Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Matos, Taynara Simão
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:
Link de acesso: http://www.repositorio.ufc.br/handle/riufc/47926
Resumo: Plectranthus ornatus Codd (Lamiaceae), popularly known as “boldo-gambá” and “boldinho”, is a medicinal plant whose leaf or aerial part decoction is used to treat gastrointestinal problems. Despite of its importance in the popular medicinal, there are few chemical and pharmacological reports on the species. Thus, the aim of this study was to investigate the chemical composition of the MeOH soluble fraction from the decoction of the aerial part of P. ornatus, cultivated at the Medicinal Plants Garden Francisco José de Abreu Matos at the Universidade Federal do Ceará –UFC. Successive chromatography procedures, including Sephadex LH-20, C18 cartridge, and HPLC resulted in the isolation of thirteen chemical constituents including two new diterpene derivatives (19-β-D-glucopyranosyl-labda-7,13-diene-15,16-dioicacidand 16-desacetyl-coleon L) and two new flavonoids (3'-β-D-glucuropyranosyl-5,4'-dihydroxy-7-methoxy-flavone and 4'-β-D-glucuropyranosyl-5,3'-dihydroxy-7-methoxy-flavone). It is noteworthy that the flavonoid 4'-β-D-glucuropyranosyl-5-hydroxy-7-methoxy-flavone is already reported in the literature, however the 1H and 13C NMR data of this compound are being presented for the first time. Addicionally, a qualitative comparison of the main isolated compounds from the methanol soluble fraction of P. ornatus with the MeOH fractions from the aerial part decoctions of specimens of three other Plectranthus species (P. barbatus, P. amboinicus, and P. grandis) common in Ceará State was performed. Rosmarinic acid was the main compound in all decoctions. It is worth mentioning the presence of highly hydroxylated and glycosylated compounds. The structural determination of all compounds was performed by interpretation of HRMS and 1H and 13C NMR spectra, and comparison with the literature data. In addition, the biosynthetic route for the isolated diterpenes was suggested. Moreover, the decoctions of the investigated species were assayed for α-glycosidase enzymatic inhibition, and cell viability on human gastric adenocarcinoma cells. None of the studied decoctions showed inhibition of the α-glucosidase enzime. Interestingly, all decoctions showed cell proliferative action and may be indicative for medicinal popular use. However, further tests need to be performed to prove this prophylactic effect against human gastric cells.
id UFC-7_65416cd64b34b2e3e8fc6525e91ea424
oai_identifier_str oai:repositorio.ufc.br:riufc/47926
network_acronym_str UFC-7
network_name_str Repositório Institucional da Universidade Federal do Ceará (UFC)
repository_id_str
spelling Matos, Taynara SimãoPessoa, Otília Deusdênia Loiola2019-11-26T14:01:53Z2019-11-26T14:01:53Z2019MATOS, Taynara Simão. Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd. 2019. 165 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.http://www.repositorio.ufc.br/handle/riufc/47926Plectranthus ornatus Codd (Lamiaceae), popularly known as “boldo-gambá” and “boldinho”, is a medicinal plant whose leaf or aerial part decoction is used to treat gastrointestinal problems. Despite of its importance in the popular medicinal, there are few chemical and pharmacological reports on the species. Thus, the aim of this study was to investigate the chemical composition of the MeOH soluble fraction from the decoction of the aerial part of P. ornatus, cultivated at the Medicinal Plants Garden Francisco José de Abreu Matos at the Universidade Federal do Ceará –UFC. Successive chromatography procedures, including Sephadex LH-20, C18 cartridge, and HPLC resulted in the isolation of thirteen chemical constituents including two new diterpene derivatives (19-β-D-glucopyranosyl-labda-7,13-diene-15,16-dioicacidand 16-desacetyl-coleon L) and two new flavonoids (3'-β-D-glucuropyranosyl-5,4'-dihydroxy-7-methoxy-flavone and 4'-β-D-glucuropyranosyl-5,3'-dihydroxy-7-methoxy-flavone). It is noteworthy that the flavonoid 4'-β-D-glucuropyranosyl-5-hydroxy-7-methoxy-flavone is already reported in the literature, however the 1H and 13C NMR data of this compound are being presented for the first time. Addicionally, a qualitative comparison of the main isolated