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Glycyrrhetinic acid (GA) is a principal bioactive pentacyclic triterpenoid from  Glycyrrhiza uralensis . Uridine diphosphate-dependent glycosyltransferases (UGTs) have been widely used to catalyze glycosylation of diverse nature products for the development of potential therapeutic compounds. In this study, we have characterized a UGT109A3 from  Bacillus subtilis , which can glycosylate both the free C3 hydroxyl and C30 carboxyl groups of GA to yield a unique 3, 30- O -β- D -diglucoside-GA. By coupling the microbial UGT109A3 to plant sucrose synthase (SUS), GA-diglucoside could be biosynthesized in an efficient and economical way. With a fed-batch glycosylation, a large scale of GA-diglucoside (6.26 mM, 4.98 g/L in 8 h) could be enzymatically transformed from GA. The obtained GA-diglucoside showed a significant water solubility improvement of around 3.4 × 10 3  fold compared with that of the parent GA (29 μM). Moreover, it also exhibited dose-dependent cytotoxicity toward human colon carcinoma Caco-2 cell line according to MTT assay, having an IC 50  at 160 μM. This study not only establishes efficient platform for producing GA-glucosides, but is also valuable for developing further the biosynthesis of other complex glycosylated natural products.

Highly Efficient Biosynthesis of Glycyrrhetinic Acid Glucosides by Coupling of Microbial Glycosyltransferase to Plant Sucrose Synthase