Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown
Ano de defesa: | 2008 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Ciências Farmacêuticas
|
Departamento: |
Farmácia
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/5889 |
Resumo: | Lippia alba (Mill.) N. E. Brown is a native medicinal plant of South America. Known popularly as false-melissa , its leaves and roots are used in the treatment of some illnesses, including some of infective etiology. The presence of essential oils, among other metabolites with recognized antimicrobial activity, can explain its medicinal use. This paper describes the chemical analyses and antimicrobial activity of the essential oils from Lippia alba at different seasons of the year, as well as the bio-guided fractionation, the isolation and the structure elucidation of its main constituents. Lippia alba was cultivated in São Luiz Gonzaga, RS, Brazil, and its leaves were collected in 2005 and 2006 in the middle period (January, April, July and October) of each season. A voucher specimen (SMDB n° 10.050) was deposited in the herbarium of the Department of Biology, UFSM. The extraction of the essential oils was performed by the hydrodistillation method of fresh leaves. The oils were analyzed by GC-MS and their constituents were identified by the comparison of Kovat s retention indexes and mass spectra with literature data. The essential oil was fractionated by CC over silica gel for the isolation of germacrene D-4-ol and linalool, both identified by GC-MS, 13C and 1H NMR, DEPT-135, COSY and HETCOR. The antimicrobial activity of the essential oils, fractions and isolated compounds were determined by the broth microdilution method. The essential oil showed qualitative and semi-quantitative variability in relation to the seasons of the year. The yield ranged from 0.3 to 0.6%, being lower in winter and higher in summer, autumn and spring. The essential oil was composed of monoterpenoids (69 - 84%) and sesquiterpenoids (6 - 24%), being most of them oxygenated and hidrocarbonated, respectively. Moreover, the major compounds (> 15%) were not the same between the years of the analysis. The seasonal variability influenced the antimicrobial activity of the essential oils. With the exception of P. aeruginosa, all other microorganisms were susceptible to the essential oil. The most sensitive ones were S. cerevisiae (MIC and MFC of 800 μg/mL for the oil obtained in January), S. aureus (MIC of 800 μg/mL and MBC of 1600 μg/mL for the oils obtained in April and July) and K. pneumoniae (MIC and MFC of 1600 μg/mL for the oil extracted in July). In view of the antimicrobial activity, winter and summer are the best seasons for the collection and extraction of essential oils. The bio-guided fractionation of the essential oil showed that the fractions containing greater amounts of oxygenates are more active than those containing hydrocarbon compounds. Germacrene D-4-ol presented activity against S. cerevisiae (MIC and MFC of 200 μg/mL), P. zopfii (MIC and MFC of 400 μg/mL) and S. aureus (MIC and MBC of 800 μg/mL), while linalool was inactive against the tested microorganisms up to 3200 mg/mL. |
id |
UFSM_6ff4c063c2984c6d7d830b23eca8a5cb |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/5889 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2009-10-092009-10-092008-06-02BARROS, Francisco Maikon Corrêa de. Seasonal variability, antimicrobial activity, bioguided fractionation, isolation and structural elucidation of the main constituents of the essential oil of Lippia alba (Mill.) N. E. Brown. 2008. 162 f. Dissertação (Mestrado em Farmacologia) - Universidade Federal de Santa Maria, Santa Maria, 2009.http://repositorio.ufsm.br/handle/1/5889Lippia alba (Mill.) N. E. Brown is a native medicinal plant of South America. Known popularly as false-melissa , its leaves and roots are used in the treatment of some illnesses, including some of infective etiology. The presence of essential oils, among other metabolites with recognized antimicrobial activity, can explain its medicinal use. This paper describes the chemical analyses and antimicrobial activity of the essential oils from Lippia alba at different seasons of the year, as well as the bio-guided fractionation, the isolation and the structure elucidation of its main constituents. Lippia alba was cultivated in São Luiz Gonzaga, RS, Brazil, and its leaves were collected in 2005 and 2006 in the middle period (January, April, July and October) of each season. A voucher specimen (SMDB n° 10.050) was deposited in the herbarium of the Department of Biology, UFSM. The extraction of the essential oils was performed by the hydrodistillation method of fresh leaves. The oils were analyzed by GC-MS and their constituents were identified by the comparison of Kovat s retention indexes and mass spectra with literature