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Catechin ((+)-Catechin) Sale

(Synonyms: 儿茶素; (+)-Catechin; Cianidanol; Catechuic acid) 目录号 : GC32841

(+)-Catechin (Cianidanol, Catechinic acid, Catechuic acid) is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.

Catechin ((+)-Catechin) Chemical Structure

Cas No.:154-23-4

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10mM (in 1mL DMSO)
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实验参考方法

Cell experiment:

The Cell viability assay is performed to assess the toxicity of different concentrations of Catechin on MCF-7 cells. Briefly, MCF-7 cells (2×104 cells/well) are plated in 96-well plates and treated with 0 μg/mL Catechin and 160 μg/mL Catechin for 24 hours. Then, 40 μL of the Cell Titer Blue solution is directly added to the wells and incubated at 37°C for 6 hours. The fluorescence is recorded with a 560 nm/590 nm (excitation/emission) filter set using a microplate fluorescence reader, and the IC50 is calculated. Quadruplet samples are run for each concentration of Catechin in three independent experiments[2].

Animal experiment:

Rats[3]Twelve weeks old, healthy male rats weighing 200 to 230 g are used in this study. Rats are divided into four experimental groups (n=9 each) for one vehicle and three groups of Catechin (three doses). The doses of Catechin are prepared at 50, 100, 200 mg/kg in 0.25% w/v sodium carboxy methylcellulose (CMC) and administered orally for 7 days prior to and during the experimental trials. Episodic memory, the conscious memory of the past experiences is evaluated in this study[3].

References:

[1]. Waffo-Téguo P, et al. Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer. 2001;40(2):173-9.
[2]. Cheruku SP, et al. Catechin ameliorates doxorubicin-induced neuronal cytotoxicity in in vitro and episodic memory deficit in in vivo in Wistar rats. Cytotechnology. 2018 Feb;70(1):245-259.
[3]. Alshatwi AA. Catechin hydrate suppresses MCF-7 proliferation through TP53/Caspase-mediated apoptosis. J Exp Clin Cancer Res. 2010 Dec 17;29:167.

产品描述

(+)-Catechin (Cianidanol, Catechinic acid, Catechuic acid) is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.

The catechin flavonoid reduces proliferation and induces apoptosis of murine lymphoma cells LB02 through modulation of antiapoptotic proteins[1]. Treatment of human prostate cancer cells with catechin induces apoptosis and results in effects on a variety of survival signals suggesting the potential of these compounds as chemopreventive agents for prostate cancer[2]. Catechin is well known to inhibit cyclooxygenase activity with reported IC50 values ranging from 4O μM to 943 μM. It has also been reported to act as an inhibitor of COX-1 and COX-2 with IC50 of about 80 ?M and 130 μM[3].

Dietary catechin significantly delayed tumor onset[5]. Continued intake of catechin, a potential antioxidant, prevents memory regression and DNA oxidative damage in senescence-accelerated (SAMP10) mice. It does not prolong the lifetime of SAMP10 mice, but it does delay brain senescence[6]. (+)-Catechin inhibits intestinal tumor formation and suppresses Focal adhesion kinase activation in the Min/+ Mouse[7].

[1] Daniela Laura Papademetrio, et al. Rev bras farmacogn. 2013, 23(3):455-463. [2] Tayyaba Afsar, et al. Scientific Reports 6. 2016, 23077. [3] Noreen Y, et al. Planta Med. 1998, 64(6):520-4.

Chemical Properties

Cas No. 154-23-4 SDF
别名 儿茶素; (+)-Catechin; Cianidanol; Catechuic acid
Canonical SMILES O[C@@H]1[C@@H](C2=CC(O)=C(O)C=C2)OC3=CC(O)=CC(O)=C3C1
分子式 C15H14O6 分子量 290.27
溶解度 DMSO : ≥ 100 mg/mL (344.51 mM) 储存条件 4°C, away from moisture and light
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1 mM 3.4451 mL 17.2253 mL 34.4507 mL
5 mM 0.689 mL 3.4451 mL 6.8901 mL
10 mM 0.3445 mL 1.7225 mL 3.4451 mL
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Research Update

Beneficial Properties of Green Tea Catechins

Int J Mol Sci 2020 Mar 4;21(5):1744.PMID:32143309DOI:10.3390/ijms21051744.

Green tea (Camellia sinesis) is widely known for its anticancer and anti-inflammatory properties. Among the biologically active compounds contained in Camellia sinesis, the main antioxidant agents are catechins. Recent scientific research indicates that the number of hydroxyl groups and the presence of characteristic structural groups have a major impact on the antioxidant activity of catechins. The best source of these compounds is unfermented green tea. Depending on the type and origin of green tea leaves, their antioxidant properties may be uneven. Catechins exhibit the strong property of neutralizing reactive oxygen and nitrogen species. The group of green tea Catechin derivatives includes: epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate. The last of these presents the most potent anti-inflammatory and anticancer potential. Notably, green tea catechins are widely described to be efficient in the prevention of lung cancer, breast cancer, esophageal cancer, stomach cancer, liver cancer and prostate cancer. The current review aims to summarize the potential anticancer effects and molecular signaling pathways of major green tea catechins. It needs to be clearly emphasized that green tea as well as green tea catechols cannot replace the standard chemotherapy. Nonetheless, their beneficial effects may support the standard anticancer approach.

