Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Mesquita, Lidivânia Silva Freitas
Orientador(a): Pessoa, Otília Deusdênia Loiola
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
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
Palavras-chave em Português:
Plectranthus ornatus
Diterpenos
Atividade citotóxica
Lamiaceae
Link de acesso: http://www.repositorio.ufc.br/handle/riufc/40954
Resumo: This work reports the chemical study of the ethanol extract from leaves of Plectranthus ornatus Codd (lamiaceae), whose goal was to isolate new bioactive secondary metabolites. Using conventional methods of chromatography were isolatted eight diterpenes, being three clerodanes [11-acetoxy-2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-1), 2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-3) and 11R*-acetoxy-2-oxoneocleroda-3,13E-dien-15-oic methyl ester (PO-12)], and five abietanes [7,12S*,17- triacetoxy-6R*,19-dihydroxy-abiet-8-ene-11,14-dione (PO-2), 12R*-acetoxy-3R*,6S*,7-trihydroxy-13,16-abiet-8-ene-11,14-dione (PO-7), 6S*,12R*-diacetoxy-3S*,7-dihydroxy-13,16-abiet-8-ene-11,14-dione (PO-6), 3S*,17-diacetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-abietatetraen-7-one (PO-9), and 3-acetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-7-one (PO-8)]. In addition, were isolated the caffeic acid (PO-4), the flavonoids pedalatin (PO-5) and circimaritin (PO-10), and a ceramide (PO-11). Their structures were elucidated by interpretation of their spectroscopic data (IR, HRESIMS and 1H and 13C NMR) and by comparison with published data of analogous compounds. The compounds compostos PO-1, PO-2, PO-5, PO-6, PO-7, PO-8, PO-9, PO-10 e PO-11were assayed on four cancer cell lines [SF-295 (glioblastoma), PC-3 (prostate), HCT-116 (colon) e HL-60 (leukemia)]. Except PO-5, which was moderately cytotoxic against the cell lines SF-295 (CI50 4,15 µg/mL) and HL-60 (CI50 4,16 µg/mL),all the compounds were inactive.
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spelling Mesquita, Lidivânia Silva FreitasPessoa, Otília Deusdênia Loiola2019-04-17T19:04:31Z2019-04-17T19:04:31Z2019MESQUITA, Lidivânia Silva Freitas. Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd. 2019. 191 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.http://www.repositorio.ufc.br/handle/riufc/40954This work reports the chemical study of the ethanol extract from leaves of Plectranthus ornatus Codd (lamiaceae), whose goal was to isolate new bioactive secondary metabolites. Using conventional methods of chromatography were isolatted eight diterpenes, being three clerodanes [11-acetoxy-2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-1), 2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-3) and 11R*-acetoxy-2-oxoneocleroda-3,13E-dien-15-oic methyl ester (PO-12)], and five abietanes [7,12S*,17- triacetoxy-6R*,19-dihydroxy-abiet-8-ene-11,14-dione (PO-2), 12R*-acetoxy-3R*,6S*,7-trihydroxy-13,16-abiet-8-ene-11,14-dione (PO-7), 6S*,12R*-diacetoxy-3S*,7-dihydroxy-13,16-abiet-8-ene-11,14-dione (PO-6), 3S*,17-diacetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-abietatetraen-7-one (PO-9), and 3-acetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-7-one (PO-8)]. In addition, were isolated the caffeic acid (PO-4), the flavonoids pedalatin (PO-5) and circimaritin (PO-10), and a ceramide (PO-11). Their structures were elucidated by interpretation of their spectroscopic data (IR, HRESIMS and 1H and 13C NMR) and by comparison with published data of analogous compounds. The compounds compostos PO-1, PO-2, PO-5, PO-6, PO-7, PO-8, PO-9, PO-10 e PO-11were assayed on four cancer cell lines [SF-295 (glioblastoma), PC-3 (prostate), HCT-116 (colon) e HL-60 (leukemia)]. Except PO-5, which was moderately cytotoxic against the cell lines SF-295 (CI50 4,15 µg/mL) and HL-60 (CI50 4,16 µg/mL),all the compounds were inactive.Este trabalho relata a investigação química do extrato etanólico das folhas de Plectranthus ornatus Codd (Lamiaceae), cujo principal objetivo foi isolar novos metabólitos secundários bioativos. Utilizando técnicas clássicas de cromatografia foram isolados oito diterpenos, sendo três de esqueleto clerodano [ácido 11-acetoxi-2-oxo-neocleroda-3,13E-dien-15-óico (PO-1), ácido 2-oxo-neocleroda-3,13E-dien-15-óico (PO-3) e 11R*-acetoxi-2-oxoneocleroda-3,13E-dien-15-oato de metila (PO-12)], e cinco abietanos [7,12S*,17- triacetoxi-6R*,19-dihidroxi-abiet-8-ene-11,14-diona (PO-2), 12R*-acetoxi-3R*,6S*,7-trihidroxi-13,16-abiet-8-ene-11,14-diona (PO-7), 6S*,12R*-Diacetoxi-3S*,7-dihidroxi-13,16-abiet-8-ene-11,14-diona (PO-6), 3S*,17-diacetoxi-6,11,12,14,16-penta-hidroxi-5,8,11,13-abietatetraen-7-ona (PO-9) e 3-acetoxi-6,11,12,14,16-penta-hidroxi-5,8,11,13-7-ona (PO-8)]. Adicionalmente, foram isolados um derivado fenólico: ácido cafeico (PO-4), os flavonoides pedalatina (PO-5) e circimaritina (PO-10), e uma ceramida (PO-11). Dos compostos codificados como