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

Abstract

A new quaternary beta-carboline alkaloid, nostocarboline (1), 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 (1) was found to be a potent butyrylcholinesterase (BChE) inhibitor, with an IC50 of 13.2 mu M. 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 mu M). These inhibitory concentrations are comparable to galanthamine, an approved drug for the treatment of Alzheimer's disease (AID). Nostocarboline (1) can thus be considered as a lead for the development of novel neurochemicals.

Published in

Journal of Natural Products
2005, volume: 68, number: 12, pages: 1793-1795
Publisher: AMER CHEMICAL SOC

SLU Authors

• Becher, Paul

  • University of Zürich

UKÄ Subject classification

Microbiology

Publication identifier

• DOI: https://doi.org/10.1021/np050312l

Permanent link to this page (URI)

https://res.slu.se/id/publ/42843