Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio )
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1055/a-1264-4302 http://hdl.handle.net/11449/210537 |
Resumo: | Tropane alkaloids are specialized plant metabolites mostly found in the Erythroxylaceae and Solanaceae families. Although tropane alkaloids have a high degree of structural similarity because of the tropane ring, their pharmacological actions are quite distinct. Brazil is one of the main hotspots of Erythroxylum spp. diversity with 123 species (almost 66% of the species catalogued in tropical America). Erythroxylum pungens occurs in the Caatinga, a promising biome that provides bioactive compounds, including tropane alkaloids. As part of our efforts to investigate this species, 15 alkaloids in specimens harvested under different environmental conditions are presented herein. The occurrence of 3-(2-methylbutyryloxy)tropan-6,7-diol in the stem bark of plants growing in their natural habitat, greenhouse controlled conditions, and after a period of water restriction, suggests that it is a potential chemical marker for the species. This alkaloid was evaluated for several parameters in zebrafish ( Danio rerio ) as a model organism. Regarding toxicity, teratogenic effects were observed at 19.5 mu M and the lethal dose for embryos was 18.4 mu M. No mortality was observed in adults, but a behavioral screen showed psychostimulatory action at 116.7 mu M. Overall, the alkaloid was able to cause zebrafish behavioral changes, prompting further investigation of its potential as a new molecule in the treatment of depression-like symptoms. In silico , targets involved in antidepressant pathways were identified by docking. |
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Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio )Erythroxylum pungensErythroxylaceaetropane alkaloidsDanio rerioCyprinidaeCaatingaTropane alkaloids are specialized plant metabolites mostly found in the Erythroxylaceae and Solanaceae families. Although tropane alkaloids have a high degree of structural similarity because of the tropane ring, their pharmacological actions are quite distinct. Brazil is one of the main hotspots of Erythroxylum spp. diversity with 123 species (almost 66% of the species catalogued in tropical America). Erythroxylum pungens occurs in the Caatinga, a promising biome that provides bioactive compounds, including tropane alkaloids. As part of our efforts to investigate this species, 15 alkaloids in specimens harvested under different environmental conditions are presented herein. The occurrence of 3-(2-methylbutyryloxy)tropan-6,7-diol in the stem bark of plants growing in their natural habitat, greenhouse controlled conditions, and after a period of water restriction, suggests that it is a potential chemical marker for the species. This alkaloid was evaluated for several parameters in zebrafish ( Danio rerio ) as a model organism. Regarding toxicity, teratogenic effects were observed at 19.5 mu M and the lethal dose for embryos was 18.4 mu M. No mortality was observed in adults, but a behavioral screen showed psychostimulatory action at 116.7 mu M. Overall, the alkaloid was able to cause zebrafish behavioral changes, prompting further investigation of its potential as a new molecule in the treatment of depression-like symptoms. In silico , targets involved in antidepressant pathways were identified by docking.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)INCT BioNatFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Univ Fed Rio Grande do Norte, Dept Pharm, Gal Gustavo Cordeiro Farias St S-N, BR-59012570 Natal, RN, BrazilUniv Fed Rio Grande do Norte, Dept Physiol & Behav, Natal, RN, BrazilUniv Fed Mato Grosso do Sul, Fac Pharmaceut Sci Food & Nutr, Campo Grande, MS, BrazilUniv Fed Rio Grande do Sul, Fac Pharm, Porto Alegre, RS, BrazilUniv Fed Rio Grande do Sul, Ctr Biotechnol & Dept Bot, Porto Alegre, RS, BrazilSao Paulo State Univ, Chem Inst, Araraquara, SP, BrazilSao Paulo State Univ, Chem Inst, Araraquara, SP, BrazilCNPq: 445149/2014-0INCT BioNat: 465637/2014-0CAPES: 001FAPESP: 2014/50926-0Georg Thieme Verlag KgUniv Fed Rio Grande do NorteUniversidade Federal de Mato Grosso do Sul (UFMS)Univ Fed Rio Grande do SulUniversidade Estadual Paulista (Unesp)Lambert Moreira, Leticia GondimLeite Ferreira, Maria ElisaSantos Reginaldo, Fernanda PriscilaGuimaraes Lourenco, Estela MarianaSilveira Zuanazzi, Jose AngeloBarbosa, Euzebio GuimaraesFerreira, Leandro de SantisFett-Neto, Arthur GermanoCavalheiro, Alberto Jose [UNESP]Luchiari, Ana CarolinaGiordani, Raquel Brandt2021-06-25T19:56:02Z2021-06-25T19:56:02Z2020-11-11info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article177-186http://dx.doi.org/10.1055/a-1264-4302Planta Medica. Stuttgart: Georg Thieme Verlag Kg, v. 87, n. 01/02, p. 177-186, 2021.0032-0943http://hdl.handle.net/11449/21053710.1055/a-1264-4302WOS:000589399300002Web of Sciencereponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengPlanta Medicainfo:eu-repo/semantics/openAccess2021-10-23T20:19:07Zoai:repositorio.unesp.br:11449/210537Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T16:01:58.794861Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
