Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Revista Brasileira de Farmacognosia (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2016000300296 |
Resumo: | Abstract Recent publications have highlighted the numerous biological activities attributed to the lignan (-)-cubebin (1), Piper cubeba L. f., Piperaceae, and ongoing studies have focused on its structural optimization, in order to obtain derivatives with greater pharmacological potential. The aim of this study was the obtainment of (1), its semisynthetic derivatives and evaluation of antibacterial activity. The extract of the seeds of P. cubeba was chromatographed, subjected to recrystallization and was analyzed by HPLC and spectrometric techniques. It was used for the synthesis of: (-)-O-methylcubebin (2), (-)-O-benzylcubebin (3), (-)-O-acetylcubebin (4), (-)-O-(N, N-dimethylamino-ethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6.6'-dinitrohinokinin (7). The evaluation of the antibacterial activity has been done by broth microdilution technique for determination of the minimum inhibitory concentration and the minimum bactericidal concentration against Porphyromonas gingivalis, Prevotella nigrescens, Actinomyces naeslundii, Bacteroides fragilis and Fusobacterium nucleatum. It was possible to make an analysis regarding the relationship between structure and antimicrobial activity of derivatives against microorganisms that cause endodontic infections. The most promising were minimum inhibitory concentration =50 µg/ml against P. gingivalis by (2) and (3), and minimum inhibitory concentration =100 µg/ml against B. fragilis by (6). Cytotoxicity assays demonstrated that (1) and its derivatives do not display toxicity. |
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Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infectionsLignansPiper cubeba(-)-cubebinSemisynthetic derivativesAntibacterial activityAbstract Recent publications have highlighted the numerous biological activities attributed to the lignan (-)-cubebin (1), Piper cubeba L. f., Piperaceae, and ongoing studies have focused on its structural optimization, in order to obtain derivatives with greater pharmacological potential. The aim of this study was the obtainment of (1), its semisynthetic derivatives and evaluation of antibacterial activity. The extract of the seeds of P. cubeba was chromatographed, subjected to recrystallization and was analyzed by HPLC and spectrometric techniques. It was used for the synthesis of: (-)-O-methylcubebin (2), (-)-O-benzylcubebin (3), (-)-O-acetylcubebin (4), (-)-O-(N, N-dimethylamino-ethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6.6'-dinitrohinokinin (7). The evaluation of the antibacterial activity has been done by broth microdilution technique for determination of the minimum inhibitory concentration and the minimum bactericidal concentration against Porphyromonas gingivalis, Prevotella nigrescens, Actinomyces naeslundii, Bacteroides fragilis and Fusobacterium nucleatum. It was possible to make an analysis regarding the relationship between structure and antimicrobial activity of derivatives against microorganisms that cause endodontic infections. The most promising were minimum inhibitory concentration =50 µg/ml against P. gingivalis by (2) and (3), and minimum inhibitory concentration =100 µg/ml against B. fragilis by (6). Cytotoxicity assays demonstrated that (1) and its derivatives do not display toxicity.Sociedade Brasileira de Farmacognosia2016-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2016000300296Revista Brasileira de Farmacognosia v.26 n.3 2016reponame:Revista Brasileira de Farmacognosia (Online)instname:Sociedade Brasileira de Farmacognosia (SBFgnosia)instacron:SBFGNOSIA10.1016/j.bjp.2015.12.006info:eu-repo/semantics/openAccessRezende,Karen C.S.Lucarini,RodrigoSímaro,Guilherme V.Pauletti,Patricia M.Januário,Ana H.Esperandim,Viviane R.Martins,Carlos H.G.Silva,Mislaine A.Cunha,Wilson R.Bastos,Jairo K.Silva,Márcio L.A.E.eng2016-06-14T00:00:00Zoai:scielo:S0102-695X2016000300296Revistahttp://www.sbfgnosia.org.br/revista/https://old.scielo.br/oai/scielo-oai.phprbgnosia@ltf.ufpb.br1981-528X0102-695Xopendoar:2016-06-14T00:00Revista Brasileira de Farmacognosia (Online) - Sociedade Brasileira de Farmacognosia (SBFgnosia)false |
