Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas

Detalhes bibliográficos
Autor(a) principal: Menezes, Paula dos Passos
Data de Publicação: 2015
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFS
Texto Completo: https://ri.ufs.br/handle/riufs/3799
Resumo: The essential oils, which are secondary metabolites produced by plants. These metabolites are part of the group of terpenes. Such organic molecules are characterized by presenting important pharmacological activities such as anti-inflammatory, antinociceptive, antimicrobial, among others. Thus, the essential oil of Hyptis pectinata (EOHP), a native fragrant plant of the states of Alagoas and Sergipe and widely used by the population, has attracted attention of researchers in order to validate its popular use. In addition, the isopulegol (ISOP), a major monoterpene in the industry for their flavoring properties and medicinal has been the subject of research in scientific research. However, EOHP present ISOP and the physico-chemical characteristics and limited water solubility, high volatilization photosensitivity and easy oxidation. In this perspective, an alternative to preserve the characteristics of these substances is the formation of supramolecular complexes involving cyclodextrins (CDs). The CDs have a molecular structure suitable for the formation of inclusion complexes since they have polar and hydrophilic surface cavity. Thus, the inclusion complex of essential oils and CDs improve the physico-chemical properties of these molecules to optimize the pharmacological activity thereof. Hence, the aim of this study was to identify the chemical constituents of OEHP by gas chromatography coupled to mass spectrometry with flame detector (GC-MS/FID) and from there to prepare the samples with β -CD and ISOP in the α- and β-CD by the methods of the physical mixture (PM), paste complexation (PC) and slurry complexation (SC). Furthermore, the physico-chemical characterization of the samples through the techniques of differential scanning calorimetry (DSC) was performed thermogravimetry/derivative thermogravimetry (TGA/DTG) absorption spectrophotometry in the infrared Fourier transform spectroscopy (FT-IR) scanning electron microscopy, X-ray diffraction (XRD), complexation efficiency by GC-MS/FID, pharmacological test formalin with the best complex obtained from OEHP and study of molecular modeling (docking) to isopulegol and CDs. Based on these results, we observed three major constituents in OEHP, (E) -caryophyllene (54.07%), caryophyllene oxide (14.91%) and germacrene-D (7.46%). The results of physicochemical characterization showed that the EC was the best method to complex (E)-caryophyllene and germacrene-D, caryophyllene oxide has not been complexed and this may be related to its low affinity for the cavity of β- CD. The formalin test showed a better antinociceptive and anti-inflammatory OEHP / β-CD when compared with pure EOHP that can be attributed to the high percentage of (E) -caryophyllene complexed. Regarding isopulegol, it was observed that α-CD complexes more stable inclusion of the β-CD, as showed in the docking analysis and PC/α-CD gave a higher ratio of complexing with respect to PM and SC. But the SC obtained with β-CD showed the highest molecular inclusion. Thus, the techniques used were efficient in the complexation of EOHP and ISOP.
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spelling Menezes, Paula dos Passoshttp://lattes.cnpq.br/5669386489328067Serafini, Mairim Russohttp://lattes.cnpq.br/95087017512984312017-09-26T12:17:31Z2017-09-26T12:17:31Z2015-02-27MENEZES, Paula dos Passos. Obtainment and physicochemical characterization of complexes supramoleculars essential oil and substance isolated on cyclodextrins. 2015. 