Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity
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2012
Authors
Veličković, DušanDimitrijević, Aleksandra
Bihelović, Filip
Bezbradica, Dejan
Knežević-Jugović, Zorica
Milosavić, Nenad
Article (Published version)
Metadata
Show full item recordAbstract
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-alpha-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 A degrees 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 activitySource:
Bioprocess and Biosystems Engineering, 2012, 35, 7, 1107-1115Publisher:
- Springer, New York
Funding / projects:
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
- Allergens, antibodies, enzymes and small physiologically important molecules: design, structure, function and relevance (RS-172049)
- Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness (RS-46010)
DOI: 10.1007/s00449-012-0695-3
ISSN: 1615-7591
PubMed: 22307809
WoS: 000307514500007
Scopus: 2-s2.0-84865357405
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Veličković, Dušan AU - Dimitrijević, Aleksandra AU - Bihelović, Filip AU - Bezbradica, Dejan AU - Knežević-Jugović, Zorica AU - Milosavić, Nenad PY - 2012 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2109 AB - 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-alpha-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 A degrees 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. PB - Springer, New York T2 - Bioprocess and Biosystems Engineering T1 - Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity EP - 1115 IS - 7 SP - 1107 VL - 35 DO - 10.1007/s00449-012-0695-3 ER -
@article{ author = "Veličković, Dušan and Dimitrijević, Aleksandra and Bihelović, Filip and Bezbradica, Dejan and Knežević-Jugović, Zorica and Milosavić, Nenad", year = "2012", 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-alpha-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 A degrees 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.", publisher = "Springer, New York", journal = "Bioprocess and Biosystems Engineering", title = "Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity", pages = "1115-1107", number = "7", volume = "35", doi = "10.1007/s00449-012-0695-3" }
Veličković, D., Dimitrijević, A., Bihelović, F., Bezbradica, D., Knežević-Jugović, Z.,& Milosavić, N.. (2012). Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity. in Bioprocess and Biosystems Engineering Springer, New York., 35(7), 1107-1115. https://doi.org/10.1007/s00449-012-0695-3
Veličković D, Dimitrijević A, Bihelović F, Bezbradica D, Knežević-Jugović Z, Milosavić N. Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity. in Bioprocess and Biosystems Engineering. 2012;35(7):1107-1115. doi:10.1007/s00449-012-0695-3 .
Veličković, Dušan, Dimitrijević, Aleksandra, Bihelović, Filip, Bezbradica, Dejan, Knežević-Jugović, Zorica, Milosavić, Nenad, "Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity" in Bioprocess and Biosystems Engineering, 35, no. 7 (2012):1107-1115, https://doi.org/10.1007/s00449-012-0695-3 . .