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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 (publishedVersion)
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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 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 / COPASI
Source:
Biochemical Engineering Journal, 2017, 128, 106-115
Publisher:
  • Elsevier Science Bv, Amsterdam
Funding / projects:
  • info:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/46010/RS// (RS-46010)
  • info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172053/RS// (RS-172053)

DOI: 10.1016/j.bej.2017.09.018

ISSN: 1369-703X

WoS: 000417008900012

Scopus: 2-s2.0-85030172007
[ Google Scholar ]
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3593
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  • Radovi istraživača / Researchers’ publications (TMF)
  • Radovi istraživača (Inovacioni centar) / Researchers’ publications (Innovation Centre)
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Tehnološko-metalurški fakultet

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