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

A new quaternary β-carboline alkaloid, nostocarboline (I), 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. I is a potent butyrylcholinesterase (BChE) inhibitor, with an IC50 of 13.2 μM. The related 2-methylnorharmane, which is present in the human brain and might be relevant to Parkinson's disease, was also detected to be a BChE inhibitor (11.2 μM). These inhibitory concentrations are comparable to galanthamine, an approved drug for the treatment of Alzheimer's disease. I can thus be considered as a lead for the development of novel neurochemicals.


Published in:
Journal of Natural Products, 68, 12, 1793-1795
Year:
2005
Keywords:
Laboratories:




 Record created 2006-11-22, last modified 2018-03-17


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