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Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity

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2015
Influence_of_fatty_acc_2015.pdf (828.0Kb)
Authors
Stojanović, Marija
Simović, Milica
Mihailović, Mladen
Veličković, Dušan
Dimitrijević, Aleksandra
Milosavić, Nenad
Bezbradica, Dejan
Article (Accepted Version)
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Abstract
Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco-friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase-catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short-chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L-1 of lipase, 50 mM of vitamin C, 10-fold molar excess of oleic acid, and 0.7 mL L-1 of initial water. Obtained results showed that even short- and medium-...chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l-ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes.

Keywords:
antioxidant / ascorbyl ester / Candida antarctica lipase B / fatty acid / vitamin C
Source:
Biotechnology and Applied Biochemistry, 2015, 62, 4, 458-466
Publisher:
  • Wiley, Hoboken
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)
Note:
  • This is the peer-reviewed version of the following article: Stojanović, M.; Simović, M.; Mihailović, M.; Veličković, D.; Dimitrijević, A.; Milosavić, N.; Bezbradica, D. Influence of Fatty Acid on Lipase-Catalyzed Synthesis of Ascorbyl Esters and Their Free Radical Scavenging Capacity. Biotechnology and Applied Biochemistry 2015, 62 (4), 458–466. https://doi.org/10.1002/bab.1296

DOI: 10.1002/bab.1296

ISSN: 0885-4513

WoS: 000360229200004

Scopus: 2-s2.0-84939574136
[ Google Scholar ]
10
8
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4720
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Stojanović, Marija
AU  - Simović, Milica
AU  - Mihailović, Mladen
AU  - Veličković, Dušan
AU  - Dimitrijević, Aleksandra
AU  - Milosavić, Nenad
AU  - Bezbradica, Dejan
PY  - 2015
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4720
AB  - Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco-friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase-catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short-chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L-1 of lipase, 50 mM of vitamin C, 10-fold molar excess of oleic acid, and 0.7 mL L-1 of initial water. Obtained results showed that even short- and medium-chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l-ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes.
PB  - Wiley, Hoboken
T2  - Biotechnology and Applied Biochemistry
T1  - Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity
EP  - 466
IS  - 4
SP  - 458
VL  - 62
DO  - 10.1002/bab.1296
ER  - 
@article{
author = "Stojanović, Marija and Simović, Milica and Mihailović, Mladen and Veličković, Dušan and Dimitrijević, Aleksandra and Milosavić, Nenad and Bezbradica, Dejan",
year = "2015",
abstract = "Fatty acid (FA) ascorbyl esters are recently emerging food, cosmetic, and pharmaceutical additives, which can be prepared in an eco-friendly way by using lipases as catalysts. Because they are amphiphilic molecules, which possess high free radical scavenging capacity, they can be applied as liposoluble antioxidants as well as emulsifiers and biosurfactants. In this study, the influence of a wide range of acyl donors on ester yield in lipase-catalyzed synthesis and ester antioxidant activity was examined. Among saturated acyl donors, higher yields and antioxidant activities of esters were achieved when short-chain FAs were used. Oleic acid gave the highest yield overall and its ester exhibited a high antioxidant activity. Optimization of experimental factors showed that the highest conversion (60.5%) in acetone was achieved with 5 g L-1 of lipase, 50 mM of vitamin C, 10-fold molar excess of oleic acid, and 0.7 mL L-1 of initial water. Obtained results showed that even short- and medium-chain ascorbyl esters could be synthesized with high yields and retained (or even exceeded) free radical scavenging capacity of l-ascorbic acid, indicating prospects of broadening their application in emulsions and liposomes.",
publisher = "Wiley, Hoboken",
journal = "Biotechnology and Applied Biochemistry",
title = "Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity",
pages = "466-458",
number = "4",
volume = "62",
doi = "10.1002/bab.1296"
}
Stojanović, M., Simović, M., Mihailović, M., Veličković, D., Dimitrijević, A., Milosavić, N.,& Bezbradica, D.. (2015). Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity. in Biotechnology and Applied Biochemistry
Wiley, Hoboken., 62(4), 458-466.
https://doi.org/10.1002/bab.1296
Stojanović M, Simović M, Mihailović M, Veličković D, Dimitrijević A, Milosavić N, Bezbradica D. Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity. in Biotechnology and Applied Biochemistry. 2015;62(4):458-466.
doi:10.1002/bab.1296 .
Stojanović, Marija, Simović, Milica, Mihailović, Mladen, Veličković, Dušan, Dimitrijević, Aleksandra, Milosavić, Nenad, Bezbradica, Dejan, "Influence of fatty acid on lipase-catalyzed synthesis of ascorbyl esters and their free radical scavenging capacity" in Biotechnology and Applied Biochemistry, 62, no. 4 (2015):458-466,
https://doi.org/10.1002/bab.1296 . .

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