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Planta Med 2013; 79(16): 1531-1535
DOI: 10.1055/s-0033-1350897
Biological and Pharmacological Activity
Letters
Georg Thieme Verlag KG Stuttgart · New York

In Vitro Evaluation of Caffeoyl and Cinnamoyl Derivatives as Potential Prolyl Oligopeptidase Inhibitors

Luciana O. Adolpho
1   Núcleo de Pesquisa de Produtos Naturais (NPPN), Chemistry Department, Universidade Federal de Santa Maria, Santa Maria – RS, Brazil
,
Daniele Marin
1   Núcleo de Pesquisa de Produtos Naturais (NPPN), Chemistry Department, Universidade Federal de Santa Maria, Santa Maria – RS, Brazil
,
Albert Puigpinos
2   Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
,
Laura Mendieta
2   Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
,
Teresa Tarragó
2   Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
,
Ademir F. Morel
1   Núcleo de Pesquisa de Produtos Naturais (NPPN), Chemistry Department, Universidade Federal de Santa Maria, Santa Maria – RS, Brazil
,
Ernest Giralt
2   Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain
,
Ionara I. Dalcol
1   Núcleo de Pesquisa de Produtos Naturais (NPPN), Chemistry Department, Universidade Federal de Santa Maria, Santa Maria – RS, Brazil
› Author Affiliations
Further Information

Publication History

received 09 April 2013
revised 29 August 2013

accepted 04 September 2013

Publication Date:
01 October 2013 (online)

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Abstract

A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase 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 dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 µM) in the range of 81.5–7.2 %. 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 activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14 mM.

Key words

prolyl oligopeptidase - dipeptidyl peptidase IV - chlorogenic acid - caffeoyl and cinnamoyl derivatives - Hypericum brasiliense - Hypericaceae

Supporting Information

 

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