Coniothyrium sp. (Ps-03) associated to the red macroalga Pyropia spiralis, collected at SP State shore. Their extracts were obtained in different culture media: rice, malt and Czapek, which induced diversified metabolic production, as shown by HPLC-DAD and NMR analyses and evidenced that the metabolic profile depends on culture media for these strains. Extracts and fractions from Sarocladium strictum and Coniothyrium sp. were evaluated in antifungal, anticholinesterasic and cytotoxic assays and presented one or more potential bioactivities. Fraction Ps-03 A-ACN from Coniothyrium sp. showed antifungal and cytotoxic activities, and was selected for reversed phase column chromatography under positive pressure and gradient elution with H2O:MeOH. Fractions purification by HPLC-DAD or normal phase column chromatography led to the isolation of one diketopiperazine, polyketides and steroids, which had their structural elucidation by UV, 1D and 2D NMR, and MS analyses. The polyketides isolated in this study include three aromatic macrolides (1 – 3): (3R,5R)-sonnerlactone and two sonnerlactone analogues: one novel compound and one novel as a natural product; the aromatic butenolide gymnoascolide A (4), and the antiviral tetralone 10-norparvulenone (7). Two steroids: ergosterol-5,8-endoperóxido-∆6,22 (5) and 22E-ergosta-7,22-dieno-3β,5,6-triol (6) were also isolated. They are structurally related, probably due to rearrangement, which includes opening of the endoperoxide ring and double bond shift. Compound 8 is a diketopiperazine, that results from one unit phenylalanine and one of threonine. Such results confirm the strong chemodiversity of marine-derived endophytic fungi and their relevant bioactivity potential, which represents an open and attractive path towards deeper bioprospection studies on such ecological niche.
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spelling Costa, Luis Paulo de Sousa [UNESP]Universidade Estadual Paulista (Unesp)Araujo, Angela ReginaRodrigues Filho, EdsonSilva, Dulce Helena Siqueira [UNESP]2016-09-01T21:00:27Z2016-09-01T21:00:27Z2016-08-05http://hdl.handle.net/11449/14376500087211633004030072P833004030072P847020049042312480000-0002-1516-7765This work dealt with the study of fungal strains Sarocladium strictum (Ps-02) e Coniothyrium sp. (Ps-03) associated to the red macroalga Pyropia spiralis, collected at SP State shore. Their extracts were obtained in different culture media: rice, malt and Czapek, which induced diversified metabolic production, as shown by HPLC-DAD and NMR analyses and evidenced that the metabolic profile depends on culture media for these strains. Extracts and fractions from Sarocladium strictum and Coniothyrium sp. were evaluated in antifungal, anticholinesterasic and cytotoxic assays and presented one or more potential bioactivities. Fraction Ps-03 A-ACN from Coniothyrium sp. showed antifungal and cytotoxic activities, and was selected for reversed phase column chromatography under positive pressure and gradient elution with H2O:MeOH. Fractions purification by HPLC-DAD or normal phase column chromatography led to the isolation of one diketopiperazine, polyketides and steroids, which had their structural elucidation by UV, 1D and 2D NMR, and MS analyses. The polyketides isolated in this study include three aromatic macrolides (1 – 3): (3R,5R)-sonnerlactone and two sonnerlactone analogues: one novel compound and one novel as a natural product; the aromatic butenolide gymnoascolide A (4), and the antiviral tetralone 10-norparvulenone (7). Two steroids: ergosterol-5,8-endoperóxido-∆6,22 (5) and 22E-ergosta-7,22-dieno-3β,5,6-triol (6) were also isolated. They are structurally related, probably due to rearrangement, which includes opening of the endoperoxide ring and double bond shift. Compound 8 is a diketopiperazine, that results from one unit phenylalanine and one of threonine. Such results confirm the strong chemodiversity of marine-derived endophytic fungi and their relevant bioactivity potential, which represents an open and attractive path towards deeper bioprospection studies on such ecological niche.Este trabalho consistiu no estudo dos micro-organismos Sarocladium strictum (Ps-02) e Coniothyrium sp. (Ps-03) associados à macroalga vermelha Pyropia spiralis, coletada no litoral paulista. Os extratos foram obtidos em diferentes meios de cultivos: arroz, malte e Czapek, e induziram produção metabólica diversificada, conforme apontado pelas análises por CLAE-DAD e RMN de 1H, evidenciando que o perfil metabólico é dependente do meio de cultivo para estas linhagens. Os extratos e frações de Sarocladium strictum e Coniothyrium sp. foram avaliados em ensaios para atividade antifúngica, anticolinesterásica e citotóxica e apresentaram uma ou mais potenciais atividades. A fração Ps-03 A-ACN de Coniothyrium sp. apresentou atividade antifúngica e citotóxica, e foi selecionada para fracionamento por cromatografia em coluna sob pressão em modo reverso (C18) com eluição em gradiente H2O:MeOH. A purificação das frações por CLAE-DAD ou cromatografia flash em modo normal levou ao isolamento de uma dicetopiperazina, policetídeos e esteroides, que tiveram suas estruturas determinadas por análises na região do UV, RMN 1D e 2D, e por espectrometria de massas. Os policetídeos isolados neste estudo incluem três macrolídeos aromáticos (1 – 3): a (3R,5R)-sonnerlactona e dois análogos à sonnerlactona, sendo um inédito na literatura e outro, inédito como produto natural; o butenolídeo aromático gymnoascolídeo A (4), e a tetralona antiviral10-norparvulenona (7). Foram também obtidos os esteroides ergosterol-5,8-endoperóxido-∆6,22 (5) e 22E-ergosta-7,22-dieno-3β,5,6-triol (6), estruturalmente relacionados, provavelmente por rearranjo que inclui a abertura do anel endoperóxido e deslocamento da ligação dupla. A substância 8 uma dicetopiperazina: formada por unidades do aminoácido fenilalanina, e outra, do aminoácido treonina. Estes resultados confirmam a expressiva quimiodiversidade de fungos endofíticos de origem marinha, e seu potencial de bioatividade relevante, abrindo perspectivas atrativas para estudos de bioprospecção neste nicho ecológico.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)porUniversidade Estadual Paulista (Unesp)Fungo endofíticoAlga marinhaMetabólitosFungos marinhosMicro-organismoEndophytic fungiMarine algaMetabolitesMarine fungiMicroorganismsLos hongos endófitosAlgasMetabolitosLos hongos marinosMicroorganismosBioprospecção de fungos endofíticos da alga vermelha Pyropia spiralisBioprospection endophytic fungi red alga Pyropia spiralisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPQuímica - IQARQuímicaQuímica de Produtos NaturaisUniversidade Estadual Paulista (UNESP), Instituto de Química, Araraquara24 meses após a data da defesa47020049042312484702004904231248[1]0000-0002-1516-7765[1]Publicationbc74a1ce-4c4c-4dad-8378-83962d76c4fdvirtual::43371-1bc74a1ce-4c4c-4dad-8378-83962d76c4fdvirtual::43371-161afcbc3-9ae1-47a5-b858-c45020d514d5virtual::37001-161afcbc3-9ae1-47a5-b858-c45020d514d5virtual::37001-1ORIGINALcosta_lps_me_araiq_par.pdfcosta_lps_me_araiq_par.pdfapplication/pdf948267https://repositorio.unesp.br/bitstreams/96af6f5a-817f-47b0-9fec-540b37361d49/downloadbbb5f6c179ff35de4a7cee21f5fc8c2aMD53trueAnonymousREADcosta_lps_me_araiq_int.pdfcosta_lps_me_araiq_int.pdfapplication/pdf3584850https://repositorio.unesp.br/bitstreams/7dbfb464-0bab-4a04-998c-b7c330e598d8/download3c9a6914d4a3b475bb1207a4145b6f7aMD54falseAnonymousREADLICENSElicense.txtWritten