Grandisines C-G, indolizidine alkaloids from the Australian rainforest tree Elaeocarpus grandis

J Nat Prod. 2006 Sep;69(9):1295-9. doi: 10.1021/np060179c.

Abstract

Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4-8), and one known indolizidine alkaloid, (-)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (-)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (-)-isoelaeocarpiline showed receptor binding affinity for the human delta-opioid receptor with IC(50) values of 14.6, 1.65, 1.55, 75.4, and 9.9 microM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / isolation & purification
  • Alkaloids* / pharmacology
  • Australia
  • Elaeocarpaceae / chemistry*
  • Humans
  • Indolizines* / chemistry
  • Indolizines* / isolation & purification
  • Indolizines* / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Pyridines / chemistry
  • Pyridines / isolation & purification
  • Pyridines / pharmacology
  • Receptors, Opioid / drug effects*
  • Trees / chemistry*

Substances

  • Alkaloids
  • Indolizines
  • Pyridines
  • Receptors, Opioid
  • grandisine G