Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth.
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFOP |
Texto Completo: | http://www.repositorio.ufop.br/handle/123456789/9933 |
Resumo: | The triterpene lupeol (1) and some of its esters are secondary metabolites produced by species of Celastraceae family, which have being associated with cytotoxic activity. We report herein the isolation of 1, the semi-synthesis of eight lupeol esters and the evaluation of their in vitro activity against nine strains of cancer cells. The reaction of carboxylic acids with 1 and DIC/DMAP was used to obtain lupeol stearate (2), lupeol palmitate (3) lupeol miristate (4), and the new esters lupeol laurate (5), lupeol caprate (6), lupeol caprilate (7), lupeol caproate (8) and lupeol 3’,4’-dimethoxybenzoate (9), with high yields. Compounds 1-9 were identified using FT-IR, 1H, 13C-NMR, CHN analysis and XRD data and were tested in vitro for proliferation of human cancer cell activity. In these assays, lupeol was inactive (GI50> 250μg/ mL) while lupeol esters 2 -4 and 7 - 9 showed a cytostatic effect. The XRD method was a suitable tool to determine the structure of lupeol and its esters in solid state. Compound 3 showed a selective growth inhibition effect on erythromyeloblastoid leukemia (K-562) cells in a concentration-dependent way. Lupeol esters 4 and 9 showed a selective cytostatic effect with low GI50 values representing promising prototypes for the development of new anticancer drugs. |
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Silva, Aline Teixeira MacielMagalhães, Cássia GonçalvesDuarte, Lucienir PainsMussel, Wagner da NovaRuiz, Ana Lucia Tasca GoisShiozawa, LarissaCarvalho, João Ernesto deTrindade, Izabel CristinaVieira Filho, Sidney Augusto2018-05-14T14:56:49Z2018-05-14T14:56:49Z2018SILVA, A. T. M. et al. Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. Brazilian Journal of Pharmaceutical Sciences, v. 53, p. 1-10, 2018. Disponível em: <http://www.scielo.br/scielo.php?script=sci_abstract&pid=S1984-82502017000300621&lng=en&nrm=iso>. Acesso em: 05 abr. 2018.15169332http://www.repositorio.ufop.br/handle/123456789/9933The triterpene lupeol (1) and some of its esters are secondary metabolites produced by species of Celastraceae family, which have being associated with cytotoxic activity. We report herein the isolation of 1, the semi-synthesis of eight lupeol esters and the evaluation of their in vitro activity against nine strains of cancer cells. The reaction of carboxylic acids with 1 and DIC/DMAP was used to obtain lupeol stearate (2), lupeol palmitate (3) lupeol miristate (4), and the new esters lupeol laurate (5), lupeol caprate (6), lupeol caprilate (7), lupeol caproate (8) and lupeol 3’,4’-dimethoxybenzoate (9), with high yields. Compounds 1-9 were identified using FT-IR, 1H, 13C-NMR, CHN analysis and XRD data and were tested in vitro for proliferation of human cancer cell activity. In these assays, lupeol was inactive (GI50> 250μg/ mL) while lupeol esters 2 -4 and 7 - 9 showed a cytostatic effect. The XRD method was a suitable tool to determine the structure of lupeol and its esters in solid state. Compound 3 showed a selective growth inhibition effect on erythromyeloblastoid leukemia (K-562) cells in a concentration-dependent way. Lupeol esters 4 and 9 showed a selective cytostatic effect with low GI50 values representing promising prototypes for the development of new anticancer drugs.Todo o conteúdo do periódico Revista Brasileira de Ciências Farmacêuticas, exceto onde identificado, está licenciado sob uma licença Creative Commons 4.0 que permite copiar, distribuir e transmitir o trabalho em qualquer suporte ou formato desde que sejam citados o autor e o licenciante. Fonte: Revista Brasileira de Ciências Farmacêuticas <http://www.scielo.br/scielo.php/script_sci_serial/lng_pt/pid_1516-9332/nrm_iso>. Acesso em: 06 jan. 2017.info:eu-repo/semantics/openAccessLupeol/in vitro evaluationAntiproliferative effectLupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOPLICENSElicense.txtlicense.txttext/plain; charset=utf-8924http://www.repositorio.ufop.br/bitstream/123456789/9933/2/license.txt62604f8d955274beb56c80ce1ee5dcaeMD52ORIGINALARTIGO_LupeolEsterNMR.pdfARTIGO_LupeolEsterNMR.pdfapplication/pdf738271http://www.repositorio.ufop.br/bitstream/123456789/9933/1/ARTIGO_LupeolEsterNMR.pdff8486b855057482c815c76142929ba04MD51123456789/99332018-05-14 10:56:49.128oai:localhost: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ório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332018-05-14T14:56:49Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false |
