Chemical and biological evaluation of amazonian medicinal plant vouacapoua americana aubl

Detalhes bibliográficos
Autor(a) principal: Çiçek, Serhat Sezai
Data de Publicação: 2022
Outros Autores: Barbosa, Anna Laís Pfeifer, Wenzel-Storjohann, Arlette, Segovia, Jorge Federico Orellana, Bezerra, Roberto Messias, Sönnichsen, Frank, Zidorn, Christian, Kanzaki, Isamu, Tasdemir, Deniz
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.
id UNB_b68dd146956248b75ce5cd7b6d1ddd43
oai_identifier_str oai:repositorio.unb.br:10482/48026
network_acronym_str UNB
network_name_str Repositório Institucional da UnB
repository_id_str
spelling 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
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.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:Repositório Institucional da UnB
instname:Universidade de Brasília (UnB)
instacron:UNB
instname_str Universidade de Brasília (UnB)
instacron_str UNB
institution UNB
reponame_str Repositório Institucional da UnB
collection Repositório Institucional da UnB
repository.name.fl_str_mv Repositório Institucional da UnB - Universidade de Brasília (UnB)
repository.mail.fl_str_mv repositorio@unb.br
_version_ 1814508271902392320