Enzymatic synthesis, antioxidant ability and oil-water distribution coefficient of troxerutin fatty acid esters

Abstract

Abstract Troxerutin fatty acid esters were prepared using troxerutin and fatty acid vinyl esters as substrates in pyridine through enzymatic route. The structures of as-prepared compounds were identified by FT-TR, NMR, and ESI-HRMS. Using alkaline protease (≥30 mg/mL) as enzyme, maximum yields reached 58% at 3:1 (vinyl hexanoate to troxerutin) in pyridine (water content ≤1%). The yields gradually declined as chain length of acyl donors rose. The antioxidation abilities of the as-obtained compounds were confirmed by both DPPH free radical scavenging and potassium ferricyanide reduction methods. The antioxidation ability of troxerutin fatty acid esters was found lower than that of troxerutin. However, the logP values of troxerutin fatty acid esters varied from 0.15 to 1.94, suggesting that troxerutin fatty acid esters had better lipophilicity than troxerutin (logP = −2.12) when compared to their oil-water distribution coefficients. Overall, these findings look promising as reference for further development of future troxerutin.