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Special Issue "Catechin in Human Health and Disease"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products".

Deadline for manuscript submissions: 30 April 2018

Special Issue Editor

Guest Editor
Prof. Dr. Mamoru Isemura

University of Shizuoka, Tea Science Center, Shizuoka, Japan
Website | E-Mail
Interests: green tea; Catechin; lectin; cancer

Special Issue Information

Dear Colleagues,

Catechins are natural polyphenolic compounds that are distributed in a variety of foods and herbs. Tea (Camellia sinensis) is a rich source of catechins, especially epigallocatechin-3-gallate (EGCG), which has many biological activities beneficial for human health. These include anti-cancer, anti-obesity, anti-diabetic, anti-cardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects. A number of human epidemiological and clinical studies on tea have provided evidence for its health benefits and these results have been supported by cell-based and animal experiments, although studies to show conflicting results have also been reported. In addition, detailed molecular mechanisms have been proposed for the action mechanism of tea’s major catechin EGCG. One of the most attractive mechanisms is the one in which reactive oxygen species (ROS) is involved. EGCG is known to have dual actions in relation to ROS as an anti-oxidant and a pro-oxidant. Several lines of evidence have indicated that EGCG can both eliminate ROS by scavenging and enhance ROS production. However, it remains unclear what factor(s) can direct EGCG to act as an anti-oxidant or a pro-oxidant.    Catechins and their oligomeric derivatives are also found in apples, persimmons, cacaos, grapes, berries, and so on. However, less information on biological activities of other catechin compounds has been available as compared with EGCG.   This Special Issue is devoted to promotion of the understanding of association of catechins and human health. Research articles and reviews related to catechin compounds to reveal their health effects and their mechanistic aspects are welcomed for inclusion in this Special Issue of Molecules. Topics will include cell-based, animal studies, and human studies and special focus will be given to mechanistically-informative studies to be useful to concinnate the dual action of EGCG and other catechin compounds on ROS. 

Prof. Dr. Mamoru Isemura
Guest Editor

Manuscript Submission Information

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Keywords

  • catechin
  • catechin-derivatives
  • anti-oxidant
  • pro-oxidant
  • ROS
  • human health

Published Papers (4 papers)

