The inhibition effects of chlorogenic acid on the formation of colored oxidation products of (−)-epigallocatechin gallate under enzymatic oxidation

Cui, Yuqing; Han, Zisheng; Lian, Li; Zhang, Liang

doi:10.1016/j.foodchem.2023.135895

Cited by 8 publications

(4 citation statements)

References 28 publications

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“…To further verify our hypothesis, we constructed the EGCG aqueous model systems and monitored the auto-browning of EGCG in both encapsulated and non-encapsulated forms using UV–vis spectrophotometry, as illustrated in Figure . The absorbance between 400 and 500 nm is generally thought to relate to yellow and red colors . For EGCG in the non-encapsulated form (i.e., pristine EGCG and the mixture of EGCG and CD-MOFs), a gradual increase of the absorbance in this range was observed, indicating the formation and accumulation of colored products with a prolonged storage time.…”

Section: Resultsmentioning

confidence: 99%

“…The absorbance between 400 and 500 nm is generally thought to relate to yellow and red colors. 21 For EGCG in the non-encapsulated form (i.e., pristine EGCG and the mixture of EGCG and CD-MOFs), a gradual increase of the absorbance in this range was observed, indicating the formation and accumulation of colored products with a prolonged storage time. In contrast, with regard to those samples from the encapsulated group, a significant change in absorbance between 400 and 500 nm was detected after the sixth week.…”

Section: Monitoring Auto-oxidative Browning Of Egcg In Aqueous Soluti...mentioning

confidence: 95%

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

Wang,

Yin,

et al. 2023

J. Agric. Food Chem.

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Catechins are widely recognized for superb antioxidant capability, but their application as food antioxidants is hindered by susceptibility to auto-browning under high-moisture conditions. Here, we proposed a strategy of ordered encapsulation with cyclodextrin-based metal–organic frameworks (CD-MOFs) to alleviate the auto-browning phenomenon of catechins while preserving their antioxidant capability and demonstrated the feasibility of this strategy via selecting epigallocatechin-3-gallate (EGCG) as a model. Even in aqueous solutions, EGCG@CD-MOFs still possessed delayed browning, in contrast with pristine EGCG, characterized by suppressed efficiencies on the generation of oxidative dimers (theasinensin A) and semiquinone radicals. Mechanism insights revealed that ordered encapsulation brought dual regulations on the self-aggregation behavior of EGCG: EGCG@CD-MOFs exhibited a gradual structural collapse from the framework toward irregular aggregates as O–K bonds broke progressively, which restricted molecular mobility of EGCG, and EGCG molecular conformations became constrained by the structure of EGCG@CD-MOFs as well as rich intermolecular forces, even after structural collapse.

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Section: Resultsmentioning

confidence: 99%

Section: Monitoring Auto-oxidative Browning Of Egcg In Aqueous Soluti...mentioning

confidence: 95%

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

Wang,

Yin,

et al. 2023

J. Agric. Food Chem.

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“…Through the continuous addition of CQA, the color of the reaction mixture of CQA and EGCG gradually became colorless. 21 Liquid chromatography quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS) analysis revealed that the formation of oolongtheanin quinone, 22 a critical chromogenic oxidation product of EGCG, was inhibited after CQA addition. However, when CQA reacted with other tea catechins (e.g., EGC), the catechol moiety of CQA could form a benzotropolone ring with the pyrogallol moiety of (epi)gallocatechins.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Moreover, a simulated enzymatic reaction of chlorogenic acid (3-caffeoylquinic acid, CQA) and (−)-epigallocatechin gallate (EGCG) showed that the oxidation degree of EGCG was inhibited with the addition of CQA. Through the continuous addition of CQA, the color of the reaction mixture of CQA and EGCG gradually became colorless . Liquid chromatography quadrupole time-of-flight mass spectrometry (LC-Q-TOF-MS) analysis revealed that the formation of oolongtheanin quinone, a critical chromogenic oxidation product of EGCG, was inhibited after CQA addition.…”

Section: Introductionmentioning

confidence: 99%

Novel Oxidation Oligomer of Chlorogenic Acid and (−)-Epigallocatechin and Its Quantitative Analysis during the Processing of Keemun Black Tea

Lai,

Wen,

Jiang

et al. 2023

J. Agric. Food Chem.

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Not only do flavan-3-ols participate in the formation of chromogenic oxidation products such as theaflavins, but chlorogenic acid (3-caffeoylquinic acid, CQA) is also involved in the enzymatic oxidation during black tea processing. The critical oxidation product of CQA and (−)-epigallocatechin (EGC) were identified as an adduct containing benzobicyclo[3.2.2]nonenone structure, which was named as the dichlorogeniccatechin (DCGC) oligomer. It was composed of two molecules of CQA and one molecule of EGC. The effects of the initial reactant ratio and reaction time on the generation of DCGC were also analyzed. A high proportion of CQA promoted the production of DCGC, but a high proportion of EGC inhibited the DCGC formation. In addition, the content of DCGC in Keemun black tea during processing was determined. The content of DCGC highly increased after withering but decreased after drying. This study provides a new perspective for the investigation of other oxidation oligomers in black tea.

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The hydrates of chlorogenic acid in its aqueous solution and in stored food products

Dawidowicz,

Typek,

Hołowiński

et al. 2024

Eur Food Res Technol

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Chlorogenic acids (CQAs), a large family of naturally occurring esters of quinic acid with one, two or even three cinnamic acids moieties and/or moieties of cinnamic acids derivatives, supplied to human organisms mainly with coffee, tea, fruit and vegetables, have been among the most frequently studied polyphenols. Of these, caffeic acid esters predominate, and 5-O-caffeoylquinic acid (5-CQA) is their main and most widespread representative. Recently performed studies have shown that after removing water from the aqueous solution of 5-CQA, its dry residue contains two hydrates of this compound, each consisting of two 5-CQA molecules and two molecules of H2O (2 × 5-CQA*2xH2O). The results presented in the paper not only define the characteristic features of 5-CQA but, more importantly, offer solid evidence that 5-CQA hydrates begin to form already in the aqueous solution of 5-CQA immediately after the dissolution of this compound and that the analogous process can occur in food products containing 5-CQA during their storage. Moreover, the performed experiments indicate the validity of the hypothesis that 5-CQA hydrates are formed by active collisions of 5-CQA molecules with monomeric/dimeric water molecules existing in trace amount in strongly associated aqueous systems. The presence of 5-CQA hydrates in liquid food products may have a significant impact on the assessment of some of their physicochemical properties as well as their biochemical activity.

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The inhibition effects of chlorogenic acid on the formation of colored oxidation products of (−)-epigallocatechin gallate under enzymatic oxidation

Cited by 8 publications

References 28 publications

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

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

Novel Oxidation Oligomer of Chlorogenic Acid and (−)-Epigallocatechin and Its Quantitative Analysis during the Processing of Keemun Black Tea

The hydrates of chlorogenic acid in its aqueous solution and in stored food products

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