Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-α-D-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity.
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.
Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
Dušan
D
Veličković
Aleksandra
A
Dimitrijević
Filip
F
Bihelović
Dejan
D
Bezbradica
Zorica
Z
Knežević-Jugović
Nenad
N
Milosavić
D000840:Anisoles / Q000737:chemistry* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology; D001592:Benzyl Alcohols / Q000737:chemistry*; D002853:Chromatography, Liquid; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry
C000591714:4-hydroxy-3-methoxybenzylglucopyranoside; D000840:Anisoles; D000975:Antioxidants; D001592:Benzyl Alcohols; D005960:Glucosides; D006027:Glycosides; C024078:vanillyl alcohol