Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica
Само за регистроване кориснике
2013
Аутори
Jakovetić, SonjaJugović, Branimir
Gvozdenović, Milica M.
Bezbradica, Dejan
Antov, Mirjana
Mijin, Dušan
Knežević Jugović, Zorica
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Immobilized lipase from Candida antarctica (Novozyme 435) was tested for the synthesis of various phenolic acid esters (ethyl and n-butyl cinnamate, ethyl p-coumarate and n-butyl p-methoxycinnamate). The second-order kinetic model was used to mathematically describe the reaction kinetics and to compare present processes quantitatively. It was found that the model agreed well with the experimental data. Further, the effect of alcohol type on the esterification of cinnamic acid was investigated. The immobilized lipase showed more ability to catalyze the synthesis of butyl cinnamate. Therefore, the process was optimized for the synthesis of butyl cinnamate as a function of solvent polarity (logP) and amount of biocatalyst. The highest ester yield of 60.7 % was obtained for the highest enzyme concentration tested (3 % w/w), but the productivity was for 34 % lower than the corresponding value obtained for the enzyme concentration of 1 % (w/w). The synthesized esters were purified, identifie...d, and screened for antioxidant activities. Both DPPH assay and cyclic voltammetry measurement have shown that cinnamic acid esters have better antioxidant properties than cinnamic acid itself.
Кључне речи:
aliphatic esters / cinnamic acid / lipophilic antioxidants / Candida antarctica / lipase B / catalysisИзвор:
Applied Biochemistry and Biotechnology, 2013, 170, 7, 1560-1573Издавач:
- Springer
Финансирање / пројекти:
- Развој нових инкапсулационих и ензимских технологија за производњу биокатализатора и биолошки активних компонената хране у циљу повећања њене конкурентности, квалитета и безбедности (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-46010)
DOI: 10.1007/s12010-013-0294-z
ISSN: 0273-2289 (Print); 1559-0291
WoS: 000322542900002
Scopus: 2-s2.0-84881231766
Институција/група
Институт техничких наука САНУ / Institute of Technical Sciences of SASATY - JOUR AU - Jakovetić, Sonja AU - Jugović, Branimir AU - Gvozdenović, Milica M. AU - Bezbradica, Dejan AU - Antov, Mirjana AU - Mijin, Dušan AU - Knežević Jugović, Zorica PY - 2013 UR - https://dais.sanu.ac.rs/123456789/355 AB - Immobilized lipase from Candida antarctica (Novozyme 435) was tested for the synthesis of various phenolic acid esters (ethyl and n-butyl cinnamate, ethyl p-coumarate and n-butyl p-methoxycinnamate). The second-order kinetic model was used to mathematically describe the reaction kinetics and to compare present processes quantitatively. It was found that the model agreed well with the experimental data. Further, the effect of alcohol type on the esterification of cinnamic acid was investigated. The immobilized lipase showed more ability to catalyze the synthesis of butyl cinnamate. Therefore, the process was optimized for the synthesis of butyl cinnamate as a function of solvent polarity (logP) and amount of biocatalyst. The highest ester yield of 60.7 % was obtained for the highest enzyme concentration tested (3 % w/w), but the productivity was for 34 % lower than the corresponding value obtained for the enzyme concentration of 1 % (w/w). The synthesized esters were purified, identified, and screened for antioxidant activities. Both DPPH assay and cyclic voltammetry measurement have shown that cinnamic acid esters have better antioxidant properties than cinnamic acid itself. PB - Springer T2 - Applied Biochemistry and Biotechnology T1 - Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica SP - 1560 EP - 1573 VL - 170 IS - 7 DO - 10.1007/s12010-013-0294-z UR - https://hdl.handle.net/21.15107/rcub_dais_355 ER -
@article{ author = "Jakovetić, Sonja and Jugović, Branimir and Gvozdenović, Milica M. and Bezbradica, Dejan and Antov, Mirjana and Mijin, Dušan and Knežević Jugović, Zorica", year = "2013", abstract = "Immobilized lipase from Candida antarctica (Novozyme 435) was tested for the synthesis of various phenolic acid esters (ethyl and n-butyl cinnamate, ethyl p-coumarate and n-butyl p-methoxycinnamate). The second-order kinetic model was used to mathematically describe the reaction kinetics and to compare present processes quantitatively. It was found that the model agreed well with the experimental data. Further, the effect of alcohol type on the esterification of cinnamic acid was investigated. The immobilized lipase showed more ability to catalyze the synthesis of butyl cinnamate. Therefore, the process was optimized for the synthesis of butyl cinnamate as a function of solvent polarity (logP) and amount of biocatalyst. The highest ester yield of 60.7 % was obtained for the highest enzyme concentration tested (3 % w/w), but the productivity was for 34 % lower than the corresponding value obtained for the enzyme concentration of 1 % (w/w). The synthesized esters were purified, identified, and screened for antioxidant activities. Both DPPH assay and cyclic voltammetry measurement have shown that cinnamic acid esters have better antioxidant properties than cinnamic acid itself.", publisher = "Springer", journal = "Applied Biochemistry and Biotechnology", title = "Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica", pages = "1560-1573", volume = "170", number = "7", doi = "10.1007/s12010-013-0294-z", url = "https://hdl.handle.net/21.15107/rcub_dais_355" }
Jakovetić, S., Jugović, B., Gvozdenović, M. M., Bezbradica, D., Antov, M., Mijin, D.,& Knežević Jugović, Z.. (2013). Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica. in Applied Biochemistry and Biotechnology Springer., 170(7), 1560-1573. https://doi.org/10.1007/s12010-013-0294-z https://hdl.handle.net/21.15107/rcub_dais_355
Jakovetić S, Jugović B, Gvozdenović MM, Bezbradica D, Antov M, Mijin D, Knežević Jugović Z. Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica. in Applied Biochemistry and Biotechnology. 2013;170(7):1560-1573. doi:10.1007/s12010-013-0294-z https://hdl.handle.net/21.15107/rcub_dais_355 .
Jakovetić, Sonja, Jugović, Branimir, Gvozdenović, Milica M., Bezbradica, Dejan, Antov, Mirjana, Mijin, Dušan, Knežević Jugović, Zorica, "Synthesis of Aliphatic Esters of Cinnamic Acid as Potential Lipophilic Antioxidants Catalyzed by Lipase B from Candida antarctica" in Applied Biochemistry and Biotechnology, 170, no. 7 (2013):1560-1573, https://doi.org/10.1007/s12010-013-0294-z ., https://hdl.handle.net/21.15107/rcub_dais_355 .