Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica

J Nat Prod. 2010 May 28;73(5):988-91. doi: 10.1021/np100009j.

Abstract

Two new (1 and 2) and six known hasubanan alkaloids (3-8) and one morphinane alkaloid (9) were isolated from the leaves of the North Queensland rainforest vine Stephania japonica. The structures of 1 and 2 were determined by interpretation of their 1D and 2D NMR spectra. The hasubanan alkaloids showed affinity for the human delta-opioid receptor with IC(50) values ranging from 0.7 to 46 microM. The compounds were also tested for their affinity to micro- and kappa-opioid receptors and shown to be inactive against kappa-opioid receptors, but were of similar potency against the micro-opioid receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Australia
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plants, Medicinal / chemistry*
  • Receptors, Opioid, delta / drug effects*
  • Receptors, Opioid, delta / metabolism
  • Receptors, Opioid, kappa / metabolism
  • Stephania / chemistry*

Substances

  • 6-cinnamoylhernandine
  • Alkaloids
  • N-methylstephisoferulin
  • Receptors, Opioid, delta
  • Receptors, Opioid, kappa