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A novel acylated derivate of phloretin and its use as antioxidant
EP22382582
The invention relates to a method for producing acylated derivate of polyphenols comprising α-glucosylation of the phloretin with a sucrose phosphorylase mutant from T. thermosaccharolyticum and acylation with the lipase from Thermomyces lanuginosus, obtaining a novel acylated derivate of phloretin, particularly the phloretin 4’-O-(6-O-lauryl)-α-D-glucopyranoside. Further,it relates the use of phloretin 4’-O-(6-O-lauryl)-α-D-glucopyranoside as antioxidant.
The ability of these compounds to cross skin barriers depends largely on their lipophilicity. Binding a fatty acid to the flavonoid molecule can enhance its affinity for the lipid membranes of skin cells and thus improve absorption. Acylation of polyphenols can also modify other bioactivities of these compounds, increase their stability or even allow the design of a prodrug. The enzymatic method developed allows the selective production of acylated polyphenol derivatives, with an overall process yield of more than 80%. Using a porcine skin model, it has been shown that the acyl-alpha-glucoside derivative of phloretin has a significantly higher percutaneous absorption than either phloretin or its alpha-glucoside.