Lupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth

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dc.creatorAline Teixeira Maciel e Silva
dc.creatorCássia Gonçalves Magalhães
dc.creatorLucienir Pains Duarte
dc.creatorWagner da Nova Mussel
dc.creatorAna Lúcia Tasca Gois Ruiz
dc.creatorLarissa Shiozawa
dc.creatorJoão Ernesto de Carvalho
dc.creatorIzabel Cristina Trindade
dc.creatorSidney Augusto Vieira Filho
dc.date.accessioned2023-03-02T18:53:44Z
dc.date.accessioned2025-09-08T22:48:58Z
dc.date.available2023-03-02T18:53:44Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.format.mimetypepdf
dc.identifier.doihttp://dx.doi.org/10.1590/s2175-97902017000300251
dc.identifier.issn2175-9790
dc.identifier.urihttps://hdl.handle.net/1843/50615
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.rightsAcesso Aberto
dc.subjectQuímica analítica
dc.subjectQuímica farmacêutica
dc.subjectCélulas cancerosas - Crescimento
dc.subjectCélulas cancerosas - Proliferação
dc.subjectAgentes antineoplásicos
dc.subjectLeucemia
dc.subjectQuímica farmacêutica
dc.subjectFourier, Espectroscopia de infravermelho por transformada de
dc.subjectEspectroscopia de ressonancia nuclear
dc.subjectRaios X - Difração
dc.subject.otherLupeol/in vitro evaluation
dc.subject.otherLupeol ester
dc.subject.otherK-562 cells
dc.subject.otherXRD method
dc.subject.otherAntiproliferative effect
dc.titleLupeol and its esters: NMR, powder XRD data and in vitro evaluation of cancer cell growth
dc.typeArtigo de periódico
local.citation.issue3
local.citation.volume53
local.description.resumoThe 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.
local.identifier.orcidhttps://orcid.org/0000-0002-8885-6625
local.identifier.orcidhttps://orcid.org/0000-0002-9768-9830
local.identifier.orcidhttps://orcid.org/0000-0002-0844-8702
local.identifier.orcidhttps://orcid.org/0000-0002-8171-8035
local.publisher.countryBrasil
local.publisher.departmentFAR - DEPARTAMENTO DE PRODUTOS FARMACÊUTICOS
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.scielo.br/j/bjps/a/QRr4cmTQN4F9frHNbwcGXYB/?lang=en

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