Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids
Abstract Lipase‐catalyzed transesterification of triolein with cinnamic and ferulic acids using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate the antioxidant activity of the lipophilized products as model systems for enhanced protection of unsaturated oil. Th...
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Online Access: | http://dx.doi.org/10.1007/s11745-008-3242-x https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-008-3242-x |
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crwiley:10.1007/s11745-008-3242-x 2024-06-23T07:47:53+00:00 Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids Choo, Wee‐Sim Birch, Edward John 2008 http://dx.doi.org/10.1007/s11745-008-3242-x https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-008-3242-x en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Lipids volume 44, issue 2 ISSN 0024-4201 1558-9307 journal-article 2008 crwiley https://doi.org/10.1007/s11745-008-3242-x 2024-06-13T04:24:16Z Abstract Lipase‐catalyzed transesterification of triolein with cinnamic and ferulic acids using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate the antioxidant activity of the lipophilized products as model systems for enhanced protection of unsaturated oil. The lipophilized products were identified using ESI‐MS. Free radical scavenging activity was determined using the DPPH radical method. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Ferulic acid showed much higher radical scavenging activity than cinnamic acid, which has limited activity. The esterification of cinnamic acid and ferulic acid with triolein resulted in significant increase and decrease in the radical scavenging activity, respectively. These opposite effects were due to the effect of addition of electron‐donating alkyl groups on the predominant mechanism of reaction (hydrogen atom transfer or electron transfer) of a species with DPPH. The effect of esterification of cinnamic acid was confirmed using ethyl cinnamate which greatly enhances the radical scavenging activity. Although, compared to the lipophilized cinnamic acid product, the activity was lower. The radical scavenging activity of the main component isolated from lipophilized cinnamic acid product using solid phase extraction, monocinnamoyl dioleoyl glycerol, was as good as the unseparated mixture of lipophilized product. Based on the ratio of a substrate to DPPH concentration, lipophilized ferulic acid was a much more efficient radical scavenger than lipophilized cinnamic acid. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Lipids 44 2 |
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Wiley Online Library |
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English |
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Abstract Lipase‐catalyzed transesterification of triolein with cinnamic and ferulic acids using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate the antioxidant activity of the lipophilized products as model systems for enhanced protection of unsaturated oil. The lipophilized products were identified using ESI‐MS. Free radical scavenging activity was determined using the DPPH radical method. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Ferulic acid showed much higher radical scavenging activity than cinnamic acid, which has limited activity. The esterification of cinnamic acid and ferulic acid with triolein resulted in significant increase and decrease in the radical scavenging activity, respectively. These opposite effects were due to the effect of addition of electron‐donating alkyl groups on the predominant mechanism of reaction (hydrogen atom transfer or electron transfer) of a species with DPPH. The effect of esterification of cinnamic acid was confirmed using ethyl cinnamate which greatly enhances the radical scavenging activity. Although, compared to the lipophilized cinnamic acid product, the activity was lower. The radical scavenging activity of the main component isolated from lipophilized cinnamic acid product using solid phase extraction, monocinnamoyl dioleoyl glycerol, was as good as the unseparated mixture of lipophilized product. Based on the ratio of a substrate to DPPH concentration, lipophilized ferulic acid was a much more efficient radical scavenger than lipophilized cinnamic acid. |
format |
Article in Journal/Newspaper |
author |
Choo, Wee‐Sim Birch, Edward John |
spellingShingle |
Choo, Wee‐Sim Birch, Edward John Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
author_facet |
Choo, Wee‐Sim Birch, Edward John |
author_sort |
Choo, Wee‐Sim |
title |
Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
title_short |
Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
title_full |
Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
title_fullStr |
Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
title_full_unstemmed |
Radical Scavenging Activity of Lipophilized Products from Lipase‐Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids |
title_sort |
radical scavenging activity of lipophilized products from lipase‐catalyzed transesterification of triolein with cinnamic and ferulic acids |
publisher |
Wiley |
publishDate |
2008 |
url |
http://dx.doi.org/10.1007/s11745-008-3242-x https://onlinelibrary.wiley.com/doi/full/10.1007/s11745-008-3242-x |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Lipids volume 44, issue 2 ISSN 0024-4201 1558-9307 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1007/s11745-008-3242-x |
container_title |
Lipids |
container_volume |
44 |
container_issue |
2 |
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1802638111225675776 |