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Research

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Open AccessArticle Antioxidant and Cytoprotective Effects of Tibetan Tea and Its Phenolic Components
Molecules 2018, 23(2), 179; doi:10.3390/molecules23020179
Received: 6 December 2017 / Revised: 22 January 2018 / Accepted: 23 January 2018 / Published: 24 January 2018
PDF Full-text (2820 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Tibetan tea (Kangzhuan) is an essential beverage of the Tibetan people. In this study, a lyophilized aqueous extract of Tibetan tea (LATT) was prepared and analyzed by HPLC. The results suggested that there were at least five phenolic components, including gallic
[...] Read more.
Tibetan tea (Kangzhuan) is an essential beverage of the Tibetan people. In this study, a lyophilized aqueous extract of Tibetan tea (LATT) was prepared and analyzed by HPLC. The results suggested that there were at least five phenolic components, including gallic acid, and four catechins (i.e., (+)-catechin, (−)-catechin gallate (CG), (−)-epicatechin gallate (ECG), and (−)-epigallocatechin gallate). Gallic acid, the four catechins, and LATT were then comparatively investigated by four antioxidant assays: ferric reducing antioxidant power, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•) scavenging, 1,1-diphenyl-2-picryl-hydrazl radical scavenging, and 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) radical scavenging assays. In these assays, LATT, along with the five phenolic components, increased their antioxidant effects in a concentration-dependent manner; however, the half maximal scavenging concentrations of ECG were always lower than those of CG. Gallic acid and the four catechins were also suggested to chelate Fe2+ based on UV-visible spectral analysis. Ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC−ESI−Q−TOF−MS/MS) analysis suggested that, when mixed with PTIO•, the five phenolic components could yield two types of radical adduct formation (RAF) products (i.e., tea phenolic dimers and tea phenolic-PTIO• adducts). In a flow cytometry assay, (+)-catechin and LATT was observed to have a cytoprotective effect towards oxidative-stressed bone marrow-derived mesenchymal stem cells. Based on this evidence, we concluded that LATT possesses antioxidative or cytoprotective properties. These effects may mainly be attributed to the presence of phenolic components, including gallic acid and the four catechins. These phenolic components may undergo electron transfer, H+-transfer, and Fe2+-chelating pathways to exhibit antioxidative or cytoprotective effects. In these effects, two diastereoisomeric CG and ECG showed differences to which a steric effect from the 2-carbon may contribute. Phenolic component decay may cause RAF in the antioxidant process. Full article
(This article belongs to the Special Issue Catechin in Human Health and Disease)
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Open AccessFeature PaperArticle Liposomal TriCurin, A Synergistic Combination of Curcumin, Epicatechin Gallate and Resveratrol, Repolarizes Tumor-Associated Microglia/Macrophages, and Eliminates Glioblastoma (GBM) and GBM Stem Cells
Molecules 2018, 23(1), 201; doi:10.3390/molecules23010201
Received: 20 November 2017 / Revised: 3 January 2018 / Accepted: 15 January 2018 / Published: 18 January 2018
PDF Full-text (10006 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Glioblastoma (GBM) is a deadly brain tumor with a current mean survival of 12–15 months. Despite being a potent anti-cancer agent, the turmeric ingredient curcumin (C) has limited anti-tumor efficacy in vivo due to its low bioavailability. We have reported earlier a strategy
[...] Read more.
Glioblastoma (GBM) is a deadly brain tumor with a current mean survival of 12–15 months. Despite being a potent anti-cancer agent, the turmeric ingredient curcumin (C) has limited anti-tumor efficacy in vivo due to its low bioavailability. We have reported earlier a strategy involving the use two other polyphenols, epicatechin gallate (E) from green tea and resveratrol (R) from red grapes at a unique, synergistic molar ratio with C (C:E:R: 4:1:12.5, termed TriCurin) to achieve superior potency against HPV+ tumors than C alone at C:E:R (μM): 32:8:100 (termed 32 μM+ TriCurin). We have now prepared liposomal TriCurin (TrLp) and demonstrated that TrLp boosts activated p53 in cultured GL261 mouse GBM cells to trigger apoptosis of GBM and GBM stem cells in vitro. TrLp administration into mice yielded a stable plasma concentration of 210 nM C for 60 min, which, though sub-lethal for cultured GL261 cells, was able to cause repolarization of M2-like tumor (GBM)-associated microglia/macrophages to the tumoricidal M1-like phenotype and intra-GBM recruitment of activated natural killer cells. The intratumor presence of such tumoricidal immune cells was associated with concomitant suppression of tumor-load, and apoptosis of GBM and GBM stem cells. Thus, TrLp is a potential onco-immunotherapeutic agent against GBM tumors. Full article
(This article belongs to the Special Issue Catechin in Human Health and Disease)
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Open AccessArticle Dietary Copper Reduces the Hepatotoxicity of (−)-Epigallocatechin-3-Gallate in Mice
Molecules 2018, 23(1), 38; doi:10.3390/molecules23010038
Received: 27 November 2017 / Revised: 22 December 2017 / Accepted: 23 December 2017 / Published: 23 December 2017
PDF Full-text (2021 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We developed Cu-deficient, -sufficient and -super nutrition mice models by feeding them with diet containing 1.68, 11.72 or 51.69 mg of Cu/kg for 28 days, respectively. Then, the mice were treated to (−)-epigallocatechin-3-gallate (EGCG, 750 mg/kg BW) by oral in order to assess
[...] Read more.
We developed Cu-deficient, -sufficient and -super nutrition mice models by feeding them with diet containing 1.68, 11.72 or 51.69 mg of Cu/kg for 28 days, respectively. Then, the mice were treated to (−)-epigallocatechin-3-gallate (EGCG, 750 mg/kg BW) by oral in order to assess the acute toxicity of the drug. Following EGCG treatment, the survival rates were 12.5%, 50% and 100% in the Cu-deficient, -sufficient and Cu-super nutrition groups of mice, respectively. Cu level and ceruloplasmin activity in serum were significantly increased with the increase of dietary Cu. However, the Cu supplementation did not produce any obvious impact on serum superoxide dismutase activity. Furthermore, ceruloplasmin, in vitro, significantly promotes EGCG oxidation accompanied with increasing oxidation products and decreasing levels of reactive oxygen species. These results, therefore, suggest that Cu can relieve EGCG hepatotoxicity, possibly by up-regulating ceruloplasmin activity, which can be used to promote EGCG applications. Full article
(This article belongs to the Special Issue Catechin in Human Health and Disease)
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Review

