Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-alpha-d-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity
Само за регистроване кориснике
2012
Аутори
Veličković, DušanDimitrijević, Aleksandra
Bihelović, Filip
Bezbradica, Dejan
Knežević-Jugović, Zorica
Milosavić, Nenad
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Кључне речи:
Vanillyl alcohol / Glucoside / Maltase / Transglucosylation / Anticonvulsive / Antioxidant activityИзвор:
Bioprocess and Biosystems Engineering, 2012, 35, 7, 1107-1115Издавач:
- Springer, New York
Финансирање / пројекти:
- 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-FP7-256716)
- Алергени, антитела, ензими и мали физиолошки значајни молекули: дизајн, структура, функција и значај (RS-MESTD-Basic Research (BR or ON)-172049)
- Развој нових инкапсулационих и ензимских технологија за производњу биокатализатора и биолошки активних компонената хране у циљу повећања њене конкурентности, квалитета и безбедности (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-46010)
DOI: 10.1007/s00449-012-0695-3
ISSN: 1615-7591
PubMed: 22307809
WoS: 000307514500007
Scopus: 2-s2.0-84865357405
Институција/група
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 . .