Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501002 |
Resumo: | Electrochemical procedures have emerged as a powerful tool for the synthesis of complex organic molecules including transformation of natural products. In this study, the electrosynthesis of biseugenol in MeOH afforded one new oxidized derivative, which was characterized as methoxyl-oxo-biseugenol (MOB) by nuclear magnetic resonance (NMR) and electrospray ionization-high resolution mass spectrometry (ESI-HRMS) analysis. Since biseugenol was previously described as a cytotoxic natural product, MOB was also tested against tumoral cells B16F10-Nex2 (murine metastatic melanoma) and SKMEL-25 (human metastatic melanoma) as well as against non-tumoral cells MØ Raw 264.7 (murine macrophage immortalized) and HUVEC (human umbilical endothelium). As results, MOB showed inhibitory concentration that affects 50% of cells (IC50) values of 9.5 ± 1.6 mg mL-1(B16F10Nex2), 13.2 ± 2.5 mg mL-1 (SKMEL-25), 19.9 ± 3.5 mg mL-1 (MØ Raw 264.7) and 36.3 ± 7.4 mg mL-1 (HUVEC). Therefore, selectivity index (SI) values of MOB to tumoral cells B16F10Nex2 and SKMEL-25 were calculated as 2.1 and 2.8, respectively, higher than biseugenol (1.4 and 1.7, respectively). Based on these results, the superior cytotoxic activity of MOB in comparison to biseugenol could be associated, at least in part, to the presence of a non-aromatic ring and a conjugated carbonyl system instead of a phenol moiety. |
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Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenolbiseugenolnatural productselectrosynthesiscytotoxic activityElectrochemical procedures have emerged as a powerful tool for the synthesis of complex organic molecules including transformation of natural products. In this study, the electrosynthesis of biseugenol in MeOH afforded one new oxidized derivative, which was characterized as methoxyl-oxo-biseugenol (MOB) by nuclear magnetic resonance (NMR) and electrospray ionization-high resolution mass spectrometry (ESI-HRMS) analysis. Since biseugenol was previously described as a cytotoxic natural product, MOB was also tested against tumoral cells B16F10-Nex2 (murine metastatic melanoma) and SKMEL-25 (human metastatic melanoma) as well as against non-tumoral cells MØ Raw 264.7 (murine macrophage immortalized) and HUVEC (human umbilical endothelium). As results, MOB showed inhibitory concentration that affects 50% of cells (IC50) values of 9.5 ± 1.6 mg mL-1(B16F10Nex2), 13.2 ± 2.5 mg mL-1 (SKMEL-25), 19.9 ± 3.5 mg mL-1 (MØ Raw 264.7) and 36.3 ± 7.4 mg mL-1 (HUVEC). Therefore, selectivity index (SI) values of MOB to tumoral cells B16F10Nex2 and SKMEL-25 were calculated as 2.1 and 2.8, respectively, higher than biseugenol (1.4 and 1.7, respectively). Based on these results, the superior cytotoxic activity of MOB in comparison to biseugenol could be associated, at least in part, to the presence of a non-aromatic ring and a conjugated carbonyl system instead of a phenol moiety.Sociedade Brasileira de Química2021-05-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501002Journal of the Brazilian Chemical Society v.32 n.5 2021reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20210002info:eu-repo/semantics/openAccessSilva,Flavia T. daGomes,Kaio S.Machado,Fabricio C.Loureiro,Leticia L.Travassos,Luiz R.Martins,Tereza S.Lago,João Henrique G.Camilo,Fernanda F.eng2021-04-28T00:00:00Zoai:scielo:S0103-50532021000501002Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2021-04-28T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
title |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
spellingShingle |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol Silva,Flavia T. da biseugenol natural products electrosynthesis cytotoxic activity |
title_short |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
title_full |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
title_fullStr |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
title_full_unstemmed |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
title_sort |
Electrochemical Preparation and Evaluation of Cytotoxic Activity of Methoxyl-oxo-biseugenol, a New Oxidized Derivative of Biseugenol |
author |
Silva,Flavia T. da |
author_facet |
Silva,Flavia T. da Gomes,Kaio S. Machado,Fabricio C. Loureiro,Leticia L. Travassos,Luiz R. Martins,Tereza S. Lago,João Henrique G. Camilo,Fernanda F. |
author_role |
author |
author2 |
Gomes,Kaio S. Machado,Fabricio C. Loureiro,Leticia L. Travassos,Luiz R. Martins,Tereza S. Lago,João Henrique G. Camilo,Fernanda F. |
author2_role |
author author author author author author author |
dc.contributor.author.fl_str_mv |
Silva,Flavia T. da Gomes,Kaio S. Machado,Fabricio C. Loureiro,Leticia L. Travassos,Luiz R. Martins,Tereza S. Lago,João Henrique G. Camilo,Fernanda F. |
dc.subject.por.fl_str_mv |
biseugenol natural products electrosynthesis cytotoxic activity |
topic |
biseugenol natural products electrosynthesis cytotoxic activity |
description |
Electrochemical procedures have emerged as a powerful tool for the synthesis of complex organic molecules including transformation of natural products. In this study, the electrosynthesis of biseugenol in MeOH afforded one new oxidized derivative, which was characterized as methoxyl-oxo-biseugenol (MOB) by nuclear magnetic resonance (NMR) and electrospray ionization-high resolution mass spectrometry (ESI-HRMS) analysis. Since biseugenol was previously described as a cytotoxic natural product, MOB was also tested against tumoral cells B16F10-Nex2 (murine metastatic melanoma) and SKMEL-25 (human metastatic melanoma) as well as against non-tumoral cells MØ Raw 264.7 (murine macrophage immortalized) and HUVEC (human umbilical endothelium). As results, MOB showed inhibitory concentration that affects 50% of cells (IC50) values of 9.5 ± 1.6 mg mL-1(B16F10Nex2), 13.2 ± 2.5 mg mL-1 (SKMEL-25), 19.9 ± 3.5 mg mL-1 (MØ Raw 264.7) and 36.3 ± 7.4 mg mL-1 (HUVEC). Therefore, selectivity index (SI) values of MOB to tumoral cells B16F10Nex2 and SKMEL-25 were calculated as 2.1 and 2.8, respectively, higher than biseugenol (1.4 and 1.7, respectively). Based on these results, the superior cytotoxic activity of MOB in comparison to biseugenol could be associated, at least in part, to the presence of a non-aromatic ring and a conjugated carbonyl system instead of a phenol moiety. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-05-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501002 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532021000501002 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20210002 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.32 n.5 2021 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318184020312064 |