Structures of compounds with antigonadotropic activity obtained by in vitro oxidation of caffeic acid

Planta Med. 1990 Aug;56(4):395-8. doi: 10.1055/s-2006-960992.

Abstract

Two new cyclolignan derivatives were isolated by HPLC from the mixture of substances obtained after oxidation of caffeic acid with KMnO4. Their structures were elucidated by spectroscopic methods as 2,3-dicarboxy-6,7-dihydroxy-1-(3', 4'-dihydroxy)-phenyl-1, 2-dihydronaphthalene (1) and 3-carboxy-6,7-dihydroxy-1-(3', 4'-dihydroxy)-phenylnaphthalene (2). Compounds 1 and 2 exhibit antigonadotropic activity as do the extracts of crude drugs of Lycopus europaeus and Lithospermum officinale after oxidation by plant enzymes.

MeSH terms

  • Animals
  • Caffeic Acids / metabolism*
  • Caffeic Acids / pharmacology
  • Catechols / isolation & purification
  • Catechols / pharmacology*
  • Chromatography, High Pressure Liquid
  • Gonadotropins / antagonists & inhibitors*
  • Leydig Cells / drug effects
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Molecular Structure
  • Naphthols / isolation & purification
  • Naphthols / pharmacology*
  • Oxidation-Reduction

Substances

  • Caffeic Acids
  • Catechols
  • Gonadotropins
  • Naphthols
  • KS IV
  • KS I
  • caffeic acid