Natural flavonoid from green tea
(+)-Gallocatechin does not have a single defined molecular target but rather exerts its effects through multiple mechanisms. As a polyphenol, it acts as a potent antioxidant by scavenging free radicals and reducing oxidative stress. The compound modulates cellular signaling pathways involved in cell proliferation, apoptosis, and inflammation. It has been shown to inhibit the adherence of bacteria, suggesting antimicrobial activity. Its anticancer activity is thought to involve induction of apoptosis, inhibition of cell proliferation, and modulation of signaling pathways such as MAPK, PI3K/AKT, and NF-κB. The compound's antimutagenic properties suggest it may protect against DNA damage.

(+)-Gallocatechin (10-300 μM, 48 h) causes apoptosis and prevents HCT-116 and SW-480 cells from proliferating [1].
In vitro, (+)-Gallocatechin demonstrates potent antioxidant activity by scavenging free radicals and reducing oxidative stress markers. It exhibits anticancer activity against various cancer cell lines, inhibiting cell proliferation and inducing apoptosis. The compound inhibits the adherence of bacteria, indicating antimicrobial potential. It also has antimutagenic properties in UV-irradiated cells. The compound's effects on cellular signaling pathways, including its ability to modulate MAPK, PI3K/AKT, and NF-κB, have been characterized in cell culture models. Its antioxidant activity is typically measured using DPPH, ABTS, or FRAP assays.

In vivo, (+)-Gallocatechin has been studied for its health-promoting effects through its ability to scavenge free radicals and modulate cellular signaling pathways. Its antioxidant properties may contribute to protective effects in models of oxidative stress-related diseases. The compound has been evaluated for its anticancer activity in animal models. However, detailed in vivo efficacy data for (+)-Gallocatechin beyond its antioxidant effects are limited in the public literature. The compound is not used as a therapeutic agent and is for research use only.

For in vitro antioxidant assays, (+)-Gallocatechin is evaluated using cell-free methods. In the DPPH assay, the compound is incubated with a DPPH radical solution, and the decrease in absorbance at 517 nm is measured. The ABTS assay uses ABTS radical cation, and the decrease in absorbance at 734 nm is measured. The FRAP assay measures the compound's ability to reduce ferric ions. In the ORAC assay, the compound's ability to protect a fluorescent probe from peroxyl radical-induced oxidation is measured. For enzyme assays, the compound's inhibition of enzymes such as xanthine oxidase, cyclooxygenase, or lipoxygenase can be measured using standard protocols.

Apoptosis analysis [1]
Cell Types: HCT-116 Cell
Tested Concentrations: 0-100 µM
Incubation Duration: 48 h
Experimental Results: Apoptosis rates at concentrations of 60, 80 and 100 µM: 14.1%, 25.0%, 23.5%.

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Cell Proliferation Analysis[1]
Tea polyphenols were dissolved in DMSO and stored at −20 °C before use. Cells were seeded in 96-well plates (1 × 10~4 cells/well). After 24 h, indicated concentrations of drugs were added to the wells. The final concentration of DMSO was 1%. Controls were exposed to culture medium containing 1% DMSO without drugs. Following the indicated incubation period, cell proliferation was evaluated using an MTS assay according to the manufacturer’s instructions. Briefly, the medium was replaced with 100 μL of fresh medium and 20 μL of MTS reagent (CellTiter 96 Aqueous Solution) in each well, and the plate was returned to the incubator for 1–2 h. A 60 μL aliquot of medium from each well was transferred to an ELISA 96-well plate and its absorbance at 490 nm was recorded. Since 1% DMSO did not influence the proliferation of the two cell lines, results were expressed as percent of control (DMSO vehicle set at 100%).

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Cell Cycle Analysis[1]
HCT-116 cells were plated at a density of 2 × 10~5 cells onto 24-well tissue culture plates. After culturing for 1 day, the medium was changed and the tea polyphenols were added. Cells were incubated for 48 h before they were harvested. These cells were fixed gently with 80% ethanol in a freezer for 2 h and were then treated with 0.25% Triton X-100 for 5 min in an ice bath. Cells were resuspended in 150 µL of PBS containing 40 µg/mL propidium iodide (PI) and 0.1 mg/mL RNase. The cells were incubated in a dark room for 20 min at room temperature, and cell cycle analysis was performed using a FACScan flow cytometer and FlowJo 9.0 software. For each measurement, at least 10,000 cells were counted.

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Apoptosis Analysis[1]
HCT-116 cells were seeded in 24-well tissue culture plates (2 × 10~5 cells/well). On the second day, the medium was changed and cells were treated with test compounds. After treatment for 48 h, the cells floating in the medium were collected. The adherent cells were detached with 0.05% trypsin. Then the culture medium containing FBS and floating cells was added to inactivate the trypsin. After being pipetted gently, the cells were centrifuged for 5 min at 1500× g. The supernatant was removed and the cells were stained with annexin V-FITC and PI according to the manufacturer’s instructions. Annexin V-FITC detects translocation of phosphatidylinositol from the inner to the outer cell membrane during early apoptosis, and PI can enter the cell in late apoptosis or necrosis. Untreated cells were used as control for the double staining. The cells were analyzed immediately after staining using a FACScan flow cytometer and FlowJo 9.0 software. For each measurement, at least 20,000 cells were counted.
For in vitro cell-based assays, cancer cell lines or other cell types are cultured in appropriate media and treated with (+)-Gallocatechin at various concentrations (typically 1-200 μM). Cell viability is measured by MTT or CCK-8 assays. Apoptosis is assessed by Annexin V staining, caspase activity assays, or DNA fragmentation analysis. Cell cycle distribution is analyzed by flow cytometry. For antimicrobial studies, bacterial cultures are treated with the compound, and the minimum inhibitory concentration (MIC) is determined by broth microdilution. For antioxidant studies, cells are exposed to oxidative stress inducers (e.g., H₂O₂) in the presence of the compound, and oxidative stress markers (ROS, MDA, GSH) are measured.

