Enzymatic acylation improves the stability and bioactivity of lutein: Protective effects of acylated lutein derivatives on L-O2 cells upon H2O2-induced oxidative stress

[Display omitted] •Three new acylated lutein derivatives were synthesized and characterized.•Acylation significantly improved the thermal and light stabilities of lutein.•Acylation significantly improved the ABTS and OH free radical scavenging abilities of lutein.•Acylated lutein showed great protective effect on L-O2 cells upon H2O2-induced oxidative stress. The instability of lutein has limited its wide application especially in the food industry. In this study, enzymatic acylation of lutein with divinyl adipate was investigated. Three new acylated lutein derivatives, lutein-3-O-adipate (compound 1), lutein-3′-O-adipate (compound 2) and lutein-di-adipate (compound 3), were identified and their stabilities and bioactivates were evaluated. Notably, compounds 1–3 showed better thermal, light stability and stronger scavenging capacity to ABTS radical cation (ABTS+) and hydroxyl radical (OH). Most importantly, these acylated lutein derivatives exhibited excellent protective effects on L-O2 cells upon hydrogen peroxide (H2O2)-induced oxidative stress. In particular, the acylated lutein derivative termed compound 3 prevented cellular oxidative stress via restraining the overproduction of reactive oxygen species (ROS), thereby increasing related antioxidant enzymes activity and inhibiting apoptosis by mitochondria pathway. Our research provides important insights into the application of acylated lutein derivatives in food, cosmetic, and pharmaceutical products.