Distinguishing between R- and S-antcin C and their cytotoxicity.
Antcin C is a bioactive compound isolated from Antrodia cinnamomea, a rare and expensive medicinal fungus endemic to Taiwan. Up to date, the absolute structure of antcin C has not been solved. In this study, the phenylglycine methyl ester (PGME) derivatives of antcin C were prepared. From NMR analysis the absolute configuration of(S)-antcin C (1) and (R)-antcin C (2) were determined. By MTT assay, (S)-antcin C presented cytotoxicity against Hep G2 and MCF-7 cells, with IC50 values of 14.5 and 12.8 microg/mL, respectively. However, (R)-antcin C did not show significant cytotoxicity. Our results showed that the configuration at C25 for antcin C is very important for its cytotoxicity. From a quality control point of view, it is necessary to identify and quantify the R- and S- enantiomers in the A. cinnamomea products.
Department of Forestry, National Chung-Hsing University, Taichung, Taiwan.
Ting-Yu
TY
Lin
Shih-Chang
SC
Chien
Yueh-Hsiung
YH
Kuo
Sheng-Yang
SY
Wang
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005658:Fungi / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000970:Antineoplastic Agents