CONICET | Buscador de Institutos y Recursos Humanos

Butenolides (substituted furan-(5H)-2-one) form a family of unsaturated five-membered lactones. The large majority among them are plant metabolites displaying a wide range of biological activities. 3-(benzyloxymethyl)furan-5H-2-one is an α,β-unsaturated lactone, which was obtained by our group during extensive research on the development of new anti-ulcer and mast cell stabilizer molecules from plant products. The general strategy for the construction of butenolides from furan was applied to 3-(benzyloxymethyl)furan, yielding the butenolide 3-(benzyloxymethyl)furan-5H-2-one. This butenolide (100% purity, flash chromatography) was identified by 1H and 13C NMR (Nuclear Magnetic Resonance), mass spectrometry, infrared spectra, and melting point analysis. Peritoneal mast cells from male adult Sprague-Dawley rats were purified in Percoll, preincubated in the presence of 3-(benzyloxymethyl)furan-5H-2-one and then challenged with the mast cell activator calcium ionophore A23187 (10 µg/ml). Concentration-response and kinetic studies of mast cell β-hexosaminidase release evoked by A23187, and evaluation of mast cell viability and morphology by light and electron microscopy were carried out. Biochemical release studies, carried out together with morphological studies, showed the effectiveness of the above butenolide to stabilize mast cells. Our findings suggest that this α,β-unsaturated lactone could be effective in the treatment of diseases associated with inappropriate mast cell activation and may provide an insight into the design of novel pharmacological agents which may be used to regulate the mast cell response.