Obtenção de derivados do (-)-Mentol e avaliação de atividades biológicas: inibição da enzima acetilcolinesterase, larvicida e ansiolítica

Detalhes bibliográficos
Ano de defesa: 2023
Autor(a) principal: Sousa, Emerson Yvay Almeida de
Orientador(a): Lemos, Telma Leda Gomes de
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:
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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spelling 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:riufc/77693Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=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
dc.date.available.fl_str_mv 2024-08-14T13:52:20Z
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 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.
dc.identifier.uri.fl_str_mv http://repositorio.ufc.br/handle/riufc/77693
identifier_str_mv 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.
url http://repositorio.ufc.br/handle/riufc/77693
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