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Novel Multifunctional Hydroxypyridinone Derivatives as Potential Shrimp Preservatives

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Abstract

In order to develop a new efficient method for the prolongation of shrimp shelf life, two novel hydroxypyridinone derivatives ((S)-2-amino-N-((S)-1-(((5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl)amino)-1-oxo-3-phenylpropan-2-yl)-3-phenylpropanamide (2) and (S)-(5-hydroxy-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-(benzyloxycarbonyl)-3- phenylpropanoate (3)) possessing strong tyrosinase inhibitory activity were investigated to explore their potential as shrimp preservatives. Their antimicrobial activities were evaluated by a disk diffusion method. Inhibition zone assays indicated that both 2 and 3 possess a stronger inhibitory effect than kojic acid. The minimum inhibition concentrations (MICs) of compound 3 against Bacillus subtilis, Staphylococcous aureus, Escherichia coli, Salmonella spp., and Pseudomonas aeruginosa were determined to be 32, 32, 32, 8, and 16 μg/mL. Both 2 and 3 were also found to possess antioxidant activity. The IC50 values of 2 and 3 for scavenging DPPH radical were measured to be 2.93 and 2.37 mg/mL, respectively. At 4 mg/mL, 2 and 3 were determined to have total antioxidant capacity of 2.43 and 2.72 U/mL, respectively. Compound 3 was further investigated for efficacy in shrimp preservation by sensory evaluation, determination of total volatile basic nitrogen (TVB-N), pH, and total bacterial count. The treatment with 3 was found to extend the shelf life of Penaeus vannamei Boone to 10 days at 4 °C, while the shelf life of shrimp treated with 4-hexylresorcinol, kojic acid, and the control group was 9, 6, and 4 days, respectively. Compound 3 could find application in the food industry, as a shrimp preservative, due to its protective properties.

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Acknowledgments

This research work was financially supported by Science Technology Department of Zhejiang Province of China (No. 2013C24006).

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Authors and Affiliations

  1. School of Food Science and Biotechnology, Zhejiang Gongshang University, Xiasha, Hangzhou, Zhejiang, 310018, People’s Republic of China

    Xiao-Yan Dai, Ming-Xia Zhang & Tao Zhou

  2. College of Tourism & Food, Shanghai Business School, Shanghai, 200235, China

    Xiao-Yi Wei

  3. Division of Pharmaceutical Science, King’s College London, Franklin-Wilkins Building, 150 Stamford Street, London, SE1 9NH, UK

    Robert C Hider

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  1. Xiao-Yan Dai
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Correspondence to Tao Zhou.

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Dai, XY., Zhang, MX., Wei, XY. et al. Novel Multifunctional Hydroxypyridinone Derivatives as Potential Shrimp Preservatives. Food Bioprocess Technol 9, 1079–1088 (2016). https://doi.org/10.1007/s11947-016-1694-1

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  • DOI: https://doi.org/10.1007/s11947-016-1694-1

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