compounds from the methanol soluble fraction of P. ornatus with the MeOH fractions from the aerial part decoctions of specimens of three other Plectranthus species (P. barbatus, P. amboinicus, and P. grandis) common in Ceará State was performed. Rosmarinic acid was the main compound in all decoctions. It is worth mentioning the presence of highly hydroxylated and glycosylated compounds. The structural determination of all compounds was performed by interpretation of HRMS and 1H and 13C NMR spectra, and comparison with the literature data. In addition, the biosynthetic route for the isolated diterpenes was suggested. Moreover, the decoctions of the investigated species were assayed for α-glycosidase enzymatic inhibition, and cell viability on human gastric adenocarcinoma cells. None of the studied decoctions showed inhibition of the α-glucosidase enzime. Interestingly, all decoctions showed cell proliferative action and may be indicative for medicinal popular use. However, further tests need to be performed to prove this prophylactic effect against human gastric cells.CAPESPlectranthus ornatus Codd (Lamiaceae), popularmente conhecida como boldo-gambá ou boldinho, é uma planta medicinal utilizada na forma de chá das folhas ou parte aérea para o tratamento de problemas gastrointestinais. Apesar de sua importância na medicina popular, são poucos os trabalhos em química e farmacologia relatados sobre a espécie. Deste modo, o objetivo do presente trabalho foi investigar a composição química da fração metanólica obtida a partir do decocto da parte aérea de P. ornatus, cultivada no Horto de Plantas Medicinais Francisco José de Abreu Matos da Universidade Federal do Ceará –UFC. Sucessivos fracionamentos cromatográficos, incluindo Sephadex LH-20, cartucho C18 e Cromatografia Líquida de Alta Eficiência (CLAE), resultou no isolamento de treze constituintes químicos, entre os quais dois novos diterpenos (ácido 19-β-D-glicopiranosil-labda-7,13-dieno-15,16-dióico e 16-desacetil-coleon L) e dois novos flavonoides glicosilados (3’-β-D-glicoropiranosil-5,4’-diidróxi-7-metóxi-flavona e 4’-β-D-glicoropiranosil-5,3’-diidróxi-7-metóxi-flavona). Vale ressaltar que já há relato do flavonoide 4’-β-D-glicoropiranosil-5-hidróxi-7-metóxi-flavona na literatura, entretanto os dados de RMN 1H e 13C do composto estão sendo apresentados pela primeira vez. Adicionalmente, foi realizado uma comparação qualitativa dos compostos isolados da fração metanólica do decocto de P. ornatus nas frações obtidas dos decoctos da parte aérea de espécimes de três outras espécies de Plectranthus (P. barbatus, P. amboinicuse P. grandis) comuns no Estado do Ceará, também cultivadas no Horto de Plantas Medicinais. O ácido rosmarínico foi o componente majoritário em todos os decoctos. Importante frisar a presença de compostos altamente hidroxilados e glicosilados. A determinação estrutural de todos os compostos foi realizada através da interpretação de espectros obtidos de métodos espectrométricos como EMAR, RMN de 1H e 13C e comparação com dados da literatura. Adicionalmente, uma proposta de rota biossintética para os diterpenos isolados do chá de P. ornatus foi sucedida. Além disso, os chás das espécies em estudo foram submetidos a teste de inibição enzimática da α-glicosidase e de viabilidade celular com células de adenocarcinoma gástrico humana. Nenhum dos chás estudados apresentou inibição da α-glicosidase. Interessantemente, todos os chás apresentaram ação proliferativa celular, podendo ser um indicativo para o uso popular medicinal. Entretanto, mais testes precisam ser realizados a fim de comprovar esse efeito profilático frente as células gástricas humanas.Plectranthus ornatusDiterpenosFlavonoidesInibição enzimáticaViabilidade celularInvestigação dos constituintes químicos do chá de Plectranthus ornatus CoddInvestigation of the chemical constituents of the tea from 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/openAccessLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/47926/4/license.txt8a4605be74aa9ea9d79846c1fba20a33MD54ORIGINAL2019_dis_tsmatos.pdf2019_dis_tsmatos.pdfapplication/pdf12781888http://repositorio.ufc.br/bitstream/riufc/47926/3/2019_dis_tsmatos.pdf056ba52b75cbdb3b4ebf2fd480414fb3MD53riufc/479262019-11-26 11:01:53.809oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2019-11-26T14:01:53Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
