In the present study, structured oils were prepared by introducing about 30% conjugated linolenic (CLN) or α-linolenic (LN) acid into olive oil in the form of CLN-triacylglycerol (CLN-TAG) or LN-TAG, respectively, by enzymatic transacylation. The anti-oxidative activities of natural polyphenolic compounds, such as tocopherol (Toc), sesamol (Se), epigallocatechin gallate (EGCG) and quercetin (Qu), in the prepared structured oils were then evaluated. It was found that these four kinds of hydrogen radical-donating anti-oxidants effectively prevented oxidation of the prepared structured oils, and the anti-oxidative effects of these polyphenols were shown to depend on DPPH radical scavenging ability. EGCG, which showed the highest anti-oxidative effect among these antioxidants by the conductometric determination method (CDM) improved the oxidative stability of the prepared CLN-TAG and LN-TAG by about six-fold when it was added at 3,600 ppm (equivalent to 20,000 ppm Toc in terms of radical scavenging ability). In addition, the oxidative stability of CLN-TAG was increased about eight-fold when EGCG was added at 5,500 ppm (30,000 ppm Toc in terms of radical scavenging ability). On the other hand, addition of EGCG at 3,600 ppm to LN-TAG did not improve the anti-oxidant activity. Thus, it was considered that the use of polyphenols with lipid solubility, thermal stability and high DPPH radical scavenging ability, such as EGCG at 5,500 ppm, is very effective for preventing the oxidation of CLN-TAG.
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