Cytotoxicity of Curcuminoids and Some Novel Compounds from Curcuma zedoaria

1998/10/17 by Wan-Jr Syu, Chien-Chang Shen, Chien‐Chang Shen +8 · 2 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Curcumin's Biomedical Applications #Natural product bioactivities and synthesis #Synthesis and biological activity

paper · doi:10.1021/np980269k

Abstract

Bioassay-directed fractionation of an EtOH extract of Curcuma zedoaria led to isolation of an active curcuminoid, which was identified as demethoxycurcumin (2) by comparison of its 1H and 13C NMR spectra with literature data and by direct comparison with synthetic material. Curcumin (1) and bisdemethoxycurcumin (3) were also obtained. Curcuminoids (1-3) were synthesized and demonstrated to be cytotoxic against human ovarian cancer OVCAR-3 cells. The observed CD50 values of 1, 2, and 3 were 4.4, 3.8, and 3.1 microg/mL, respectively. Three additional novel compounds, 3, 7-dimethylindan-5-carboxylic acid (4), curcolonol (5), and guaidiol (6), were also isolated from the EtOH extract. The structures and relative stereochemistry of 4-6 were determined by spectroscopic methods and X-ray crystallographic analysis.

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