Document Detail


Gastroprotective effect of carnosic acid gamma-lactone derivatives.
MedLine Citation:
PMID:  20359186     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid gamma-lactone (3). To determine structure-activity relationships, a series of 17 esters of 3 were prepared including aliphatic, aromatic, and heterocyclic derivatives. Also, two units of 3 were coupled with succinic and phthalic acid as linkers. The compounds were assessed for their gastroprotective effect in the HCl/EtOH-induced gastric lesions model in mice and for cytotoxicity in human lung fibroblasts, human adenocarcinoma AGS cells, and Hep G2 hepatocellular carcinoma cells. At a single oral dose of 40 mg/kg, the gastroprotective effect increased moderately with the length of the alkyl chain. The best effects were observed for the butyrate (9) and chloroacetate (6) derivatives. Activity of fatty acid esters increased with chain length but decreased with unsaturation. The best gastroprotective effect, with lowest cytotoxicity, was found for the palmitate (11) and oleate (12) derivatives.
Authors:
Mariano Walter Pertino; Cristina Theoduloz; Jaime A Rodr?guez; Tania Y??ez; Viviana Lazo; Guillermo Schmeda-Hirschmann
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of natural products     Volume:  73     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2010 Apr 
Date Detail:
Created Date:  2010-04-23     Completed Date:  2010-06-03     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  639-43     Citation Subset:  IM    
Affiliation:
Laboratorio de Quimica de Productos Naturales, Instituto de Quimica de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile.
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MeSH Terms
Descriptor/Qualifier:
Anti-Ulcer Agents / chemistry*,  pharmacology*
Diterpenes, Abietane / chemical synthesis*,  chemistry,  pharmacology*
Dose-Response Relationship, Drug
Gastric Mucosa / drug effects*
Humans
Lactones / chemistry*,  pharmacology*
Molecular Structure
Oleic Acid / chemical synthesis,  chemistry,  pharmacology*
Palmitates / chemical synthesis,  chemistry,  pharmacology*
Plant Extracts / chemical synthesis*,  chemistry,  pharmacology*
Stereoisomerism
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Anti-Ulcer Agents; 0/Diterpenes, Abietane; 0/Lactones; 0/Palmitates; 0/Plant Extracts; 112-80-1/Oleic Acid; 3650-09-7/salvin

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