Enzymatic synthesis and antioxidation characterization of various acylated chlorogenic acids via regioselective and recyclable immobilized lipases

Liposoluble antioxidants are widely used in food, cosmetic and pharmacy, but the green synthesis remains the big challenge limiting their industrial clean production. In our study, an immobilized lipase (CSL@OMS-C 18 ) was prepared by immobilizing Candida sp. Lipase (CSL) on hydrophobically modified ordered mesoporous silicon (OMS-C 18 ) for the enzymatic production of acylated chlorogenic acids (ACDs). The results showed that CSL@OMS-C 18 facilitated 97.2% of chlorogenic acid in 45 min with the corresponding CE value of 1463.1 μmol/(g·h). Besides, CSL@OMS-C 18 maintained 82.5% of initial activity after 10 cycles of reuse, demonstrating its catalytic stability and reusability. The broad applicability of CSL@OMS-C 18 was confirmed by the enzymatic synthesis of acetylated chlorogenic acid, butylated chlorogenic acid, octanoylated chlorogenic acid and laurylated chlorogenic acid, which were analyzed using molecular docking simulation to reveal the bonding mechanism between lipase CSL and different substrates. Finally, the antioxidant capacity of chlorogenic acid and its derivatives were assessed based on the DPPH, ABTS, hydroxyl radical scavenging activity, ferric reducing ability, and oils oxidation induction assay. This study provides new insights into the sustainable enzymatic synthesis of liposoluble and antioxidant acylated chlorogenic acids for food industries.