data. The essential oil was fractionated by CC over silica gel for the isolation of germacrene D-4-ol and linalool, both identified by GC-MS, 13C and 1H NMR, DEPT-135, COSY and HETCOR. The antimicrobial activity of the essential oils, fractions and isolated compounds were determined by the broth microdilution method. The essential oil showed qualitative and semi-quantitative variability in relation to the seasons of the year. The yield ranged from 0.3 to 0.6%, being lower in winter and higher in summer, autumn and spring. The essential oil was composed of monoterpenoids (69 - 84%) and sesquiterpenoids (6 - 24%), being most of them oxygenated and hidrocarbonated, respectively. Moreover, the major compounds (> 15%) were not the same between the years of the analysis. The seasonal variability influenced the antimicrobial activity of the essential oils. With the exception of P. aeruginosa, all other microorganisms were susceptible to the essential oil. The most sensitive ones were S. cerevisiae (MIC and MFC of 800 μg/mL for the oil obtained in January), S. aureus (MIC of 800 μg/mL and MBC of 1600 μg/mL for the oils obtained in April and July) and K. pneumoniae (MIC and MFC of 1600 μg/mL for the oil extracted in July). In view of the antimicrobial activity, winter and summer are the best seasons for the collection and extraction of essential oils. The bio-guided fractionation of the essential oil showed that the fractions containing greater amounts of oxygenates are more active than those containing hydrocarbon compounds. Germacrene D-4-ol presented activity against S. cerevisiae (MIC and MFC of 200 μg/mL), P. zopfii (MIC and MFC of 400 μg/mL) and S. aureus (MIC and MBC of 800 μg/mL), while linalool was inactive against the tested microorganisms up to 3200 mg/mL.Lippia alba (Mill.) N. E. Brown é uma planta medicinal nativa da América do Sul. Conhecida popularmente como falsa-melissa , suas folhas e raízes são empregadas no tratamento de várias doenças, incluindo algumas de etiologia infecciosa. A presença dos óleos essenciais, entre outros metabólitos com reconhecida atividade antimicrobiana, pode explicar o seu uso como medicinal. Este trabalho descreve a analise química e a atividade antimicrobiana dos óleos essenciais de Lippia alba nas diferentes estações do ano, bem como o fracionamento bio-guiado, o isolamento e a elucidação estrutural dos seus principais constituintes. Lippia alba foi cultivada no município de São Luiz Gonzaga, RS, Brasil, e suas partes aéreas foram coletadas no período médio de cada estação (janeiro, abril, julho e outubro) durante o ano de 2005 e 2006. Material testemunha (SMDB n° 10.050) encontra-se depositado no Herbário do Departamento de Biologia da UFSM. Para a realização dos experimentos, foram utilizadas as folhas frescas. A extração dos óleos essenciais foi realizada pelo método da hidrodestilação. Os óleos foram analisados por CG-EM e seus constituintes identificados pela comparação dos índices de retenção de Kovats e espectros de massas com dados da literatura. O óleo essencial também foi fracionado por CC sobre gel de sílica até o isolamento do germacreno D-4- ol e do linalol, ambos identificados por CG-EM, RMN 13C e 1H, DEPT-135, COSY e HETCOR. A atividade antimicrobiana dos óleos essenciais, das frações e das substâncias isoladas foi determinada pelo método de microdiluição em caldo. O óleo essencial apresentou variabilidade qualitativa e semiquantitativa em relação às estações do ano. O rendimento variou na ordem de 0,3 a 0,6%, sendo menor no inverno, e maior no verão, outono e primavera. O óleo essencial foi composto de monoterpenóides (69 - 84%) e sesquiterpenóides (6 24%), sendo a maioria deles oxigenados e hidrocarbonados, respectivamente. Os compostos majoritários (>15%) não foram os mesmos entre os diferentes anos de análise. A variabilidade sazonal, por sua vez, influenciou a atividade antimicrobiana dos óleos essenciais. Com exceção de P. aeruginosa, todos os outros microorganismos foram sensíveis ao óleo essencial de pelo menos uma estação. Os microorganismos com menor CIM foram S. cerevisiae (CIM e CFM de 800 μg/mL para o óleo obtido em janeiro), S. aureus (CIM de 800 μg/mL e CBM 1600 μg/mL para os óleos obtidos em abril e julho) e K. pneumoniae (CIM e CBM de 1600 μg/mL para o óleo extraído em julho). Tendo em vista a atividade antimicrobiana, o inverno e o verão constituem as melhores épocas para a coleta e extração dos óleos essenciais. O fracionamento bio-guiado do óleo essencial mostrou que frações contendo maiores quantidades de compostos oxigenados são mais ativas do que aquelas contendo compostos hidrocarbonados. Germacreno D-4-ol apresentou atividade contra S. cerevisiae (CIM e CFM de 200 μg/mL), P. zopfii (CIM e CFM de 400 μg/mL) e S. aureus (CIM e CBM de 800 μg/mL), ao passo que linalol foi inativo contra os microorganismos testados até a concentração de 3200 mg/mL.