Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Ávila, Fábio do Nascimento
Orientador(a): Pessoa, Otília Deusdênia Loiola
Banca de defesa: Não Informado pela instituição
Tipo de documento: Tese
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Não Informado pela instituição
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufc.br/handle/riufc/77957
Resumo: In this work, the extracts from the algae Lobophora variegata, Dictyota menstrualis and Dictyota mertensii (Phaeophyceae, Dictyotaceae) were investigated, resulting in the isolation of twenty-two compounds. From Dictyota species were isolated diterpenes of different skeletons such as prenilated guaiane and cadinane, crenulidane and dollabelane. Among these compounds, four have been described for the first time. From L. variegata were isolated long-chain alcohol and epoxide, two of which are new compounds. The compounds were isolated using classic methods of chromatography including chromatography on silica gel, sephadex LH-20 and high performance liquid chromatography. The structure elucidation of compounds was performed by spectroscopic methods such as: mass spectrometry (HRESIMS, APCI and GC-MS) and nuclear magnetic resonance (1H and 13C NMR) including bidimensional techniques (COSY, HSQC e HMBC), and comparison with literature data. The isolated compounds were evaluated for their cytotoxicity against the cancer cell line (HCT-116 and RAW-264.7), antimicrobial properties against Gram-positive (S. aureus ATCC 6538P) and Gram-negative (E. coli ATCC 10536) bacteria strains, antioxidant (DPPH) and anti-inflammatory effects. The long-chain epoxides designated as epoxy-lobophorenes A and B (isolated of L. variegata) showed anti-inflammatory and antioxidant effects, while the diterpenes designated dictyols K, M, N and O (isolated of D. menstrualis) showed anti-inflammatory activity comparable to dexamethasone, a potent anti-inflammatory drug in clinical use.
id UFC-7_148edded158b2d2a83543a6105ce79d5
oai_identifier_str oai:repositorio.ufc.br:riufc/77957
network_acronym_str UFC-7
network_name_str Repositório Institucional da Universidade Federal do Ceará (UFC)
repository_id_str
spelling Ávila, Fábio do NascimentoPessoa, Otília Deusdênia Loiola2024-08-29T15:15:10Z2024-08-29T15:15:10Z2019ÁVILA, Fábio do Nascimento. Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados. 2019. 211 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.http://repositorio.ufc.br/handle/riufc/77957In this work, the extracts from the algae Lobophora variegata, Dictyota menstrualis and Dictyota mertensii (Phaeophyceae, Dictyotaceae) were investigated, resulting in the isolation of twenty-two compounds. From Dictyota species were isolated diterpenes of different skeletons such as prenilated guaiane and cadinane, crenulidane and dollabelane. Among these compounds, four have been described for the first time. From L. variegata were isolated long-chain alcohol and epoxide, two of which are new compounds. The compounds were isolated using classic methods of chromatography including chromatography on silica gel, sephadex LH-20 and high performance liquid chromatography. The structure elucidation of compounds was performed by spectroscopic methods such as: mass spectrometry (HRESIMS, APCI and GC-MS) and nuclear magnetic resonance (1H and 13C NMR) including bidimensional techniques (COSY, HSQC e HMBC), and comparison with literature data. The isolated compounds were evaluated for their cytotoxicity against the cancer cell line (HCT-116 and RAW-264.7), antimicrobial properties against Gram-positive (S. aureus ATCC 6538P) and Gram-negative (E. coli ATCC 10536) bacteria strains, antioxidant (DPPH) and anti-inflammatory effects. The long-chain epoxides designated as epoxy-lobophorenes A and B (isolated of L. variegata) showed anti-inflammatory and antioxidant effects, while the diterpenes designated dictyols K, M, N and O (isolated of D. menstrualis) showed anti-inflammatory activity comparable to dexamethasone, a potent anti-inflammatory drug in clinical use.Neste trabalho foram investigados os extratos das algas pardas Lobophora variegata, Dictyota menstrualis e Dictyota mertensii (Phaeophyceae, Dictyotaceae), resultando no isolamento de vinte e dois compostos. Das espécies de Dictyota foram isolados diterpenos de esqueletos variados como, guaiano e cadinano prenilados, crenulidano e dollabelano. Destes compostos, quatro foram descritos pela primeira vez. A partir da alga D. mertensii foi também isolado sais de aminas quaternárias. De L. variegata os compostos isolados foram alcoóis e epóxidos de cadeia longa, dois dos quais inéditos. Para o isolamento dos compostos foram utilizados métodos cromatográficos clássicos, incluindo cromatografia em coluna sobre gel de sílica, Sephadex LH-20 e cromatografia líquida de alta eficiência. A determinação estrutural dos compostos foi realizada através de técnicas espectroscópicas e espectrométricas como: espectrometria de massas (EMAR-ESI, APCI, CG-EM) e ressonância magnética nuclear de hidrogênio (RMN 1H C13, incluindo técnicas bidimensionais (COSY, HSQC e HMBC), além de comparação com dados registrados na literatura. Os compostos foram submetidos a ensaios de atividade citotóxica, utilizando linhagens de células cancerígenas (HCT-116) e normal (RAW-264.7), antimicrobiana, contra cepas de bactérias Gram-positiva (S. aureus ATCC 6538P) e Gram-negativa (E. coli ATCC 10536), antioxidante (DPPH) e anti-inflamatório. Os epóxidos de cadeia longa designados de epóxi-lobophorenos A e B (isolados de L. variegata) apresentaram efeito anti-inflamatório e antioxidante, enquanto os diterpenos designados de dictyois K, M, N, O (isolados de D. menstrualis) mostraram atividade anti-inflamatória semelhante ao da dexametasona, um potente anti-inflamatório de uso clínico.Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isoladosChemical study of brown algae Lobophora variegata, Dictyota menstrualis, Dictyota mertensii and pharmacological investigation of isolated compoundsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisLobophora variegataDictyota menstrualisAtividade citotóxicaAtividade antimicrobianaLobophora variegataDictyota menstrualisCytotoxic activityAntimicrobial activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAinfo:eu-repo/semantics/openAccessporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFChttps://orcid.org/0000-0002-1617-7586http://lattes.cnpq.br/6852350815216385https://orcid.org/0000-0002-1617-7586http://lattes.cnpq.br/03506187005128642024-08-29LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/77957/6/license.txt8a4605be74aa9ea9d79846c1fba20a33MD56ORIGINAL2019_tese_fnavila.pdf2019_tese_fnavila.pdfapplication/pdf8293089http://repositorio.ufc.br/bitstream/riufc/77957/5/2019_tese_fnavila.pdf5724e1343ca781b2d28b8c382bd2c6dfMD55riufc/779572024-08-29 12:15:11.371oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-08-29T15:15:11Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
dc.title.en.pt_BR.fl_str_mv Chemical study of brown algae Lobophora variegata, Dictyota menstrualis, Dictyota mertensii and pharmacological investigation of isolated compounds
title Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
spellingShingle Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
Ávila, Fábio do Nascimento
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Lobophora variegata
Dictyota menstrualis
Atividade citotóxica
Atividade antimicrobiana
Lobophora variegata
Dictyota menstrualis
Cytotoxic activity
Antimicrobial activity
title_short Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
title_full Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
title_fullStr Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
title_full_unstemmed Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
title_sort Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados
author Ávila, Fábio do Nascimento
author_facet Ávila, Fábio do Nascimento
author_role author
dc.contributor.author.fl_str_mv Ávila, Fábio do Nascimento
dc.contributor.advisor1.fl_str_mv Pessoa, Otília Deusdênia Loiola
contributor_str_mv Pessoa, Otília Deusdênia Loiola
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Lobophora variegata
Dictyota menstrualis
Atividade citotóxica
Atividade antimicrobiana
Lobophora variegata
Dictyota menstrualis
Cytotoxic activity
Antimicrobial activity
dc.subject.ptbr.pt_BR.fl_str_mv Lobophora variegata
Dictyota menstrualis
Atividade citotóxica
Atividade antimicrobiana
dc.subject.en.pt_BR.fl_str_mv Lobophora variegata
Dictyota menstrualis
Cytotoxic activity
Antimicrobial activity
description In this work, the extracts from the algae Lobophora variegata, Dictyota menstrualis and Dictyota mertensii (Phaeophyceae, Dictyotaceae) were investigated, resulting in the isolation of twenty-two compounds. From Dictyota species were isolated diterpenes of different skeletons such as prenilated guaiane and cadinane, crenulidane and dollabelane. Among these compounds, four have been described for the first time. From L. variegata were isolated long-chain alcohol and epoxide, two of which are new compounds. The compounds were isolated using classic methods of chromatography including chromatography on silica gel, sephadex LH-20 and high performance liquid chromatography. The structure elucidation of compounds was performed by spectroscopic methods such as: mass spectrometry (HRESIMS, APCI and GC-MS) and nuclear magnetic resonance (1H and 13C NMR) including bidimensional techniques (COSY, HSQC e HMBC), and comparison with literature data. The isolated compounds were evaluated for their cytotoxicity against the cancer cell line (HCT-116 and RAW-264.7), antimicrobial properties against Gram-positive (S. aureus ATCC 6538P) and Gram-negative (E. coli ATCC 10536) bacteria strains, antioxidant (DPPH) and anti-inflammatory effects. The long-chain epoxides designated as epoxy-lobophorenes A and B (isolated of L. variegata) showed anti-inflammatory and antioxidant effects, while the diterpenes designated dictyols K, M, N and O (isolated of D. menstrualis) showed anti-inflammatory activity comparable to dexamethasone, a potent anti-inflammatory drug in clinical use.
publishDate 2019
dc.date.issued.fl_str_mv 2019
dc.date.accessioned.fl_str_mv 2024-08-29T15:15:10Z
dc.date.available.fl_str_mv 2024-08-29T15:15:10Z
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 ÁVILA, Fábio do Nascimento. Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados. 2019. 211 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.
dc.identifier.uri.fl_str_mv http://repositorio.ufc.br/handle/riufc/77957
identifier_str_mv ÁVILA, Fábio do Nascimento. Estudo químico das algas pardas Lobophora variegata, Dictyota menstrualis, Dictyota mertensii e investigação farmacológica dos compostos isolados. 2019. 211 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.
url http://repositorio.ufc.br/handle/riufc/77957
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.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Ceará (UFC)
instname:Universidade Federal do Ceará (UFC)
instacron:UFC
instname_str Universidade Federal do Ceará (UFC)
instacron_str UFC
institution UFC
reponame_str Repositório Institucional da Universidade Federal do Ceará (UFC)
collection Repositório Institucional da Universidade Federal do Ceará (UFC)
bitstream.url.fl_str_mv http://repositorio.ufc.br/bitstream/riufc/77957/6/license.txt
http://repositorio.ufc.br/bitstream/riufc/77957/5/2019_tese_fnavila.pdf
bitstream.checksum.fl_str_mv 8a4605be74aa9ea9d79846c1fba20a33
5724e1343ca781b2d28b8c382bd2c6df
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)
repository.mail.fl_str_mv bu@ufc.br || repositorio@ufc.br
_version_ 1847793064633958400

Registros relacionados