C18 dibenzocyclooctadiene lignans from Kadsura philippinensis

J Nat Prod. 2006 Jun;69(6):963-6. doi: 10.1021/np058134j.

Abstract

Four new C18 dibenzocyclooctadiene lignans, kadsuphilins A (1) and B (3), 6-epi-gomisin (2), and 1-demethylkadsuphilin A (4), along with eight known related metabolites, were isolated from an EtOAc fraction of an alcoholic extract of the aerial parts of Kadsura philippinensis growing in Taiwan. The structures of 1-4 were elucidated on the basis of spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The configurations of the biphenyl and cyclooctadiene moieties were deduced from circular dichroism (CD) and NOESY NMR spectra, respectively. Some of the compounds showed radical-scavenging activity in a DPPH-HPLC method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds
  • Cyclooctanes / chemistry*
  • Cyclooctanes / isolation & purification*
  • Cyclooctanes / pharmacology
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology
  • Kadsura / chemistry*
  • Lignans / chemistry*
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Picrates / pharmacology
  • Plants, Medicinal / chemistry*
  • Taiwan

Substances

  • Biphenyl Compounds
  • Cyclooctanes
  • Free Radical Scavengers
  • Lignans
  • Picrates
  • dibenzocyclooctadiene
  • 1,1-diphenyl-2-picrylhydrazyl