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Ursolic and oleanolic acid derivatives with cholinesterase inhibiting potential.

Abstract：

:Triterpenoids are in the focus of scientific interest, and they were evaluated for many pharmacological applications among them their ability to act as inhibitors of cholinesterases. These inhibitors are still of interest as drugs that improve the life quality of patients suffering from age-related dementia illnesses especially of Alzheimer's disease. Herein, we prepared several derivatives of ursolic and oleanolic acid and screened them in Ellman's assays for their ability to inhibit acetylcholinesterase and/or butyrylcholinesterase, and for each of the active compounds the type of inhibition was determined. As a result, several compounds were shown as good inhibitors for acetylcholinesterase and butyrylcholinesterase even in a micromolar range. An ursolic acid derived hydroxyl-propinyl derivative 10 was a competitive inhibitor for butyrylcholinesterase with an inhibition constant of Ki = 4.29 μM, and therefore being twice as active as gold standard galantamine hydrobromide. The best inhibitor for acetylcholinesterase, however, was 2-methyl-3-oxo-methyl-ursoloate (18), acting as a mixed-type inhibitor showing Ki = 1.72 µM and Ki' = 1.28 μM, respectively.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Loesche A,Köwitsch A,Lucas SD,Al-Halabi Z,Sippl W,Al-Harrasi A,Csuk R

doi

10.1016/j.bioorg.2018.12.013

subject

Has Abstract

pub_date

2019-04-01 00:00:00

pages

23-32

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(18)31228-8

journal_volume

85

pub_type

杂志文章

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