Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.
Two new (1 and 2) and six known hasubanan alkaloids (3-8) and one morphinane alkaloid (9) were isolated from the leaves of the North Queensland rainforest vine Stephania japonica. The structures of 1 and 2 were determined by interpretation of their 1D and 2D NMR spectra. The hasubanan alkaloids showed affinity for the human delta-opioid receptor with IC(50) values ranging from 0.7 to 46 microM. The compounds were also tested for their affinity to micro- and kappa-opioid receptors and shown to be inactive against kappa-opioid receptors, but were of similar potency against the micro-opioid receptor.
Carroll
Anthony R
AR
Eskitis Institute, Griffith University, Brisbane, Queensland 4111, Australia.
Arumugan
Thirumavalavan
T
Redburn
Joanne
J
Ngo
Ana
A
Guymer
Gordon P
GP
Forster
Paul I
PI
Quinn
Ronald J
RJ
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001315:Australia; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D017465:Receptors, Opioid, delta / Q000187:drug effects* / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000378:metabolism; D031607:Stephania / Q000737:chemistry*
C550030:6-cinnamoylhernandine; D000470:Alkaloids; C550031:N-methylstephisoferulin; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa