Inhibition Mechanism of Chitooligosaccharide-Polyphenol Conjugates toward Polyphenoloxidase from Shrimp Cephalothorax

Author:

Mittal Ajay1,Singh Avtar1ORCID,Zhang Bin2,Zhao Qiancheng3,Benjakul Soottawat14ORCID

Affiliation:

1. International Center of Excellence in Seafood Science and Innovation, Faculty of Agro-Industry, Prince of Songkla University, Hat Yai 90110, Thailand

2. Key Laboratory of Health Risk Factors for Seafood of Zhejiang Province, College of Food Science and Pharmacy, Zhejiang Ocean University, Zhoushan 316022, China

3. School of Food Science and Engineering, Dalian Ocean University, Dalian 116023, China

4. Department of Food and Nutrition, Kyung Hee University, Seoul 02447, Republic of Korea

Abstract

Crustaceans are perishable with a short shelf-life. They are prone to deterioration after capture, particularly during handling, processing, and storage due to melanosis caused by polyphenoloxidase (PPO). Therefore, inhibitory effects of chitooligosaccharide (CHOS) in comparison with CHOS-catechin (CHOS-CAT), CHOS-epigallocatechin gallate (CHOS-EGCG), and CHOS-gallic acid (CHOS-GAL) conjugates on Pacific white shrimp cephalothorax PPO were studied. IC50 of CHOS-CAT (0.32 mg/mL) toward PPO was less than those of all conjugates tested (p < 0.05). CHOS-CAT exhibited the mixed-type inhibition. Kic (0.58 mg/mL) and Kiu (0.02 mg/mL) of CHOS-CAT were lower than those of other conjugates (p < 0.05). CHOS-CAT showed static fluorescence-quenching, suggesting a change in micro-environment around the active site of PPO. Moreover, CHOS-CAT was linked with various amino acid residues, including Tyr208 or Tyr209 of proPPO via van der Waals, hydrophobic interaction, and hydrogen bonding as elucidated by the molecular docking of proPPO. Although CHOS-CAT had the highest PPO inhibitory activity, it showed a lower binding energy (−8.5 kcal/mol) than other samples, except for CHOS-EGCG (−10.2 kcal/mol). Therefore, CHOS-CAT could act as an anti-melanosis agent in shrimp and other crustaceans to prevent undesirable discoloration associated with quality losses.

Funder

National Science and Technology Development Agency (NSTDA), Thailand

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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