by org.dspace.content.LicenseUtilstext/plain; charset=utf-83044https://repositorio.unesp.br/bitstreams/17205fdc-99f6-477c-92b6-94324d7fb49d/download1fd791b974bd86ceec067287edf6c685MD52falseAnonymousREADTEXTcosta_lps_me_araiq_par.pdf.txtWritten by FormatFilter org.dspace.app.mediafilter.TikaTextExtractionFilter on 2023-12-14T06:19:45Z (GMT).Extracted texttext/plain58123https://repositorio.unesp.br/bitstreams/df17fec6-d6af-4f53-acd6-67a4efb73a64/downloadf9e1b8d7c4c1523155a7a4e322a15840MD59falseAnonymousREADcosta_lps_me_araiq_int.pdf.txtWritten by FormatFilter org.dspace.app.mediafilter.TikaTextExtractionFilter on 2023-12-14T06:19:45Z (GMT).Extracted texttext/plain102397https://repositorio.unesp.br/bitstreams/ebda97b0-96a4-4b59-b923-aed73fb1b3d7/download1bbe8bb45433e25de3813c392e3bab11MD510falseAnonymousREADTHUMBNAILcosta_lps_me_araiq_par.pdf.jpgWritten by FormatFilter org.dspace.app.mediafilter.ImageMagickPdfThumbnailFilter on 2016-11-18T18:45:56Z (GMT).IM Thumbnailimage/jpeg3788https://repositorio.unesp.br/bitstreams/1c71d6bc-3d45-432d-a548-f8a122ff5636/downloadf8d61ba9d8d80d45d95065ef910cfa90MD57falseAnonymousREADcosta_lps_me_araiq_int.pdf.jpgWritten by FormatFilter org.dspace.app.mediafilter.ImageMagickPdfThumbnailFilter on 2016-11-18T18:45:57Z (GMT).IM Thumbnailimage/jpeg4261https://repositorio.unesp.br/bitstreams/e3e3db50-90b9-438c-a933-7a8e51b8b5f2/download9264f844bbedbc1d3dcc6d55e1ace42eMD58falseAnonymousREAD11449/1437652026-03-10T18:59:02.817964Zopen.accessoai:repositorio.unesp.br:11449/143765https://repositorio.unesp.brRepositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestrepositoriounesp@unesp.bropendoar:29462026-03-10T18:59:02Repositório Institucional da UNESP - 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dc.title.pt.fl_str_mv Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
dc.title.alternative.en.fl_str_mv Bioprospection endophytic fungi red alga Pyropia spiralis
title Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
spellingShingle Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
Costa, Luis Paulo de Sousa [UNESP]
Fungo endofítico
Alga marinha
Metabólitos
Fungos marinhos
Micro-organismo
Endophytic fungi
Marine alga
Metabolites
Marine fungi
Microorganisms
Los hongos endófitos
Algas
Metabolitos
Los hongos marinos
Microorganismos
title_short Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
title_full Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
title_fullStr Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
title_full_unstemmed Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
title_sort Bioprospecção de fungos endofíticos da alga vermelha Pyropia spiralis
author Costa, Luis Paulo de Sousa [UNESP]
author_facet Costa, Luis Paulo de Sousa [UNESP]
author_role author
dc.contributor.institution.none.fl_str_mv Universidade Estadual Paulista (Unesp)
dc.contributor.committeeMember.none.fl_str_mv Araujo, Angela Regina
Rodrigues Filho, Edson
dc.contributor.author.fl_str_mv Costa, Luis Paulo de Sousa [UNESP]
dc.contributor.advisor1.fl_str_mv Silva, Dulce Helena Siqueira [UNESP]
contributor_str_mv Silva, Dulce Helena Siqueira [UNESP]
dc.subject.por.fl_str_mv Fungo endofítico
Alga marinha
Metabólitos
Fungos marinhos
Micro-organismo
topic Fungo endofítico
