Milivojević, Ana

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  • Milivojević, Ana (3)
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Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate

Ćorović, Marija; Milivojević, Ana; Carević, Milica B.; Banjanac, Katarina; Vujisić, Ljubodrag V.; Pjanović, Rada V.; Bezbradica, Dejan

(2018)

TY  - JOUR
AU  - Ćorović, Marija
AU  - Milivojević, Ana
AU  - Carević, Milica B.
AU  - Banjanac, Katarina
AU  - Vujisić, Ljubodrag V.
AU  - Pjanović, Rada V.
AU  - Bezbradica, Dejan
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/217
AB  - Lipophilic derivatives of vitamin C are additives with antioxidant properties, attractive for application in food, cosmetics and pharmaceutics. They could be synthesized in lipase-catalyzed processes by using various acyl donors. Hereby, we present application of linoleic acid, which is polyunsaturated fatty acid essential in human nutrition, for esterification of vitamin C catalyzed by immobilized enzyme preparation Novozym® 435 in acetone. Highest specific ester yield, 9.7 mmol/g of immobilized lipase, was accomplished with 0.15 M of vitamin C, 0.6 M of linoleic acid, 3 g/l of enzyme and 0.07% (v/v) of water, at 60°C. NMR analyses of purified product proved that synthesized molecule was identical to 6-O-ascorbyl linoleate. Capacity of ester for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals was two times higher comparing to parent molecule, vitamin C. Its diffusion coefficient, determined using Franz cell and cellulose acetate membrane, was 40% higher than palmitate and 62% higher than oleate. Obtained results showed that L-ascorbyl linoleate could be successfully synthesized in biocatalyzed processes. Furthermore, it was demonstrated that it possess high potential for application in different lipophilic products due to its liposolubility, high antioxidant efficiency and good diffusion properties.
AB  - Lipofilni derivati vitamina C su aditivi sa antioksidativnim dejstvom pogodni za primenu u prehrambenim, kozmetičkim i farmaceutskim proizvodima. Mogu biti sintetisani u procesima katalizovanim lipazama korišćenjem različitih acil-donora. U ovom radu, opisana je primena linolne kiseline, polinezasićene masne kiseline esencijalne u ljudskoj ishrani, u esterifikaciji vitamina C katalizovanoj imobilisanim enzimskim preparatom Novozym® 435 u acetonu. Najviši specifični prinos estra od 9,7 mmol/g imobilisane lipaze, ostvaren je sa 0,15 M vitamina C, 0,6 M linolne kiseline, 3 g/l enzima i 0,07 zapr. % vode, na 60°C. NMR analize prečišćenog proizvoda dokazale su da je sintetisani molekul identičan 6-O-askorbil-linolatu. Kapacitet estra za vezivanje 2,2- difenil-1-pikrilhidrazil radikala bio je dva puta viši u odnosu na sam vitamin C. Njegov koeficijent difuzije, određen korišćenjem Franz-ove ćelije i celuloza-acetatne membrane, bio je za 40% viši u odnosu na palmitat i za 62% u odnosu na oleat. Ostvareni rezultati pokazali su da L-askorbil-linolat može uspešno biti sintetisan u biokatalizovanom procesu. Pored toga, dokazano je da ovaj estar poseduje značajan potencijal za primenu u različitim lipofilnim proizvodima zbog svoje liposolubilnosti, snažnog antioksidativnog dejstva i pogodnih difuzionih karakteristika.
T2  - Food and Feed Research
T1  - Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate
T1  - enzimska lipofilizacija vitamina C linolnom kiselinom - određivanje antioksidativnih i difuzionih svojstava L-askorbil-linolata
VL  - 45
IS  - 1
SP  - 1
EP  - 10
DO  - 10.5937/FFR1801001C
UR  - Kon_157
ER  - 
@article{
author = "Ćorović, Marija and Milivojević, Ana and Carević, Milica B. and Banjanac, Katarina and Vujisić, Ljubodrag V. and Pjanović, Rada V. and Bezbradica, Dejan",
year = "2018",
