Comparing the inhibitory abilities of epigallocatechin-3-gallate and gallocatechin gallate against tyrosinase and their combined effects with kojic acid

Song, Xin; Ni, Mengting; Zhang, Ying; Zhang, Guowen; Pan, Junhui; Gong, Deming

doi:10.1016/j.foodchem.2021.129172

Cited by 80 publications

(44 citation statements)

References 40 publications

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“…The characteristic spectra of Tyr and Trp residues were obtained at Δλ of 15 and 60 nm, respectively. As shown in Figure 3 C,D, the addition of ECG caused the fluorescence of Tyr and Trp residues to be gradually quenched with no significant peak shift, suggesting that ECG had almost no effect on the polarity and hydrophobicity of the microenvironment around Tyr and Trp residues [ 49 ]. In addition, the ratio of synchronous fluorescence quenching (RSFQ = 1 − F / F 0 ) value of Tyr residue was higher than that of Trp residue, indicating that Tyr residue was closer to the binding site of ECG in XO and thus had a greater contribution to the fluorescence quenching.…”

Section: Resultsmentioning

confidence: 99%

“…The radius of gyration (Rg) is a common index to evaluate the compactness of protein structure [ 49 ]. The Rg value of XO was slightly lower than that of free XO during the whole simulation ( Figure 6 B), indicating that ECG induced XO to form a more compact conformation.…”

Section: Resultsmentioning

confidence: 99%

“…These differences implied that the presence of ECG affected the freedom of the XO structure, and ECG-XO complex had higher stability than the free XO. The radius of gyration (Rg) is a common index to evaluate the compactness of protein structure [49]. The Rg value of XO was slightly lower than that of free XO during the whole simulation (Figure 6B), indicating that ECG induced XO to form a more compact conformation.…”

Section: Simulationmentioning

confidence: 99%

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Epicatechin Gallate as Xanthine Oxidase Inhibitor: Inhibitory Kinetics, Binding Characteristics, Synergistic Inhibition, and Action Mechanism

Zhu

Pan

et al. 2021

Foods

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Epicatechin gallate (ECG) is one of the main components of catechins and has multiple bioactivities. In this work, the inhibitory ability and molecular mechanism of ECG on XO were investigated systematically. ECG was determined as a mixed xanthine oxidase (XO) inhibitor with an IC50 value of 19.33 ± 0.45 μM. The promotion of reduced XO and the inhibition of the formation of uric acid by ECG led to a decrease in O2− radical. The stable ECG–XO complex was formed by hydrogen bonds and van der Waals forces, with the binding constant of the magnitude of 104 L mol−1, and ECG influenced the stability of the polypeptide skeleton and resulted in a more compact conformation of XO. Computational simulations further characterized the binding characteristics and revealed that the inhibitory mechanism of ECG on XO was likely that ECG bound to the vicinity of flavin adenine dinucleotide (FAD) and altered the conformation of XO, hindering the entry of substrate and the diffusion of catalytic products. ECG and allopurinol bound to different active sites of XO and exerted a synergistic inhibitory effect through enhancing their binding stability with XO and changing the target amino acid residues of XO. These findings may provide a theoretical basis for the further application of ECG in the fields of food nutrition and functional foods.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Simulationmentioning

confidence: 99%

See 1 more Smart Citation

Epicatechin Gallate as Xanthine Oxidase Inhibitor: Inhibitory Kinetics, Binding Characteristics, Synergistic Inhibition, and Action Mechanism

Zhu

Pan

et al. 2021

Foods

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“…Tyrosinase activity was found to be related with Parkinson’s disease [ 40 ]. Due to the critical role of tyrosinase in melanogenesis, tyrosinase inhibitors have gained popularity in the cosmetic and pharmaceutical industries to prevent hyperpigmentation and skin-related disorders by inhibiting melanin production and controlling food browning processes [ 41 ]. Because of the side effects of the long-term or excessive use of kojic acid, a tyrosinase inhibitor, natural products have received extensive attention from researchers.…”

