Journal
PLANTA MEDICA
Volume 79, Issue 16, Pages 1531-1535Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1350897
Keywords
prolyl oligopeptidase; dipeptidyl peptidase IV; chlorogenic acid; caffeoyl and cinnamoyl derivatives; Hypericum brasiliense; Hypericaceae
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Funding
- CAPES-Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (Ministerio da Educacao-Brazil)
- MECD (Ministerio de Educacion, Cultura y Deporte de Espana)
- MCI-FEDER [BIO2008-00799]
- Fundacio la Marato de TV3
- Generalitat de Catalunya [2005SGR-00663]
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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 mu M) 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 14mM.
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