Cytotoxic cordiaquinones from the roots of Cordia polycephala

Abstract

The chemical investigation of roots of Cordia polycephala resulted in the isolation of two new terpenoid naphtoquinones, 6-[10-(12,12-dimethyl-13α- (22-methyl-21-butenoyloxy)-16- methenylcyclohexyl)ethyl]-naphtalene-1,4-dione and (6-[10-(12,12-dimethyl-13α-(tigloyloxy)- 16-methenylcyclohexyl)ethyl]- naphtalene-1,4-dione, named as cordiaquinone N (1) and O (2), respectively. The known cordiaquinones B (3), L (4) and E (5) were also isolated. Their structures were elucidated after detailed 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HRESIMS) data analysis. All cordiaquinones (1-5) were evaluated against four human cancer cell lines: HCT-8 (colon), HL-60 (leukemia), MDA-MB-435 (melanoma) and SF295 (glioblastoma), showing IC 50 values in the range of 1.2 to 11.1 mmol L-1. The new cordiaquinones 1 and 2 were the most active against all cancer cell lines, while compound 3 was selective to leukemia HL-60 cells (IC50 2.2 μmol L-1). ©2012 Sociedade Brasileira de Química.