PO-2 e PO-7 são inéditos na literatura. A determinação estrutural foi realizada através de técnicas espectroscópicas como EMAR-ESI, IV, RMN de 1H e de 13C (1D e 2D), além de comparação com os dados descritos na literatura. Os compostos PO-1, PO-2, PO-5, PO-6, PO-7, PO-8, PO-9, PO-10 e PO-11 foram testados frente a quatro linhagens de células cancerígenas [SF-295 (glioblastoma), PC-3 (próstata), HCT-116 (colon) e HL-60 (leucemia)]. Exceto PO-5, que mostrou moderada toxicidade frente às linhagens SF-295 (CI50 4,15 µg/mL ) e HL-60 (CI50 4,16 µg/mL, todos os compostos foram inativos.Plectranthus ornatusDiterpenosAtividade citotóxicaLamiaceaeProspecção química do extrato etanólico das folhas de Plectranthus ornatus CoddChemical prospection of ethanolic extract from the leaves of Plectranthus ornatus Coddinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccessORIGINAL2016_dis_lsfmesquita.pdf2016_dis_lsfmesquita.pdfapplication/pdf12434007http://repositorio.ufc.br/bitstream/riufc/40954/4/2016_dis_lsfmesquita.pdf55d3bc92b90041b7fe4f892b15b153d3MD54LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/40954/5/license.txt8a4605be74aa9ea9d79846c1fba20a33MD55riufc/409542020-06-18 16:02:29.755oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2020-06-18T19:02:29Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
dc.title.en.pt_BR.fl_str_mv Chemical prospection of ethanolic extract from the leaves of Plectranthus ornatus Codd
title Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
spellingShingle Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
Mesquita, Lidivânia Silva Freitas
Plectranthus ornatus
Diterpenos
Atividade citotóxica
Lamiaceae
title_short Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
title_full Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
title_fullStr Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
title_full_unstemmed Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
title_sort Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd
author Mesquita, Lidivânia Silva Freitas
author_facet Mesquita, Lidivânia Silva Freitas
author_role author
dc.contributor.author.fl_str_mv Mesquita, Lidivânia Silva Freitas
dc.contributor.advisor1.fl_str_mv Pessoa, Otília Deusdênia Loiola
contributor_str_mv Pessoa, Otília Deusdênia Loiola
dc.subject.por.fl_str_mv Plectranthus ornatus
Diterpenos
Atividade citotóxica
Lamiaceae
topic Plectranthus ornatus
Diterpenos
Atividade citotóxica
Lamiaceae
description This work reports the chemical study of the ethanol extract from leaves of Plectranthus ornatus Codd (lamiaceae), whose goal was to isolate new bioactive secondary metabolites. Using conventional methods of chromatography were isolatted eight diterpenes, being three clerodanes [11-acetoxy-2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-1), 2-oxo-neocleroda-3,13E-dien-15-oic acid (PO-3) and 11R*-acetoxy-2-oxoneocleroda-3,13E-dien-15-oic methyl ester (PO-12)], and five abietanes [7,12S*,17- triacetoxy-6R*,19-dihydroxy-abiet-8-ene-11,14-dione (PO-2), 12R*-acetoxy-3R*,6S*,7-trihydroxy-13,16-abiet-8-ene-11,14-dione (PO-7), 6S*,12R*-diacetoxy-3S*,7-dihydroxy-13,16-abiet-8-ene-11,14-dione (PO-6), 3S*,17-diacetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-abietatetraen-7-one (PO-9), and 3-acetoxy-6,11,12,14,16-penta-hydroxy-5,8,11,13-7-one (PO-8)]. In addition, were isolated the caffeic acid (PO-4), the flavonoids pedalatin (PO-5) and circimaritin (PO-10), and a ceramide (PO-11). Their structures were elucidated by interpretation of their spectroscopic data (IR, HRESIMS and 1H and 13C NMR) and by comparison with published data of analogous compounds. The compounds compostos PO-1, PO-2, PO-5, PO-6, PO-7, PO-8, PO-9, PO-10 e PO-11were assayed on four cancer cell lines [SF-295 (glioblastoma), PC-3 (prostate), HCT-116 (colon) e HL-60 (leukemia)]. Except PO-5, which was moderately cytotoxic against the cell lines SF-295 (CI50 4,15 µg/mL) and HL-60 (CI50 4,16 µg/mL),all the compounds were inactive.
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-04-17T19:04:31Z
dc.date.available.fl_str_mv 2019-04-17T19:04:31Z
dc.date.issued.fl_str_mv 2019
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.citation.fl_str_mv MESQUITA, Lidivânia Silva Freitas. Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd. 2019. 191 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/40954
identifier_str_mv MESQUITA, Lidivânia Silva Freitas. Prospecção química do extrato etanólico das folhas de Plectranthus ornatus Codd. 2019. 191 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2016.
url http://www.repositorio.ufc.br/handle/riufc/40954
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/40954/4/2016_dis_lsfmesquita.pdf
http://repositorio.ufc.br/bitstream/riufc/40954/5/license.txt
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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
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