Journal
CARBOHYDRATE RESEARCH
Volume 483, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2019.107741
Keywords
Glucansucrase; Modification; NMR spectroscopy; Acceptor reaction; Structural characterization; Purification
Funding
- Carl-Zeiss Foundation
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Flavonoids are commonly abundant, plant-derived polyphenolic compounds which are responsible for color, taste, and antioxidant properties of certain plant based foods. Glucosylation by glucansucrases or other glycosyltransferases/glycoside hydrolases has been described to be a promising approach to modify stability, solubility, bioavailability, and taste profile of flavonoids and other compounds. In this study, we modified and applied a recombinant dextransucrase from Lactobacillus reuteri TMW 1.106 to glucosylate various flavonoids and flavonoid glycosides. The glucoconjugates were subsequently isolated and characterized by using two-dimensional NMR spectroscopy. Efficient glucosylation was achieved for quercetin and its glycosides quercetin-3-O-beta-glucoside and rutin. Significant portions of alpha-glucose conjugates were also obtained for epigallocatechin gallate, dihydromyricetin, and cyanidin-3-O-beta-glucoside, whereas glucosylation efficiency was low for naringin and neohesperidin dihydrochalcone. Most of the flavonoids with a catechol or pyrogallol group at the B-ring were predominantly glucosylated at position O4'. However, glycosyl substituents such as beta-glucose, rutinose, or neohesperidose were glucosylated at varying positions. Therefore, mutant dextransucrase from L. reuteri TMW 1.106 can be applied for versatile structural modification of flavonoids.
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