Alkaloids with human delta-opioid receptor binding affinity from the Australian rainforest tree Peripentadenia mearsii.
Three new pyrrolidine alkaloids, peripentonine A-C ( 2- 4), one known pyrrolidine alkaloid, peripentadenine ( 1), and one novel indolizidine alkaloid, mearsamine ( 5), were isolated from the leaves of Peripentadenia mearsii and their structures determined by 1D and 2D NMR spectroscopy. Peripentonines A ( 2) and B ( 3) were isolated as a 1:1 mixture of inseparable diastereomers. Mearsamine ( 5) contains a novel tricyclic ring system. Peripentadenine and peripentonines A/B and C showed receptor binding affinity for the human delta-opioid receptor with IC 50 values of 11.4, 69.2, and 30.9 microM, respectively. Mearsamine did not bind to the delta-opioid receptor.
Natural Product Discovery, Eskitis Institute, Griffith University, Brisbane, Queensland, Australia.
Peter L
PL
Katavic
Debra A
DA
Venables
Gordon P
GP
Guymer
Paul I
PI
Forster
Anthony R
AR
Carroll
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001315:Australia; D045467:Elaeocarpaceae / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D017465:Receptors, Opioid, delta / Q000187:drug effects*
D000470:Alkaloids; D011759:Pyrrolidines; D017465:Receptors, Opioid, delta; C526832:peripentadenine; C526829:peripentonine A; C526830:peripentonine B; C526831:peripentonine C