Leonuketal, a Spiroketal Diterpenoid from Leonurus japonicus

Org Lett. 2015 Dec 18;17(24):6238-41. doi: 10.1021/acs.orglett.5b03227. Epub 2015 Dec 4.

Abstract

An architecturally complex spiroketal diterpenoid, leonuketal (1), was isolated from the aerial parts of the plant Leonurus japonicus. This compound possessed an unprecedented tetracyclic skeleton that comprised a bridged spiroketal moiety fused with a ketal-γ-lactone unit. The structure and absolute configuration were determined by spectroscopic analyses, a modified Mosher's method, and ECD (electronic circular dichroism) calculations. Leonuketal (1) showed significant vasorelaxant activity against KCl-induced contraction of rat aorta, with the EC50 value of 2.32 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aortic Coarctation / chemically induced
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology
  • Leonurus / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Components, Aerial / chemistry
  • Potassium Chloride / pharmacology
  • Rats
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology

Substances

  • Diterpenes
  • Furans
  • Spiro Compounds
  • leonuketal
  • spiroketal
  • Potassium Chloride