Alkaloids from Chelidonium majus L.: Fractionated supercritical CO2 extraction with co-solvents

Chelidonium majus L. is rich in many isoquinoline alkaloids which are responsible for the anti-inflammatory, antitumor and cytotoxic bioactivities known for this plant. The main alkaloids identified in C. majus L. include chelidonine, berberine, coptisine, sanguinarine and chelerythrine, which are present in different parts of the plant. In this work, alkaloids from C. majus aerial and terrestrial parts were extracted using a two step extraction procedure which consisted in a first step (SFE) using only supercritical carbon dioxide (scCO2) as solvent followed by a second step (ESE) using scCO2 and a co-solvent mixture composed by an alcohol (ethanol or isopropanol) and diethylamine (alkaline conditions). The effect of operation temperature, pressure, solvent density and solvent pH on extraction yields, kinetic profiles and alkaloids? selectivity was evaluated. Results showed that SFE presents high selectivity for alkaloids (particularly for chelidonine) at solvent densities in the range 813-850 kg/m3 and for both the aerial and terrestrial parts of the plant. The highest lipoxygenase inhibition capacity was observed for extracts obtained by SFE, in particular those obtained from the aerial parts of C. majus L. at higher solvent density conditions. The highest alkaloids extraction yield was observed at higher solvent density conditions using the scCO2/isopropanol/diethylamine mixture (ESE extraction step). The highest antioxidant capacity was observed for the extracts obtained from the terrestrial parts of C. majus L. using this co-solvent mixture at lower solvent density. Chelidonine was found to be highly soluble in scCO2. Therefore, the fractioned high pressure extraction procedure proposed in this work can be successfully applied to separate enriched chelidonine fractions, while other alkaloids can be obtained using basified isopropanol as co-solvent. This procedure demonstrates that alkaloids fractionation during extraction is an important tool to be used before further purification/isolation steps.Fil: Gañan, Nicolas Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Dias, Ana M. A.. Universidad de Coimbra; PortugalFil: Bombaldi, Fernanda. Universidad de Coimbra. Facultad de Ciencias E Tecnología; Portugal. Universidad de Coimbra; PortugalFil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Brignole, Esteban Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Sousa, Herminio C. de. Universidad de Coimbra; PortugalFil: Braga, Mara E. M.. Universidad de Coimbra; Portuga