Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).

Detalhes bibliográficos
Autor(a) principal: Brandão, Geraldo Célio
Data de Publicação: 2013
Outros Autores: Kroon, Erna Geessien, Souza, Danielle E. R., Souza Filho, José Dias de, Oliveira, Alaíde Braga de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFOP
Texto Completo: http://www.repositorio.ufop.br/handle/123456789/3630
https://doi.org/10.3390/molecules18089919
Resumo: The aim of the present work was to carry out a bioguided isolation of antiviral chemical constituents from an ethanol extract of leaves from Arrabidaea pulchra (Cham.) Sandwith (EEAPL) that had shown in vitro activity in a previous screening using DNA and RNA viruses. The activity of EEPAL was evaluated against the DNA viruses Human herpesvirus 1 (HSV-1) and Vaccinia virus Western Reserve (VACV-WR) as well as against the RNA viruses Murine encephalomyocarditis virus (EMCV), and Dengue virus 2 (DENV-2) by the 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) colorimetric assay. Cytotoxicity was determined in LLCMK2 and Vero cells and the Selectivity Indexes (SI) were calculated. The most potent effect was observed against DENV-2 (EC50 46.8 ± 1.6 μg mL−1; SI 2.7). For HSV-1 and VACV-WR EC50 values > 200 μg mL−1 were determined, while no inhibition of the cytopathic effect was observed with EMCV. Bioguided fractionation of EEAPL by partition between immiscible solvents followed by chromatography over a Sephadex LH20 column afforded two arylpropanoid glycosides, verbascoside (AP 1) and caffeoylcalleryanin (AP 2), along with a terpenoid, ursolic acid (AP 3). AP 1 and AP 3 exhibited similar anti-DENV-2 profiles, with SI values of 3.8 and 3.1, respectively, while AP 2 was the most effective anti-DENV-2 constituent, with a SI of 20.0. Our results show that A. pulchra leaves ethanol extract (EEAPL) affords compounds with antiviral activity, mainly against DENV-2.
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spelling Brandão, Geraldo CélioKroon, Erna GeessienSouza, Danielle E. R.Souza Filho, José Dias deOliveira, Alaíde Braga de2014-09-09T18:26:23Z2014-09-09T18:26:23Z2013BRANDÃO, G. C. et al. Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae). Molecules, v. 18, p. 9919-9932, 2013. Disponível em: <http://www.mdpi.com/1420-3049/18/8/9919>. Acesso em: 20 ago. 2014.1420-3049http://www.repositorio.ufop.br/handle/123456789/3630https://doi.org/10.3390/molecules18089919The aim of the present work was to carry out a bioguided isolation of antiviral chemical constituents from an ethanol extract of leaves from Arrabidaea pulchra (Cham.) Sandwith (EEAPL) that had shown in vitro activity in a previous screening using DNA and RNA viruses. The activity of EEPAL was evaluated against the DNA viruses Human herpesvirus 1 (HSV-1) and Vaccinia virus Western Reserve (VACV-WR) as well as against the RNA viruses Murine encephalomyocarditis virus (EMCV), and Dengue virus 2 (DENV-2) by the 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) colorimetric assay. Cytotoxicity was determined in LLCMK2 and Vero cells and the Selectivity Indexes (SI) were calculated. The most potent effect was observed against DENV-2 (EC50 46.8 ± 1.6 μg mL−1; SI 2.7). For HSV-1 and VACV-WR EC50 values > 200 μg mL−1 were determined, while no inhibition of the cytopathic effect was observed with EMCV. Bioguided fractionation of EEAPL by partition between immiscible solvents followed by chromatography over a Sephadex LH20 column afforded two arylpropanoid glycosides, verbascoside (AP 1) and caffeoylcalleryanin (AP 2), along with a terpenoid, ursolic acid (AP 3). AP 1 and AP 3 exhibited similar anti-DENV-2 profiles, with SI values of 3.8 and 3.1, respectively, while AP 2 was the most effective anti-DENV-2 constituent, with a SI of 20.0. Our results show that A. pulchra leaves ethanol extract (EEAPL) affords compounds with antiviral activity, mainly against DENV-2.Antiviral activityDengue virusArrabidaea pulchraVerbascosideCaffeoylcallerianinChemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).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/123456789/3630/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52ORIGINALARTIGO_ChemistryAntiviralActivity.pdfARTIGO_ChemistryAntiviralActivity.pdfapplication/pdf824204http://www.repositorio.ufop.br/bitstream/123456789/3630/1/ARTIGO_ChemistryAntiviralActivity.pdfc45404df4e8233152fff15fbbd27bfabMD51123456789/36302019-04-30 10:01:40.525oai:localhost: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Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-04-30T14:01:40Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false
dc.title.pt_BR.fl_str_mv Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
title Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
spellingShingle Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
Brandão, Geraldo Célio
Antiviral activity
Dengue virus
Arrabidaea pulchra
Verbascoside
Caffeoylcallerianin
title_short Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
title_full Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
title_fullStr Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
title_full_unstemmed Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
title_sort Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae).