abstract = "Lipophilic derivatives of vitamin C are additives with antioxidant properties, attractive for application in food, cosmetics and pharmaceutics. They could be synthesized in lipase-catalyzed processes by using various acyl donors. Hereby, we present application of linoleic acid, which is polyunsaturated fatty acid essential in human nutrition, for esterification of vitamin C catalyzed by immobilized enzyme preparation Novozym® 435 in acetone. Highest specific ester yield, 9.7 mmol/g of immobilized lipase, was accomplished with 0.15 M of vitamin C, 0.6 M of linoleic acid, 3 g/l of enzyme and 0.07% (v/v) of water, at 60°C. NMR analyses of purified product proved that synthesized molecule was identical to 6-O-ascorbyl linoleate. Capacity of ester for scavenging 2,2-diphenyl-1-picrylhydrazyl radicals was two times higher comparing to parent molecule, vitamin C. Its diffusion coefficient, determined using Franz cell and cellulose acetate membrane, was 40% higher than palmitate and 62% higher than oleate. Obtained results showed that L-ascorbyl linoleate could be successfully synthesized in biocatalyzed processes. Furthermore, it was demonstrated that it possess high potential for application in different lipophilic products due to its liposolubility, high antioxidant efficiency and good diffusion properties., Lipofilni derivati vitamina C su aditivi sa antioksidativnim dejstvom pogodni za primenu u prehrambenim, kozmetičkim i farmaceutskim proizvodima. Mogu biti sintetisani u procesima katalizovanim lipazama korišćenjem različitih acil-donora. U ovom radu, opisana je primena linolne kiseline, polinezasićene masne kiseline esencijalne u ljudskoj ishrani, u esterifikaciji vitamina C katalizovanoj imobilisanim enzimskim preparatom Novozym® 435 u acetonu. Najviši specifični prinos estra od 9,7 mmol/g imobilisane lipaze, ostvaren je sa 0,15 M vitamina C, 0,6 M linolne kiseline, 3 g/l enzima i 0,07 zapr. % vode, na 60°C. NMR analize prečišćenog proizvoda dokazale su da je sintetisani molekul identičan 6-O-askorbil-linolatu. Kapacitet estra za vezivanje 2,2- difenil-1-pikrilhidrazil radikala bio je dva puta viši u odnosu na sam vitamin C. Njegov koeficijent difuzije, određen korišćenjem Franz-ove ćelije i celuloza-acetatne membrane, bio je za 40% viši u odnosu na palmitat i za 62% u odnosu na oleat. Ostvareni rezultati pokazali su da L-askorbil-linolat može uspešno biti sintetisan u biokatalizovanom procesu. Pored toga, dokazano je da ovaj estar poseduje značajan potencijal za primenu u različitim lipofilnim proizvodima zbog svoje liposolubilnosti, snažnog antioksidativnog dejstva i pogodnih difuzionih karakteristika.",
journal = "Food and Feed Research",
title = "Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate, enzimska lipofilizacija vitamina C linolnom kiselinom - određivanje antioksidativnih i difuzionih svojstava L-askorbil-linolata",
volume = "45",
number = "1",
pages = "1-10",
doi = "10.5937/FFR1801001C",
url = "Kon_157"
}
Ćorović, M., Milivojević, A., Carević, M. B., Banjanac, K., Vujisić, L. V., Pjanović, R. V.,& Bezbradica, D.. (2018). Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate. in Food and Feed Research, 45(1), 1-10.
https://doi.org/10.5937/FFR1801001C
Kon_157
Ćorović M, Milivojević A, Carević MB, Banjanac K, Vujisić LV, Pjanović RV, Bezbradica D. Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate. in Food and Feed Research. 2018;45(1):1-10.
doi:10.5937/FFR1801001C
Kon_157 .
Ćorović, Marija, Milivojević, Ana, Carević, Milica B., Banjanac, Katarina, Vujisić, Ljubodrag V., Pjanović, Rada V., Bezbradica, Dejan, "Enzymatic lipophilization of vitamin C with linoleic acid: Determination of antioxidant and diffusion properties of L-ascorbyl linoleate" in Food and Feed Research, 45, no. 1 (2018):1-10,
https://doi.org/10.5937/FFR1801001C .,
Kon_157 .