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Open AccessReview Food-Grade Encapsulation Systems for (−)-Epigallocatechin Gallate
Molecules 2018, 23(2), 445; doi:10.3390/molecules23020445
Received: 2 February 2018 / Revised: 12 February 2018 / Accepted: 15 February 2018 / Published: 17 February 2018
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Abstract
(−)-Epigallocatechin gallate (EGCG) has attracted significant research interest due to its health-promoting effects such as antioxidation, anti-inflammation and anti-cancer activities. However, its instability and poor bioavailability have largely limited its efficacy and application. Food-grade materials such as proteins, carbohydrates and lipids show biodegradability,
[...] Read more.
(−)-Epigallocatechin gallate (EGCG) has attracted significant research interest due to its health-promoting effects such as antioxidation, anti-inflammation and anti-cancer activities. However, its instability and poor bioavailability have largely limited its efficacy and application. Food-grade materials such as proteins, carbohydrates and lipids show biodegradability, biocompatibility and biofunctionality properties. Food-grade encapsulation systems are usually used to improve the bioavailability of EGCG. In the present paper, we provide an overview of materials and techniques used in encapsulating EGCG, in which the adsorption mechanisms of food-grade systems during in vitro digestion are reviewed. Moreover, the potential challenges and future work using food-grade encapsulates for delivering EGCG are also discussed. Full article
(This article belongs to the Special Issue Catechin in Human Health and Disease)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Binding of catechins to staphylococcal enterotoxin A
Authors: Shimamura Y.1, Utsumi M.1, Hirai C.1, Nakano S.1, Ito S.1, Tsuji A.2, Ishii T.2, Hosoya T.3, Kan T.4, Ohashi N.1, Masuda S.1
Full name: Shimamura Yuko1, Utsumi Mio1, Hirai Chikako1, Nakano Shogo1, Ito Sohei1, Tsuji Ai.2, Ishii Takeshi2, Hosoya Takahiro3, Kan Toshiyuki4, Ohashi Norio1, Masuda Shuichi1
Affiliations: 1 School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga- ku, Shizuoka 422-8526, Japan
2 Faculty of Nutrition, Kobe Gakuin University, 518 Arise, Ikawadani-cho, Nishi-ku, Kobe 651-2180, Japan
3 Yokohama University of Pharmacy, Department of Kampo Pharmacy, 601 Matano-cho, Totsuka-ku, Yokohama, 245-0066, Japan
4 Department of Synthetic Organic & Medicinal Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
Abstract: Staphylococcal enterotoxin A (SEA) is a toxin protein, and is the most common cause of staphylococcal food poisoning. Polyphenols are known to interact with proteins. In this study, we investigated the binding of catechins to SEA using SPR (Biacore), fourier transform infrared spectroscopy (FT-IR), isothermal titration calorimetry (ITC) and protein-ligand docking. We found that (-)-epigallocatechin gallate (EGCG) could strongly bind to SEA. According to thermodynamic parameters, a negative ΔG indicated that the interaction between EGCG and SEA was spontaneous, and the electrostatic force accompanied by hydrophobic binding forces may play a major role in the binding. Data from Western blot analysis and docking simulation suggest that the hydroxyl group at position 3 of the galloyl group in the catechin structure was responsible for binding affinity with the Y91 of A-6 region of SEA active sites. Our results provide further understanding of the binding interactions between catechins and SEA and the inhibition of toxin activities by catechins.

Title: Vacuum heating enhances the bone forming capability of epigallocatechin gallate-modified gelatin sponge by reinforcing its scaffold effect and by retaining the pharmacological effect of catechin.
Authors: Yoshitomo Honda, et al
Abstract: More recently, we have fabricated and reported the epigallocatechin gallate (EGCG)-modified gelatin sponge (EGCG-GS) as a bone substitute materials (Honda Y, Int J Mol Sci, 2015). The modification of EGCG by gelatin significantly enhanced the bone forming capability of this polyphenol in vivo. However, the EGCG-GS was fragile; further improvement was required to enhance its bone forming capability when the material is compared with autogenous bone graft, gold standard of bone regeneration therapy. In the present study, we newly developed vacuum heated EGCG-GS (vhEGCG-GS) and evaluated its bone forming capability using critical sized defect of rat calvaria model.
New findings were as follows:
1) Vacuum heating process remarkably enhanced the bone formation by reinforcing the scaffold effect of EGCG-GS
2) In vitro experiment revealed that osteoblastic cell line UMR106 readily elongated and proliferated on the vhEGCG-GS. Short intercellular membrane nanotube like image could be observed between two UMR106 cells cultured on the vhEGCG-GS. vhEGCG-GS might not only increase the proliferation of host osteoblasts from calvaria but also promote cell-cell contact of those cells.
3) Given the results of in vivo experiment, there seems to be negligible effect for hindering the pharmacological effect of EGCG by vacuum heating process.

Title: Effects of catechins on Alzheimer’s disease: Recent updates and perspectives
Authors: Kazuki Ide 1,2,3, Norihiro Matsuoka 4, Hiroshi Yamada 3, Daisuke Furushima 3, Koji Kawakami 1, 2
Affiliations: 1 Department of Pharmacoepidemiology, Graduate School of Medicine and Public Health, Kyoto University; Kyoto 606–8501, Japan
2 Center for the Promotion of Interdisciplinary Education and Research, Kyoto University; Kyoto
606–8501, Japan
3 Department of Drug Evaluation and Informatics, Graduate School of Pharmaceutical Sciences, University of Shizuoka; Shizuoka 422–8526, Japan
4 Jyoto Hospital, 11-22 Hanatenhigashi 2-chome, Tsurumi-ku Osaka-shi, Osaka, 538-0044, Japan
Abstract: Alzheimer’s disease (AD) is one of the most frequent neurodegenerative disorders worldwide. Its incidence is gradually increasing because of demographic aging. Therefore, AD prevention and modification is important to improve the elderly health status. Oxidative stress is a component of pathological mechanisms underlying AD. It is caused by a disruption of the balance between reactive oxygen species and antioxidant molecules. This imbalance also causes neuroinflammation. Catechins, which are bioactive components of tea, have antioxidative and anti-inflammatory effects. Moreover, their other potential properties related to AD prevention and modification have been reported in in vitro and in vivo studies. Several clinical studies have also been conducted to date. The current review summarizes recent updates and perspectives of the effects of catechins on AD based on the molecular mechanisms and related clinical studies.
Keywords: Alzheimer’s disease, catechins, molecular mechanisms, clinical study

Title: Lipid peroxidation diminishing perspective of isolated oxidized catechins (theaflavins and thearubigins) from black tea in arginine induced renal malfunctional Rats.
Author: Ali Imran
Abstract: Background: Recently oxidative stress induced maladies have amplified owing to sedentary lifestyle and monotonous diet. Introduction of plant based biomolecules may be a suitable strategy to cope with the lipid peroxidation. In this context, black tea polyphenols (theaflavin & thearubigins) are in fame among the scientific community as cost effective therapeutic agents owing to their safety, economics, structural diversity and ability to modulate various lipid peroxidation responses by halting the expression of different metabolic targets. Methods: The mandate of present investigation was to test the synergism among theaflavins & thearubigins against lipid peroxidative indicators both in vitro and in vivo. Purposely, theaflavins and thearubigins were isolated from black tea through solvent partition methods by using different solvents (Aqueous ethanol, Aqueous methanol & Water) and time intervals (30, 60 & 90 minutes) and subjected to in vitro characterization through different antioxidant indices to access the in vitro lipid peroxidation shooting effect of these bioactive moieties. Moreover, individual theaflavins contents also estimate through HPLC. For evaluation of in vivo antioxidant effect, renal malfunction was induced through arginine and forty rats were divided in four groups (10 each after power analysis) and 04 types of diets were given i.e. T0 (control diet without supplementation), T1 (Basic experimental Diet+ theaflavins supplementation @ 1g), T2 (Basic experimental Diet+ Thearubigins supplementation @ 1g) & T3 (Basic experimental Diet+ Supplementation of theaflavins+ thearubigins @ 0.5+0.5 g, respectively) for the period of 56 days. The body weight, lipid profile, glycemic responses, Renal function test, liver function test, antioxidant indices and hematological parameters were estimated at the termination of study.
Results: The results indicated that theaflavins and thearubigins isolation was significantly affected by time of extraction and solvent. In this context, aqueous ethanol at 60 minute extraction interval caused maximum extraction. Likewise, theaflavins isolate exhibited more antioxidant activity as compared to thearubigins. Moreover, the theaflavins and thearubigins based experimental diets imparted significant reduction in Lipid profile, glucose content, renal function tests and TBARS with enhancement in insulin, HDL and hematological parameters. In this context, theaflavin based diet caused maximum reduction in lipid profile and TBARS better as compared to thearubigins and theaflavins + thearubigins based. However, theaflavin+ thearubigins based diet caused highest glucose, urea & creatinine decline and maximum insulin increase & antioxidant indices as compared to other nutraceuticals.
Conclusions: it was deduced that theaflavins & thearubigins have strong antioxidative potential both in in vitro as well as in vivo to tackle the menace associated with lipid peroxidation.

