Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica
| Ano de defesa: | 2023 |
|---|---|
| Autor(a) principal: | |
| Orientador(a): | |
| Banca de defesa: | |
| 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: | |
| Link de acesso: | http://repositorio.ufc.br/handle/riufc/77693 |
Resumo: | In this work, menthol and menthone derivatives were synthesized, including nine esters, one thiosemicarbazone and two hydrazones. All were characterized by nuclear magnetic resonance (1H NMR), gas chromatography coupled to mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (FTIR). Considering that menthol and menthone are the major constituents present in many essential oils of plants with proven larvicidal activity, mainly in the Mentha genus, the main objective of this work was to evaluate the larvicidal potential of the derivatives obtained against the larvae of the Aedes aegypti mosquito, the main vector responsible for the transmission of diseases such as Chikungunya Fever, Zika and Dengue. The compounds were evaluated for larvicidal activity using 3rd stage larvae of the Aedes aegypti mosquito, at different concentrations (4 – 10 – 20 – 40 – 100) ppm of the bioproducts. The compounds MDODEC, MBENZ, MBENZ 4-OCH3, MBENZ 4-Cl, MAC, MCINAM, MCINAM 4-OCH3, MENTIO and MENTISO, obtained potent larvicidal activity with LC50 values lower than 100 ppm, highlighting MDODEC with LC50 of 8 ppm and MENTIO with LC50 of 22 ppm, values close to the larvicide temephos. The samples were also evaluated for their anxiolytic activity, modifying the lomotor and behavioral activity of zebrafish, acting via GABA. All compounds were tested for inhibitory action of the enzyme Acetylcholinesterase (AChE), presenting inhibition halos close to and, in some cases, greater than the Eserine standard. |
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Sousa, Emerson Yvay Almeida deMonte, Francisco José QueriozLemos, Telma Leda Gomes de2024-08-14T13:52:20Z2024-08-14T13:52:20Z2023SOUSA, Emerson Yvay Almeida De. Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: Inibição da enzima acetilcolinesterase, larvicida e ansiolítica. 2023. 107 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2023.http://repositorio.ufc.br/handle/riufc/77693In this work, menthol and menthone derivatives were synthesized, including nine esters, one thiosemicarbazone and two hydrazones. All were characterized by nuclear magnetic resonance (1H NMR), gas chromatography coupled to mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (FTIR). Considering that menthol and menthone are the major constituents present in many essential oils of plants with proven larvicidal activity, mainly in the Mentha genus, the main objective of this work was to evaluate the larvicidal potential of the derivatives obtained against the larvae of the Aedes aegypti mosquito, the main vector responsible for the transmission of diseases such as Chikungunya Fever, Zika and Dengue. The compounds were evaluated for larvicidal activity using 3rd stage larvae of the Aedes aegypti mosquito, at different concentrations (4 – 10 – 20 – 40 – 100) ppm of the bioproducts. The compounds MDODEC, MBENZ, MBENZ 4-OCH3, MBENZ 4-Cl, MAC, MCINAM, MCINAM 4-OCH3, MENTIO and MENTISO, obtained potent larvicidal activity with LC50 values lower than 100 ppm, highlighting MDODEC with LC50 of 8 ppm and MENTIO with LC50 of 22 ppm, values close to the larvicide temephos. The samples were also evaluated for their anxiolytic activity, modifying the lomotor and behavioral activity of zebrafish, acting via GABA. All compounds were tested for inhibitory action of the enzyme Acetylcholinesterase (AChE), presenting inhibition halos close to and, in some cases, greater than the Eserine standard.Neste trabalho foram sintetizados derivados do mentol e da mentona entre estes, nove ésteres, uma tiossemicarbazona e duas hidrazonas. Todos caracterizados por ressonância magnética nuclear (RMN 1H), cromatografia gasosa acoplada ao espectrômetro de massas (CG-EM) e espectroscopia no infravermelho com transformada de Fourier (FTIR). Considerando que mentol e mentona são os constituintes majoritários presentes em muitos óleos essenciais de plantas com atividade larvicida comprovada, principalmente no gênero Mentha, o trabalho teve como objetivo central avaliar o potencial larvicida dos derivados obtidos frente as larvas do mosquito Aedes aegypti, principal vetor responsável pela transmissão de doenças como Febre Chikungunya, Zika e Dengue. Os compostos foram avaliados quanto a atividade larvicida usando larvas de 3º estágio do mosquito Aedes aegypti, em diferentes concentrações (4 – 10 – 20 – 40 – 100) ppm dos bioprodutos. Os compostos MDODEC, MBENZ, MBENZ 4-OCH3, MBENZ 4-Cl, MAC, MCINAM, MCINAM 4-OCH3, MENTIO E MENTISO, obtiveram pontencil larvicida com valores de CL50 menor que 100 ppm, destacando-se MDODEC com CL50 de 8ppm e MENTIO com CL50 de 22ppm, valores próximos ao larvicida temefos. As amostras também foram avaliadas quanto a sua atividade ansiolítica, modificando a atividade lomotora e comportamental do zebrafish, atuando via GABA. Todos os compostos foram testados quanto a ação inibitória da enzima Acetilcolinesterase (AChE), apresentando halos de inibição próximos e, em alguns casos, maior que o padrão Eserina.Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolíticaObtaining (-)-menthol derivatives and evaluation of biological activities: inhibition of the acetylcholinesterase enzyme, larvicidic and anxiolyticinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesis-)-MentolDerivados do (-)-mentolAtividade larvicidaAtividade acetilcolinesterásica(-)-MentholDerivatives of (-)-mentholLarvicidal activityAcetylcholinesterase 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/0000-0002-8877-8604https://lattes.cnpq.br/9333522198578201https://orcid.org/0000-0002-7031-860Xhttp://lattes.cnpq.br/6012129579229029https://orcid.org/0000-0003-1472-8396http://lattes.cnpq.br/51892637616820192024-08-14LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/77693/4/license.txt8a4605be74aa9ea9d79846c1fba20a33MD54ORIGINAL2023_tese_eyasousa.pdf2023_tese_eyasousa.pdfapplication/pdf2900374http://repositorio.ufc.br/bitstream/riufc/77693/5/2023_tese_eyasousa.pdf12d66c40c297ae3968371939528f8ad2MD55riufc/776932024-08-14 10:53:39.053oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-08-14T13:53:39Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false |
| dc.title.pt_BR.fl_str_mv |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| dc.title.en.pt_BR.fl_str_mv |
Obtaining (-)-menthol derivatives and evaluation of biological activities: inhibition of the acetylcholinesterase enzyme, larvicidic and anxiolytic |
| title |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| spellingShingle |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica Sousa, Emerson Yvay Almeida de CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA -)-Mentol Derivados do (-)-mentol Atividade larvicida Atividade acetilcolinesterásica (-)-Menthol Derivatives of (-)-menthol Larvicidal activity Acetylcholinesterase activity |
| title_short |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| title_full |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| title_fullStr |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| title_full_unstemmed |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| title_sort |
Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica |
| author |
Sousa, Emerson Yvay Almeida de |
| author_facet |
Sousa, Emerson Yvay Almeida de |
| author_role |
author |
| dc.contributor.co-advisor.none.fl_str_mv |
Monte, Francisco José Querioz |
| dc.contributor.author.fl_str_mv |
Sousa, Emerson Yvay Almeida de |
| dc.contributor.advisor1.fl_str_mv |
Lemos, Telma Leda Gomes de |
| contributor_str_mv |
Lemos, Telma Leda Gomes de |
| dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
| topic |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA -)-Mentol Derivados do (-)-mentol Atividade larvicida Atividade acetilcolinesterásica (-)-Menthol Derivatives of (-)-menthol Larvicidal activity Acetylcholinesterase activity |
| dc.subject.ptbr.pt_BR.fl_str_mv |
-)-Mentol Derivados do (-)-mentol Atividade larvicida Atividade acetilcolinesterásica |
| dc.subject.en.pt_BR.fl_str_mv |
(-)-Menthol Derivatives of (-)-menthol Larvicidal activity Acetylcholinesterase activity |
| description |
In this work, menthol and menthone derivatives were synthesized, including nine esters, one thiosemicarbazone and two hydrazones. All were characterized by nuclear magnetic resonance (1H NMR), gas chromatography coupled to mass spectrometry (GC-MS) and Fourier transform infrared spectroscopy (FTIR). Considering that menthol and menthone are the major constituents present in many essential oils of plants with proven larvicidal activity, mainly in the Mentha genus, the main objective of this work was to evaluate the larvicidal potential of the derivatives obtained against the larvae of the Aedes aegypti mosquito, the main vector responsible for the transmission of diseases such as Chikungunya Fever, Zika and Dengue. The compounds were evaluated for larvicidal activity using 3rd stage larvae of the Aedes aegypti mosquito, at different concentrations (4 – 10 – 20 – 40 – 100) ppm of the bioproducts. The compounds MDODEC, MBENZ, MBENZ 4-OCH3, MBENZ 4-Cl, MAC, MCINAM, MCINAM 4-OCH3, MENTIO and MENTISO, obtained potent larvicidal activity with LC50 values lower than 100 ppm, highlighting MDODEC with LC50 of 8 ppm and MENTIO with LC50 of 22 ppm, values close to the larvicide temephos. The samples were also evaluated for their anxiolytic activity, modifying the lomotor and behavioral activity of zebrafish, acting via GABA. All compounds were tested for inhibitory action of the enzyme Acetylcholinesterase (AChE), presenting inhibition halos close to and, in some cases, greater than the Eserine standard. |
| publishDate |
2023 |
| dc.date.issued.fl_str_mv |
2023 |
| dc.date.accessioned.fl_str_mv |
2024-08-14T13:52:20Z |
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2024-08-14T13:52:20Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/doctoralThesis |
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doctoralThesis |
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publishedVersion |
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SOUSA, Emerson Yvay Almeida De. Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: Inibição da enzima acetilcolinesterase, larvicida e ansiolítica. 2023. 107 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2023. |
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http://repositorio.ufc.br/handle/riufc/77693 |
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SOUSA, Emerson Yvay Almeida De. Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: Inibição da enzima acetilcolinesterase, larvicida e ansiolítica. 2023. 107 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2023. |
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