One-pot biocatalytic synthesis and antioxidant activities of highly lipophilic naringin derivatives by using bi-functional whole-cells

Citrus peel wastes are an important renewable resource and rich in naringin, a flavonoid compound with multiple bioactivities. To cope with the low bioavailability of naringin, a new bienzyme whole-cell system was developed for bioconversion of naringin into two lipophilic derivatives. A series of naringin esters with different fatty acid chain length were successfully synthesized via cell-bound lipase catalyzed acylation, and another lipophilic product naringenin was simultaneously yielded via intracellular naringinase-catalyzed hydrolysis. The naringin esters obtained showed higher log P values and free radical-scavenging capacities against DPPH and ABTS than naringin itself. These esters also showed markedly enhanced permeability across the human intestinal Caco-2 cells. The whole-cell mediated conversion of naringin offers a two-fold advantage: naringin esters are produced as new high-valued derivatives with high lipophilicity and antioxidant activity; and the tasteless product naringenin was obtained simultaneously, which can reduce the bitterness of the total product and benefited its industrial applications.