Akuammine and Dihydroakuammine, Two Indolomonoterpene Alkaloids Displaying Affinity for Opioid Receptors

J Nat Prod. 1992 Mar;55(3):380-4. doi: 10.1021/np50081a017.

Abstract

Akuammine [1], an indolomonoterpene alkaloid, which is the major component of the seeds of Picralima nitida, was reduced to dihydroakuammine [4]. This compound has structural analogy with eseroline [7], for which affinity for opiate receptors was reported. The present investigation showed that 1 and 4 also bind (with lower affinity however) to mu and kappa opiate receptors. 1H- and 13C-nmr spectra of 1 and 4 have been fully assigned by 2D nmr experiments.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Animals
  • Binding, Competitive / drug effects
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Male
  • Plants / chemistry
  • Rats
  • Receptors, Opioid / drug effects*
  • Receptors, Opioid / metabolism
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Structure-Activity Relationship
  • Terpenes / chemistry
  • Terpenes / pharmacology*

Substances

  • Alkaloids
  • Receptors, Opioid
  • Receptors, Opioid, kappa
  • Receptors, Opioid, mu
  • Terpenes
  • dihydroakuammine
  • akuammine