Novel enzymatic synthesis of 3-Hydroxybutyryl Naringin and its molecular identification and bioactive characterization

In this study, we synthesized 6 ''-O-((+/-)-3-hydroxybutyryl)naringin (3HBN) for the first time through enzymatic esterification of naringin with 3-hydroxybutyric acid (3HB), achieving a high conversion of 80.19 % under optimized conditions within 8 h. Structural analysis via FT-IR and 1H NMR confirmed esterification at the C-6 '' hydroxyl position on the glucose moiety of naringin. Although the antioxidant capacity of 3HBN was slightly reduced compared to naringin, its enhanced lipophilicity (log P = -0.05) indicates improved bioavailability and potential for cellular absorption. Bioactivity evaluations confirmed that 3HBN exhibited stronger antiinflammatory effects than naringin by reducing TNF-alpha and increasing IL-10 in LPS-stimulated immune cells. These findings suggest that 3HBN is a promising bioactive compound with potential applications across the food, cosmetic, and pharmaceutical industries, offering both enhanced stability and effective bioactivity for targeted health benefits.