Selective cytotoxicity and apoptosis induction in glioma cell lines by 5-oxygenated-6,7-methylenedioxycoumarins from Pterocaulon species

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 IC50...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 57; pp. 268 - 274
Main Authors:	Vianna, D.R., Hamerski, L., Figueiró, F., Bernardi, A., Visentin, L.C., Pires, E.N.S., Teixeira, H.F., Salbego, C.G., Eifler-Lima, V.L., Battastini, A.M.O., von Poser, G.L., Pinto, A.C.
Format:	Journal Article
Language:	English
Published:	Kidlington Elsevier Masson SAS 01-11-2012 Elsevier
Subjects:	5-Oxygenated-6,7-methylenedioxycoumarin Animals Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Apoptosis Apoptosis - drug effects Asteraceae - chemistry Benzodioxoles - isolation & purification Benzodioxoles - pharmacology Biological and medical sciences Cell Line, Tumor Cell Survival - drug effects Central Nervous System Neoplasms - drug therapy Central Nervous System Neoplasms - pathology Coumarins - isolation & purification Coumarins - pharmacology Crystal structure Cytotoxic activity Cytotoxins - isolation & purification Cytotoxins - pharmacology Glioma Glioma - drug therapy Glioma - pathology Hippocampal organotypic culture Hippocampus - cytology Hippocampus - drug effects Humans Hydrogen Bonding Inhibitory Concentration 50 Male Medical sciences Miscellaneous Organ Specificity Pharmacology. Drug treatments Pterocaulon Rats Rats, Wistar Structure-Activity Relationship Tissue Culture Techniques Pterocaulon Glioma Hippocampal organotypic culture 5-Oxygenated-6,7-methylenedioxycoumarin Cytotoxic activity Crystal structure Apoptosis
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Summary:	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 IC50 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. [Display omitted] ► The report deals with the isolation of coumarins from Pterocaulon species. ► 5-Oxygenated-6,7-methylenedioxycoumarins were obtained. ► 5-Methoxy-6,7-methylenedioxycoumarin showed significant cytotoxicity against glioma cells. ► Cytotoxic effect induced in glioma cells was not observed in the organotypic cultures.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0223-5234 1768-3254
DOI:	10.1016/j.ejmech.2012.09.007