Novel Biotransformation of Maslinic Acid to MA-2-O-β-D-Glucoside by UDP-Glycosyltransferases from Bacillus subtilis

Abstract

Maslinic acid (MA) is a pentacyclic triterpenoid which originates from olive and other plants. Though MA possesses multiple biological activities, it has limitations due to its poor water solubility. YojK, YjiC, and UGT109A3 UDP-glycosyltransferases (UGTs) from Bacillus subtilis (B. subtilis) were utilized to catalyze the conjugation of MA with UDP-Glucose to generate a new MA glycosylation product, MA-2-O-β-D-glucoside (MA-2-O-β-D-Glu). The experimental results indicated that the resultant water solubility of MA-2-O-β-D-Glu is 1.69 times higher than that of MA. In addition, the recombinant YojK showed maximum activity at 40 °C with a pH range of 8.0−10.0, while the recombinant YjiC showed maximum activity at 45 °C with a pH of 8.0, and the recombinant UGT109A3 showed maximum activity at 40 °C with a pH of 8.0. Mg2+ is an important factor for efficient catalysis by three recombinant glycosyltransferases. The chemical conversion rate of the recombinant YojK, YjiC, and UGT109A3 is nearly 100% at their optimum pH, temperature, and metal ions. Furthermore, eight essential residues of three UGTs for MA glycosylation modification were further determined by molecular docking and site-directed mutagenesis. Thus, efficient glycosylation modification improves the water solubility of MA and provides a new potential method for the glycosylation modification of other pentacyclic triterpenoids.