Cytotoxic epimeric withaphysalins from leaves of Acnistus arborescens

Planta medica
Maria Leopoldina VerasLetícia Veras Costa-Lutufo

Abstract

Phytochemical analysis of the leaves of Acnistus arborescens (Solanaceae) resulted in the isolation of two new epimeric withaphysalins (17S,20R,22R)-5beta,6beta: 18,20-diepoxy-4beta,18-dihydroxy-1-oxowitha-24-enolide (2, 18R and 18S), together with the known withaphysalin F (1, 18R and 18S). Their structures were established by spectroscopic methods, including 2D NMR data and comparison with literature data. Compounds 1 and 2 dis-played potent cytotoxic activities against several cancer cell lines with IC50 values in the range of 0.20 to 1.46 microg/mL for 1 and 0.89 to 8.08 microg/mL for 2. The strong cytotoxicity presented by 1 suggests that in this series of compounds, the 2,3-unsaturated ketone moiety is an important pharmacophoric unit. The cytotoxic activity seemed to be related to DNA synthesis inhibition, as revealed by the reduction of 5-bromo-2'-deoxyuridine incorporation after 24 hours of incubation on leukemic cells.

Citations

Oct 1, 2013·Phytochemistry·Maria Conceição M TorresOtília Deusdênia L Pessoa
Feb 24, 2011·Natural Product Reports·Li-Xia ChenFeng Qiu
Jul 22, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luciana Nalone AndradeDamião Pergentino de Sousa
Jul 11, 2006·Life Sciences·Danilo Damasceno RochaLetícia Veras Costa-Lotufo
May 23, 2006·Journal of Ethnopharmacology·G GaravitoE Deharo
Aug 9, 2016·Phytochemistry·Pedro Henrique J BatistaOtília Deusdenia L Pessoa
Feb 3, 2006·The Journal of Pharmacy and Pharmacology·Hemerson Iury Ferreira MagalhãesCláudia Pessoa
May 10, 2019·Journal of Natural Products·Sebastián J CastroViviana E Nicotra
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