Galactosylation of Monosaccharide Derivatives of Glycyrrhetinic Acid by UDP-Glycosyltransferase GmSGT2 from Glycine max

Glycyrrhetinic acid (GA), a pentacyclic triterpenoid aglycone, is the major functional component in licorice which mainly exists in the form of functional glycosides in licorice. The introduction of a sugar moiety to the C-3 OH of GA to yield glycosylated derivatives has been reported, but the late-stage glycosylation of GA-3-O-sugar to form rare GA glycosides with more complexed glycosyl decoration has been rarely reported. In this study, a unique UDP-galactosyltransferase GmSGT2 from Glycine max was found to transfer a galactose to the C2 position of the sugar moiety of GA-3-O-monoglucuronide (GAMG) and GA-3-O-monoglucose. In addition to UDP-galactose, GmSGT2 also recognizes UDP-glucose, UDP-xylose, and UDP-arabinose with relative activities of 32.1-89.2%. Based on a test of 12 typical natural products, GmSGT2 showed high specificity toward the pentacyclic triterpenoid skeleton as the sugar acceptor. Molecular docking was performed to elucidate the substrate recognition mechanism of GmSGT2 toward GAMG.