EVALUATION OF CAFFEOYL AND CINNAMOYL DERIVATIVES AS POTENTIAL PROLYL OLIGOPEPTIDASE INHIBITORS

DALCOL I.I.¹, ADOLPHO L.O.², MARIN D.³, PUIGPINOS A.⁴, MENDIETA L.⁵, TARRAGÓ T.⁶, MOREL A.F.⁷, GIRALT E.^8
1Núcleo de Pesquisa de Produtos Naturais, Chemistry Department, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil.
²Núcleo de Pesquisa de Produtos Naturais, Chemistry Department, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil.
³Núcleo de Pesquisa de Produtos Naturais, Chemistry Department, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil.
⁴Institute for Research in Biomedicine, Barcelona Science Park, E-08028, Barcelona, Spain.
⁵Institute for Research in Biomedicine, Barcelona Science Park, E-08028, Barcelona, Spain.
⁶Institute for Research in Biomedicine, Barcelona Science Park, E-08028, Barcelona, Spain.
⁷Núcleo de Pesquisa de Produtos Naturais, Chemistry Department, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil.
⁸Institute for Research in Biomedicine, Barcelona Science Park, E-08028, Barcelona, Spain.

Received : 23-11-2012     Accepted : 11-07-2013     Published : 19-08-2013
Volume : 1     Issue : 1       Pages : 4 - 9
World Res J Chem 1.1 (2013):4-9

A bioassay-guided study of the inhibitory capacity of the natural products chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid and p-methoxycinnamic acid, and of caffeoylquinic, caffeoyl and cinnamoyl derivatives against the enzymes prolyl oligopeptidase (POP) and dipeptidyl peptidase IV (DPP IV) was carried out. Caffeoylquinic, caffeoyl and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The capacity of the compounds to inhibit DPP IV was not exceptional. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and interesting performance as POP inhibitors from natural products, with IC50 values of 3 to 14 mM.