New neoclerodane diterpenoids isolated from the leaves of Salvia divinorum and their binding affinities for human kappa opioid receptors

Bioorg Med Chem. 2005 Oct 1;13(19):5635-9. doi: 10.1016/j.bmc.2005.05.054.

Abstract

Bioactivity-guided fractionation of the leaves of Salvia divinorum has resulted in the isolation of three new neoclerodane diterpenoids: divinatorin D (1), divinatorin E (2), and salvinorin G (3), together with 10 known terpenoids, divinatorin C (4), hardwickiic acid (5), salvinorin-A (6), -B (7), -C (8), -D (9), -E (10), and -F (11), presqualene alcohol (12), and (E)-phytol (13). The structures of these three new compounds were characterized by spectroscopic methods. All these compounds were evaluated for their binding affinities to the human kappa opioid receptors. In comparison with divinatorin D (1), divinatorin E (2), and salvinorin G (3), salvinorin A (6) is still the most potent kappa agonist.

MeSH terms

  • Binding, Competitive / drug effects*
  • Diterpenes, Clerodane / chemistry*
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology*
  • Humans
  • Molecular Conformation
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry*
  • Receptors, Opioid, kappa / antagonists & inhibitors*
  • Salvia / chemistry*
  • Structure-Activity Relationship

Substances

  • Diterpenes, Clerodane
  • Plant Extracts
  • Receptors, Opioid, kappa