author Brandão, Geraldo Célio
author_facet Brandão, Geraldo Célio
Kroon, Erna Geessien
Souza, Danielle E. R.
Souza Filho, José Dias de
Oliveira, Alaíde Braga de
author_role author
author2 Kroon, Erna Geessien
Souza, Danielle E. R.
Souza Filho, José Dias de
Oliveira, Alaíde Braga de
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Brandão, Geraldo Célio
Kroon, Erna Geessien
Souza, Danielle E. R.
Souza Filho, José Dias de
Oliveira, Alaíde Braga de
dc.subject.por.fl_str_mv Antiviral activity
Dengue virus
Arrabidaea pulchra
Verbascoside
Caffeoylcallerianin
topic Antiviral activity
Dengue virus
Arrabidaea pulchra
Verbascoside
Caffeoylcallerianin
description The aim of the present work was to carry out a bioguided isolation of antiviral chemical constituents from an ethanol extract of leaves from Arrabidaea pulchra (Cham.) Sandwith (EEAPL) that had shown in vitro activity in a previous screening using DNA and RNA viruses. The activity of EEPAL was evaluated against the DNA viruses Human herpesvirus 1 (HSV-1) and Vaccinia virus Western Reserve (VACV-WR) as well as against the RNA viruses Murine encephalomyocarditis virus (EMCV), and Dengue virus 2 (DENV-2) by the 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) colorimetric assay. Cytotoxicity was determined in LLCMK2 and Vero cells and the Selectivity Indexes (SI) were calculated. The most potent effect was observed against DENV-2 (EC50 46.8 ± 1.6 μg mL−1; SI 2.7). For HSV-1 and VACV-WR EC50 values > 200 μg mL−1 were determined, while no inhibition of the cytopathic effect was observed with EMCV. Bioguided fractionation of EEAPL by partition between immiscible solvents followed by chromatography over a Sephadex LH20 column afforded two arylpropanoid glycosides, verbascoside (AP 1) and caffeoylcalleryanin (AP 2), along with a terpenoid, ursolic acid (AP 3). AP 1 and AP 3 exhibited similar anti-DENV-2 profiles, with SI values of 3.8 and 3.1, respectively, while AP 2 was the most effective anti-DENV-2 constituent, with a SI of 20.0. Our results show that A. pulchra leaves ethanol extract (EEAPL) affords compounds with antiviral activity, mainly against DENV-2.
publishDate 2013
dc.date.issued.fl_str_mv 2013
dc.date.accessioned.fl_str_mv 2014-09-09T18:26:23Z
dc.date.available.fl_str_mv 2014-09-09T18:26:23Z
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dc.identifier.citation.fl_str_mv BRANDÃO, G. C. et al. Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae). Molecules, v. 18, p. 9919-9932, 2013. Disponível em: <http://www.mdpi.com/1420-3049/18/8/9919>. Acesso em: 20 ago. 2014.
dc.identifier.uri.fl_str_mv http://www.repositorio.ufop.br/handle/123456789/3630
dc.identifier.issn.none.fl_str_mv 1420-3049
dc.identifier.doi.none.fl_str_mv https://doi.org/10.3390/molecules18089919
identifier_str_mv BRANDÃO, G. C. et al. Chemistry and antiviral activity of Arrabidaea pulchra (Bignoniaceae). Molecules, v. 18, p. 9919-9932, 2013. Disponível em: <http://www.mdpi.com/1420-3049/18/8/9919>. Acesso em: 20 ago. 2014.
1420-3049
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https://doi.org/10.3390/molecules18089919
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