C13-norisoprenoids are carotenoid-derived aroma compounds responsible for the characteristic aroma and flavors of wine. The majority of C13-norisoprenoids present in grapes exist either as free volatiles or as non-volatile glycoconjugates. The glucosidic forms of these compounds can undergo either acid or enzymatic hydrolysis to trigger the release of free volatiles contributing to the wine aroma and flavors. This research aims to investigate the glycosides of C13-norisoprenoids and the corresponding chemical pathways for their formation in grapevine leaves, grape berries and as wine metabolites. A combined approach involving the total synthesis of megastigm-4-en-3,6,9-triol-9-O-glucoside, megastigm-4-en-3,6,9-triol-3-O-glucoside, 4,5-dihydrovomifoliol 9-O-β-D-glucopyranoside tetra-acetate and 4,5-dihydrovomifoliol 3-O-β-D-glucopyranoside (<b>Figure 1</b>), will allow analysis of these molecules from natural sources using mass-spectrometry (MS). In addition, computational modelling by high-level quantum chemical modelling will provide complementary structural, energetic and dynamic details to support total synthesis mechanisms of these glycosides.

Total synthesis, analysis and theoretical studies towards the characterisation of bioactive grape and wine metabolites

254th National Meeting (2017)

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