Identification of polyphenols in grape pomace and new synthetic approaches to 2,3-diaryl-2,3- dihydrobenzofurans, useful active ingredients against degenerative diseases

The PhD project is divided in two main studies, the first concerning in the identification of polyphenols in Grape Pomace and the second in developing new synthetic approaches to 2,3-disubstituted-2,3- dihydlobenzofurans. The Grape Pomace (a mixture of mainly skins and seeds) is one of the most abundant by-products of the winemaking process, which represents a waste management issue both ecologically and economically. However, it is considered a potential source of bioactive phenolic compounds that, thank to thanks to their innumerable beneficial properties for human health, it can be applied in the food and pharmaceutical industries. In this context, the aim of the first study, carried out at Osun Solution S.r.l. (Lauria, Italy), was analyzed the content of total polyphenol compounds and of trans-resu,eraîrol into three different varieties of grape pomace ("Aglianico del Vulture", "Yuko" and "Piedirosso') using two different extràction procedures, the first one using classical alcoholic aqueous conditions, the second one carried out by spray-drying microencapsulation using maltodextrin as camier material. The amount of the total soluble polyphenols obtained in all three extracts, using the Folin-Ciocalteau (FQ method, was very good, so these wine byproducts could be a potential matrices for the formulation of new drugs and supplements food. The HPLC-UV method applied for the quantification of trans-resveratrol in the three GP extracts gave a bad to quite good separation in the chromatographic runs. This method, although it will need to be optimized, is the only one, among the many methods tested, to allow a preliminary quantitative evaluation of trans-resveratrol in the GP extracts. In the GP from "Piedirosso " analysis the peak of trans-resveratrol was not much resolved and for this reason the content of trans-resveratrol obtained could not be accurately evaluated. A better separation was obtained in the chromatographic runs of GP from "Aglianico del Vulture" and the content of trans-resveratrol was found quite in agreement with the results obtained in previous research on different red grape. Finally, the best separation was obtained in the chromatographic runs of GP from "Yuko ", in which the peak of trans-resveratrol was quite resolved and the content obtained very high. The 2,3-dihydrobenfuran-2,3-disubstituted system constitute the key structural motif of numerous biologically active compounds, as resveratrol dimers. These natural compounds, that have a broad spectrum of beneficial effect, are present in very small quantities in plants and for this reason they have recently received significant attention from the scientific community in order to obtain them and their derivatives synthetically. In this context, the aim of the second shrdy carried out at "University of Basilicata" (Potenza,Italy) and at "Université de Strasbourg" (Strasbourg, France), was focused on the development of two new synthetic approach for stereo- and entantioselective synthesis of trans-2,3-diaryl- 2,3-dihydrobenzofurans systems, the first one via regio- and diastereoselective arylation of trans 2.3-diaryloxiranes and the second one via metal-catalyzed C- H functionalisation of diarylacetaldehyde. [edited by Author]