Document Detail

Synthesis, gastroprotective effect and cytotoxicity of new amino acid diterpene monoamides and diamides.
MedLine Citation:
PMID:  20966879     Owner:  NLM     Status:  In-Process    
Following our studies on the gastroprotective effect and cytotoxicity of terpene derivatives, new amides were prepared from the diterpene 8(17)-labden-15,19-dioic acid (junicedric acid) and its 8(9)-en isomer with C-protected amino acids (amino acid esters). The new compounds were evaluated for their gastroprotective effect in the ethanol/HCl-induced gastric lesions model in mice, as well as for cytotoxicity using the following human cell lines: normal lung fibroblasts (MRC-5), gastric adenocarcinoma cells (AGS) and liver hepatocellular carcinoma (Hep G2). A dose-response experiment showed that at 25 mg/kg the C-15 leucyl and C-15,19-dileucylester amides of junicedric acid reduced gastric lesions by about 65.6 and 49.6%, respectively, with an effect comparable to lansoprazole at 20 mg/kg (79.3% lesion reduction). The comparison of the gastroprotective effect of 18 new amino acid ester amides was carried out at a single oral dose of 25 mg/kg. Several compounds presented a strong gastroprotective effect, reducing gastric lesions in the 70.9-87.8% range. The diprolyl derivative of junicedric acid, the most active product of this study (87.8% lesion reduction at 25 mg/kg) presented a cytotoxicity value comparable with that of the reference compound lansoprazole. The structure-activity relationships are discussed.
Guillermo Schmeda-Hirschmann; Mariano Walter Pertino; Jaime A Rodriguez; Francisco Monsalve; Daniel Droguett; Cristina Theoduloz
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-10-21
Journal Detail:
Title:  Molecules (Basel, Switzerland)     Volume:  15     ISSN:  1420-3049     ISO Abbreviation:  Molecules     Publication Date:  2010  
Date Detail:
Created Date:  2010-10-22     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100964009     Medline TA:  Molecules     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  7378-94     Citation Subset:  IM    
Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile.
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