New 29-nor-cycloartanes with a 3,4-seco- and a novel 2,3-seco-structure from the leaves of Sinocalycanthus chinensis

Bioorg Med Chem. 2011 May 1;19(9):2790-6. doi: 10.1016/j.bmc.2011.03.055. Epub 2011 Mar 29.

Abstract

Eight new triterpenoids, including sinocalycanchinensins A-E (1-5) with a 3,4-seco-29-nor-cycloartane skeleton, sinocalycanchinensin F (6) possessing a novel 2,3-seco-29-nor-cycloartane skeleton, and 29-nor-cycloartanes, sinocalycanchinensins G and H (7 and 8), have been isolated from the leaves of Sinocalycanthus chinensis. Their structures were elucidated on the basis of spectroscopic examinations. The cytotoxicities of the isolated new triterpenes against a panel of human cancer cell lines, including multi-drug resistant (MDR) cancer cell lines, were also evaluated. Compound 5 demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine, although all the compounds showed moderate or no cytotoxicities.

MeSH terms

  • Calycanthaceae / chemistry*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Leaves / chemistry
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / toxicity

Substances

  • Triterpenes
  • sinocalycanchinensin E