Catechin prodrugs and analogs: a new array of chemical entities with improved pharmacological and pharmacokinetic properties

Nat Prod Rep 2013 Oct 11;30(11):1438-54.PMID:24056761DOI:10.1039/c3np70038k.

Extensive research on tea catechins, mainly (-)-epigallocatechin gallate, has shown numerous health promoting effects. However, various clinical studies demonstrated several issues associated with tea catechins which account for their poor systemic bioavailability. In order to improve pharmacological activity and bioavailability of natural tea catechins, two major strategies have been adopted to date which include synthesizing Catechin analogs/prodrugs and the development of novel drug delivery systems. In this review, we provide a detailed account of novel synthetic analogs/prodrugs as well as novel drug delivery approaches used for natural tea catechins to make them therapeutically potent drug-like molecules.

New insights into the role of the Nrf2 signaling pathway in green tea Catechin applications

Phytother Res 2021 Jun;35(6):3078-3112.PMID:33569875DOI:10.1002/ptr.7033.

Nuclear factor-erythroid 2-related factor 2 (Nrf2) is a transcriptional signaling pathway that plays a crucial role in numerous clinical complications. Pivotal roles of Nrf2 have been proved in cancer, autoimmune diseases, neurodegeneration, cardiovascular diseases, diabetes mellitus, renal injuries, respiratory conditions, gastrointestinal disturbances, and general disorders related to oxidative stress, inflammation, apoptosis, gelatinolysis, autophagy, and fibrogenesis processes. Green tea catechins as a rich source of phenolic compounds can deal with various clinical problems and manifestations. In this review, we attempted to focus on intervention between green tea catechins and Nrf2. Green tea catechins especially epigallocatechin gallate (EGCG) elucidated the protective role of Nrf2 and its downstream molecules in various disorders through Keap-1, HO-1, NQO-1, GPx, GCLc, GCLm, NF-kB cross-link, kinases, and apoptotic proteins. Subsequently, we compiled an updated expansions of the Nrf2 role as a gate to manage and protect different disorders and feasible indications of green tea catechins through this signaling pathway. The present review highlighted recent evidence-based data in silico, in vitro, and in vivo studies on an outline for future clinical trials.

ORAC and DPPH assay comparison to assess antioxidant capacity of tea infusions: relationship between total polyphenol and individual Catechin content

Int J Food Sci Nutr 2010 Mar;61(2):109-24.PMID:20109129DOI:10.3109/09637480903292601.

Commercially available tea infusions are the major source of catechins for preparing bottled tea beverages and tea supplements available in the market today. In the present study, we analyzed five tea infusions to measure the total antioxidant capacity (TAC) by oxygen radical absorbance capacity (ORAC) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging capacity (DRSC) assays, total polyphenol content by the colorimetric method and individual Catechin content by high-performance liquid chromatography. Four major tea catechins were also analyzed for their TAC to reveal differential antioxidant behavior of the tea infusions, resulting in the ORAC and DRSC methods. The correlation coefficients between DRSC and the total polyphenol or total Catechin content of the tea infusions were 1.0 and 0.99. However, the values fall to 0.73 and 0.69, respectively, while the ORAC activity was correlated with total polyphenol and total Catechin content. Determining the TAC of individual tea catechins showed that ORAC of epicatechin was seven-fold higher than that of epigallocatechin gallate; on the contrary, epigallocatechin gallate showed significantly (P < 0.05) stronger DRSC activity than epicatechin. By evaluating the structure-activity relationship, this study further revealed that OH substitution at the 3' position in pyrogallol moieties contributes to the lower ORAC value of epigallocatechin and epigallocatechin gallate comparing with their non-3'-OH counterparts, such as epicatechin and epicatechin gallate, respectively. Also, numbers of OH substitutions were poorly correlated with the observed ORAC value unlike the DRSC. Overall, results of this study enabled us to hypothesize that substances having a lower TAC value in the ORAC assay compared with that in DPPH assays may pertain to a pro-oxidant effect by generating reactive oxygen species in an aqueous buffer, at a physiological pH. We also propose that substances exhibiting lower TAC value in the ORAC assay compared with that in the DPPH assay are powerful pro-oxidants compared with the substances showing a higher TAC value in the ORAC assay than that in the DPPH assay.

Estimating the Catechin concentrations of new shoots in green tea fields using ground-based hyperspectral imagery

Food Chem 2022 Feb 15;370:130987.PMID:34536779DOI:10.1016/j.foodchem.2021.130987.

Hyperspectral imagery was applied to estimating non-galloyl (EC, EGC) and galloyl (ECG, EGCG) types of catechins in new shoots of green tea. Partial least squares regression models were developed to consider the effects of commercial fertilizer (CF) and organic fertilizer (OF). The models could explain each type of Catechin with a precision of more than 0.79, with a few exceptions. When the CF model was applied to the OF hyperspectral reflectance and the OF model was applied to the CF hyperspectral reflectance for mutual prediction, the prediction accuracy was better with the OF models than CF models. The prediction models using both CF and OF data (hyperspectral reflectances, and concentrations of catechins) had a precision of more than 0.76 except for the non-galloyl-type catechins as a group and EGC alone. These results provide useful data for maintaining and improving the quality of green tea.