For in vivo animal studies, (+)-Gallocatechin is typically administered orally or intraperitoneally. In models of cancer, tumor-bearing mice are treated with the compound, and tumor growth is monitored. In models of oxidative stress-related diseases, the compound is administered, and markers of oxidative stress and inflammation are assessed. In models of bacterial infection, the compound's antimicrobial efficacy is evaluated. Pharmacokinetic and toxicological studies may also be performed.

Pharmacokinetic properties of (+)-Gallocatechin are not extensively characterized. As a polyphenol, the compound is expected to have limited oral bioavailability due to poor absorption and extensive metabolism. It is metabolized in the liver and gut by phase I and phase II enzymes, and its metabolites may be excreted in urine and feces. The compound's distribution to various tissues, including the brain, has been studied to some extent. Detailed parameters such as Cmax, Tmax, half-life, and bioavailability vary depending on the route of administration and the formulation used.

(+)-Gallocatechin is generally recognized as safe as a natural component of green tea. No significant toxicity has been reported at typical dietary levels. However, high doses of catechins may cause hepatotoxicity in susceptible individuals. The compound is not intended for therapeutic use and is for research purposes only. Standard laboratory safety precautions should be observed when handling the compound. Comprehensive toxicological studies for (+)-Gallocatechin specifically are limited.

[1]. Epigallocatechin Gallate (EGCG) is the most effective cancer chemopreventive polyphenol in green tea. Nutrients. 2012 Nov 8;4(11):1679-91.

Gallocatechin is a catechin belonging to the flavanoids, with hydroxyl groups substituted at the 3, 3', 4', 5, 5', and 7 positions (trans isomer). It is isolated from black locust (Acacia mearnsii) as a metabolite. It is a catechin and also a flavanoid-3,3',4',5,5',7-hexanol. (+)-Gallocatechin has been reported in tea (Camellia sinensis), oak (Quercus acutissima), and other organisms with relevant data. See also: anthocyanin alcohols (subclass); Croferlemer (monomer); green tea leaves (partial). Green tea is a popular beverage consumed daily by millions worldwide. Previous studies have shown that some polyphenolic compounds in green tea possess anticancer activity. However, systematic evaluation remains limited. This study determined the cancer chemopreventive potential of 10 representative polyphenols (caffeic acid, CA; gallic acid, GA; catechin, C; epicatechin, EC; gallocatechin, GC; catechin gallate, CG; gallocatechin gallate, GCG; epicatechin gallate, ECG; epigallocatechin, EGC; epigallocatechin gallate, EGCG) and explored their structure-activity relationships. The effects of these 10 polyphenols on the proliferation of HCT-116 and SW-480 human colorectal cancer cells were assessed using the MTS assay. Cell cycle distribution and apoptosis were analyzed by flow cytometry after staining with propidium iodide (PI)/RNase or Annexin V/PI. Among the 10 polyphenols, EGCG exhibited the strongest antiproliferative effect and significantly induced cell cycle arrest in the G1 phase and apoptosis. Studies on the relationship between chemical structure and anticancer activity have revealed that C and EC do not have antiproliferative effects, while GA does have certain antiproliferative effects. When C and EC are esterified with GA to generate CG and ECG, their antiproliferative effects are significantly enhanced. A similar association exists between EGC and EGCG. Gallic acid groups significantly enhance the anticancer potential of catechins. This property can be used for the semi-synthesis of flavonoid derivatives in the future to develop novel anticancer drugs. [1]
(+)-Gallocatechin is a research compound with no clinical trial or regulatory approval status. It is a naturally occurring polyphenol found in green tea. The compound is used primarily as a reference standard and in pharmacological studies of antioxidant, anticancer, antimicrobial, and antimutagenic activities. It is also used as a standard in analytical chemistry for the quantification of catechins in tea and other plant extracts. The compound is commercially available from chemical suppliers for research purposes only.

C15H14O7

306.2675

306.073

C, 58.83; H, 4.61; O, 36.57

970-73-0

(-)-Epigallocatechin;970-74-1;(+)-Gallocatechin-13C3

65084

White to off-white solid powder

1.7±0.1 g/cm3

685.6±55.0 °C at 760 mmHg

189 - 191 °C

368.5±31.5 °C

0.0±2.2 mmHg at 25°C

1.776

-0.1

6

7

1

22

380

2

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

XMOCLSLCDHWDHP-SWLSCSKDSA-N

InChI=1S/C15H14O7/c16-7-3-9(17)8-5-12(20)15(22-13(8)4-7)6-1-10(18)14(21)11(19)2-6/h1-4,12,15-21H,5H2/t12-,15+/m0/s1

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

(+)-Gallocatechin; Gallocatechin; 970-73-0; Gallocatechol; (+)-gallocatechol; d-Gallocatechin; 1617-55-6; (2R,3S)-gallocatechin;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

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

DMSO : ~100 mg/mL (~326.51 mM)
H2O : ~3.33 mg/mL (~10.87 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (8.16 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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