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Soybean is considered one of the most important crops globally, being ranked ninth among the most cultivated species. Its high production levels are associated with the generation of substantial amounts of waste. These residues are regarded as valuable due to the presence of high-value-added molecules, including glycosides such as daidzin, genistin, and glycitin, which have been extensively studied for their potent antioxidant properties. However, due to their low bioavailability and limited solubility in lipidic media, lipophilization strategies have been increasingly pursued to enhance the application of these glycosides as multifunctional additives in the food, pharmaceutical, and cosmetic industries.
In this context, two parallel approaches were undertaken starting from soybean-derived glycosides: hydrolysis to obtain the corresponding aglycones with improved pharmacokinetic profiles, and esterification of the sugar primary alcohol with short-chain fatty acids. Aglycones were prepared using a homemade extremophilic glycosidase (HOR) from Halothermothrix orenii, with molar conversions of 96–99% achieved in both aqueous and biphasic media (water/2,2,5,5-tetramethyloxolane, 1:1). Subsequently, lipophilization reactions with butanoic, hexanoic, and octanoic acids were performed under flow conditions using commercially available immobilized lipase B from Candida antarctica (CaLB), resulting in modified glycosides with improved physicochemical properties suitable for cosmetic applications. Notably, in comparison to the batch process, compound 1 (6-O-octanoildaidzin) was obtained with a significant reduction in reaction time (30 minutes vs 18 hours) and a ninefold increase in specific reaction rates (0.15 vs 0.017 μmol/(min·g)).
- Corti, M
- Annunziata, F
- Colacicco, A
- Tamborini, L
- Molinari, F
- Contente, ML
- Pinto, A
- Department of Food Environmental and Nutritional Sciences (DeFENS), University of Milan, via Celoria 2, 20133 Milano, Italy
