Improved antioxidant activity of rutin via lipase‐mediated esterification with oleic acid

作者：Yihang Liu, Qingzhi Wang, Chen Liu, Haonan Yang, Li Jia, Litao Zhao, Fayong Gong, Chen Tan, Hongxun Tao, Wen‐Sen He · 发表于：Journal of the Science of Food and Agriculture · 年份：2023 · DOI：10.1002/jsfa.12486 · 被引用次数：29 · 研究领域：Enzyme Catalysis and Immobilization、Phytochemicals and Antioxidant Activities、Nuts composition and effects

Abstract BACKGROUND Oxidation is a major problem for oils and fats, which can be mitigated by antioxidants. Rutin has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. In this study, an efficient enzymatic synthesis route of lipophilic rutin ester was established using oleic acid as an acyl donor, and the antioxidant potential of rutin oleate was evaluated for the first time by proton ( 1 H) nuclear magnetic resonance (NMR) spectroscopy. RESULTS The synthesized product was finally identified as rutin oleate by Fourier transform infrared, high‐performance liquid chromatography–mass spectrometry, and 1 H, carbon‐13, and DEPT‐135 NMR analyses, and the acylation site was the 4‴‐OH of the rhamnose group in the rutin molecule. The maximum conversion was over 93% after 48 h of reaction using Novozym 435 as catalyst under the best conditions among these tests. The conversion of rutin ester decreased with the increase of carbon chain length and the number of carbon–carbon double bonds of the fatty acid molecule. Most importantly, rutin oleate exhibited antioxidant capacity comparable to butylated hydroxytoluene and its counterparts (rutin and oleic acid) at low temperatures (60° C), but had a significant advantage at high temperatures (120° C). CONCLUSION The antioxidant activity of rutin was significantly enhanced by lipase‐mediated esterification with oleic acid. Therefore, rutin oleate could be further developed as a novel antio...