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The native tree Geoffroea decorticans (cha ar) grows in the arid lands of northern Chile. It has been used as a food plant since prehistoric times. Phenolic-enriched extracts (PEEs) of Chilean cha ar fruits were assessed for their chemical composition, antioxidant properties and inhibition of pro-inflammatory and metabolic syndrome-associated enzymes. Phenolic profiles were determined by HPLC-DAD-MS/MS. The PEEs of G. decorticans showed a strong effect towards the enzymes COX-1/COX-2, with inhibition percentages ranging from inactive to 92.1% and inactive to 76.0% at 50 µg PEE/mL, respectively. The IC50 values of the PEEs towards lipoxygenase and phospholipase A2 inhibitory activity were between 43.6–96.8 and 98.9–156.0 µg PEE/mL, respectively. Samples inhibited α-glucosidase (IC50 0.8–7.3 µg PEE/mL) and lipase (9.9 to 100 µg PEE/mL). However, samples did not inhibit α-amylase. The HPLC-DAD-MS analysis of the PEEs allowed the tentative identification of 53 compounds, mainly flavonol glycosides and procyanidins. The procyanidin content of the Chilean G. decorticans pulp was positively correlated with the antioxidant activity and the inhibition of the enzyme α-glucosidase. These results indicate that the Chilean cha ar fruit contains bioactive polyphenols with functional properties. Fil: Jiménez Aspee, Felipe. Universidad de Talca; Chile Fil: Theoduloz, Cristina. Universidad de Talca; Chile Fil: Soriano, María del Pilar C.. Universidad de Talca; Chile Fil: Ugalde Arbizu, Maider. Universidad de Talca; Chile Fil: Alberto, Maria Rosa. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Zampini, Iris Catiana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Isla, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Simirgiotis, Mario J.. Universidad Austral de Chile; Chile Fil: Schmeda Hirschmann, Guillermo. Universidad de Talca; Chile

A concise diastereotioselective strategy for the synthesis of noscapine, bicuculline, and egenine ( 1a – c ), as well as capnoidine and corytensine ( 2a , b ), was developed using diastereoselective addition of 1-siloxy-isobenzofurans 4a and 4b to iminium ion 5 in a one-pot approach. The synthesis features the use of imine 13 obtained through Bischler–Napieralsky reaction from amine 11 . The addition of ionic liquids as addictives in the reactions afforded erythro configuration in major adduct compounds. The synthetic route can also be applied in the total synthesis of promising tubulin binding agent EM105 ( 3 ).

Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe β-carboline imine reductions employing cell-free extracts from red Californian earthworms ( Eisenia foetida ) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a – g substituents to afford amines with an ( R )-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed.