Bioprocess and Biosystems Engineering

, Volume 35, Issue 7, pp 1107–1115

Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-α-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity

  • Dušan Veličković
  • Aleksandra Dimitrijević
  • Filip Bihelović
  • Dejan Bezbradica
  • Zorica Knežević-Jugović
  • Nenad Milosavić
Original Paper

DOI: 10.1007/s00449-012-0695-3

Cite this article as:
Veličković, D., Dimitrijević, A., Bihelović, F. et al. Bioprocess Biosyst Eng (2012) 35: 1107. doi:10.1007/s00449-012-0695-3

Abstract

Novel glucoside of physiological active vanillyl alcohol was synthesized for the first time using maltase from Saccharomyces cerevisiae as catalyst, and established its structure as 4-hydroxy-3-methoxybenzyl-α-d-glucopyranoside. The key reaction factors for this transglucosylation reaction were optimized using response surface methodology and the highest yield so far in maltase catalyzed transglucosylation reaction was obtained. It was found out that optimum temperature of reaction was 37 °C, optimal maltose concentration was 60% (w/v), optimal pH was 6.6, and optimal concentration of vanillyl alcohol was 158 mM. Under these conditions, yield of glucoside was 90 mM with no by product formation. It was shown that this compound posses good antioxidant activity as well as stability in gastrointestinal tract. It was demonstrated that it is hydrolyzed on brush border membrane of enterocytes, so it can serve in protecting gastrointestinal system from oxidation, as well as source of anticonvulsive drug after the hydrolysis of glucoside on brush border membrane of small intestine.

Keywords

Vanillyl alcohol Glucoside Maltase Transglucosylation Anticonvulsive Antioxidant activity 

Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Dušan Veličković
    • 1
  • Aleksandra Dimitrijević
    • 1
  • Filip Bihelović
    • 1
  • Dejan Bezbradica
    • 2
  • Zorica Knežević-Jugović
    • 2
  • Nenad Milosavić
    • 1
  1. 1.Faculty of ChemistryUniversity of BelgradeBelgradeSerbia
  2. 2.Faculty of Technology and MetallurgyBelgradeSerbia

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