Triterpenes and phytosterols are classes of natural compounds widespread in
plants possessing a great number of pharmacological activities. In our continued search
for new compounds from natural sources with pharmacological potential, we prepared a
series of novel stigmasterol and ursolic acid (UA) derivatives by coupling with L-proline,
L-cysteine and L-glutamic acid. Unlike stigmasterol, the eight derivatives obtained
showed good inhibitory capacity against acetylcholinesterase (AChE) or prolyl oligopeptidase
(POP). Among these derivatives, we highlight 3 and 5 with IC50 values of 99.0 ± 8.8
and 97.5 ± 5.0 µM against AChE, respectively, and derivative 8 with a POP IC50 value of
75.7 ± 6.3 µM. The ursolic acid derivative 19 was the most promising compound of its
class, with IC50 against AChE of 98.3 ± 7.7 µM. These results demonstrate that simple
structural modifications on triterpenes and phytosterols can enhance their performance as enzymatic inhibitors.
Keywords: Sterols, triterpenes, stigmasterol derivatives, ursolic acid derivatives, acetylcholinesterase, prolyl oligopeptidase.
Kaur, N.; Chaudhary, J.; Jain, A.; Kishore, L. Stigmasterol: A comprehensive review. Int. J. Pharm. Sci. Res., 2011, 2, 2259-2265.
Park, Y.; Jang, H.; Paik, Y. Prolyl endopeptidase inhibitory activity of ursolic and oleanolic acids from Corni fructus. Agric. Chem. Biotechnol., 2005, 48, 207-212.
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