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em Ciências FarmacêuticasUFSMBRFarmáciaLippia albaVerbenaceaeÓleos essenciaisVariabilidade sazonalAtividade antimicrobianaFracionamento bio-guiadoGermacreno D-4-olLinalolLippia albaVerbenaceaeEssential oilsSeasonal variabilityAntimicrobial activityBioguided fractionationGermacrene D-4-olLinaloolCNPQ::CIENCIAS DA SAUDE::FARMACIAVariabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. BrownSeasonal variability, antimicrobial activity, bioguided fractionation, isolation and structural elucidation of the main constituents of the essential oil of Lippia alba (Mill.) N. E. Browninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisHeinzmann, Berta Mariahttp://lattes.cnpq.br/0786124562427815Burger, Marilise Escobarhttp://lattes.cnpq.br/9128090974948413Horner, Rosmarihttp://lattes.cnpq.br/5907084134183708http://lattes.cnpq.br/3640649127516310Barros, Francisco Maikon Corrêa de201000000000400500300500300ef52d431-0698-40fb-ab56-1dbd415cc5d7a57a4a72-1d5a-4c0c-8d51-35f37b1aa66d9ba38641-32d0-45d3-92ea-7987f1ae97da9b9181b8-425f-4fcc-867c-dd8dca30a2ddinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALBARROS, FRANCISCO MAIKON CORREA DE.pdfapplication/pdf4079739http://repositorio.ufsm.br/bitstream/1/5889/1/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf77cc6320fa5f671e4e938443da21431aMD51TEXTBARROS, FRANCISCO MAIKON CORREA DE.pdf.txtBARROS, FRANCISCO MAIKON CORREA DE.pdf.txtExtracted texttext/plain270393http://repositorio.ufsm.br/bitstream/1/5889/2/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf.txt3a1a96f79193c279a9113ab8adbef8feMD52THUMBNAILBARROS, FRANCISCO MAIKON CORREA DE.pdf.jpgBARROS, FRANCISCO MAIKON CORREA DE.pdf.jpgIM Thumbnailimage/jpeg5318http://repositorio.ufsm.br/bitstream/1/5889/3/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf.jpg4402190e6280f21a10da6343481228eeMD531/58892023-04-11 09:56:09.084oai:repositorio.ufsm.br:1/5889Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-04-11T12:56:09Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
dc.title.alternative.eng.fl_str_mv |
Seasonal variability, antimicrobial activity, bioguided fractionation, isolation and structural elucidation of the main constituents of the essential oil of Lippia alba (Mill.) N. E. Brown |
title |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
spellingShingle |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown Barros, Francisco Maikon Corrêa de Lippia alba Verbenaceae Óleos essenciais Variabilidade sazonal Atividade antimicrobiana Fracionamento bio-guiado Germacreno D-4-ol Linalol Lippia alba Verbenaceae Essential oils Seasonal variability Antimicrobial activity Bioguided fractionation Germacrene D-4-ol Linalool CNPQ::CIENCIAS DA SAUDE::FARMACIA |
title_short |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
title_full |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
title_fullStr |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
title_full_unstemmed |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
title_sort |
Variabilidade sazonal, atividade antimicrobiana, fracionamento bio-guiado, isolamento e elucidação estrural dos prinicpais constituintes do óleo essencial de Lippia alba (Mill.) N. E. Brown |
author |
Barros, Francisco Maikon Corrêa de |
author_facet |
Barros, Francisco Maikon Corrêa de |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Heinzmann, Berta Maria |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0786124562427815 |
dc.contributor.referee1.fl_str_mv |
Burger, Marilise Escobar |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/9128090974948413 |
dc.contributor.referee2.fl_str_mv |
Horner, Rosmari |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/5907084134183708 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3640649127516310 |
dc.contributor.author.fl_str_mv |
Barros, Francisco Maikon Corrêa de |
contributor_str_mv |
Heinzmann, Berta Maria Burger, Marilise Escobar Horner, Rosmari |
dc.subject.por.fl_str_mv |
Lippia alba Verbenaceae Óleos essenciais Variabilidade sazonal Atividade antimicrobiana Fracionamento bio-guiado Germacreno D-4-ol Linalol |
topic |
Lippia alba Verbenaceae Óleos essenciais Variabilidade sazonal Atividade antimicrobiana Fracionamento bio-guiado Germacreno D-4-ol Linalol Lippia alba Verbenaceae Essential oils Seasonal variability Antimicrobial activity Bioguided fractionation Germacrene D-4-ol Linalool CNPQ::CIENCIAS DA SAUDE::FARMACIA |
dc.subject.eng.fl_str_mv |
Lippia alba Verbenaceae Essential oils Seasonal variability Antimicrobial activity Bioguided fractionation Germacrene D-4-ol Linalool |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS DA SAUDE::FARMACIA |
description |
