Grandisine A and B, novel indolizidine alkaloids with human delta-opioid receptor binding affinity from the leaves of the Australian rainforest tree Elaeocarpus grandis.
Two novel indolizidine alkaloids, grandisine A (1) and B (2), and the known alkaloid (-) isoelaeocarpiline (3) were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. The compounds showed affinity for the human delta-opioid receptor. Grandisine A contains a unique tetracyclic skeleton, while grandisine B possesses the unique combination of isoquinuclidinone and indolizidine groups in one molecule.
Carroll
Anthony R
AR
Natural Product Discovery, Eskitis Institute, Griffith University, Brisbane, Queensland 4111, Australia. a.carroll@griffith.edu.au
Arumugan
Garrie
G
Quinn
Ronald J
RJ
Redburn
Joanne
J
Guymer
Gordon
G
Grimshaw
Paul
P
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D001667:Binding, Competitive / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D045467:Elaeocarpaceae / Q000737:chemistry*; D006801:Humans; D007212:Indolizines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D009842:Oligopeptides / Q000037:antagonists & inhibitors; D018515:Plant Leaves / Q000737:chemistry; D017465:Receptors, Opioid, delta / Q000737:chemistry / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000470:Alkaloids; D007212:Indolizines; D009842:Oligopeptides; D017465:Receptors, Opioid, delta; C499760:grandisine A; C499761:grandisine B; C060209:deltorphin II, Ala(2)-