Unusual sesquiterpene lactones from Ligularia virgaurea spp. oligocephala

Org Lett. 2004 Jul 8;6(14):2313-6. doi: 10.1021/ol049571c.

Abstract

[structure: see text] [structure: see text] Sesquiterpene lactones, ligulolide A (1) and 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide (2), were isolated from Ligularia virgaurea spp. oligocephala. Their structures were established by analysis of one- and two-dimensional NMR data. The relative stereostructures were determined on the basis of NOESY and single-crystal X-ray experiments. 1 represents a novel sesquiterpene carbon framework, and a possible biosynthetic process is proposed. 2 is a novel eremophilane-type sesquiterpene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Asteraceae / chemistry*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemistry*
  • Lactones / isolation & purification*
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • 6beta,8alpha-dihydroxy-1-oxoeremophila-7(11),9(10)-diene-12,8-olide
  • Antineoplastic Agents
  • Lactones
  • Naphthalenes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • eremophilane compounds
  • ligulolide A