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Gypsogenin Derivatives: An Unexpected Class of Inhibitors of Cholinesterases
Author(s) -
Heller Lucie,
Schwarz Stefan,
Weber Björn A.,
Csuk René
Publication year - 2014
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201400103
Subject(s) - butyrylcholinesterase , chemistry , acetylcholinesterase , stereochemistry , cholinesterase , aché , enzyme , galantamine , pharmacology , biochemistry , medicine , dementia , disease , pathology , donepezil
Gypsogenin ( 1 ) was obtained by acidic hydrolysis from its saponin. While the parent compound 1 acted as a selective inhibitor for butyrylcholinesterase (from equus) possessing a moderate mixed‐type inhibition of the enzyme, K i values as low as 2.67 ± 0.59 μM were determined for (3β,4α) 3‐ O ‐acetyl‐olean‐12‐ene‐23,28‐dinitrile ( 11 ) and acetylcholinesterase (AChE, from electric eel). Thus, 11 possesses one‐fifth of the inhibitory activity of the “gold standard” galantamine hydrobromide; this compound is one of the first pentacyclic triterpenoids described as a potent AChE‐selective inhibitor.