Variable-temperature NMR and conformational analysis of oenothein B
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000200011 |
Resumo: | Oenothein B is a dimeric hydrolysable tannin with a wide range of biological activities, such as antitumour, anti-inflammatory and antiviral. Its nuclear magnetic resonance (NMR) at room temperature show duplications and broadening of signals. Experiments of 1D and 2D NMR at lower temperatures were useful for the complete NMR assignments of all hydrogens and carbons. The 3D structure of the most stable conformer was determined for the first time by nuclear Overhauser effect spectroscopy (NOESY) experiment (-20 ºC) and density functional theory (DFT)(B3LYP/6-31G)/ polarizable continuum model (PCM) quantum chemical calculations. The favoured conformation showed a highly compacted geometry and a lack of symmetry, in which the two valoneoyl groups showed distinct conformational parameters and stabilities. |
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Journal of the Brazilian Chemical Society (Online) |
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Variable-temperature NMR and conformational analysis of oenothein Boenothein Bvariable-temperature NMRmacrocyclic dimerconformational analysisOenothein B is a dimeric hydrolysable tannin with a wide range of biological activities, such as antitumour, anti-inflammatory and antiviral. Its nuclear magnetic resonance (NMR) at room temperature show duplications and broadening of signals. Experiments of 1D and 2D NMR at lower temperatures were useful for the complete NMR assignments of all hydrogens and carbons. The 3D structure of the most stable conformer was determined for the first time by nuclear Overhauser effect spectroscopy (NOESY) experiment (-20 ºC) and density functional theory (DFT)(B3LYP/6-31G)/ polarizable continuum model (PCM) quantum chemical calculations. The favoured conformation showed a highly compacted geometry and a lack of symmetry, in which the two valoneoyl groups showed distinct conformational parameters and stabilities.Sociedade Brasileira de Química2014-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000200011Journal of the Brazilian Chemical Society v.25 n.2 2014reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130295info:eu-repo/semantics/openAccessSantos,Suzana C.Carvalho,Ariadne G.Fortes,Gilmara A. C.Ferri,Pedro H.Oliveira,Anselmo E. deeng2014-02-14T00:00:00Zoai:scielo:S0103-50532014000200011Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2014-02-14T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Variable-temperature NMR and conformational analysis of oenothein B |
title |
Variable-temperature NMR and conformational analysis of oenothein B |
spellingShingle |
Variable-temperature NMR and conformational analysis of oenothein B Santos,Suzana C. oenothein B variable-temperature NMR macrocyclic dimer conformational analysis |
title_short |
Variable-temperature NMR and conformational analysis of oenothein B |
title_full |
Variable-temperature NMR and conformational analysis of oenothein B |
title_fullStr |
Variable-temperature NMR and conformational analysis of oenothein B |
title_full_unstemmed |
Variable-temperature NMR and conformational analysis of oenothein B |
title_sort |
Variable-temperature NMR and conformational analysis of oenothein B |
author |
Santos,Suzana C. |
author_facet |
Santos,Suzana C. Carvalho,Ariadne G. Fortes,Gilmara A. C. Ferri,Pedro H. Oliveira,Anselmo E. de |
author_role |
author |
author2 |
Carvalho,Ariadne G. Fortes,Gilmara A. C. Ferri,Pedro H. Oliveira,Anselmo E. de |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Santos,Suzana C. Carvalho,Ariadne G. Fortes,Gilmara A. C. Ferri,Pedro H. Oliveira,Anselmo E. de |
dc.subject.por.fl_str_mv |
oenothein B variable-temperature NMR macrocyclic dimer conformational analysis |
topic |
oenothein B variable-temperature NMR macrocyclic dimer conformational analysis |
description |
Oenothein B is a dimeric hydrolysable tannin with a wide range of biological activities, such as antitumour, anti-inflammatory and antiviral. Its nuclear magnetic resonance (NMR) at room temperature show duplications and broadening of signals. Experiments of 1D and 2D NMR at lower temperatures were useful for the complete NMR assignments of all hydrogens and carbons. The 3D structure of the most stable conformer was determined for the first time by nuclear Overhauser effect spectroscopy (NOESY) experiment (-20 ºC) and density functional theory (DFT)(B3LYP/6-31G)/ polarizable continuum model (PCM) quantum chemical calculations. The favoured conformation showed a highly compacted geometry and a lack of symmetry, in which the two valoneoyl groups showed distinct conformational parameters and stabilities. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-02-01 |
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=S0103-50532014000200011 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000200011 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20130295 |
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 Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.25 n.2 2014 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318175714541568 |