dc.title.none.fl_str_mv |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
title |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
spellingShingle |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections Rezende,Karen C.S. Lignans Piper cubeba (-)-cubebin Semisynthetic derivatives Antibacterial activity |
title_short |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
title_full |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
title_fullStr |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
title_full_unstemmed |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
title_sort |
Antibacterial activity of (-)-cubebin isolated from Piper cubeba and its semisynthetic derivatives against microorganisms that cause endodontic infections |
author |
Rezende,Karen C.S. |
author_facet |
Rezende,Karen C.S. Lucarini,Rodrigo Símaro,Guilherme V. Pauletti,Patricia M. Januário,Ana H. Esperandim,Viviane R. Martins,Carlos H.G. Silva,Mislaine A. Cunha,Wilson R. Bastos,Jairo K. Silva,Márcio L.A.E. |
author_role |
author |
author2 |
Lucarini,Rodrigo Símaro,Guilherme V. Pauletti,Patricia M. Januário,Ana H. Esperandim,Viviane R. Martins,Carlos H.G. Silva,Mislaine A. Cunha,Wilson R. Bastos,Jairo K. Silva,Márcio L.A.E. |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Rezende,Karen C.S. Lucarini,Rodrigo Símaro,Guilherme V. Pauletti,Patricia M. Januário,Ana H. Esperandim,Viviane R. Martins,Carlos H.G. Silva,Mislaine A. Cunha,Wilson R. Bastos,Jairo K. Silva,Márcio L.A.E. |
dc.subject.por.fl_str_mv |
Lignans Piper cubeba (-)-cubebin Semisynthetic derivatives Antibacterial activity |
topic |
Lignans Piper cubeba (-)-cubebin Semisynthetic derivatives Antibacterial activity |
description |
Abstract Recent publications have highlighted the numerous biological activities attributed to the lignan (-)-cubebin (1), Piper cubeba L. f., Piperaceae, and ongoing studies have focused on its structural optimization, in order to obtain derivatives with greater pharmacological potential. The aim of this study was the obtainment of (1), its semisynthetic derivatives and evaluation of antibacterial activity. The extract of the seeds of P. cubeba was chromatographed, subjected to recrystallization and was analyzed by HPLC and spectrometric techniques. It was used for the synthesis of: (-)-O-methylcubebin (2), (-)-O-benzylcubebin (3), (-)-O-acetylcubebin (4), (-)-O-(N, N-dimethylamino-ethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6.6'-dinitrohinokinin (7). The evaluation of the antibacterial activity has been done by broth microdilution technique for determination of the minimum inhibitory concentration and the minimum bactericidal concentration against Porphyromonas gingivalis, Prevotella nigrescens, Actinomyces naeslundii, Bacteroides fragilis and Fusobacterium nucleatum. It was possible to make an analysis regarding the relationship between structure and antimicrobial activity of derivatives against microorganisms that cause endodontic infections. The most promising were minimum inhibitory concentration =50 µg/ml against P. gingivalis by (2) and (3), and minimum inhibitory concentration =100 µg/ml against B. fragilis by (6). Cytotoxicity assays demonstrated that (1) and its derivatives do not display toxicity. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-06-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2016000300296 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2016000300296 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1016/j.bjp.2015.12.006 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Farmacognosia |
publisher.none.fl_str_mv |
Sociedade Brasileira de Farmacognosia |
dc.source.none.fl_str_mv |
Revista Brasileira de Farmacognosia v.26 n.3 2016 reponame:Revista Brasileira de Farmacognosia (Online) instname:Sociedade Brasileira de Farmacognosia (SBFgnosia) instacron:SBFGNOSIA |
instname_str |
Sociedade Brasileira de Farmacognosia (SBFgnosia) |
instacron_str |
SBFGNOSIA |
institution |
SBFGNOSIA |
reponame_str |
Revista Brasileira de Farmacognosia (Online) |
collection |
Revista Brasileira de Farmacognosia (Online) |
repository.name.fl_str_mv |
Revista Brasileira de Farmacognosia (Online) - Sociedade Brasileira de Farmacognosia (SBFgnosia) |
repository.mail.fl_str_mv |
rbgnosia@ltf.ufpb.br |
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1752122469745950720 |