Lippia alba (Mill.) N. E. Brown is a native medicinal plant of South America. Known popularly as false-melissa , its leaves and roots are used in the treatment of some illnesses, including some of infective etiology. The presence of essential oils, among other metabolites with recognized antimicrobial activity, can explain its medicinal use. This paper describes the chemical analyses and antimicrobial activity of the essential oils from Lippia alba at different seasons of the year, as well as the bio-guided fractionation, the isolation and the structure elucidation of its main constituents. Lippia alba was cultivated in São Luiz Gonzaga, RS, Brazil, and its leaves were collected in 2005 and 2006 in the middle period (January, April, July and October) of each season. A voucher specimen (SMDB n° 10.050) was deposited in the herbarium of the Department of Biology, UFSM. The extraction of the essential oils was performed by the hydrodistillation method of fresh leaves. The oils were analyzed by GC-MS and their constituents were identified by the comparison of Kovat s retention indexes and mass spectra with literature data. The essential oil was fractionated by CC over silica gel for the isolation of germacrene D-4-ol and linalool, both identified by GC-MS, 13C and 1H NMR, DEPT-135, COSY and HETCOR. The antimicrobial activity of the essential oils, fractions and isolated compounds were determined by the broth microdilution method. The essential oil showed qualitative and semi-quantitative variability in relation to the seasons of the year. The yield ranged from 0.3 to 0.6%, being lower in winter and higher in summer, autumn and spring. The essential oil was composed of monoterpenoids (69 - 84%) and sesquiterpenoids (6 - 24%), being most of them oxygenated and hidrocarbonated, respectively. Moreover, the major compounds (> 15%) were not the same between the years of the analysis. The seasonal variability influenced the antimicrobial activity of the essential oils. With the exception of P. aeruginosa, all other microorganisms were susceptible to the essential oil. The most sensitive ones were S. cerevisiae (MIC and MFC of 800 μg/mL for the oil obtained in January), S. aureus (MIC of 800 μg/mL and MBC of 1600 μg/mL for the oils obtained in April and July) and K. pneumoniae (MIC and MFC of 1600 μg/mL for the oil extracted in July). In view of the antimicrobial activity, winter and summer are the best seasons for the collection and extraction of essential oils. The bio-guided fractionation of the essential oil showed that the fractions containing greater amounts of oxygenates are more active than those containing hydrocarbon compounds. Germacrene D-4-ol presented activity against S. cerevisiae (MIC and MFC of 200 μg/mL), P. zopfii (MIC and MFC of 400 μg/mL) and S. aureus (MIC and MBC of 800 μg/mL), while linalool was inactive against the tested microorganisms up to 3200 mg/mL. |
publishDate |
2008 |
dc.date.issued.fl_str_mv |
2008-06-02 |
dc.date.accessioned.fl_str_mv |
2009-10-09 |
dc.date.available.fl_str_mv |
2009-10-09 |
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 |
BARROS, Francisco Maikon Corrêa de. Seasonal variability, antimicrobial activity, bioguided fractionation, isolation and structural elucidation of the main constituents of the essential oil of Lippia alba (Mill.) N. E. Brown. 2008. 162 f. Dissertação (Mestrado em Farmacologia) - Universidade Federal de Santa Maria, Santa Maria, 2009. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/5889 |
identifier_str_mv |
BARROS, Francisco Maikon Corrêa de. Seasonal variability, antimicrobial activity, bioguided fractionation, isolation and structural elucidation of the main constituents of the essential oil of Lippia alba (Mill.) N. E. Brown. 2008. 162 f. Dissertação (Mestrado em Farmacologia) - Universidade Federal de Santa Maria, Santa Maria, 2009. |
url |
http://repositorio.ufsm.br/handle/1/5889 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
201000000000 |
dc.relation.confidence.fl_str_mv |
400 500 300 500 300 |
dc.relation.authority.fl_str_mv |
ef52d431-0698-40fb-ab56-1dbd415cc5d7 a57a4a72-1d5a-4c0c-8d51-35f37b1aa66d 9ba38641-32d0-45d3-92ea-7987f1ae97da 9b9181b8-425f-4fcc-867c-dd8dca30a2dd |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Ciências Farmacêuticas |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
BR |
dc.publisher.department.fl_str_mv |
Farmácia |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/5889/1/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf http://repositorio.ufsm.br/bitstream/1/5889/2/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf.txt http://repositorio.ufsm.br/bitstream/1/5889/3/BARROS%2c%20FRANCISCO%20MAIKON%20CORREA%20DE.pdf.jpg |
bitstream.checksum.fl_str_mv |
77cc6320fa5f671e4e938443da21431a 3a1a96f79193c279a9113ab8adbef8fe 4402190e6280f21a10da6343481228ee |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793239996325429248 |