Section: Resultsmentioning

confidence: 99%

Identification of Phenolic Compounds by LC-MS/MS and Evaluation of Bioactive Properties of Two Edible Halophytes: Limonium effusum and L. sinuatum

et al. 2021

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This work aimed to evaluate the phenolic content and in vitro antioxidant, antimicrobial and enzyme inhibitory activities of the methanol extracts and their fractions of two edible halophytic Limonium species, L. effusum (LE) and L. sinuatum (LS). The total phenolic content resulted about two-fold higher in the ethyl acetate fraction of LE (522.82 ± 5.67 mg GAE/g extract) than in that of LS (274.87 ± 1.87 mg GAE/g extract). LC-MS/MS analysis indicated that tannic acid was the most abundant phenolic acid in both species (71,439.56 ± 3643.3 µg/g extract in LE and 105,453.5 ± 5328.1 µg/g extract in LS), whereas hyperoside was the most abundant flavonoid (14,006.90 ± 686.1 µg/g extract in LE and 1708.51 ± 83.6 µg/g extract in LS). The antioxidant capacity was evaluated by DPPH and TAC assays, and the stronger antioxidant activity in ethyl acetate fractions was highlighted. Both species were more active against Gram-positive bacteria than Gram negatives and showed considerable growth inhibitions against tested fungi. Interestingly, selective acetylcholinesterase (AChE) activity was observed with LE and LS. Particularly, the water fraction of LS strongly inhibited AChE (IC50 = 0.199 ± 0.009 µg/mL). The ethyl acetate fractions of LE and LS, as well as the n-hexane fraction of LE, exhibited significant antityrosinase activity (IC50 = 245.56 ± 3.6, 295.18 ± 10.57 and 148.27 ± 3.33 µg/mL, respectively). The ethyl acetate fraction and methanol extract of LS also significantly inhibited pancreatic lipase (IC50 = 83.76 ± 4.19 and 162.2 ± 7.29 µg/mL, respectively). Taken together, these findings warrant further investigations to assess the potential of LE and LS as a bioactive source that can be exploited in pharmaceutical, cosmetics and food industries.

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“…Turmeric extract, salidroside and paeonol had potential for preventing pigmentation induced by UVB radiation via inhibiting the tyrosinase activity and melanin synthesis, and they were used as melanin formation inhibitors for hyperpigmentation therapy 38 , 39 . Molecular docking showed that GCG and EGCG bound to the active center of tyrosinase and interacted with copper ions and key amino acid residues via hydrogen bonding and hydrophobic interactions, resulting in a looser conformation of tyrosinase and decrease in tyrosinase activity, during which the half maximal inhibitory concentration (IC 50 ) was 36.8 ± 0.21 μmol/L for GCG and 39.4 ± 0.54 μmol/L for EGCG 40 , 41 . These suggest that GCG alleviated UVB-induced melanosome formation via suppressing tyrosinase activity.…”

Section: Discussionmentioning

confidence: 99%

Protective effects of gallocatechin gallate against ultraviolet B induced skin damages in hairless mice

Sheng

Xiang

et al. 2022

Sci Rep

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Epigallocatechin gallate (EGCG) has the effect to protect skin from ultraviolet B (UVB) induced damages, but it is unstable under ambient conditions, being susceptible to become brown in color. Gallocatechin gallate (GCG), an epimer counterpart of EGCG, is more stable chemically than EGCG. The potential effects of GCG against UVB-induced skin damages has not been available. The objective of this study was to investigate the protective effects of GCG against UVB-induced skin photodamages. GCG was topically applied on the skin of hairless mice at three dosage levels (LL, 12.5 mg/mL; ML 25 mg/mL; HL, 50 mg/mL), with EGCG and a commercially available baby sunscreen lotion SPF50 PA+++ as control. The mice were then irradiated by UVB (fluence rate 1.7 µmol/m2 s) for 45 min. The treatments were carried out once a day for 6 consecutive days. Skin measurements and histological studies were performed at the end of experiment. The results show that GCG treatments at ML and HL levels inhibited the increase in levels of skin oil and pigmentation induced by UVB irradiation, and improved the skin elasticity and collagen fibers. GCG at ML and HL levels inhibited the formation of melanosomes and aberrations in mitochondria of UVB-irradiated skin in hairless mice. It is concluded that GCG protected skin from UVB-induced photodamages by improving skin elasticity and collagen fibers, and inhibiting aberrations in mitochondria and formation of melanosomes.

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Comparing the inhibitory abilities of epigallocatechin-3-gallate and gallocatechin gallate against tyrosinase and their combined effects with kojic acid

Cited by 80 publications

References 40 publications

Epicatechin Gallate as Xanthine Oxidase Inhibitor: Inhibitory Kinetics, Binding Characteristics, Synergistic Inhibition, and Action Mechanism

Epicatechin Gallate as Xanthine Oxidase Inhibitor: Inhibitory Kinetics, Binding Characteristics, Synergistic Inhibition, and Action Mechanism

Identification of Phenolic Compounds by LC-MS/MS and Evaluation of Bioactive Properties of Two Edible Halophytes: Limonium effusum and L. sinuatum

Protective effects of gallocatechin gallate against ultraviolet B induced skin damages in hairless mice

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