Cytotoxic biotransformed products from cinobufagin by Mucor spinosus and Aspergillus Niger

Steroids. 2006 May;71(5):392-402. doi: 10.1016/j.steroids.2005.12.003. Epub 2006 Feb 15.

Abstract

Cinobufagin (1) was one of important cardenolidal steroids and major components of Chan'Su, a famous traditional Chinese medicine. Bioconversion of cinobufagin by the fungi of Mucor spinosus and Aspergillus niger were investigated. Nine bioconversion products were obtained from M. spinosus and seven products from A. niger. Their structures were elucidated by high-resolution fast atom bombardment mass spectroscopy (HR-FAB-MS), extensive NMR techniques, including (1)H NMR, (13)C NMR, DEPT, (1)H-(1)H correlation spectroscopy (COSY), two-dimensional nuclear Overhauser effect correlation spectroscopy (NOESY), heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple bond coherence (HMBC). The in vitro cytotoxic activities against human hepatoma cells (HepG2, SMMC-7221 and BEL-7402) and human leukemia cells (K562, HL-60 and HEL) of all bioconversion products were determined by the MTT method, and their structure-activity relationships (SAR) were discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / metabolism*
  • Aspergillus niger / metabolism*
  • Biotransformation
  • Bufanolides / chemistry
  • Bufanolides / metabolism*
  • Carcinoma, Hepatocellular / drug therapy*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Humans
  • Leukemia / drug therapy*
  • Molecular Conformation
  • Mucor / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Bufanolides
  • Drugs, Chinese Herbal
  • cinobufagin