Polyphenol–caffeine complexation

Martin, Russell; Lilley, Terence H.; Bailey, Neil A.; Falshaw, C. P.; Haslam, Edwin; Magnolato, Daniéle; Begley, Michael J.

doi:10.1039/c39860000105

Cited by 71 publications

(56 citation statements)

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“…To our knowledge, only two crystal structure determinations involving quinic acid have been published, the free quinic acid (Abell, Allen, Bugg, Doyle & Raithby, 1988) and the caffeine-potassium chlorogenate complex (Martin et al, 1986(Martin et al, , 1987.…”

Section: Ho Coohmentioning

confidence: 99%

Structure and absolute configuration of a quinic acid–copper(II) complex

Bkouche-Waksman¹

1994

Acta Crystallogr C

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Section: Ho Coohmentioning

confidence: 99%

Structure and absolute configuration of a quinic acid–copper(II) complex

Bkouche-Waksman¹

1994

Acta Crystallogr C

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“…25) Interestingly, it is known that polyphenols form complexes with caffeine, especially in black tea and coffee. [26][27][28][29] Maruyama et al have noted that some gallate-type catechins have a strong affinity with caffeine, and assumed that these catechins bound a caffeine molecule in the space formed from the galloyl group and the B-ring on the basis of 1 H-NMR chemical shift changes in the catechins. 30) Such complexation seemed to be an interesting chemical phenomenon, because there might be a possibility that this complexation regulates the foregoing biological activities.…”

mentioning

confidence: 99%

Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with¹H-NMR

Hayashi¹,

Ujihara²,

Kohata³

2004

Bioscience, Biotechnology, and Biochemistry

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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 (ÀÁG) 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, respectively, by the titration method with 1 H-NMR. An investigation of the 1 H-NMR chemical shift change and NOESY spectra in the catechin/caffeine solutions showed the participation of the A-rings of the catechins in complexation, as well as that of the galloyl groups or B-rings.

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“…Crystalline complexes of caffeine with the following organic substrates have been determined, namely, 5-chlorosalicylic acid [1], barbital [2], hydrochloride dihydrate [3], methyl gallate and m-nitrobenzoic acid [4], potassium chlorogenate dihydrate [5], N-acetylsulfanilamide [6]. In the asymmetric unit of the title crystal structure, there are one water molecule, one caffeinium cation and one perchlorate anion, whereas perchlorate anion and water molecule are disordered.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of caffeinium perchlorate monohydrate, (C8H11N4O2)[ClO4] · H2O

Wang

Feng

et al. 2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialCaffeine and perchloric acid in a molar ratio of 1:1 were mixed and dissolved in sufficient amount of water by heating to a temperature where a clear solution resulted. Crystals of the title compound were formed by gradual evaporation of water over a period of one week at 293 K. Experimental detailsPerchlorate anion (including Cl atoms) is disordered and described by two positions with occupancies of 0.5. ClO and O···O distances were restrained to 1.42(3) Å and 2.34(3) Å, respectively. H atom attached to N atom was deduced from Fourier difference map and refined freely. H atoms of water molecule could not be localized. Other H atoms were placed in calculated positions and allowed to ride on their parent atoms at distances of 0.93 Å (C5H5) and 0.96 Å (methyl) with U iso (H) values 1.2 times U eq of the parent atoms. DiscussionCaffeine (3,7-dihydro-1,3,7-trimethyl-1,4-purine-2,6-di-one) is a purine alkaloid possessing pharmacological properties as a therapeutic agent with analeptic activity.

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Polyphenol–caffeine complexation

Cited by 71 publications

References 0 publications

Structure and absolute configuration of a quinic acid–copper(II) complex

Structure and absolute configuration of a quinic acid–copper(II) complex

Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with¹H-NMR

Crystal structure of caffeinium perchlorate monohydrate, (C8H11N4O2)[ClO4] · H2O

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Polyphenol–caffeine complexation

Cited by 71 publications

References 0 publications

Structure and absolute configuration of a quinic acid–copper(II) complex

Structure and absolute configuration of a quinic acid–copper(II) complex

Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with1H-NMR

Crystal structure of caffeinium perchlorate monohydrate, (C8H11N4O2)[ClO4] · H2O

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Binding Energy of Tea Catechin/Caffeine Complexes in Water Evaluated by Titration Experiments with¹H-NMR