Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation
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2017
Authors
Milivojević, Ana
Ćorović, Marija

Simović, Milica

Banjanac, Katarina

Vujisić, Ljubodrag V.

Veličković, Dušan
Bezbradica, Dejan

Article (Published version)

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Solubility and stability of flavonoid glycosides, valuable natural constituents of cosmetics and pharmaceuticals, could be improved by lipase-catalyzed acylation. Focus of this study was on development of eco-friendly process for the production of flavonoid acetates. By using phloridzin as model compound and triacetin as acetyl donor and solvent, 100% conversion and high productivity (23.32 gl(-1) day(-1)) were accomplished. Complete conversions of two other glycosylated flavonoids, naringin and esculin, in solvent-free system were achieved, as well. Comprehensive kinetic mechanism based on two con-secutive mono-substrate reactions was established where first one represents formation of flavonoid monoacetate and within second reaction diacetate is being produced from monoacetate. Both steps were regarded as reversible Michaelis-Menten reactions without inhibition. Apparent kinetic parameters for two consecutive reactions (V-m constants for substrates and products and Km constants for f...orward and reverse reactions) were estimated for three examined acetyl acceptors and excellent fitting of experimental data (R-2 gt 0.97) was achieved. Obtained results showed that derived kinetic model could be applicable for solvent-free esterifications of different flavonoid glycosides. It was valid for entire transesterification course (72 h of reaction) which, combined with complete conversions and green character of synthesis, represents firm basis for further process development.
Keywords:
Flavonoid acetylation / Lipase / Solvent-free / Kinetic parameters / COPASISource:
Biochemical Engineering Journal, 2017, 128, 106-115Publisher:
- Elsevier Science Bv, Amsterdam
Funding / projects:
- Novel encapsulation and enzyme technologies for designing of new biocatalysts and biologically active compounds targeting enhancement of food quality, safety and competitiveness (RS-46010)
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
DOI: 10.1016/j.bej.2017.09.018
ISSN: 1369-703X
WoS: 000417008900012
Scopus: 2-s2.0-85030172007
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Tehnološko-metalurški fakultetTY - JOUR AU - Milivojević, Ana AU - Ćorović, Marija AU - Simović, Milica AU - Banjanac, Katarina AU - Vujisić, Ljubodrag V. AU - Veličković, Dušan AU - Bezbradica, Dejan PY - 2017 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3593 AB - Solubility and stability of flavonoid glycosides, valuable natural constituents of cosmetics and pharmaceuticals, could be improved by lipase-catalyzed acylation. Focus of this study was on development of eco-friendly process for the production of flavonoid acetates. By using phloridzin as model compound and triacetin as acetyl donor and solvent, 100% conversion and high productivity (23.32 gl(-1) day(-1)) were accomplished. Complete conversions of two other glycosylated flavonoids, naringin and esculin, in solvent-free system were achieved, as well. Comprehensive kinetic mechanism based on two con-secutive mono-substrate reactions was established where first one represents formation of flavonoid monoacetate and within second reaction diacetate is being produced from monoacetate. Both steps were regarded as reversible Michaelis-Menten reactions without inhibition. Apparent kinetic parameters for two consecutive reactions (V-m constants for substrates and products and Km constants for forward and reverse reactions) were estimated for three examined acetyl acceptors and excellent fitting of experimental data (R-2 gt 0.97) was achieved. Obtained results showed that derived kinetic model could be applicable for solvent-free esterifications of different flavonoid glycosides. It was valid for entire transesterification course (72 h of reaction) which, combined with complete conversions and green character of synthesis, represents firm basis for further process development. PB - Elsevier Science Bv, Amsterdam T2 - Biochemical Engineering Journal T1 - Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation EP - 115 SP - 106 VL - 128 DO - 10.1016/j.bej.2017.09.018 ER -
@article{ author = "Milivojević, Ana and Ćorović, Marija and Simović, Milica and Banjanac, Katarina and Vujisić, Ljubodrag V. and Veličković, Dušan and Bezbradica, Dejan", year = "2017", abstract = "Solubility and stability of flavonoid glycosides, valuable natural constituents of cosmetics and pharmaceuticals, could be improved by lipase-catalyzed acylation. Focus of this study was on development of eco-friendly process for the production of flavonoid acetates. By using phloridzin as model compound and triacetin as acetyl donor and solvent, 100% conversion and high productivity (23.32 gl(-1) day(-1)) were accomplished. Complete conversions of two other glycosylated flavonoids, naringin and esculin, in solvent-free system were achieved, as well. Comprehensive kinetic mechanism based on two con-secutive mono-substrate reactions was established where first one represents formation of flavonoid monoacetate and within second reaction diacetate is being produced from monoacetate. Both steps were regarded as reversible Michaelis-Menten reactions without inhibition. Apparent kinetic parameters for two consecutive reactions (V-m constants for substrates and products and Km constants for forward and reverse reactions) were estimated for three examined acetyl acceptors and excellent fitting of experimental data (R-2 gt 0.97) was achieved. Obtained results showed that derived kinetic model could be applicable for solvent-free esterifications of different flavonoid glycosides. It was valid for entire transesterification course (72 h of reaction) which, combined with complete conversions and green character of synthesis, represents firm basis for further process development.", publisher = "Elsevier Science Bv, Amsterdam", journal = "Biochemical Engineering Journal", title = "Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation", pages = "115-106", volume = "128", doi = "10.1016/j.bej.2017.09.018" }
Milivojević, A., Ćorović, M., Simović, M., Banjanac, K., Vujisić, L. V., Veličković, D.,& Bezbradica, D.. (2017). Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation. in Biochemical Engineering Journal Elsevier Science Bv, Amsterdam., 128, 106-115. https://doi.org/10.1016/j.bej.2017.09.018
Milivojević A, Ćorović M, Simović M, Banjanac K, Vujisić LV, Veličković D, Bezbradica D. Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation. in Biochemical Engineering Journal. 2017;128:106-115. doi:10.1016/j.bej.2017.09.018 .
Milivojević, Ana, Ćorović, Marija, Simović, Milica, Banjanac, Katarina, Vujisić, Ljubodrag V., Veličković, Dušan, Bezbradica, Dejan, "Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation" in Biochemical Engineering Journal, 128 (2017):106-115, https://doi.org/10.1016/j.bej.2017.09.018 . .