Nostocarboline: isolation and synthesis of a new
cholinesterase inhibitor from Nostoc 78-12A

Becher PG, Beuchat J, Gademann K, Juttner F.
Limnological Station, Institute of Plant Biology,
University of Zurich, Seestrasse 187,
8802 Kilchberg, Switzerland.
J Nat Prod. 2005 Dec;68(12):1793-5.


A new quaternary beta-carboline alkaloid, nostocarboline, was isolated from the freshwater cyanobacterium Nostoc 78-12A, and its constitution was assigned by 2D-NMR methods. The structure was proven by its total synthesis starting from norharmane via chlorination at C-6 and methylation at N-2. Nostocarboline was found to be a potent butyrylcholinesterase (BChE) inhibitor, with an IC(50) of 13.2 microM. The related 2-methylnorharmane, which is present in the human brain and might be relevant to Parkinson's disease (PD), was also determined to be a BChE inhibitor (11.2 microM). These inhibitory concentrations are comparable to galanthamine, an approved drug for the treatment of Alzheimer's disease (AD). Nostocarboline can thus be considered as a lead for the development of novel neurochemicals.

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