Title: Probing the in vitro antioncogenic potential of isolated oxidized black tea polyphenols(theaflavins and thearubigins) against HCT-116 and HT 460 Colon and lung cancer cells"
Authors: Ali Imran1, Masood sadiq Butt2 and Hang Xiao3
Abstract: Theaflavins and thearubigins are the flavanols-3-ols found in black tea and have promising antioncogenic potential.  In current research, these fractions were isolated from black tea and probe for their in vitro inhibitory effect against colon and lung cancer cell lines. Results indicated that theaflavin, thearubigins and their combination caused significant inhibition in cell viability in dose dependent manner however, theaflavin imparted maximum reduction in cell viability of HCT 116 & HT460. The flow cytometry results indicated that theaflavin, thearubigins and their combination caused substantial cell arrest at G2/M phase. The effect was more obvious in lung cancer cells (HT 460) as compared to colon cells (HCT 116). Likewise, all treatments caused apoptosis however, the combination of theaflavin and thearubigins showed highest apoptotic ability in comparison of their alone treatments.  Conclusively, it was revealed that theaflavin and thearubigins showed synergistic effect and significantly inhibited the cell proliferation of HCT 116 & HT 460 in time and dose dependent manner by inducing apoptosis and cell cycle arrest however, theaflavin exhibited more pronounced effect.  
Keywords: HCT 116; HT 460; Lung cancer; Theaflavins; Thearubigins; synergistic effects

Type: Review
Title: Synthesis of theaflavins and their functions
Authors: Masumi Takemoto 1,*, and Hiroaki Takemoto 2,*
Affiliation:
1 School of Pharmaceutical Sciences, Ohu University, 31-1 Tomitamachi-Aza Misumido, Koriyama 963-8611, Japan
2 School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan
* Correspondence: Tel.: +81-24-932-92181), +81-3-5791-62402)
Abstract: Epidemiological and interventional clinical studies have reported that black tea is good for human health. The polyphenolic compound theaflavin and its galloyl esters (theaflavins) are the primary red pigments in black tea, which possesses several beneficial properties, such as fat-reducing and glucose-lowering capabilities; lifestyle-related disease prevention; and anti-obesity, anti-cancer, anti-atherosclerotic, anti-inflammatory, anti-viral, anti-bacterial, anti-osteoporotic, and anti-dental caries effects. These compounds are produced from their parent green tea catechins in fresh green tea leaves by key enzymes, such as polyphenoloxidase or peroxidase, during the production of black tea leaves or the fermentation of green tea. Because of the extremely low concentration of theaflavins in black tea, their extraction from black tea leaves at levels sufficient for use in medical studies has been difficult. Therefore, different procedures for the synthesis of theaflavins using chemical oxidizing reagents or enzyme have been studied. Using these methods, theaflavin and its galloyl esters can be synthesized, but at low yields. However, recently, several biosynthetic methods have been reported for the mass production of theaflavins. Using these methods, physiological functions of theaflavins against lifestyle-related diseases in mice and humans were also studied. The detailed functions of theaflavins can be elucidated by undertaking more precise animal experiments and human intervention tests. In this review, we introduce reports on the synthesis of theaflavins and their functions performed over the last 10 years.
Keywords: black tea; theaflavin: polyphenoloxidase; peroxidase: physiological functions

Tentative title: Roles of binding affinity of epigallocatechin-3-O-gallate with proteins in health benefits of green tea
Type: Review
Authors: Kouichi Saeki, Sumio Hayakawa, Shogo Nakano, Sohei Itoh, Yumiko Oishi and Mamoru Isemura
Abstract: Green tea has been shown to have beneficial effects on a variety of diseases such as cancer, obesity, diabetes, cardiovascular disease, and neurodegenerative disease. Green tea component, epigallocatechin-3-O-gallate (EGCG), has been believed to contribute to these effects through antioxidative and prooxidative actions. In addition, several lines of evidence have demonstrated that the binding affinity of EGCG to proteins involves in its action mechanism. There are several methods to demonstrate EGCG-protein bindings. These include dot assays, affinity chromatography, surface plasmon resonance, and computational docking analysis. The present review is aimed to update information from such studies on EGCG-protein interaction and discuss the molecular mechanism by which green tea exerts its health-promoting actions.

 

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