A Comparative Investigation of Synthesized Coumarin-Chalcone with Vitamin C for the Inhibition of Enzymatic Browning in Potato

The enzymatic browning reaction is one of the primary factors contributing to the deterioration of food products, such as fruits and vegetables, after harvest. This phenomenon is primarily caused by the enzyme polyphenol oxidase (PPO), which alters the organoleptic properties and nutritional value, ultimately leading to economic losses worldwide. The inhibition of PPO prevents this reaction and preserves food products. Coumarin chalcone bearing a hydroxyl group has shown promising antioxidant and enzyme-inhibitory activities. Here, a novel coumarin chalcone, ۳-(۳-(۴-hydroxy-۳-methoxyphenyl) acryloyl)-۲H-chromen-۲-one (CCh), was synthesized, characterized, and tested for its ability to inhibit enzymatic browning in potatoes. The compound was produced through a condensation reaction between ۳-acetylcoumarin and vanillin. Its structure was confirmed using ۱H, ۱۳C-NMR, and FT-IR spectroscopy. The anti-browning effect of CCh, compared to the known antioxidant, vitamin C, was evaluated over five days of frozen storage. Results showed that CCh effectively inhibited PPO activity and slowed the browning process. Molecular docking simulations with PPO (PDB ID: ۲P۳X) confirmed CCh’s binding to amino acid residues GLN A۳۳۱, LYS A۶۱, LEU A۵۳, PRO A۸۹, and THR A۱۳۶ through hydrogen bonds and hydrophobic interactions. The calculated binding energy of CCh was −۴.۷۱ kcal/mol, similar to vitamin C (−۵.۲ kcal/mol). These findings highlight CCh as a potential natural food preservative and capable of inhibiting enzymatic browning in potatoes, and could extend the shelf life of fruits and vegetables.

کلیدواژه ها:

Food preservatives ، Enzymatic browning ، Polyphenol oxidase ، coumarin chalcone ، molecular docking