Small molecules interfacial assembly regulate the crystallization transition process for nobiletin stabilization

Xiaojuan Chen; Bojia Li; Sicheng Ji; Di Wu; Bing Cui; Xingling Ren; Bin Zhou; Bin Li; Hongshan Liang

doi:10.1016/j.foodchem.2023.136519

Small molecules interfacial assembly regulate the crystallization transition process for nobiletin stabilization

Food Chem. 2023 Nov 15:426:136519. doi: 10.1016/j.foodchem.2023.136519. Epub 2023 Jun 5.

Authors

Xiaojuan Chen¹, Bojia Li², Sicheng Ji², Di Wu¹, Bing Cui¹, Xingling Ren², Bin Zhou³, Bin Li⁴, Hongshan Liang⁵

Affiliations

¹ College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, China.
² College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China.
³ Key Laboratory of Fermentation Engineering, Ministry of Education, National "111" Center for Cellular Regulation and Molecular Pharmaceutics, Hubei Key Laboratory of Industrial Microbiology, School of Biological Engineering and Food, Hubei University of Technology, Wuhan 430068, China.
⁴ College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, China; Functional Food Engineering and Technology Research Center of Hubei Province, China.
⁵ College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China; Key Laboratory of Environment Correlative Dietology (Huazhong Agricultural University), Ministry of Education, China. Electronic address: lianghongshan@mail.hzau.edu.cn.

PMID: 37329798
DOI: 10.1016/j.foodchem.2023.136519

Abstract

Many bioactive nutraceuticals naturally occurring in food materials possess beneficial biological activities, while their use as functional supplements is subjected to hydrophobicity and crystallinity. Currently, inhibiting crystallization for such nutrients is of immense scientific interest. Here, we exploited diverse structural polyphenols as potential inhibitors for restraining Nobiletin crystallization. Specifically, the crystallization transition process could be influenced by the polyphenol gallol density, Nobiletin supersaturation (1, 1.5, 2, 2.5 mM), temperature (4, 10, 15, 25 and 37 ℃), and pH (3.5, 4, 4.5, 5), important factors for regulating the binding attachment and interactions. The optimized samples could be guided by NT100 lied in 4 ℃ at pH 4. Besides, the main assembly driving force was hydrogen-bonding cooperated with π-π stacking and electrostatic interaction, leading to a Nobiletin/TA combination ratio of ∼ 3:1. Our findings proposed an innovative synergistic strategy for inhibiting crystallization and broaden potential applications of polyphenol-based materials in advanced biological fields.

Keywords: Antisolvent; Crystallization inhibition; Interface assembly; Nucleation; Small molecules interaction; Supersaturation.

MeSH terms

Crystallization
Flavones*
Polyphenols* / chemistry
Temperature

Substances

nobiletin
Polyphenols
Flavones