Lignans, phenylpropanoids and polyacetylenes from Chaerophyllum aureum L. (Apiaceae)

Z Naturforsch C J Biosci. 2003 Jul-Aug;58(7-8):553-7. doi: 10.1515/znc-2003-7-818.

Abstract

Sub-aerial parts of Chaerophyllum aureum L. yielded two polyacetylenes, falcarinol (1), falcarindiol (2), three lignans, namely nemerosin (3), deoxypodorhizone (4), deoxypodo-phyllotoxin (5), two phenylpropanoids, 1'-hydroxymyristicin (6) and its angeloyl ester (7). Compounds 6 and 7 were isolated for the first time from plant material and their structures were elucidated by means of extensive 1- and 2-dimensional NMR spectroscopy and high resolution mass spectrometry. In bioautographic tests on TLC plates the dichloromethane extract showed a significant antimicrobial activity. Falcarindiol was identified as the main active principle whereas the phenylpropanoids and lignans showed no activity.

MeSH terms

  • Acetylene / analogs & derivatives*
  • Acetylene / chemistry*
  • Acetylene / isolation & purification
  • Apiaceae / chemistry*
  • Lignans / chemistry*
  • Lignans / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Methylene Chloride
  • Models, Molecular
  • Molecular Conformation
  • Optical Rotation
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Roots / chemistry
  • Polymers / chemistry*
  • Polymers / isolation & purification
  • Polyynes
  • Propanols / chemistry*
  • Propanols / isolation & purification
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Lignans
  • Plant Extracts
  • Polymers
  • Propanols
  • Polyynes
  • Methylene Chloride
  • Acetylene