Enzymatic Synthesis of Phloretin ??Glucosides Using a Sucrose Phosphorylase Mutant and its Effect on Solubility, Antioxidant Properties and Skin Absorption

Glycosylation of polyphenols may increase their aqueous solubility, stability, bioavailability and pharmacological activity. Herein, we used a mutant sucrose phosphorylase from Thermoanaerobacterium thermosaccharolyticum engineered to accept large (variant TtSPP_R134A) produce phloretin glucosides. The reaction was performed using 10% (v/v) acetone as cosolvent. selective formation monoglucoside or diglucoside (53% 73% maximum conversion percentage, respectively) can be kinetically controlled. MS 2D-NMR determined that the 4’-O-?-D-glucopyranoside phloretin-4’-O-[?-D-glucopyranosyl-(1?3)-O-?-D-glucopyranoside], novel compound. molecular features determine specificity this enzyme for 4’-OH phenolic group were analysed by induced-fit docking analysis each putative derivative, crystal structure TtSPP changing mutated residue. mono- were, respectively, 71- 1200-fold more soluble in water than at room temperature. ?-glucosylation decreased antioxidant capacity phloretin, measured DPPH ABTS assays; however, loss moderate activity could recovered upon deglycosylation vivo. Since attracts great interest dermocosmetic applications, analyzed percutaneous absorption glucosides aglycon employing pig skin model. Although three compounds detected all layers (except fluid receptor), present mainly on superficial layers.