Alga marinha
Metabólitos
Fungos marinhos
Micro-organismo
Endophytic fungi
Marine alga
Metabolites
Marine fungi
Microorganisms
Los hongos endófitos
Algas
Metabolitos
Los hongos marinos
Microorganismos
dc.subject.eng.fl_str_mv Endophytic fungi
Marine alga
Metabolites
Marine fungi
Microorganisms
dc.subject.spa.fl_str_mv Los hongos endófitos
Algas
Metabolitos
Los hongos marinos
Microorganismos
description This work dealt with the study of fungal strains Sarocladium strictum (Ps-02) e Coniothyrium sp. (Ps-03) associated to the red macroalga Pyropia spiralis, collected at SP State shore. Their extracts were obtained in different culture media: rice, malt and Czapek, which induced diversified metabolic production, as shown by HPLC-DAD and NMR analyses and evidenced that the metabolic profile depends on culture media for these strains. Extracts and fractions from Sarocladium strictum and Coniothyrium sp. were evaluated in antifungal, anticholinesterasic and cytotoxic assays and presented one or more potential bioactivities. Fraction Ps-03 A-ACN from Coniothyrium sp. showed antifungal and cytotoxic activities, and was selected for reversed phase column chromatography under positive pressure and gradient elution with H2O:MeOH. Fractions purification by HPLC-DAD or normal phase column chromatography led to the isolation of one diketopiperazine, polyketides and steroids, which had their structural elucidation by UV, 1D and 2D NMR, and MS analyses. The polyketides isolated in this study include three aromatic macrolides (1 – 3): (3R,5R)-sonnerlactone and two sonnerlactone analogues: one novel compound and one novel as a natural product; the aromatic butenolide gymnoascolide A (4), and the antiviral tetralone 10-norparvulenone (7). Two steroids: ergosterol-5,8-endoperóxido-∆6,22 (5) and 22E-ergosta-7,22-dieno-3β,5,6-triol (6) were also isolated. They are structurally related, probably due to rearrangement, which includes opening of the endoperoxide ring and double bond shift. Compound 8 is a diketopiperazine, that results from one unit phenylalanine and one of threonine. Such results confirm the strong chemodiversity of marine-derived endophytic fungi and their relevant bioactivity potential, which represents an open and attractive path towards deeper bioprospection studies on such ecological niche.
publishDate 2016
dc.date.accessioned.fl_str_mv 2016-09-01T21:00:27Z
dc.date.available.fl_str_mv 2016-09-01T21:00:27Z
dc.date.issued.fl_str_mv 2016-08-05
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/11449/143765
dc.identifier.aleph.none.fl_str_mv 000872116
dc.identifier.capes.none.fl_str_mv 33004030072P8
33004030072P8
dc.identifier.lattes.none.fl_str_mv 4702004904231248
dc.identifier.orcid.none.fl_str_mv 0000-0002-1516-7765
url http://hdl.handle.net/11449/143765
identifier_str_mv 000872116
33004030072P8
4702004904231248
0000-0002-1516-7765
dc.language.iso.fl_str_mv por
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 Estadual Paulista (Unesp)
publisher.none.fl_str_mv Universidade Estadual Paulista (Unesp)
dc.source.none.fl_str_mv reponame:Repositório Institucional da UNESP
instname:Universidade Estadual Paulista (UNESP)
instacron:UNESP
instname_str Universidade Estadual Paulista (UNESP)
instacron_str UNESP
institution UNESP
reponame_str Repositório Institucional da UNESP
collection Repositório Institucional da UNESP
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repository.name.fl_str_mv Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)
repository.mail.fl_str_mv repositoriounesp@unesp.br
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