Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with 1H-NMR

@article{Hayashi2004BindingEO,
  title={Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with 1H-NMR},
  author={Nobuyuki Hayashi and Tomomi Ujihara and Katsunori Kohata},
  journal={Bioscience, Biotechnology, and Biochemistry},
  year={2004},
  volume={68},
  pages={2512 - 2518}
}
Evaluating the binding energy of a catechin/caffeine complex in water is important in order to elucidate the ability for molecular recognition of tea catechins. The results of this study revealed that the stoichiometric ratio of the complexation between tea chatechins (EGCg, ECg, EGC, and EC) and caffeine was 1:1 at least up to a concentration of 5.0 mM. The free energy (−ΔG) values for binding in water at 301 K were evaluated to be 2.7, 2.6, 2.2, and 2.0 kcal/mol for EGCg, ECg, EGC, and EC… 
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Association of Catechin Molecules in Water: Quantitative Binding Study and Complex Structure Analysis.

Structural analyses of the complexes by ROESY experiments and density functional theory calculations demonstrated that the higher binding abilities of gallate-type catechins are due to providing multiple intermolecular interactions that remain effective in an aqueous environment, such as aromatic/aromatic or CH/π interactions.

A theoretical study on structures of an epigallocatechin-3-O-gallate/caffeine complex in aqueous solution

Experimental Evidence of the Presence of Bimolecular Caffeine/Catechin Complexes in Green Tea Extracts.

Both MSE and product ion MS/MS methods confirm the nature of caffeine/catechin complexes of the detected ions, showing the formation of protonated caffeine.

Configurational studies of complexes of various tea catechins and caffeine in crystal state.

A solution of two kinds of non-galloylated catechin, CA and (-)-epicatechin (EC), and caffeine in water afforded a 1 : 1 : 2 complex, the crystal structure of which had two layers, one layer in which CA and caffeine formed alternate lines and an other layer inWhich EC and caffeine form alternate lines.

Recognition of caffeine by a water-soluble acyclic phane compound

Stereochemical structure and intermolecular interaction of complexes of (-)-Gallocatechin-3-O-gallate and caffeine.

A suspension containing an equimolecular amount of (-)-gallocatechin-3-O-gallate and caffeine in water was heated at 90 °C for 30 min to give a 1 : 2 complex, which contained GCg, caffeine, and water at a molar ratio of 1 : 1 : 22 based on measurement of the integral volume of (1)H-NMR signals.

Intermolecular hydrogen bonds between catechin and theanine in tea: slow release of the antioxidant capacity by a synergetic effect

The health benefits of drinking tea stem from it being rich in polyphenols and other physiologically-active substances. Thus, exploring the synergistic effect between polyphenols and a variety of…

Configurational studies of complexes of tea catechins with caffeine and various cyclodextrins.

A suspension of an equimolecular amount of ENT-gallocatechin-3-O-gallate ( ENTGCg) and caffeine in water afforded two kinds of crystals, which were 1 : 2 and 2 : 2 complexes of ENTGCg and caffeine.…

The use of diffusion-ordered spectroscopy and complexation agents to analyze mixtures of catechins

Mixtures of catechins, (+)-catechin (C), (−)-epicatechin (EC), (−)-epigallocatechin (EGC) and (−)-epigallocatechin gallate (EGCG) have been analyzed by diffusion-ordered spectroscopy (DOSY) using…

NMR Reinvestigation of the Caffeine–Chlorogenate Complex in Aqueous Solution and in Coffee Brews

Caffeine complexation by chlorogenic acid (3-caffeoylquinic acid, CAS Number [327-97-9]) in aqueous solution as well as caffeine–chlorogenate complex in freshly prepared coffee brews have been…

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