The conjugate prepared from (-)-epigallocatechin gallate (EGCG) and soy protein isolate (SPI) under alkaline and aerobic conditions was analyzed using a Nano-LC-Q-Orbitrap-MS/MS technique. The sulfhydryl and free amino groups of SPI were involved in covalent binding. Fifty-one peptides were conjugated with EGCG. Fifty-nine modified sites were identified, located on Cys, His, Arg, and Lys, respectively. It is the first time to confirm that each of the two phenolic rings of EGCG contained a reactive site that bound to an amino acid residue. The amino acid residue reactivity, amino acid sequence and composition affected the EGCG binding site in SPI. Lys and Arg residues are the most likely sites for modification, and modification appears to reduce IgE binding. This study is helpful to elucidate the pattern of covalent binding of polyphenols to proteins in food systems and provides a theoretical basis for the directional modification of soy proteins with polyphenols.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.foodchem.2020.127400 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Proximity-enhanced cysteine-histidine crosslinking for elucidating intrinsically disordered and other protein complexes.
Chem Sci
January 2025
Laboratory of Chemical Biology, Department of Biomedical Engineering and Institute for Complex Molecular Systems, Eindhoven University of Technology Netherlands
Disordered proteins and domains are ubiquitous throughout the proteome of human cell types, yet the biomolecular sciences lack effective tool compounds and chemical strategies to study this class of proteins. In this context, we introduce a novel covalent tool compound approach that combines proximity-enhanced crosslinking with histidine trapping. Utilizing a maleimide-cyclohexenone crosslinker for efficient cysteine-histidine crosslinking, we elucidated the mechanism of this dual-reactive tool compound class.
View Article and Find Full Text PDFEffects of catechins with different structure characteristics on the structure and properties of gluten-catechin covalent complex.
Food Res Int
February 2025
Antioxidant Polyphenols Team, Department of Food Engineering, Sichuan University, Chengdu 610065, PR China; The Key Laboratory of Food Science and Technology of Sichuan Province of Education, Sichuan University, Chengdu 610065, PR China. Electronic address:
Effects of catechins with different structure characteristics on the structure and properties of gluten-catechin covalent complex were investigated, and the structure-activity relationship was further explored. Catechins including epicatechin (EC), epigallocatechin (EGC), epicatechin-3-gallate (ECG), and epigallocatechin-3-gallate (EGCG) could successfully covalently bind with gluten through C-N and/or C-S bonds. The physicochemical properties of covalent complex, including particle size, thermal stability, content of free amino groups, free sulfhydryl groups and disulfide bonds, were significantly affected by different catechins, and the action order was: EGCG > ECG > EGC > EC.
View Article and Find Full Text PDFMolecular Design, Synthesis and Anti-cancer Activity of Novel Pyrazolo[3,4-b]pyridine-based Glycohybrid Molecules.
Bioorg Chem
January 2025
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India; Glycochemistry Laboratory, School of Physical Sciences, Jawaharlal Nehru University, New Delhi 110067, India. Electronic address:
Molecular hybridization is an emerging strategy in medicinal chemistry for designing new bioactive molecules that link pharmacophores covalently and shows synergistic enhanced properties. Herein, we have developed pyrazolo[3,4-b]pyridine-based new glycohybrids considering the Warburg effect. A microwave-assisted, copper-catalyzed efficient synthesis of new triazole-linked glycohybrids based on pyrazolo[3,4-b]pyridines scaffold was achieved successfully in high yields with inherent stereochemical diversity from d-glucose, d-galactose, and d-mannose.
View Article and Find Full Text PDFA Unique Case of 'in Situ' Bifluoride Triggered Formation of Supramolecular Organogels Using Isophthalamide Hydrogen Bond Donating Receptors.
Chemistry
January 2025
Department of Chemical and Geological Science, University of Cagliari, S.S. 554 Bivio per Sestu, 09042, Monserrato (CA), Italy.
A novel isopthalamide based receptor HL2 featuring two p-benzoic acid units has been synthesised and its anion binding properties analysed by H-NMR spectroscopy in DMSO-d/0.5 % HO. As expected, in the presence of tetrabutylammonium (TBA) fluoride the deprotonation of the carboxylic acid moieties was observed.
View Article and Find Full Text PDFFundamental Understanding of Bio-Nano Interface of Lysozyme on Polyphenol Coated Silver Nanoparticles: Mechanistic Insights into the Effect of Protein Corona on the Antibacterial Efficacy.
Langmuir
January 2025
Department of Chemical and Biological Sciences, National Institute of Technology Meghalaya, Shillong 793003, India.
Recent times have witnessed revolutionary progress in the design and development of functionalized nanomaterials as promising tools for biomedicinal applications. However, the gap in the fundamental understanding of the "biological responses" of the nanomaterials after the formation of "protein-corona" when it is exposed to the body system has drawn a thin line from its discoveries to real clinical trial. In this article we have synthesized two different silver NPs capped with the polyphenols of (guava) leaf extract and the other with one of its major polyphenolic groups, morin.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!