Choerosponins A and B, Two New Cytotoxic Bridged-Ring Ketones and the Determination of Their Absolute Configurations

Molecules. 2017 Mar 27;22(4):531. doi: 10.3390/molecules22040531.

Abstract

Bioactivity-directed fractionation of antitumor compounds from the stem barks of Choerospondias axillaries (Roxb.) Burtt et Hill (Anacardiaceae) afforded two new cytotoxic bridged-ring ketones, choerosponins A (1) and B (2), and their structures were elucidated by spectroscopic methods; their stereochemistry was determined by NOE difference experiments, CD spectra and the modified Mosher's method. Compound 1 has a rare dioxatricyclo skeleton. Flow cytometry and SRB methods were employed to evaluate the antitumor activity of the two compounds against tsFT210, HCT-15, HeLa, A2780 and MCF-7 cell lines, and both of them showed strong cytotoxicity. MTT and paper disc methods were also used to evaluate their anti-hypoxia and antibacterial activities, and both of them showed no apparent activities.

Keywords: Choerospondias axillaries; absolute configuration; bridged ring ketones; cytotoxicity.

MeSH terms

  • Anacardiaceae / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Hypoxia / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / pharmacology
  • HeLa Cells
  • Humans
  • Ketones / chemistry*
  • Ketones / pharmacology*
  • MCF-7 Cells
  • Molecular Structure

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Ketones