3-Hydroxypyridinone-l-phenylalanine conjugates with antimicrobial and tyrosinase inhibitory activities as potential shrimp preservatives



To explore the potential of novel tyrosinase inhibitors, 3-hydroxypyridinone-l-phenylalanine conjugates, as shrimp preservatives, compounds 1 and 2 were evaluated for the antimicrobial activity, and compound 2 was investigated for the shrimp preservative efficacy. It was found that they both possess a stronger antibacterial effect than kojic acid against two Gram-positive bacteria and three Gram-negative bacteria. The minimum inhibitory concentrations (MICs) of compound 2 against Escherichia coli, Staphylococcous aureus, Salmonella gallinarum, Vibrio parahaemolyticus and Bacillus subtilis were determined as 18.5, 37, 148, 37 and 295 μg mL−1, respectively, whereas MICs of kojic acid against the same 5 bacterial strains were determined to be 355, 178, 1420, 1420 and 355 μg mL−1, respectively. It has also been demonstrated that treatment with compound 2 improves the sensory properties, retards the growth of spoilage bacteria, decreases the total volatile basic nitrogen (TVB-N) and increases the pH of Penaeus vannamei Boone, thereby extending the shelf life to 10 days. In contrast, the shelf life of shrimp treated with kojic acid and the control group was 7 and 6 days, respectively. Clearly, 3-hydroxypyridinone-l-phenylalanine conjugates could find application as shrimp preservatives by inhibiting melanosis and by preventing the growth of bacteria during the storage.