Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UnB |
Texto Completo: | http://repositorio2.unb.br/jspui/handle/10482/48026 https://doi.org/10.3390/plants12010099 https://orcid.org/0000-0002-3038-8523 https://orcid.org/0000-0002-4539-3755 https://orcid.org/0000-0001-8956-9874 https://orcid.org/0000-0002-7841-6271 |
Resumo: | Vouacapoua americana (Fabaceae) is an economically important tree in the Amazon region and used for its highly resistant heartwood as well as for medicinal purposes. Despite its frequent use, phytochemical investigations have been limited and rather focused on ecological properties than on its pharmacological potential. In this study, we investigated the phytochemistry and bioactivity of V. americana stem bark extract and its constituents to identify eventual lead structures for further drug development. Applying hydrodistillation and subsequent GC-MS analysis, we investigated the composition of the essential oil and identified the 15 most abundant components. Moreover, the diterpenoids deacetylchagresnone (1), cassa-13(14),15-dien-oic acid (2), isoneocaesalpin H (3), (+)-vouacapenic acid (4), and (+)-methyl vouacapenate (5) were isolated from the stem bark, with compounds 2 and 4 showing pronounced effects on Methicillin-resistant Staphylococcus aureus and Enterococcus faecium, respectively. During the structure elucidation of deacetylchagresnone (1), which was isolated from a natural source for the first time, we detected inconsistencies regarding the configuration of the cyclopropane ring. Thus, the structure was revised for both deacetylchagresnone (1) and the previously isolated chagresnone. Following our works on Copaifera reticulata and Vatairea guianensis, the results of this study further contribute to the knowledge of Amazonian medicinal plants. |
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Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aublAntimicrobianoAcapuPlantas medicinaisVouacapoua americana (Fabaceae) is an economically important tree in the Amazon region and used for its highly resistant heartwood as well as for medicinal purposes. Despite its frequent use, phytochemical investigations have been limited and rather focused on ecological properties than on its pharmacological potential. In this study, we investigated the phytochemistry and bioactivity of V. americana stem bark extract and its constituents to identify eventual lead structures for further drug development. Applying hydrodistillation and subsequent GC-MS analysis, we investigated the composition of the essential oil and identified the 15 most abundant components. Moreover, the diterpenoids deacetylchagresnone (1), cassa-13(14),15-dien-oic acid (2), isoneocaesalpin H (3), (+)-vouacapenic acid (4), and (+)-methyl vouacapenate (5) were isolated from the stem bark, with compounds 2 and 4 showing pronounced effects on Methicillin-resistant Staphylococcus aureus and Enterococcus faecium, respectively. During the structure elucidation of deacetylchagresnone (1), which was isolated from a natural source for the first time, we detected inconsistencies regarding the configuration of the cyclopropane ring. Thus, the structure was revised for both deacetylchagresnone (1) and the previously isolated chagresnone. Following our works on Copaifera reticulata and Vatairea guianensis, the results of this study further contribute to the knowledge of Amazonian medicinal plants.Faculdade de Ciências da Saúde (FS)Departamento de Farmácia (FS FAR)MDPIKiel University, Department of Pharmaceutical BiologyKiel University, Department of Pharmaceutical BiologyGEOMAR Helmholtz Centre for Ocean Research Kiel, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products ChemistryBrazilian Agricultural Research Corporation, Ecoregional Research UnitFederal University of Amapá, Laboratory of Bioprospection and Atomic AbsorptionKiel University, Otto Diels Institute for Organic ChemistryKiel University, Department of Pharmaceutical BiologyUniversity of Brasilia, Darcy Ribeiro Campus, Laboratory of BioprospectionGEOMAR Helmholtz Centre for Ocean Research Kiel, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products ChemistryKiel University, Faculty of Mathematics and Natural SciencesÇiçek, Serhat SezaiBarbosa, Anna Laís PfeiferWenzel-Storjohann, ArletteSegovia, Jorge Federico OrellanaBezerra, Roberto MessiasSönnichsen, FrankZidorn, ChristianKanzaki, IsamuTasdemir, Deniz2024-03-25T12:10:37Z2024-03-25T12:10:37Z2022-12-25info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfÇIÇEK, Serhat Seai et al. Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl. Plants, [S.l.], v. 12, n. 99, 25 dez 2022. Disponível em: https://doi.org/10.3390/plants12010099. Acesso em: 20 mar 2024.http://repositorio2.unb.br/jspui/handle/10482/48026https://doi.org/10.3390/plants12010099https://orcid.org/0000-0002-3038-8523https://orcid.org/0000-0002-4539-3755https://orcid.org/0000-0001-8956-9874https://orcid.org/0000-0002-7841-6271eng© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UnBinstname:Universidade de Brasília (UnB)instacron:UNB2024-03-25T12:19:18Zoai:repositorio.unb.br:10482/48026Repositório InstitucionalPUBhttps://repositorio.unb.br/oai/requestrepositorio@unb.bropendoar:2024-03-25T12:19:18Repositório Institucional da UnB - Universidade de Brasília (UnB)false |
