Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors.
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.
Lewin
G
G
Laboratoire de Chimie des Substances Thérapeutiques Naturelles, Centre d'Etudes Pharmaceutiques, Châtenay-Malabry, France.
Le Ménez
P
P
Rolland
Y
Y
Renouard
A
A
Giesen-Crouse
E
E
D000470:Alkaloids / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010944:Plants / Q000737:chemistry; D051381:Rats; D011957:Receptors, Opioid / Q000187:drug effects* / Q000378:metabolism; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry / Q000494:pharmacology*
D000470:Alkaloids; D011957:Receptors, Opioid; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D013729:Terpenes; C074724:dihydroakuammine; C074723:akuammine