dc.title.pt_BR.fl_str_mv |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
title |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
spellingShingle |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. Silva, Aline Teixeira Maciel Lupeol/in vitro evaluation Antiproliferative effect |
title_short |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
title_full |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
title_fullStr |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
title_full_unstemmed |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
title_sort |
Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. |
author |
Silva, Aline Teixeira Maciel |
author_facet |
Silva, Aline Teixeira Maciel Magalhães, Cássia Gonçalves Duarte, Lucienir Pains Mussel, Wagner da Nova Ruiz, Ana Lucia Tasca Gois Shiozawa, Larissa Carvalho, João Ernesto de Trindade, Izabel Cristina Vieira Filho, Sidney Augusto |
author_role |
author |
author2 |
Magalhães, Cássia Gonçalves Duarte, Lucienir Pains Mussel, Wagner da Nova Ruiz, Ana Lucia Tasca Gois Shiozawa, Larissa Carvalho, João Ernesto de Trindade, Izabel Cristina Vieira Filho, Sidney Augusto |
author2_role |
author author author author author author author author |
dc.contributor.author.fl_str_mv |
Silva, Aline Teixeira Maciel Magalhães, Cássia Gonçalves Duarte, Lucienir Pains Mussel, Wagner da Nova Ruiz, Ana Lucia Tasca Gois Shiozawa, Larissa Carvalho, João Ernesto de Trindade, Izabel Cristina Vieira Filho, Sidney Augusto |
dc.subject.por.fl_str_mv |
Lupeol/in vitro evaluation Antiproliferative effect |
topic |
Lupeol/in vitro evaluation Antiproliferative effect |
description |
The triterpene lupeol (1) and some of its esters are secondary metabolites produced by species of Celastraceae family, which have being associated with cytotoxic activity. We report herein the isolation of 1, the semi-synthesis of eight lupeol esters and the evaluation of their in vitro activity against nine strains of cancer cells. The reaction of carboxylic acids with 1 and DIC/DMAP was used to obtain lupeol stearate (2), lupeol palmitate (3) lupeol miristate (4), and the new esters lupeol laurate (5), lupeol caprate (6), lupeol caprilate (7), lupeol caproate (8) and lupeol 3’,4’-dimethoxybenzoate (9), with high yields. Compounds 1-9 were identified using FT-IR, 1H, 13C-NMR, CHN analysis and XRD data and were tested in vitro for proliferation of human cancer cell activity. In these assays, lupeol was inactive (GI50> 250μg/ mL) while lupeol esters 2 -4 and 7 - 9 showed a cytostatic effect. The XRD method was a suitable tool to determine the structure of lupeol and its esters in solid state. Compound 3 showed a selective growth inhibition effect on erythromyeloblastoid leukemia (K-562) cells in a concentration-dependent way. Lupeol esters 4 and 9 showed a selective cytostatic effect with low GI50 values representing promising prototypes for the development of new anticancer drugs. |
publishDate |
2018 |
dc.date.accessioned.fl_str_mv |
2018-05-14T14:56:49Z |
dc.date.available.fl_str_mv |
2018-05-14T14:56:49Z |
dc.date.issued.fl_str_mv |
2018 |
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.citation.fl_str_mv |
SILVA, A. T. M. et al. Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. Brazilian Journal of Pharmaceutical Sciences, v. 53, p. 1-10, 2018. Disponível em: <http://www.scielo.br/scielo.php?script=sci_abstract&pid=S1984-82502017000300621&lng=en&nrm=iso>. Acesso em: 05 abr. 2018. |
dc.identifier.uri.fl_str_mv |
http://www.repositorio.ufop.br/handle/123456789/9933 |
dc.identifier.issn.none.fl_str_mv |
15169332 |
identifier_str_mv |
SILVA, A. T. M. et al. Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth. Brazilian Journal of Pharmaceutical Sciences, v. 53, p. 1-10, 2018. Disponível em: <http://www.scielo.br/scielo.php?script=sci_abstract&pid=S1984-82502017000300621&lng=en&nrm=iso>. Acesso em: 05 abr. 2018. 15169332 |
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http://www.repositorio.ufop.br/handle/123456789/9933 |
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eng |
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eng |
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info:eu-repo/semantics/openAccess |
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openAccess |
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