New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.

Detalhes bibliográficos
Autor(a) principal: Sousa, Grasiely Faria de
Data de Publicação: 2012
Outros Autores: Duarte, Lucienir Pains, Alcântara, Antônio Flávio de Carvalho, Silva, Grácia Divina de Fátima, Vieira Filho, Sidney Augusto, Miranda, Roqueline Rodrigues Silva de, Oliveira, Djalma Menezes de, Takahashi, Jacqueline Aparecida
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFOP
Texto Completo: http://www.repositorio.ufop.br/handle/123456789/3853
https://doi.org/10.3390/molecules171113439
Resumo: Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β- olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties.
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spelling New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.Maytenus robustaPentacyclic triterpenesAcetylcholinesterase inhibitory activityLeaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β- olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties.2014-11-14T18:05:21Z2014-11-14T18:05:21Z2012info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfSOUSA, G. F. de et al. New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations. Molecules, v. 17, p. 13439-13456, 2012. Disponível em: <http://www.mdpi.com/1420-3049/17/11/13439> Acesso em: 20 ago. 2014.1420-3049http://www.repositorio.ufop.br/handle/123456789/3853https://doi.org/10.3390/molecules171113439This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Fonte: Molecules <http://www.mdpi.com/1420-3049/18/8/9919> Acesso em: 08 set. 2014.info:eu-repo/semantics/openAccessSousa, Grasiely Faria deDuarte, Lucienir PainsAlcântara, Antônio Flávio de CarvalhoSilva, Grácia Divina de FátimaVieira Filho, Sidney AugustoMiranda, Roqueline Rodrigues Silva deOliveira, Djalma Menezes deTakahashi, Jacqueline Aparecidaengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOP2019-05-09T17:50:12Zoai:repositorio.ufop.br:123456789/3853Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-05-09T17:50:12Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false
dc.title.none.fl_str_mv New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
title New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
spellingShingle New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
Sousa, Grasiely Faria de
Maytenus robusta
Pentacyclic triterpenes
Acetylcholinesterase inhibitory activity
title_short New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
title_full New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
title_fullStr New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
title_full_unstemmed New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
title_sort New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
author Sousa, Grasiely Faria de
author_facet Sousa, Grasiely Faria de
Duarte, Lucienir Pains
Alcântara, Antônio Flávio de Carvalho
Silva, Grácia Divina de Fátima
Vieira Filho, Sidney Augusto
Miranda, Roqueline Rodrigues Silva de
Oliveira, Djalma Menezes de
Takahashi, Jacqueline Aparecida
author_role author
author2 Duarte, Lucienir Pains
Alcântara, Antônio Flávio de Carvalho
Silva, Grácia Divina de Fátima
Vieira Filho, Sidney Augusto
Miranda, Roqueline Rodrigues Silva de
Oliveira, Djalma Menezes de
Takahashi, Jacqueline Aparecida
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Sousa, Grasiely Faria de
Duarte, Lucienir Pains
Alcântara, Antônio Flávio de Carvalho
Silva, Grácia Divina de Fátima
Vieira Filho, Sidney Augusto
Miranda, Roqueline Rodrigues Silva de
Oliveira, Djalma Menezes de
Takahashi, Jacqueline Aparecida
dc.subject.por.fl_str_mv Maytenus robusta
Pentacyclic triterpenes
Acetylcholinesterase inhibitory activity
topic Maytenus robusta
Pentacyclic triterpenes
Acetylcholinesterase inhibitory activity
description Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β- olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties.
publishDate 2012
dc.date.none.fl_str_mv 2012
2014-11-14T18:05:21Z
2014-11-14T18:05:21Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv SOUSA, G. F. de et al. New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations. Molecules, v. 17, p. 13439-13456, 2012. Disponível em: <http://www.mdpi.com/1420-3049/17/11/13439> Acesso em: 20 ago. 2014.
1420-3049
http://www.repositorio.ufop.br/handle/123456789/3853
https://doi.org/10.3390/molecules171113439
identifier_str_mv SOUSA, G. F. de et al. New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations. Molecules, v. 17, p. 13439-13456, 2012. Disponível em: <http://www.mdpi.com/1420-3049/17/11/13439> Acesso em: 20 ago. 2014.
1420-3049
url http://www.repositorio.ufop.br/handle/123456789/3853
https://doi.org/10.3390/molecules171113439
dc.language.iso.fl_str_mv eng
language eng
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.source.none.fl_str_mv reponame:Repositório Institucional da UFOP
instname:Universidade Federal de Ouro Preto (UFOP)
instacron:UFOP
instname_str Universidade Federal de Ouro Preto (UFOP)
instacron_str UFOP
institution UFOP
reponame_str Repositório Institucional da UFOP
collection Repositório Institucional da UFOP
repository.name.fl_str_mv Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)
repository.mail.fl_str_mv repositorio@ufop.edu.br
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