Sensitized photooxidation of furanoeremophilane with singlet oxygen and their biogenetic relationship

Nat Prod Res. 2006 Jul 10;20(8):724-30. doi: 10.1080/14786410500185733.

Abstract

In an attempt to explore the biogenetic relationship of furanoeremophilane derivatives and eremophilan-8alpha,12-olides, produced in Ligularia and their structure-activity relationship, we studied the photosensitized oxidation of furanoeremophilane-type sesquiterpenes. Under the condition of several solvents solution Irradiation with a 200 W incandescent lamp of furanoeremophilan-14beta,6alpha-olide isolated from Ligularia vellerea, in various solutions with methylene blue, rose bengal, toluidine blue and safranine T gave several products. The products were isolated by chromatographic procedure and their structures were elucidated as eremophilan-14beta,6alpha,8alpha,12-diolide derivatives by NMR, IR and MS methods. A reaction mechanism has been proposed.

MeSH terms

  • Animals
  • Asteraceae / chemistry*
  • Hepatocytes / drug effects
  • Light
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Oxidation-Reduction
  • Plant Roots / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / metabolism
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes / radiation effects
  • Singlet Oxygen

Substances

  • Sesquiterpenes
  • furanoeremophilan-14,6-olide
  • Singlet Oxygen