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  • Title: Inhibition of acetylcholinesterase from electric eel by (-)-and (+)-physostigmine and related compounds.
    Author: Brossi A, Schönenberger B, Clark OE, Ray R.
    Journal: FEBS Lett; 1986 Jun 09; 201(2):190-2. PubMed ID: 3709808.
    Abstract:
    Unnatural (+)-physostigmine (2) inhibited acetylcholinesterase (AChE) from electric eel considerably less than natural (-)-physostigmine (1), but 2 may because of its possible lower toxicity still be an interesting anticholinesterase agent. (-)-Eseroline (3), a major metabolite of (-)-physostigmine (1) and a potent narcotic analgetic, and its unnatural (+)-antipode (4), were both poor inhibitors of the enzyme. (-)-Dihydrosecophysostigmine (5), a ring-open analog of (-)-physostigmine was less, but (-)-N-methylphysostigmine (6) much more potent than the natural alkaloid. The availability of compounds related to (-)- and (+)-physostigmine by improved chemical synthesis suggests that further structural variation may well lead to other biologically interesting AChE inhibitors.
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