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Title: Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation

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 g l –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 consecutive 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 K m constants for forward and reverse reactions) were estimated for three examined acetyl acceptors and excellent fitting of experimental data (R 2 > 0.97) was achieved. Obtained results showed that derived kinetic model could be applicable for solvent-free esterifications of different flavonoid glycosides. As a result, it was valid for entire transesterification course (72 h of reaction) which, combined with complete conversions and green character of synthesis,more » represents firm basis for further process development.« less

Authors:
 [1];  [1];  [1];  [1];  [1];  [2];  [1]
  1. Univ. of Belgrade, Belgrade (Serbia)
  2. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Publication Date:
Research Org.:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1395352
Grant/Contract Number:
AC05-76RL01830
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Biochemical Engineering Journal
Additional Journal Information:
Journal Volume: 128; Journal Issue: C; Journal ID: ISSN 1369-703X
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES; Flavonoid acetylation; Lipase; Solvent-free; Kinetic parameters; COPASI

Citation Formats

Milivojevic, Ana, Corovic, Marija, Carevic, Milica, Banjanac, Katarina, Vujisic, Ljubodrag, Velickovic, Dusan, and Bezbradica, Dejan. Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation. United States: N. p., 2017. Web. doi:10.1016/J.BEJ.2017.09.018.
Milivojevic, Ana, Corovic, Marija, Carevic, Milica, Banjanac, Katarina, Vujisic, Ljubodrag, Velickovic, Dusan, & Bezbradica, Dejan. Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation. United States. doi:10.1016/J.BEJ.2017.09.018.
Milivojevic, Ana, Corovic, Marija, Carevic, Milica, Banjanac, Katarina, Vujisic, Ljubodrag, Velickovic, Dusan, and Bezbradica, Dejan. Sat . "Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation". United States. doi:10.1016/J.BEJ.2017.09.018.
@article{osti_1395352,
title = {Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation},
author = {Milivojevic, Ana and Corovic, Marija and Carevic, Milica and Banjanac, Katarina and Vujisic, Ljubodrag and Velickovic, Dusan and Bezbradica, Dejan},
abstractNote = {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 g l–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 consecutive 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 (Vm 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 (R2 > 0.97) was achieved. Obtained results showed that derived kinetic model could be applicable for solvent-free esterifications of different flavonoid glycosides. As a result, 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.},
doi = {10.1016/J.BEJ.2017.09.018},
journal = {Biochemical Engineering Journal},
number = C,
volume = 128,
place = {United States},
year = {Sat Sep 23 00:00:00 EDT 2017},
month = {Sat Sep 23 00:00:00 EDT 2017}
}

Journal Article:
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