Natural flavonoid in green tea; COX-1/cyclooxygenase-1

Catechin, the name of which is derived from catechu of the extract of Acacia catechu L., is 3,3’,4’,5,7-pentahydroxyflavan with two steric forms of (+)-catechin (Figure 1) and its enantiomer. In addition, in a broad sense, catechin represents the chemical family name of the compounds derived from catechin. Catechins are distributed in a variety of foods and herbs including tea, apples, persimmons, cacaos, grapes, and berries. This special issue is devoted to information on catechin’s activities related to human health[1].

[1]. Mamoru Isemura. Catechin in Human Health and Disease. Molecules. 2019 Feb 1;24(3):528.

(+)-Catechin is the (+)-enantiomer of catechin and is a polyphenolic antioxidant plant metabolite. It has dual functions of antioxidation and plant metabolism. It is the enantiomer of (-)-catechin. An antioxidant flavonoid compound, mainly found in woody plants, exists in both (+)-catechin and (-)-epicatechin (cis) forms. It has been reported that anthocyanin alcohols are found in tea (Camellia sinensis), peony (Paeonia obovata), and other organisms with relevant data. Catechins are metabolites found or produced in Saccharomyces cerevisiae. An antioxidant flavonoid compound, mainly found in woody plants, exists in both (+)-catechin and (-)-epicatechin (cis) forms. See also: gallic catechin (with subclasses); Kroefeller (monomer). Blueberry (partial)...

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Tea, a product made from the leaves and buds of the tea plant (Camellia sinensis), is one of the richest sources of catechins, with its main catechin component being (−)-epigallocatechin-3-gallate (EGCG) (Figure 1). EGCG has numerous health benefits, such as anti-cancer, anti-obesity, anti-diabetic, anti-cardiovascular disease, anti-infection, hepatoprotective, and neuroprotective effects. Numerous human epidemiological and clinical studies on tea have confirmed its anti-cancer efficacy, supported by cell and animal experiments, although some studies have reported conflicting results. Furthermore, detailed molecular mechanisms of action of EGCG and other catechins have been proposed. One of the most intriguing mechanisms involves reactive oxygen species (ROS). EGCG is known to have a dual role with respect to ROS, acting as both an antioxidant and a pro-oxidant. Multiple pieces of evidence suggest that EGCG can both eliminate ROS by scavenging them and promote their production.
Regarding the anticancer effects of green tea catechins, Shirakami and Shimizu provided updated information on their various mechanisms, including antioxidant, pro-oxidative and anti-inflammatory activities, immune and epigenetic modifications, and receptor tyrosine kinase inhibition. They noted that due to the low bioavailability of EGCG, it is currently unclear whether observations of high concentrations of EGCG in vitro can be directly extrapolated to cancer chemoprevention in animals and humans. [1]

C15H14O6

290.26806

308.089

7295-85-4

(+)-Catechin hydrate;225937-10-0;Catechin;154-23-4

9064

White to off-white solid powder

214 °C

1.481

5

6

1

21

364

2

C1[C@@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O

PFTAWBLQPZVEMU-DZGCQCFKSA-N

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol; L-Epicatechin; 13392-26-2; 7295-85-4; (+/-)-Catechin; (+/-)-Epicatechin; 17334-50-8; CHEBI:23053;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~125 mg/mL (~430.63 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)