Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine sponge Petrosia n. sp.
Two pyridoacridine alkaloids, including a known petrosamine and a new 2-bromoamphimedine were isolated from a Thai marine sponge Petrosia n. sp. The alkaloids were characterized on the basis of 1D and 2D NMR, MS, and IR spectroscopy. Only petrosamine showed strong acetylcholinesterase inhibitory activity approximately six times higher than that of the reference galanthamine. A computational docking study of petrosamine with the enzyme from the electric eel Torpedo californica (TcAChE) showed the major contribution to the petrosamine-TcAChE interaction to be arising from the quaternary ammonium group of petrosamine.
Department of Pharmacognosy, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand.
Veena S
VS
Nukoolkarn
Suwipa
S
Saen-oon
Thanyada
T
Rungrotmongkol
Supot
S
Hannongbua
Kornkanok
K
Ingkaninan
Khanit
K
Suwanborirux
D000166:Acridines / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D002800:Cholinesterase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D009792:Oceans and Seas; D047130:Petrosia / Q000737:chemistry*; D010618:Phenanthrolines / Q000737:chemistry*; D055672:Static Electricity; D013329:Structure-Activity Relationship; D013785:Thailand
D000166:Acridines; D000470:Alkaloids; D002800:Cholinesterase Inhibitors; D010618:Phenanthrolines; C475900:pyridoacridine