16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia

Detalhes bibliográficos
Autor(a) principal: Garcez, Walmir Silva
Data de Publicação: 2008
Outros Autores: Garcez, Fernanda Rodrigues, Soares, Luzinátia Ramos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFMS
Texto Completo: https://repositorio.ufms.br/handle/123456789/158
http://dx.doi.org/10.1590/S0103-50532008000600004
Resumo: Two new seco- and di-seco-pregnanes, 2α,3β-dihydroxy-16,17-seco-pregn-17-ene-16-oic acid methyl ester 2β,19-hemiketal (1) and 2,3:16,17-di-seco-pregn-17-ene-3-oic acid-16-oic acid methyl ester-19-hydroxy-2-carboxylic acid-2,19-lactone (2), have been obtained from the trunk bark of Guarea guidonia. Their structures have been established by a combination of 1D- and 2D-NMR spectroscopic techniques and MS data. The unique seco- and di-seco-pregnane carbocyclic skeletal types as found in compounds 1 and 2 are being reported in the Meliaceae for the first time as well as the occurrence of pregnanes in the genus Guarea.
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spelling 2011-07-21T14:18:46Z2021-09-30T19:56:46Z2008GARCEZ, Walmir Silva; GARCEZ, Fernanda Rodrigues; SOARES, Luzinátia Ramos. 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia. J. Braz. Chem. Soc., São Paulo, v. 19, n. 6, 2008 . Available from <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000600004&lng=en&nrm=iso>. access on 21 July 2011. http://dx.doi.org/10.1590/S0103-50532008000600004.https://repositorio.ufms.br/handle/123456789/158http://dx.doi.org/10.1590/S0103-50532008000600004Two new seco- and di-seco-pregnanes, 2α,3β-dihydroxy-16,17-seco-pregn-17-ene-16-oic acid methyl ester 2β,19-hemiketal (1) and 2,3:16,17-di-seco-pregn-17-ene-3-oic acid-16-oic acid methyl ester-19-hydroxy-2-carboxylic acid-2,19-lactone (2), have been obtained from the trunk bark of Guarea guidonia. Their structures have been established by a combination of 1D- and 2D-NMR spectroscopic techniques and MS data. The unique seco- and di-seco-pregnane carbocyclic skeletal types as found in compounds 1 and 2 are being reported in the Meliaceae for the first time as well as the occurrence of pregnanes in the genus Guarea.Dois novos seco- e di-seco-pregnanos, 2α,3β-diidrσxi-2β,19-hemicetal-16,17-seco-pregn-17-en-16-oato de metila (1) e ácido 2,3:16,17-di-seco-pregn-17-en-3-óico-16-oato de metila-19-hidróxi-2-carboxílico-2,19-lactona (2), foram isolados da casca do caule de Guarea guidonia. Suas estruturas foram determinadas com base em dados espectrais, particularmente RMN uni- e bidimensionais e massas. Os esqueletos pregnânicos incomuns seco- e di-seco destes compostos estão sendo relatados pela primeira vez em Meliaceae, assim como a ocorrência de pregnanos no gênero Guarea.engJournal of the Brazilian Chemical SocietyGuarea trichiloidesMeliaceaeSeco-pregnaneDi-seco-pregnane16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidoniainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleGarcez, Walmir SilvaGarcez, Fernanda RodriguesSoares, Luzinátia Ramosinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMSinstname:Universidade Federal de Mato Grosso do Sul (UFMS)instacron:UFMSTHUMBNAIL16 17 Seco.pdf.jpg16 17 Seco.pdf.jpgGenerated Thumbnailimage/jpeg1630https://repositorio.ufms.br/bitstream/123456789/158/4/16%2017%20Seco.pdf.jpg32f26851949c93949e0fab060382a14bMD54ORIGINAL16 17 Seco.pdf16 17 Seco.pdfapplication/pdf2152553https://repositorio.ufms.br/bitstream/123456789/158/1/16%2017%20Seco.pdf4c5d20fb0d3bab865445febbb4dede56MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://repositorio.ufms.br/bitstream/123456789/158/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52TEXT16 17 Seco.pdf.txt16 17 Seco.pdf.txtExtracted texttext/plain25514https://repositorio.ufms.br/bitstream/123456789/158/3/16%2017%20Seco.pdf.txte778fa3d2691ab8d8fe3122427c967c2MD53123456789/1582021-09-30 15:56:46.772oai:repositorio.ufms.br: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Repositório InstitucionalPUBhttps://repositorio.ufms.br/oai/requestri.prograd@ufms.bropendoar:21242021-09-30T19:56:46Repositório Institucional da UFMS - Universidade Federal de Mato Grosso do Sul (UFMS)false
