Hydrangenone, a new isoprenoid with an unprecedented skeleton from Salvia hydrangea

Org Lett. 2012 Jan 6;14(1):166-9. doi: 10.1021/ol202953b. Epub 2011 Dec 1.

Abstract

Hydrangenone, a new heptacyclic isoprenoid with a 6/7/6/5/5 membered carbon ring skeleton, was isolated from the aerial parts of Salvia hydrangea. The structure was established by extensive NMR spectroscopic methods. The relative and absolute configuration of 1 was assigned by NOESY and X-ray crystallographic analysis and by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed in vitro antiplasmodial activity, with an IC(50) value of 1.4 μM against P. falciparum. A plausible biosynthetic pathway of 1 was also proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimalarials / chemistry*
  • Antimalarials / pharmacology
  • Models, Molecular
  • Molecular Conformation
  • Norisoprenoids / chemistry*
  • Norisoprenoids / pharmacology
  • Plasmodium falciparum / drug effects
  • Salvia / chemistry*

Substances

  • Antimalarials
  • Norisoprenoids
  • hydrangenone