Increase of Theaflavin Gallates and Thearubigins by Acceleration of Catechin Oxidation in a New Fermented Tea Product Obtained by the Tea-Rolling Processing of Loquat (Eriobotrya japonica) and Green Tea Leaves

Tanaka, Takashi; Miyata, Yuji; Tamaya, Kei; Kusano, Rie; Matsuo, Yosuke; Tamaru, Shizuka; Tanaka, Kazunari; Matsui, Toshiro; Maeda, Masamichi; Kouno, Isao

doi:10.1021/jf900963p

Cited by 38 publications

(41 citation statements)

References 26 publications

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“…26,27) However, their biological activities have not been fully evaluated because of difficulties with supply of pure compounds, due to the complexity of black tea polyphenols. Our results provide a facile and efficient method for preparation of pure theasinensins.…”

Section: Biomimetic One-pot Preparation Of a Black Tea Polyphenol Thementioning

confidence: 99%

Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid

et al. 2011

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Chromatographic separation of black tea polyphenols is too difficult to supply sufficient quantities of pure compounds for biological experiments. Thus, facile methods to prepare black tea constituents were desired. Treatment of epigallocatechin gallate with copper(II) chloride efficiently afforded an unstable quinone dimer, dehydrotheasinensin A, and subsequent treatment with ascorbic acid stereoselectively yielded theasinensin A. The latter is a dimer with an R-biphenyl bond, one of the major polyphenols found in black tea. The method is simpler and more effective than enzymatic preparation.

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Section: Biomimetic One-pot Preparation Of a Black Tea Polyphenol Thementioning

confidence: 99%

Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid

et al. 2011

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“…Fresh green tea leaves are particularly rich in catechin (CTN) which constitutes 30-45% of solid green tea extract (Tanaka et al ., 2009). In addition, CTN is a major, abundant flavonoid present in grape seed and black tea (Yilmaz and Toledo, 2004).…”

Section: Introductionmentioning

confidence: 99%

Chronic Administration of Catechin Decreases Depression and Anxiety-Like Behaviors in a Rat Model Using Chronic Corticosterone Injections

Lee¹,

Sur²,

Kwon³

et al. 2013

Biomolecules and Therapeutics

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Previous studies have demonstrated that repeated administration of the exogenous stress hormone corticosterone (CORT) induces dysregulation in the hypothalamic-pituitary-adrenal (HPA) axis and results in depression and anxiety. The current study sought to verify the impact of catechin (CTN) administration on chronic CORT-induced behavioral alterations using the forced swimming test (FST) and the elevated plus maze (EPM) test. Additionally, the effects of CTN on central noradrenergic systems were examined by observing changes in neuronal tyrosine hydroxylase (TH) immunoreactivity in rat brains. Male rats received 10, 20, or 40 mg/kg CTN (i.p.) 1 h prior to a daily injection of CORT for 21 consecutive days. The activation of the HPA axis in response to the repeated CORT injections was confirmed by measuring serum levels of CORT and the expression of corticotrophin-releasing factor (CRF) in the hypothalamus. Daily CTN administration significantly decreased immobility in the FST, increased open-arm exploration in the EPM test, and significantly blocked increases of TH expression in the locus coeruleus (LC). It also significantly enhanced the total number of line crossing in the open-field test (OFT), while individual differences in locomotor activities between experimental groups were not observed in the OFT. Taken together, these findings indicate that the administration of CTN prior to high-dose exogenous CORT significantly improves helpless behaviors, possibly by modulating the central noradrenergic system in rats. Therefore, CTN may be a useful agent for the treatment or alleviation of the complex symptoms associated with depression and anxiety disorders.

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“…Hashimoto et al [22] demonstrated that THSNs A-G (THSNs F/G are dimers of ECG-EGCG) are components of oolong tea. Nonaka et al [23] and Tanaka et al [24] demonstrated the presence of THSNs A and B in mildly oxidized green tea (at 0.061% of total tea leaf weight and 0.5% of dry tea leaf weight, respectively). EGCG and EGC, predominant catechins present in green tea, are present at 4–12% and 2–6%, respectively, of the dry leaf weight [25–26].…”

Section: Introductionmentioning

confidence: 99%

Tea catechin auto-oxidation dimers are accumulated and retained by Caco-2 human intestinal cells

et al. 2010

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Despite the presence of bioactive catechin B-ring auto-oxidation dimers in tea, little is known regarding their absorption in humans. Our hypothesis for this research is that catechin auto-oxidation dimers are present in teas and are absorbable by human intestinal epithelial cells. Dimers [theasinensins (THSNs) and P-2 analogs) were quantified in commercial teas by HPLC-MS. (−)-Epigallocatechin (EGC) and (−)-epigallocatechin gallate (EGCG) homodimers were present at 10-43 and 0-62 µmol/g leaf, respectively. EGC-EGCG heterodimers were present at 0-79 µmol/g. The potential intestinal absorption of these dimers was assessed using Caco-2 intestinal cells. Catechin monomers and dimers were detected in cells exposed to media containing monomers and preformed dimers. Accumulation of dimers was significantly greater than monomers from test media. Three h accumulation of EGC and EGCG was 0.19-0.55% and 1.24-1.35% respectively. Comparatively, 3h accumulation of the EGC P-2 analog, and THSNs C/E was 0.89 ± 0.28% and 1.53 ± 0.36%. Accumulation of P-2, and THSNs A/D was 6.93 ± 2.1%, and 10.1 ± 3.6%. EGCG-EGC heterodimer P-2 analog, and THSN B 3h accumulation was 4.87 ± 2.2%, and 4.65 ± 2.8% respectively. One h retention of P-2, and THSNs A/D was 171 ± 22%, and 29.6 ± 9.3% of accumulated amount suggesting intracellular oxidative conversion of THSNs to P-2. These data suggest that catechin dimers present in the gut lumen may be readily absorbed by intestinal epithelium.

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Increase of Theaflavin Gallates and Thearubigins by Acceleration of Catechin Oxidation in a New Fermented Tea Product Obtained by the Tea-Rolling Processing of Loquat (Eriobotrya japonica) and Green Tea Leaves

Cited by 38 publications

References 26 publications

Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid

Biomimetic One-Pot Preparation of a Black Tea Polyphenol Theasinensin A from Epigallocatechin Gallate by Treatment with Copper(II) Chloride and Ascorbic Acid

Chronic Administration of Catechin Decreases Depression and Anxiety-Like Behaviors in a Rat Model Using Chronic Corticosterone Injections

Tea catechin auto-oxidation dimers are accumulated and retained by Caco-2 human intestinal cells

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