title |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
spellingShingle |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) Lambert Moreira, Leticia Gondim Erythroxylum pungens Erythroxylaceae tropane alkaloids Danio rerio Cyprinidae Caatinga |
title_short |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
title_full |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
title_fullStr |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
title_full_unstemmed |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
title_sort |
Erythroxylum pungens Tropane Alkaloids: GC-MS Analysis and the Bioactive Potential of 3-(2-methylbutyryloxy)tropan-6,7-diol in Zebrafish ( Danio rerio ) |
author |
Lambert Moreira, Leticia Gondim |
author_facet |
Lambert Moreira, Leticia Gondim Leite Ferreira, Maria Elisa Santos Reginaldo, Fernanda Priscila Guimaraes Lourenco, Estela Mariana Silveira Zuanazzi, Jose Angelo Barbosa, Euzebio Guimaraes Ferreira, Leandro de Santis Fett-Neto, Arthur Germano Cavalheiro, Alberto Jose [UNESP] Luchiari, Ana Carolina Giordani, Raquel Brandt |
author_role |
author |
author2 |
Leite Ferreira, Maria Elisa Santos Reginaldo, Fernanda Priscila Guimaraes Lourenco, Estela Mariana Silveira Zuanazzi, Jose Angelo Barbosa, Euzebio Guimaraes Ferreira, Leandro de Santis Fett-Neto, Arthur Germano Cavalheiro, Alberto Jose [UNESP] Luchiari, Ana Carolina Giordani, Raquel Brandt |
author2_role |
author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Univ Fed Rio Grande do Norte Universidade Federal de Mato Grosso do Sul (UFMS) Univ Fed Rio Grande do Sul Universidade Estadual Paulista (Unesp) |
dc.contributor.author.fl_str_mv |
Lambert Moreira, Leticia Gondim Leite Ferreira, Maria Elisa Santos Reginaldo, Fernanda Priscila Guimaraes Lourenco, Estela Mariana Silveira Zuanazzi, Jose Angelo Barbosa, Euzebio Guimaraes Ferreira, Leandro de Santis Fett-Neto, Arthur Germano Cavalheiro, Alberto Jose [UNESP] Luchiari, Ana Carolina Giordani, Raquel Brandt |
dc.subject.por.fl_str_mv |
Erythroxylum pungens Erythroxylaceae tropane alkaloids Danio rerio Cyprinidae Caatinga |
topic |
Erythroxylum pungens Erythroxylaceae tropane alkaloids Danio rerio Cyprinidae Caatinga |
description |
Tropane alkaloids are specialized plant metabolites mostly found in the Erythroxylaceae and Solanaceae families. Although tropane alkaloids have a high degree of structural similarity because of the tropane ring, their pharmacological actions are quite distinct. Brazil is one of the main hotspots of Erythroxylum spp. diversity with 123 species (almost 66% of the species catalogued in tropical America). Erythroxylum pungens occurs in the Caatinga, a promising biome that provides bioactive compounds, including tropane alkaloids. As part of our efforts to investigate this species, 15 alkaloids in specimens harvested under different environmental conditions are presented herein. The occurrence of 3-(2-methylbutyryloxy)tropan-6,7-diol in the stem bark of plants growing in their natural habitat, greenhouse controlled conditions, and after a period of water restriction, suggests that it is a potential chemical marker for the species. This alkaloid was evaluated for several parameters in zebrafish ( Danio rerio ) as a model organism. Regarding toxicity, teratogenic effects were observed at 19.5 mu M and the lethal dose for embryos was 18.4 mu M. No mortality was observed in adults, but a behavioral screen showed psychostimulatory action at 116.7 mu M. Overall, the alkaloid was able to cause zebrafish behavioral changes, prompting further investigation of its potential as a new molecule in the treatment of depression-like symptoms. In silico , targets involved in antidepressant pathways were identified by docking. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-11-11 2021-06-25T19:56:02Z 2021-06-25T19:56:02Z |
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 |
http://dx.doi.org/10.1055/a-1264-4302 Planta Medica. Stuttgart: Georg Thieme Verlag Kg, v. 87, n. 01/02, p. 177-186, 2021. 0032-0943 http://hdl.handle.net/11449/210537 10.1055/a-1264-4302 WOS:000589399300002 |
url |
http://dx.doi.org/10.1055/a-1264-4302 http://hdl.handle.net/11449/210537 |
identifier_str_mv |
Planta Medica. Stuttgart: Georg Thieme Verlag Kg, v. 87, n. 01/02, p. 177-186, 2021. 0032-0943 10.1055/a-1264-4302 WOS:000589399300002 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Planta Medica |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
177-186 |
dc.publisher.none.fl_str_mv |
Georg Thieme Verlag Kg |
publisher.none.fl_str_mv |
Georg Thieme Verlag Kg |
dc.source.none.fl_str_mv |
Web of Science reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128596066172928 |