Glucansucrase catalyzed synthesis and functional characterization of nordihydroguaiaretic acid glucosides

Publication date: Available online 5 October 2018Source: Enzyme and Microbial TechnologyAuthor(s): Johannes Nolte, Lara-Alina Pöttgen, Julia Sperlich, Alessandra Grossert, Alexander Kempa, Nicole Teusch, Ulrich SchörkenAbstractNordihydroguaiaretic acid (NDGA) is the major lignan of the creosote bush Larrea tridentata known for its antioxidative and pharmacological properties. Here we present the identification of glucansucrases for NDGA glucosylation and the physicochemical and biological characterization of the glucosides. Extracellular glucansucrase of L. pseudomesenteroides DSM 20193 was selected from 19 glucansucrase positive Leuconostoc and Weissella strains. Kinetic analysis of the PEG-fractionated enzyme revealed a KM of 6.6 mM and a kcat of 2.6 s-1 for NDGA. Full-factorial design methodology was used to optimize conversion resulting in 95.5 % total NDGA glucosides. In total 7 glucosides were detected by LC-MS ranging from mono- to triglucoside. The 4-O-α-D-monoglucoside and the symmetrical 4,4’-O-α-D-diglucoside were the major products in all biotransformations. Water solubility and half-life stability at 45 °C increased significantly in the order diglucoside > monoglucoside > aglycon. Analysis of cellular antioxidative capacity exhibited a time-dependent activity increase pointing towards glucoside hydrolysis. Accordingly, NDGA-glucosides impaired metastasis of triple negative breast cancer cells to the same degree as the aglycon with 35 % reductio...
Source: Enzyme and Microbial Technology - Category: Biotechnology Source Type: research