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

Milivojević, Ana; Ćorović, Marija; Carević, Milica; Banjanac, Katarina; Vujisić, Ljubodrag V.; Veličković, Dusan; Bezbradica, Dejan

(Elsevier Science Bv, Amsterdam, 2017)

TY  - JOUR
AU  - Milivojević, Ana
AU  - Ćorović, Marija
AU  - Carević, Milica
AU  - Banjanac, Katarina
AU  - Vujisić, Ljubodrag V.
AU  - Veličković, Dusan
AU  - Bezbradica, Dejan
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2558
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. (C) 2017 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Biochemical Engineering Journal
T1  - Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation
VL  - 128
SP  - 106
EP  - 115
DO  - 10.1016/j.bej.2017.09.018
UR  - Kon_3374
ER  - 
@article{
author = "Milivojević, Ana and Ćorović, Marija and Carević, Milica and Banjanac, Katarina and Vujisić, Ljubodrag V. and Veličković, Dusan 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. (C) 2017 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Biochemical Engineering Journal",
title = "Highly efficient enzymatic acetylation of flavonoids: Development of solvent-free process and kinetic evaluation",
volume = "128",
pages = "106-115",
doi = "10.1016/j.bej.2017.09.018",
url = "Kon_3374"
}
Milivojević, A., Ćorović, M., Carević, 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
Kon_3374
Milivojević A, Ćorović M, Carević 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
Kon_3374 .
Milivojević, Ana, Ćorović, Marija, Carević, Milica, Banjanac, Katarina, Vujisić, Ljubodrag V., Veličković, Dusan, 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 .,
Kon_3374 .
6
6
6

Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018.

Milivojević, Ana; Ćorović, Marija; Carević, Milica; Banjanac, Katarina; Vujisić, Ljubodrag V.; Veličković, Dusan; Bezbradica, Dejan

(Elsevier Science Bv, Amsterdam, 2017)

TY  - DATA
AU  - Milivojević, Ana
AU  - Ćorović, Marija
AU  - Carević, Milica
AU  - Banjanac, Katarina
AU  - Vujisić, Ljubodrag V.
AU  - Veličković, Dusan
AU  - Bezbradica, Dejan
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2974
PB  - Elsevier Science Bv, Amsterdam
T2  - Biochemical Engineering Journal
T1  - Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018.
ER  - 
@misc{
author = "Milivojević, Ana and Ćorović, Marija and Carević, Milica and Banjanac, Katarina and Vujisić, Ljubodrag V. and Veličković, Dusan and Bezbradica, Dejan",
year = "2017",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Biochemical Engineering Journal",
title = "Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018."
}
Milivojević, A., Ćorović, M., Carević, M., Banjanac, K., Vujisić, L. V., Veličković, D.,& Bezbradica, D.. (2017). Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018.. in Biochemical Engineering Journal
Elsevier Science Bv, Amsterdam..
Milivojević A, Ćorović M, Carević M, Banjanac K, Vujisić LV, Veličković D, Bezbradica D. Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018.. in Biochemical Engineering Journal. 2017;..
Milivojević, Ana, Ćorović, Marija, Carević, Milica, Banjanac, Katarina, Vujisić, Ljubodrag V., Veličković, Dusan, Bezbradica, Dejan, "Supplementary data for article: Milivojević, A.; Ćorović, M.; Carevic, M.; Banjanac, K.; Vujisić, L. V.; Velickovic, D.; Bezbradica, D. Highly Efficient Enzymatic Acetylation of Flavonoids: Development of Solvent-Free Process and Kinetic Evaluation. Biochemical Engineering Journal 2017, 128, 106–115. https://doi.org/10.1016/j.bej.2017.09.018." in Biochemical Engineering Journal (2017).