dc.title.en.pt_BR.fl_str_mv Investigation of the chemical constituents of the tea from Plectranthus ornatus Codd
title Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
spellingShingle Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
Matos, Taynara Simão
Plectranthus ornatus
Diterpenos
Flavonoides
Inibição enzimática
Viabilidade celular
title_short Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
title_full Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
title_fullStr Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
title_full_unstemmed Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
title_sort Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd
author Matos, Taynara Simão
author_facet Matos, Taynara Simão
author_role author
dc.contributor.author.fl_str_mv Matos, Taynara Simão
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
Flavonoides
Inibição enzimática
Viabilidade celular
topic Plectranthus ornatus
Diterpenos
Flavonoides
Inibição enzimática
Viabilidade celular
description Plectranthus ornatus Codd (Lamiaceae), popularly known as “boldo-gambá” and “boldinho”, is a medicinal plant whose leaf or aerial part decoction is used to treat gastrointestinal problems. Despite of its importance in the popular medicinal, there are few chemical and pharmacological reports on the species. Thus, the aim of this study was to investigate the chemical composition of the MeOH soluble fraction from the decoction of the aerial part of P. ornatus, cultivated at the Medicinal Plants Garden Francisco José de Abreu Matos at the Universidade Federal do Ceará –UFC. Successive chromatography procedures, including Sephadex LH-20, C18 cartridge, and HPLC resulted in the isolation of thirteen chemical constituents including two new diterpene derivatives (19-β-D-glucopyranosyl-labda-7,13-diene-15,16-dioicacidand 16-desacetyl-coleon L) and two new flavonoids (3'-β-D-glucuropyranosyl-5,4'-dihydroxy-7-methoxy-flavone and 4'-β-D-glucuropyranosyl-5,3'-dihydroxy-7-methoxy-flavone). It is noteworthy that the flavonoid 4'-β-D-glucuropyranosyl-5-hydroxy-7-methoxy-flavone is already reported in the literature, however the 1H and 13C NMR data of this compound are being presented for the first time. Addicionally, a qualitative comparison of the main isolated compounds from the methanol soluble fraction of P. ornatus with the MeOH fractions from the aerial part decoctions of specimens of three other Plectranthus species (P. barbatus, P. amboinicus, and P. grandis) common in Ceará State was performed. Rosmarinic acid was the main compound in all decoctions. It is worth mentioning the presence of highly hydroxylated and glycosylated compounds. The structural determination of all compounds was performed by interpretation of HRMS and 1H and 13C NMR spectra, and comparison with the literature data. In addition, the biosynthetic route for the isolated diterpenes was suggested. Moreover, the decoctions of the investigated species were assayed for α-glycosidase enzymatic inhibition, and cell viability on human gastric adenocarcinoma cells. None of the studied decoctions showed inhibition of the α-glucosidase enzime. Interestingly, all decoctions showed cell proliferative action and may be indicative for medicinal popular use. However, further tests need to be performed to prove this prophylactic effect against human gastric cells.
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-11-26T14:01:53Z
dc.date.available.fl_str_mv 2019-11-26T14:01:53Z
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 MATOS, Taynara Simão. Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd. 2019. 165 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufc.br/handle/riufc/47926
identifier_str_mv MATOS, Taynara Simão. Investigação dos constituintes químicos do chá de Plectranthus ornatus Codd. 2019. 165 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2019.
url http://www.repositorio.ufc.br/handle/riufc/47926
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/47926/4/license.txt
http://repositorio.ufc.br/bitstream/riufc/47926/3/2019_dis_tsmatos.pdf
bitstream.checksum.fl_str_mv 8a4605be74aa9ea9d79846c1fba20a33
056ba52b75cbdb3b4ebf2fd480414fb3
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_ 1847793365408546816