112 f. Dissertação (Mestrado em Ciências da Saúde) - Universidade Federal de Sergipe, São Cristóvão, 2015.https://ri.ufs.br/handle/riufs/3799The essential oils, which are secondary metabolites produced by plants. These metabolites are part of the group of terpenes. Such organic molecules are characterized by presenting important pharmacological activities such as anti-inflammatory, antinociceptive, antimicrobial, among others. Thus, the essential oil of Hyptis pectinata (EOHP), a native fragrant plant of the states of Alagoas and Sergipe and widely used by the population, has attracted attention of researchers in order to validate its popular use. In addition, the isopulegol (ISOP), a major monoterpene in the industry for their flavoring properties and medicinal has been the subject of research in scientific research. However, EOHP present ISOP and the physico-chemical characteristics and limited water solubility, high volatilization photosensitivity and easy oxidation. In this perspective, an alternative to preserve the characteristics of these substances is the formation of supramolecular complexes involving cyclodextrins (CDs). The CDs have a molecular structure suitable for the formation of inclusion complexes since they have polar and hydrophilic surface cavity. Thus, the inclusion complex of essential oils and CDs improve the physico-chemical properties of these molecules to optimize the pharmacological activity thereof. Hence, the aim of this study was to identify the chemical constituents of OEHP by gas chromatography coupled to mass spectrometry with flame detector (GC-MS/FID) and from there to prepare the samples with β -CD and ISOP in the α- and β-CD by the methods of the physical mixture (PM), paste complexation (PC) and slurry complexation (SC). Furthermore, the physico-chemical characterization of the samples through the techniques of differential scanning calorimetry (DSC) was performed thermogravimetry/derivative thermogravimetry (TGA/DTG) absorption spectrophotometry in the infrared Fourier transform spectroscopy (FT-IR) scanning electron microscopy, X-ray diffraction (XRD), complexation efficiency by GC-MS/FID, pharmacological test formalin with the best complex obtained from OEHP and study of molecular modeling (docking) to isopulegol and CDs. Based on these results, we observed three major constituents in OEHP, (E) -caryophyllene (54.07%), caryophyllene oxide (14.91%) and germacrene-D (7.46%). The results of physicochemical characterization showed that the EC was the best method to complex (E)-caryophyllene and germacrene-D, caryophyllene oxide has not been complexed and this may be related to its low affinity for the cavity of β- CD. The formalin test showed a better antinociceptive and anti-inflammatory OEHP / β-CD when compared with pure EOHP that can be attributed to the high percentage of (E) -caryophyllene complexed. Regarding isopulegol, it was observed that α-CD complexes more stable inclusion of the β-CD, as showed in the docking analysis and PC/α-CD gave a higher ratio of complexing with respect to PM and SC. But the SC obtained with β-CD showed the highest molecular inclusion. Thus, the techniques used were efficient in the complexation of EOHP and ISOP.Os óleos essenciais são metabólitos secundários das plantas constituídos de terpenos. Tais moléculas orgânicas caracterizam-se por apresentar atividades farmacológicas importantes como anti-inflamatória, antinociceptiva, antimicrobiana, dentre outras. Dessa forma, o óleo essencial da Hyptis pectinata (OEHP), uma planta odorífera nativa dos estados de Alagoas e Sergipe e bastante utilizada pela população, tem despertado interesse dos pesquisadores com o objetivo de validar o seu uso popular. Além disso, o isopulegol (ISOP), um monoterpeno importante na indústria por suas propriedades flavorizantes e medicinais tem sido objeto de investigação na pesquisa científica. Entretanto, o OEHP, bem como o ISOP apresentam características físico-químicas como solubilidade limitada em água, elevada volatilização, fotossensibilidade e fácil oxidação. Nessa perspectiva, uma alternativa para preservar as características dessas substâncias é a formação de complexos supramoleculares envolvendo ciclodextrinas (CDs). As CDs apresentam uma estrutura molecular adequada para a formação de complexos de inclusão uma vez que possuem cavidade apolar e superfície hidrofílica. Assim, os complexos de inclusão de óleos essenciais e CDs melhoram as características físico-químicas dessas moléculas de modo a otimizar a atividade farmacológica das mesmas. Diante disto, o objetivo do presente estudo foi realizar a identificação dos constituintes químicos do OEHP através da cromatografia gasosa acoplada a espectrômetro de massas com detector de chamas (CG-EM/DIC) e a partir daí preparar as amostras com β-CD e do ISOP em α- e β-CDs através dos métodos da mistura física (MF), malaxagem (MA) e co-evaporação (CE). Além disso, foi realizada a caracterização físico-química das amostras