Lupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2017 |
| Outros Autores: | , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UFMG |
| Texto Completo: | http://dx.doi.org/10.1590/s2175-97902017000300251 http://hdl.handle.net/1843/50615 https://orcid.org/0000-0002-8885-6625 https://orcid.org/0000-0002-9768-9830 https://orcid.org/0000-0002-0844-8702 https://orcid.org/0000-0002-8171-8035 |
Resumo: | CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
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2023-03-02T18:53:44Z2023-03-02T18:53:44Z2017533http://dx.doi.org/10.1590/s2175-979020170003002512175-9790http://hdl.handle.net/1843/50615https://orcid.org/0000-0002-8885-6625https://orcid.org/0000-0002-9768-9830https://orcid.org/0000-0002-0844-8702https://orcid.org/0000-0002-8171-8035CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas GeraisThe 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.engUniversidade Federal de Minas GeraisUFMGBrasilFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOSICX - DEPARTAMENTO DE QUÍMICAQuímica analíticaQuímica farmacêuticaCélulas cancerosas - CrescimentoCélulas cancerosas - ProliferaçãoAgentes antineoplásicosLeucemiaQuímica farmacêuticaFourier, Espectroscopia de infravermelho por transformada deEspectroscopia de ressonancia nuclearRaios X - DifraçãoLupeol/in vitro evaluationLupeol esterK-562 cellsXRD methodAntiproliferative effectLupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growthinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.scielo.br/j/bjps/a/QRr4cmTQN4F9frHNbwcGXYB/?lang=enAline Teixeira Maciel e SilvaCássia Gonçalves MagalhãesLucienir Pains DuarteWagner da Nova MusselAna Lúcia Tasca Gois RuizLarissa ShiozawaJoão Ernesto de CarvalhoIzabel Cristina TrindadeSidney Augusto Vieira Filhoapplication/pdfinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGORIGINALLupeol and its esters.pdfLupeol and its esters.pdfapplication/pdf665268https://repositorio.ufmg.br/bitstream/1843/50615/2/Lupeol%20and%20its%20esters.pdfdaa725b4181ba845c6d171fa0170436dMD52LICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/50615/1/License.txtfa505098d172de0bc8864fc1287ffe22MD511843/506152023-03-02 15:53:44.82oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-03-02T18:53:44Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)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 Aline Teixeira Maciel e Silva Lupeol/in vitro evaluation Lupeol ester K-562 cells XRD method Antiproliferative effect Química analítica Química farmacêutica Células cancerosas - Crescimento Células cancerosas - Proliferação Agentes antineoplásicos Leucemia Química farmacêutica Fourier, Espectroscopia de infravermelho por transformada de Espectroscopia de ressonancia nuclear Raios X - Difração |
| 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 |
Aline Teixeira Maciel e Silva |
| author_facet |
Aline Teixeira Maciel e Silva Cássia Gonçalves Magalhães Lucienir Pains Duarte Wagner da Nova Mussel Ana Lúcia Tasca Gois Ruiz Larissa Shiozawa João Ernesto de Carvalho Izabel Cristina Trindade Sidney Augusto Vieira Filho |
| author_role |
author |
| author2 |
Cássia Gonçalves Magalhães Lucienir Pains Duarte Wagner da Nova Mussel Ana Lúcia Tasca Gois Ruiz Larissa Shiozawa João Ernesto de Carvalho Izabel Cristina Trindade Sidney Augusto Vieira Filho |
| author2_role |
author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Aline Teixeira Maciel e Silva Cássia Gonçalves Magalhães Lucienir Pains Duarte Wagner da Nova Mussel Ana Lúcia Tasca Gois Ruiz Larissa Shiozawa João Ernesto de Carvalho Izabel Cristina Trindade Sidney Augusto Vieira Filho |
| dc.subject.por.fl_str_mv |
Lupeol/in vitro evaluation Lupeol ester K-562 cells XRD method Antiproliferative effect |
| topic |
Lupeol/in vitro evaluation Lupeol ester K-562 cells XRD method Antiproliferative effect Química analítica Química farmacêutica Células cancerosas - Crescimento Células cancerosas - Proliferação Agentes antineoplásicos Leucemia Química farmacêutica Fourier, Espectroscopia de infravermelho por transformada de Espectroscopia de ressonancia nuclear Raios X - Difração |
| dc.subject.other.pt_BR.fl_str_mv |
Química analítica Química farmacêutica Células cancerosas - Crescimento Células cancerosas - Proliferação Agentes antineoplásicos Leucemia Química farmacêutica Fourier, Espectroscopia de infravermelho por transformada de Espectroscopia de ressonancia nuclear Raios X - Difração |
| description |
CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
| publishDate |
2017 |
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2017 |
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2023-03-02T18:53:44Z |
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2023-03-02T18:53:44Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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http://hdl.handle.net/1843/50615 |
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http://dx.doi.org/10.1590/s2175-97902017000300251 |
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2175-9790 |
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https://orcid.org/0000-0002-8885-6625 https://orcid.org/0000-0002-9768-9830 https://orcid.org/0000-0002-0844-8702 https://orcid.org/0000-0002-8171-8035 |
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http://dx.doi.org/10.1590/s2175-97902017000300251 http://hdl.handle.net/1843/50615 https://orcid.org/0000-0002-8885-6625 https://orcid.org/0000-0002-9768-9830 https://orcid.org/0000-0002-0844-8702 https://orcid.org/0000-0002-8171-8035 |
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2175-9790 |
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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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application/pdf |
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Universidade Federal de Minas Gerais |
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UFMG |
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Brasil |
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FAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS ICX - DEPARTAMENTO DE QUÍMICA |
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Universidade Federal de Minas Gerais |
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reponame:Repositório Institucional da UFMG instname:Universidade Federal de Minas Gerais (UFMG) instacron:UFMG |
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