Distinguishing between R- and S-antcin C and their cytotoxicity

Nat Prod Commun. 2012 Jul;7(7):835-6.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Fungi / chemistry*
  • Hep G2 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Antineoplastic Agents