Trigocherrin A, the first natural chlorinated daphnane diterpene orthoester from Trigonostemon cherrieri

Org Lett. 2012 Jan 6;14(1):342-5. doi: 10.1021/ol2030907. Epub 2011 Dec 19.

Abstract

Trigocherrin A, a chlorinated and highly oxygenated daphnane diterpenoid orthoester (DDO), was isolated from the bark of Trigonostemon cherrieri. Trigocherrin A is the first example of a naturally occurring halogenated DDO. Its structure was elucidated by comprehensive analysis of NMR spectroscopic data, and its absolute configuration was determined by comparison of experimental and theoretically calculated ECD spectra. Trigocherrin A exhibited a potent and selective effect against Chikungunya virus in Vero cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemistry*
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Biological Products / chemistry*
  • Biological Products / isolation & purification
  • Biological Products / pharmacology
  • Chikungunya virus / drug effects
  • Chlorocebus aethiops
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Euphorbiaceae / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Vero Cells

Substances

  • Antiviral Agents
  • Biological Products
  • Diterpenes
  • trigocherrin A