através das técnicas de calorimetria exploratória diferencial (DSC), termogravimetria/termogravimetria derivada (TG/DTG), espectrofotometria de absorção na região do infravermelho com transformada de Fourier (FT-IR), microscopia eletrônica de varredura, difração de raios-X (DRX), eficiência de complexação através da CG-EM/DIC, ensaio farmacológico de formalina com o melhor complexo obtido do OEHP e estudo de modelagem molecular (Docking) para o ISOP e CDs. Diante dos resultados obtidos, foram observados três constituintes majoritários no OEHP, (E)-cariofileno (54,07%), óxido de cariofileno (14,91%) e germacreno-D (7,46%). Os resultados de caracterização físico-química demonstraram que o CE foi o melhor método para complexar o (E)-cariofileno e o germacreno-D, o óxido de cariofileno não foi complexado e isso pode estar relacionado a sua baixa afinidade pela cavidade da β-CD. O teste de formalina demonstrou melhor atividade antinociceptiva e anti-inflamatória do OEHP/β-CD quando comparado com o OEHP puro que pode ser atribuída ao elevado percentual de (E)-cariofileno complexado. Em relação ao ISOP, foi observado que a α-CD forma complexos de inclusão mais estáveis que a β-CD, pela análise de Docking, e a MA/α-CD forneceu uma maior razão de complexação em relação a MF e CE. Já o CE obtido com β-CD apresentou maior taxa de inclusão molecular. Assim, as técnicas utilizadas foram eficientes na complexação do OEHP e ISOP.application/pdfporUniversidade Federal de SergipePós-Graduação em Ciências da SaúdeUFSBRα-Ciclodextrinab-CiclodextrinaMonoterpenoPlantas medicinaisEssências e óleos essenciaisFísico-químicaCiclodextrinasTerpenosMonoterpeneMedicinal herbsCNPQ::CIENCIAS DA SAUDEObtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinasObtainment and physicochemical characterization of complexes supramoleculars essential oil and substance isolated on cyclodextrinsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSinstname:Universidade Federal de Sergipe (UFS)instacron:UFSTEXTPAULA_PASSOS_MENEZES.pdf.txtPAULA_PASSOS_MENEZES.pdf.txtExtracted texttext/plain215170https://ri.ufs.br/jspui/bitstream/riufs/3799/2/PAULA_PASSOS_MENEZES.pdf.txt15e9d3e0de535ab9624fd5417d7416f8MD52THUMBNAILPAULA_PASSOS_MENEZES.pdf.jpgPAULA_PASSOS_MENEZES.pdf.jpgGenerated Thumbnailimage/jpeg1385https://ri.ufs.br/jspui/bitstream/riufs/3799/3/PAULA_PASSOS_MENEZES.pdf.jpgb79f94452854b0dd24439b8560c22df7MD53ORIGINALPAULA_PASSOS_MENEZES.pdfapplication/pdf2446078https://ri.ufs.br/jspui/bitstream/riufs/3799/1/PAULA_PASSOS_MENEZES.pdf569a6317c9440370a78e29ed47482d2fMD51riufs/37992017-11-28 16:51:47.783oai:ufs.br:riufs/3799Repositório InstitucionalPUBhttps://ri.ufs.br/oai/requestrepositorio@academico.ufs.bropendoar:2017-11-28T19:51:47Repositório Institucional da UFS - Universidade Federal de Sergipe (UFS)false
dc.title.por.fl_str_mv Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
dc.title.alternative.eng.fl_str_mv Obtainment and physicochemical characterization of complexes supramoleculars essential oil and substance isolated on cyclodextrins
title Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
spellingShingle Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
Menezes, Paula dos Passos
α-Ciclodextrina
b-Ciclodextrina
Monoterpeno
Plantas medicinais
Essências e óleos essenciais
Físico-química
Ciclodextrinas
Terpenos
Monoterpene
Medicinal herbs
CNPQ::CIENCIAS DA SAUDE
title_short Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
title_full Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
title_fullStr Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
title_full_unstemmed Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
title_sort Obtenção e caracterização físico-química de complexos supramoleculares de óleo essencial e substância isolada em ciclodextrinas
author Menezes, Paula dos Passos
author_facet Menezes, Paula dos Passos
author_role author
dc.contributor.author.fl_str_mv Menezes, Paula dos Passos
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/5669386489328067
dc.contributor.advisor1.fl_str_mv Serafini, Mairim Russo
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/9508701751298431
contributor_str_mv Serafini, Mairim Russo
dc.subject.por.fl_str_mv α-Ciclodextrina
b-Ciclodextrina
Monoterpeno
Plantas medicinais
Essências e óleos essenciais
Físico-química
Ciclodextrinas
Terpenos
topic α-Ciclodextrina
b-Ciclodextrina
