New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | , , , , , , |
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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Sousa, Grasiely Faria deDuarte, Lucienir PainsAlcântara, Antônio Flávio de CarvalhoSilva, Grácia Divina de FátimaVieira Filho, Sidney AugustoMiranda, Roqueline Rodrigues Silva deOliveira, Djalma Menezes deTakahashi, Jacqueline Aparecida2014-11-14T18:05:21Z2014-11-14T18:05:21Z2012SOUSA, 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/molecules171113439Leaves 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.Maytenus robustaPentacyclic triterpenesAcetylcholinesterase inhibitory activityNew triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleThis 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/openAccessengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://www.repositorio.ufop.br/bitstream/123456789/3853/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINALARTIGO_NewTriterpenesMaytenus.pdfARTIGO_NewTriterpenesMaytenus.pdfapplication/pdf237995http://www.repositorio.ufop.br/bitstream/123456789/3853/1/ARTIGO_NewTriterpenesMaytenus.pdf2e8b8597888a72b6725d3095f57de12cMD51123456789/38532019-05-09 13:50:12.487oai:localhost:123456789/3853Tk9URTogUExBQ0UgWU9VUiBPV04gTElDRU5TRSBIRVJFClRoaXMgc2FtcGxlIGxpY2Vuc2UgaXMgcHJvdmlkZWQgZm9yIGluZm9ybWF0aW9uYWwgcHVycG9zZXMgb25seS4KCk5PTi1FWENMVVNJVkUgRElTVFJJQlVUSU9OIExJQ0VOU0UKCkJ5IHNpZ25pbmcgYW5kIHN1Ym1pdHRpbmcgdGhpcyBsaWNlbnNlLCB5b3UgKHRoZSBhdXRob3Iocykgb3IgY29weXJpZ2h0Cm93bmVyKSBncmFudHMgdG8gRFNwYWNlIFVuaXZlcnNpdHkgKERTVSkgdGhlIG5vbi1leGNsdXNpdmUgcmlnaHQgdG8gcmVwcm9kdWNlLAp0cmFuc2xhdGUgKGFzIGRlZmluZWQgYmVsb3cpLCBhbmQvb3IgZGlzdHJpYnV0ZSB5b3VyIHN1Ym1pc3Npb24gKGluY2x1ZGluZwp0aGUgYWJzdHJhY3QpIHdvcmxkd2lkZSBpbiBwcmludCBhbmQgZWxlY3Ryb25pYyBmb3JtYXQgYW5kIGluIGFueSBtZWRpdW0sCmluY2x1ZGluZyBidXQgbm90IGxpbWl0ZWQgdG8gYXVkaW8gb3IgdmlkZW8uCgpZb3UgYWdyZWUgdGhhdCBEU1UgbWF5LCB3aXRob3V0IGNoYW5naW5nIHRoZSBjb250ZW50LCB0cmFuc2xhdGUgdGhlCnN1Ym1pc3Npb24gdG8gYW55IG1lZGl1bSBvciBmb3JtYXQgZm9yIHRoZSBwdXJwb3NlIG9mIHByZXNlcnZhdGlvbi4KCllvdSBhbHNvIGFncmVlIHRoYXQgRFNVIG1heSBrZWVwIG1vcmUgdGhhbiBvbmUgY29weSBvZiB0aGlzIHN1Ym1pc3Npb24gZm9yCnB1cnBvc2VzIG9mIHNlY3VyaXR5LCBiYWNrLXVwIGFuZCBwcmVzZXJ2YXRpb24uCgpZb3UgcmVwcmVzZW50IHRoYXQgdGhlIHN1Ym1pc3Npb24gaXMgeW91ciBvcmlnaW5hbCB3b3JrLCBhbmQgdGhhdCB5b3UgaGF2ZQp0aGUgcmlnaHQgdG8gZ3JhbnQgdGhlIHJpZ2h0cyBjb250YWluZWQgaW4gdGhpcyBsaWNlbnNlLiBZb3UgYWxzbyByZXByZXNlbnQKdGhhdCB5b3VyIHN1Ym1pc3Npb24gZG9lcyBub3QsIHRvIHRoZSBiZXN0IG9mIHlvdXIga25vd2xlZGdlLCBpbmZyaW5nZSB1cG9uCmFueW9uZSdzIGNvcHlyaWdodC4KCklmIHRoZSBzdWJtaXNzaW9uIGNvbnRhaW5zIG1hdGVyaWFsIGZvciB3aGljaCB5b3UgZG8gbm90IGhvbGQgY29weXJpZ2h0LAp5b3UgcmVwcmVzZW50IHRoYXQgeW91IGhhdmUgb2J0YWluZWQgdGhlIHVucmVzdHJpY3RlZCBwZXJtaXNzaW9uIG9mIHRoZQpjb3B5cmlnaHQgb3duZXIgdG8gZ3JhbnQgRFNVIHRoZSByaWdodHMgcmVxdWlyZWQgYnkgdGhpcyBsaWNlbnNlLCBhbmQgdGhhdApzdWNoIHRoaXJkLXBhcnR5IG93bmVkIG1hdGVyaWFsIGlzIGNsZWFybHkgaWRlbnRpZmllZCBhbmQgYWNrbm93bGVkZ2VkCndpdGhpbiB0aGUgdGV4dCBvciBjb250ZW50IG9mIHRoZSBzdWJtaXNzaW9uLgoKSUYgVEhFIFNVQk1JU1NJT04gSVMgQkFTRUQgVVBPTiBXT1JLIFRIQVQgSEFTIEJFRU4gU1BPTlNPUkVEIE9SIFNVUFBPUlRFRApCWSBBTiBBR0VOQ1kgT1IgT1JHQU5JWkFUSU9OIE9USEVSIFRIQU4gRFNVLCBZT1UgUkVQUkVTRU5UIFRIQVQgWU9VIEhBVkUKRlVMRklMTEVEIEFOWSBSSUdIVCBPRiBSRVZJRVcgT1IgT1RIRVIgT0JMSUdBVElPTlMgUkVRVUlSRUQgQlkgU1VDSApDT05UUkFDVCBPUiBBR1JFRU1FTlQuCgpEU1Ugd2lsbCBjbGVhcmx5IGlkZW50aWZ5IHlvdXIgbmFtZShzKSBhcyB0aGUgYXV0aG9yKHMpIG9yIG93bmVyKHMpIG9mIHRoZQpzdWJtaXNzaW9uLCBhbmQgd2lsbCBub3QgbWFrZSBhbnkgYWx0ZXJhdGlvbiwgb3RoZXIgdGhhbiBhcyBhbGxvd2VkIGJ5IHRoaXMKbGljZW5zZSwgdG8geW91ciBzdWJtaXNzaW9uLgo=Repositório 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.pt_BR.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.issued.fl_str_mv |
2012 |
dc.date.accessioned.fl_str_mv |
2014-11-14T18:05:21Z |
dc.date.available.fl_str_mv |
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.citation.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. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/3853 |
dc.identifier.issn.none.fl_str_mv |
1420-3049 |
dc.identifier.doi.none.fl_str_mv |
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 |
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eng |
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