One-step semisynthesis method of spirocurcasone and pyracurcasone from curcusones A and B

Org Lett. 2014 Apr 18;16(8):2196-9. doi: 10.1021/ol500692j. Epub 2014 Apr 3.

Abstract

High contents of curcusones A and B and trace amounts of spirocurcasone exist in the roots of Jatropha curcas. Here, a one-step semisynthesis method of spirocurcasone and pyracurcasone was built, not only resulted an increased yield of spirocurcasone but also produced pyracurcasone, which exhibited greater cytotoxicity compared to curcusones A and B. The plausible mechanism of the formation of pyracurcasone was proposed, and the proposed biogenetic origin for spirocurcasone by Taglialatela-Scafati was confirmed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cisplatin / pharmacology
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Female
  • HL-60 Cells
  • Humans
  • Jatropha / chemistry
  • Molecular Structure
  • Plant Roots / chemistry
  • Structure-Activity Relationship

Substances

  • Diterpenes
  • curcusone B
  • spirocurcasone
  • Cisplatin