dc.title.none.fl_str_mv |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
title |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
spellingShingle |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl Çiçek, Serhat Sezai Antimicrobiano Acapu Plantas medicinais |
title_short |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
title_full |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
title_fullStr |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
title_full_unstemmed |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
title_sort |
Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl |
author |
Çiçek, Serhat Sezai |
author_facet |
Çiçek, Serhat Sezai Barbosa, Anna Laís Pfeifer Wenzel-Storjohann, Arlette Segovia, Jorge Federico Orellana Bezerra, Roberto Messias Sönnichsen, Frank Zidorn, Christian Kanzaki, Isamu Tasdemir, Deniz |
author_role |
author |
author2 |
Barbosa, Anna Laís Pfeifer Wenzel-Storjohann, Arlette Segovia, Jorge Federico Orellana Bezerra, Roberto Messias Sönnichsen, Frank Zidorn, Christian Kanzaki, Isamu Tasdemir, Deniz |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
Kiel University, Department of Pharmaceutical Biology Kiel University, Department of Pharmaceutical Biology GEOMAR Helmholtz Centre for Ocean Research Kiel, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry Brazilian Agricultural Research Corporation, Ecoregional Research Unit Federal University of Amapá, Laboratory of Bioprospection and Atomic Absorption Kiel University, Otto Diels Institute for Organic Chemistry Kiel University, Department of Pharmaceutical Biology University of Brasilia, Darcy Ribeiro Campus, Laboratory of Bioprospection GEOMAR Helmholtz Centre for Ocean Research Kiel, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry Kiel University, Faculty of Mathematics and Natural Sciences |
dc.contributor.author.fl_str_mv |
Çiçek, Serhat Sezai Barbosa, Anna Laís Pfeifer Wenzel-Storjohann, Arlette Segovia, Jorge Federico Orellana Bezerra, Roberto Messias Sönnichsen, Frank Zidorn, Christian Kanzaki, Isamu Tasdemir, Deniz |
dc.subject.por.fl_str_mv |
Antimicrobiano Acapu Plantas medicinais |
topic |
Antimicrobiano Acapu Plantas medicinais |
description |
Vouacapoua americana (Fabaceae) is an economically important tree in the Amazon region and used for its highly resistant heartwood as well as for medicinal purposes. Despite its frequent use, phytochemical investigations have been limited and rather focused on ecological properties than on its pharmacological potential. In this study, we investigated the phytochemistry and bioactivity of V. americana stem bark extract and its constituents to identify eventual lead structures for further drug development. Applying hydrodistillation and subsequent GC-MS analysis, we investigated the composition of the essential oil and identified the 15 most abundant components. Moreover, the diterpenoids deacetylchagresnone (1), cassa-13(14),15-dien-oic acid (2), isoneocaesalpin H (3), (+)-vouacapenic acid (4), and (+)-methyl vouacapenate (5) were isolated from the stem bark, with compounds 2 and 4 showing pronounced effects on Methicillin-resistant Staphylococcus aureus and Enterococcus faecium, respectively. During the structure elucidation of deacetylchagresnone (1), which was isolated from a natural source for the first time, we detected inconsistencies regarding the configuration of the cyclopropane ring. Thus, the structure was revised for both deacetylchagresnone (1) and the previously isolated chagresnone. Following our works on Copaifera reticulata and Vatairea guianensis, the results of this study further contribute to the knowledge of Amazonian medicinal plants. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-12-25 2024-03-25T12:10:37Z 2024-03-25T12:10:37Z |
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 |
ÇIÇEK, Serhat Seai et al. Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl. Plants, [S.l.], v. 12, n. 99, 25 dez 2022. Disponível em: https://doi.org/10.3390/plants12010099. Acesso em: 20 mar 2024. http://repositorio2.unb.br/jspui/handle/10482/48026 https://doi.org/10.3390/plants12010099 https://orcid.org/0000-0002-3038-8523 https://orcid.org/0000-0002-4539-3755 https://orcid.org/0000-0001-8956-9874 https://orcid.org/0000-0002-7841-6271 |
identifier_str_mv |
ÇIÇEK, Serhat Seai et al. Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl. Plants, [S.l.], v. 12, n. 99, 25 dez 2022. Disponível em: https://doi.org/10.3390/plants12010099. Acesso em: 20 mar 2024. |
url |
http://repositorio2.unb.br/jspui/handle/10482/48026 https://doi.org/10.3390/plants12010099 https://orcid.org/0000-0002-3038-8523 https://orcid.org/0000-0002-4539-3755 https://orcid.org/0000-0001-8956-9874 https://orcid.org/0000-0002-7841-6271 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
MDPI |
publisher.none.fl_str_mv |
MDPI |
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reponame:Repositório Institucional da UnB instname:Universidade de Brasília (UnB) instacron:UNB |
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Universidade de Brasília (UnB) |
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Repositório Institucional da UnB |
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Repositório Institucional da UnB - Universidade de Brasília (UnB) |
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