Abstract
The coumarins 5-methoxy-6,7-methylenedioxycoumarin 1 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin 2 and 5-(2,3-dihydroxy-3-methylbutyloxy)-6,7-methylenedioxycoumarin 3 isolated from Pterocaulon species showed significant cytotoxicity against two glioma cells lines. Compound 1 presented IC(50) values of 34.6 μM and 31.6 μM against human (U138-MG) and rat (C6) glioma cells, respectively, and this compound was at least two times more potent than compounds 2 and 3. This result could be explained by the planar conformation adopted by 1 through a non-classical hydrogen bond between a hydrogen of the methoxy and the oxygen of the methylenedioxy groups. Another important finding was that the cytotoxic effect induced by 1 in glioma cells was not observed in organotypic cultures, indicating a selective cytotoxicity for tumor cells.
Copyright © 2012 Elsevier Masson SAS. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antineoplastic Agents / isolation & purification*
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Antineoplastic Agents / pharmacology
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Apoptosis / drug effects*
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Asteraceae / chemistry*
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Benzodioxoles / isolation & purification*
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Benzodioxoles / pharmacology
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Cell Line, Tumor
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Cell Survival / drug effects
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Central Nervous System Neoplasms / drug therapy
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Central Nervous System Neoplasms / pathology
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Coumarins / isolation & purification*
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Coumarins / pharmacology
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Cytotoxins / isolation & purification*
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Cytotoxins / pharmacology
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Glioma / drug therapy
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Glioma / pathology
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Hippocampus / cytology
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Hippocampus / drug effects
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Humans
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Hydrogen Bonding
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Inhibitory Concentration 50
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Male
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Organ Specificity
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Rats
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Rats, Wistar
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Structure-Activity Relationship
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Tissue Culture Techniques
Substances
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5-(2,3-dihydroxy-3-methylbutyloxy)-6,7-methylenedioxycoumarin
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5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin
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5-methoxy-6,7-methylenedioxycoumarin
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Antineoplastic Agents
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Benzodioxoles
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Coumarins
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Cytotoxins