Document Detail


Gastroprotective effect and cytotoxicity of labdeneamides with amino acids.
MedLine Citation:
PMID:  20862639     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
Semisynthetic aromatic amides from ARAUCARIA ARAUCANA diterpene acids have been shown to display a relevant gastroprotective effect with low cytotoxicity. The aim of this work was to assess the gastroprotective effect of amino acid amides from imbricatolic acid and its 8 (9)-en isomer in the ethanol/HCl-induced gastric lesions model in mice as well as to determine the cytotoxicity of the obtained compounds on the following human cell lines: normal lung fibroblasts (MRC-5), gastric adenocarcinoma (AGS), and liver hepatocellular carcinoma (Hep G2). The diterpenes 15-acetoxyimbricatolic acid, its 8 (9)-en isomer, 15-hydroxyimbricatolic acid, and the 8 (9)-en derivative, bearing a COOH function at C-19, were used as starting compounds. New amides with C-protected amino acids were prepared. The study reports the effect of a single oral administration of either compound 50 min before the induction of gastric lesions by ethanol/HCl. Some 20 amino acid monoamides were obtained. Dose-response experiments on the glycyl derivatives showed that at a single oral dose of 100 mg/kg, the compounds presented an effect comparable to the reference drug lansoprazole at 20 mg/kg and at 50 mg/kg reduced gastric lesions by about 50 %. All derivatives obtained in amounts > 30 mg were compared at a single oral dose of 50 mg/kg. The best gastroprotective effect was observed for the exomethylene derivatives bearing a valine residue at C-19 either with an acetoxy or free hydroxy group at C-15. The tryptophanyl derivative from the acetate belonging to the 8,9-en series presented selective cytotoxicity against hepatocytes. The glycyl amide of 15-acetoxyimbricatolic acid was the most cytotoxic and less selective compound with IC (50) values between 47 and 103 µM for the studied cell lines. This is the first report on the obtention of semisynthetic amino acid amides from labdane diterpenes.
Authors:
Guillermo Schmeda-Hirschmann; Jaime A Rodríguez; Cristina Theoduloz; Jaime A Valderrama
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Publication Detail:
Type:  Journal Article     Date:  2010-09-22
Journal Detail:
Title:  Planta medica     Volume:  77     ISSN:  1439-0221     ISO Abbreviation:  Planta Med.     Publication Date:  2011 Mar 
Date Detail:
Created Date:  2011-03-08     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0066751     Medline TA:  Planta Med     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  340-5     Citation Subset:  IM    
Copyright Information:
© Georg Thieme Verlag KG Stuttgart · New York.
Affiliation:
Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, Chile.
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