Nanoprecipitates of γ‐cyclodextrin/epigallocatechin‐3‐gallate inclusion complexes as efficient antioxidants for preservation of shrimp surimi products: synthesis, performance and mechanism

Abstract

BACKGROUND Epigallocatechin‐3‐gallate (EGCG) is well known for excellent chain‐breaking antioxidant capability. However, browning by oxidation and aggregation of EGCG is a non‐negligible defect that hinders its applications as an antioxidant in various foodstuffs. Therefore, how to eliminate or mitigate browning efficiently, while retaining functionalities as food additive is a challenge in the food industry. RESULTS Our results demonstrated that EGCG could be anchored within the internal cavity of γ‐cyclodextrin (γ‐CD) to form an inclusion structure, where hydrophobic interaction, hydrogen bonding, and π‐stacking were identified to be the primary drivers. The interplay between two molecules and the steric hindrance from γ‐CD could restrict the motion and aggregation of EGCG efficiently, thus alleviating the browning effect. In addition, the conformational adaption of EGCG within the inclusions would result in general decreases in hydrogen‐bond dissociation enthalpies for the pyrogallol‐type structure on the b ring, thus enhancing the antioxidant capability. In practical application, the nanoscale γ‐CD/EGCG inclusion complexes were validated preliminarily as efficient additives in the preservation of shrimp surimi, presenting significant effects on prolonging the shelf‐life of products. CONCLUSION Here, nanoscale γ‐CD/EGCG inclusion complexes as alternatives to EGCG were tailored as food antioxidants for the preservation of shrimp surimi products, exerting antioxidant effects while mitigating the browning effects of EGCG on products. Through self‐assembly, EGCG would be anchored with the cavity of γ‐CD, which could regulate the release modes and restrict the aggregation of EGCG. This facile strategy has great potential in food preservation. © 2023 Society of Chemical Industry.

Encapsulation Alleviates the Auto-browning of Epigallocatechin-3-gallate in Aqueous Solutions through Regulating Molecular Self-Aggregation Behavior

“…For instance, in a 28 day observation by Ho et al, cyclodextrin-based inclusion complexes were found to be effective in alleviating the browning of catechins under the conditions with a relative humidity of 10–75% yet still were observed to collapse, aggregate, as well as brown progressively when exposed to a higher relative humidity of above 85% . A subsequent study in our lab showed that the use of cyclodextrin-based inclusion complexes exhibited excellent mitigation on the auto-browning phenomenon of EGCG within 3 weeks in the preservation of shrimp surimi (with a moisture content of about 75%) . In addition, our investigation indicated that, in the complexes, the arrangement of the inclusion structure as the fundamental unit followed a random mode via the interactions of the outer surface of cyclodextrins and was susceptible to disruption by water molecules .…”

“…9 A subsequent study in our lab showed that the use of cyclodextrin-based inclusion complexes exhibited excellent mitigation on the auto-browning phenomenon of EGCG within 3 weeks in the preservation of shrimp surimi (with a moisture content of about 75%). 10 In addition, our investigation indicated that, in the complexes, the arrangement of the inclusion structure as the fundamental unit followed a random mode via the interactions of the outer surface of cyclodextrins and was susceptible to disruption by water molecules. 10 Therefore, it was speculated that an ordered rather than random arrangement of the inclusion structure could further prolong the intervention effects on the auto-browning of EGCG in high-humidity conditions.…”

“…10 In addition, our investigation indicated that, in the complexes, the arrangement of the inclusion structure as the fundamental unit followed a random mode via the interactions of the outer surface of cyclodextrins and was susceptible to disruption by water molecules. 10 Therefore, it was speculated that an ordered rather than random arrangement of the inclusion structure could further prolong the intervention effects on the auto-browning of EGCG in high-humidity conditions.…”

Fabrication of EGCG‐loaded Spirulina platensis microcarrier with sustained release properties and their application in extending the shelf‐life of minced lamb meat

“…However, the application and efficacy of EGCG is still limited due to its poor stability. EGCG is susceptible to the effects of temperature, pH, ambient light intensity or metal ions when exposed to air (Song et al ., 2022; Wang et al ., 2023). Numerous studies have reported the encapsulation of EGCG in biomolecules such as proteins (Song et al ., 2022), polysaccharides (Zhou et al ., 2023) and lipids (Shtay et al ., 2019) to form nano‐microcapsules to improve the stability of EGCG, enhance the bioavailability and control the release rate of the encapsulated EGCG.…”