dc.title.pt_BR.fl_str_mv 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
title 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
spellingShingle 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
Garcez, Walmir Silva
Guarea trichiloides
Meliaceae
Seco-pregnane
Di-seco-pregnane
title_short 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
title_full 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
title_fullStr 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
title_full_unstemmed 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
title_sort 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia
author Garcez, Walmir Silva
author_facet Garcez, Walmir Silva
Garcez, Fernanda Rodrigues
Soares, Luzinátia Ramos
author_role author
author2 Garcez, Fernanda Rodrigues
Soares, Luzinátia Ramos
author2_role author
author
dc.contributor.author.fl_str_mv Garcez, Walmir Silva
Garcez, Fernanda Rodrigues
Soares, Luzinátia Ramos
dc.subject.por.fl_str_mv Guarea trichiloides
Meliaceae
Seco-pregnane
Di-seco-pregnane
topic Guarea trichiloides
Meliaceae
Seco-pregnane
Di-seco-pregnane
description Two new seco- and di-seco-pregnanes, 2α,3β-dihydroxy-16,17-seco-pregn-17-ene-16-oic acid methyl ester 2β,19-hemiketal (1) and 2,3:16,17-di-seco-pregn-17-ene-3-oic acid-16-oic acid methyl ester-19-hydroxy-2-carboxylic acid-2,19-lactone (2), have been obtained from the trunk bark of Guarea guidonia. Their structures have been established by a combination of 1D- and 2D-NMR spectroscopic techniques and MS data. The unique seco- and di-seco-pregnane carbocyclic skeletal types as found in compounds 1 and 2 are being reported in the Meliaceae for the first time as well as the occurrence of pregnanes in the genus Guarea.
publishDate 2008
dc.date.issued.fl_str_mv 2008
dc.date.accessioned.fl_str_mv 2011-07-21T14:18:46Z
dc.date.available.fl_str_mv 2021-09-30T19:56:46Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.citation.fl_str_mv GARCEZ, Walmir Silva; GARCEZ, Fernanda Rodrigues; SOARES, Luzinátia Ramos. 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia. J. Braz. Chem. Soc., São Paulo, v. 19, n. 6, 2008 . Available from <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000600004&lng=en&nrm=iso>. access on 21 July 2011. http://dx.doi.org/10.1590/S0103-50532008000600004.
dc.identifier.uri.fl_str_mv https://repositorio.ufms.br/handle/123456789/158
dc.identifier.doi.none.fl_str_mv http://dx.doi.org/10.1590/S0103-50532008000600004
identifier_str_mv GARCEZ, Walmir Silva; GARCEZ, Fernanda Rodrigues; SOARES, Luzinátia Ramos. 16,17-Seco- and 2,3:16,17-di-Seco-pregnanes from Guarea guidonia. J. Braz. Chem. Soc., São Paulo, v. 19, n. 6, 2008 . Available from <http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000600004&lng=en&nrm=iso>. access on 21 July 2011. http://dx.doi.org/10.1590/S0103-50532008000600004.
url https://repositorio.ufms.br/handle/123456789/158
http://dx.doi.org/10.1590/S0103-50532008000600004
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dc.publisher.none.fl_str_mv Journal of the Brazilian Chemical Society
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