| Synthesis, gastroprotective effect and cytotoxicity of new amino acid diterpene monoamides and diamides. | |
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MedLine Citation:
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PMID: 20966879 Owner: NLM Status: In-Process |
Abstract/OtherAbstract:
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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. |
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Authors:
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Guillermo Schmeda-Hirschmann; Mariano Walter Pertino; Jaime A Rodriguez; Francisco Monsalve; Daniel Droguett; Cristina Theoduloz |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-10-21 |
Journal Detail:
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Title: Molecules (Basel, Switzerland) Volume: 15 ISSN: 1420-3049 ISO Abbreviation: Molecules Publication Date: 2010 |
Date Detail:
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Created Date: 2010-10-22 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100964009 Medline TA: Molecules Country: Switzerland |
Other Details:
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Languages: eng Pagination: 7378-94 Citation Subset: IM |
Affiliation:
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Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile. schmeda@utalca.cl |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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