Monoterpeno
Plantas medicinais
Essências e óleos essenciais
Físico-química
Ciclodextrinas
Terpenos
Monoterpene
Medicinal herbs
CNPQ::CIENCIAS DA SAUDE
dc.subject.eng.fl_str_mv Monoterpene
Medicinal herbs
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS DA SAUDE
description The essential oils, which are secondary metabolites produced by plants. These metabolites are part of the group of terpenes. Such organic molecules are characterized by presenting important pharmacological activities such as anti-inflammatory, antinociceptive, antimicrobial, among others. Thus, the essential oil of Hyptis pectinata (EOHP), a native fragrant plant of the states of Alagoas and Sergipe and widely used by the population, has attracted attention of researchers in order to validate its popular use. In addition, the isopulegol (ISOP), a major monoterpene in the industry for their flavoring properties and medicinal has been the subject of research in scientific research. However, EOHP present ISOP and the physico-chemical characteristics and limited water solubility, high volatilization photosensitivity and easy oxidation. In this perspective, an alternative to preserve the characteristics of these substances is the formation of supramolecular complexes involving cyclodextrins (CDs). The CDs have a molecular structure suitable for the formation of inclusion complexes since they have polar and hydrophilic surface cavity. Thus, the inclusion complex of essential oils and CDs improve the physico-chemical properties of these molecules to optimize the pharmacological activity thereof. Hence, the aim of this study was to identify the chemical constituents of OEHP by gas chromatography coupled to mass spectrometry with flame detector (GC-MS/FID) and from there to prepare the samples with β -CD and ISOP in the α- and β-CD by the methods of the physical mixture (PM), paste complexation (PC) and slurry complexation (SC). Furthermore, the physico-chemical characterization of the samples through the techniques of differential scanning calorimetry (DSC) was performed thermogravimetry/derivative thermogravimetry (TGA/DTG) absorption spectrophotometry in the infrared Fourier transform spectroscopy (FT-IR) scanning electron microscopy, X-ray diffraction (XRD), complexation efficiency by GC-MS/FID, pharmacological test formalin with the best complex obtained from OEHP and study of molecular modeling (docking) to isopulegol and CDs. Based on these results, we observed three major constituents in OEHP, (E) -caryophyllene (54.07%), caryophyllene oxide (14.91%) and germacrene-D (7.46%). The results of physicochemical characterization showed that the EC was the best method to complex (E)-caryophyllene and germacrene-D, caryophyllene oxide has not been complexed and this may be related to its low affinity for the cavity of β- CD. The formalin test showed a better antinociceptive and anti-inflammatory OEHP / β-CD when compared with pure EOHP that can be attributed to the high percentage of (E) -caryophyllene complexed. Regarding isopulegol, it was observed that α-CD complexes more stable inclusion of the β-CD, as showed in the docking analysis and PC/α-CD gave a higher ratio of complexing with respect to PM and SC. But the SC obtained with β-CD showed the highest molecular inclusion. Thus, the techniques used were efficient in the complexation of EOHP and ISOP.
publishDate 2015
dc.date.issued.fl_str_mv 2015-02-27
dc.date.accessioned.fl_str_mv 2017-09-26T12:17:31Z
dc.date.available.fl_str_mv 2017-09-26T12:17:31Z
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dc.identifier.citation.fl_str_mv MENEZES, Paula dos Passos. Obtainment and physicochemical characterization of complexes supramoleculars essential oil and substance isolated on cyclodextrins. 2015. 112 f. Dissertação (Mestrado em Ciências da Saúde) - Universidade Federal de Sergipe, São Cristóvão, 2015.
dc.identifier.uri.fl_str_mv https://ri.ufs.br/handle/riufs/3799
identifier_str_mv MENEZES, Paula dos Passos. Obtainment and physicochemical characterization of complexes supramoleculars essential oil and substance isolated on cyclodextrins. 2015. 112 f. Dissertação (Mestrado em Ciências da Saúde) - Universidade Federal de Sergipe, São Cristóvão, 2015.
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dc.publisher.initials.fl_str_mv UFS
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