Lupeol and its esters : NMR, powder XRD data and in vitro evaluation of cancer cell growth.
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2018
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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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Lupeol/in vitro evaluation, Antiproliferative effect
Citação
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.