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Radical Scavenging Activity of Lipophilized Products from Lipase-Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids

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Lipids

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.

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Abbreviations

CA:

Cinnamic acid

DPPH:

2, 2-Diphenyl-1-picrylhydrazyl radical

EC:

Ethyl cinnamate

ESI-MS:

Electrospray ionization-mass spectroscopy

ESI-MS–MS:

Electrospray ionization-mass spectroscopy–mass spectroscopy

ET:

Electron transfer

FA:

Ferulic acid

HAT:

Hydrogen atom transfer

HBA:

Hydrogen bond accepting

HPLC:

High performance liquid chromatography

RSA:

Radical scavenging activity

SPE:

Solid phase extraction

TO:

Triolein

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Acknowledgments

The funding provided by University of Otago Research and Enterprise Office to the author Wee Sim Choo for writing up this paper was greatly appreciated.

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Authors and Affiliations

  1. Department of Food Science, University of Otago, P.O. Box 56, Dunedin, 9054, New Zealand

    Wee-Sim Choo & Edward John Birch

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  1. Wee-Sim Choo
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  2. Edward John Birch
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Correspondence to Edward John Birch.

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Choo, WS., Birch, E.J. Radical Scavenging Activity of Lipophilized Products from Lipase-Catalyzed Transesterification of Triolein with Cinnamic and Ferulic Acids. Lipids 44, 145–152 (2009). https://doi.org/10.1007/s11745-008-3242-x

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  • DOI: https://doi.org/10.1007/s11745-008-3242-x

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