Page last updated: 2024-12-06

1,2,3,6-tetragalloylglucose

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,2,3,6-Tetragalloylglucose: A Powerful Antioxidant with Research Potential

1,2,3,6-Tetragalloylglucose, also known as **tetragalloyl glucose**, is a naturally occurring polyphenol found in various plants, including oak, chestnut, and tea. It is a complex molecule formed by the attachment of four gallic acid molecules to a glucose molecule. This structure gives it several unique properties that make it a promising subject for research:

**1. Powerful Antioxidant:**

- Tetragalloylglucose exhibits strong antioxidant activity, which stems from its ability to scavenge free radicals and prevent oxidative damage. This makes it a potential candidate for protecting against various diseases linked to oxidative stress, such as cancer, cardiovascular disease, and neurodegenerative disorders.

**2. Anti-inflammatory Effects:**

- Studies have shown that this compound possesses anti-inflammatory properties, possibly by inhibiting the production of pro-inflammatory cytokines. This opens possibilities for its use in treating inflammatory conditions like arthritis and inflammatory bowel disease.

**3. Antibacterial and Antifungal Activity:**

- Tetragalloylglucose has been shown to exhibit antibacterial and antifungal activity against various microorganisms. This makes it a potential candidate for the development of new antibiotics and antifungals.

**4. Antiviral Properties:**

- Research suggests that tetragalloylglucose may possess antiviral activity, potentially inhibiting viral replication and spread. This opens the door for exploring its use in treating viral infections.

**5. Potential for Cancer Treatment:**

- Some studies indicate that tetragalloylglucose may have anticancer properties, potentially inhibiting tumor growth and inducing apoptosis (programmed cell death) in cancer cells. However, further research is necessary to confirm these findings.

**Current Research Focus:**

- **Exploring its therapeutic potential:** Research is ongoing to further explore the therapeutic benefits of tetragalloylglucose in treating a wide range of diseases, including inflammatory conditions, cancer, and infections.
- **Developing more efficient extraction and synthesis methods:** Researchers are working on developing more efficient methods to extract and synthesize tetragalloylglucose for potential use in pharmaceuticals and supplements.
- **Investigating its mechanisms of action:** Researchers are actively studying the mechanisms by which tetragalloylglucose exerts its beneficial effects, aiming to better understand its interaction with biological systems.

**In conclusion:** 1,2,3,6-Tetragalloylglucose is a promising molecule with significant potential for various applications in the medical field. Its powerful antioxidant, anti-inflammatory, and antimicrobial properties, along with its potential for cancer treatment, make it an attractive target for further research and development.

1,2,3,6-tetragalloylglucose: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2,3,6-tetrakis-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having four galloyl groups in the 1-, 2-, 3- and 6-positions. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID73178
CHEMBL ID449947
CHEBI ID17527
SCHEMBL ID2370043
MeSH IDM0167992

Synonyms (38)

Synonym
CHEBI:17527 ,
1,2,3,6-tetrakis-o-(3,4,5-trihydroxybenzoyl)-beta-d-glucopyranose
79886-50-3
C04516
1,2,3,6-tetra-o-galloyl-beta-d-glucose
1,2,3,6-tetrakis-o-galloyl-beta-d-glucose
1,2,3,6-tetragalloylglucose
[(2r,3r,4s,5r,6s)-3-hydroxy-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate
ACON1_000379
MEGXP0_001175
NCGC00169133-01
[(2r,3r,4s,5r,6s)-3-hydroxy-4,5,6-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
CHEMBL449947 ,
1,2,3,6-tgg
unii-4648s0g699
beta-d-glucopyranose, 1,2,3,6-tetrakis(3,4,5-trihydroxybenzoate)
4648s0g699 ,
b-d-glucopyranose,1,2,3,6-tetrakis(3,4,5-trihydroxybenzoate)
SCHEMBL2370043
84297-48-3
np-003686
1,2,3,6-tetra-o-galloyl-.beta.-d-glucose
.beta.-d-glucopyranose 1,2,3,6-tetragallate
1(.beta.),2,3,6-tetra-o-galloylglucose
.beta.-d-glucopyranose, 1,2,3,6-tetrakis(3,4,5-trihydroxybenzoate)
1,2,3,6-tetra-o-galloyl-.beta.-d-glucopyranose
1,2,3,6-tetra-o-galloyl-beta-d-glucopyranose
beta-d-glucopyranose 1,2,3,6-tetragallate
1(beta),2,3,6-tetra-o-galloylglucose
tetra-o-galloyl-?-d-glucose
Q27102438
CS-0093043
MS-31445
DTXSID80904234
HY-111832
bdbm50595060
E87174
AKOS040760170
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
galloyl beta-D-glucoseA class of beta-D-glucose compounds having an unspecified number of O-galloyl groups in undeined positions.
gallate esterA benzoate ester that is any ester resulting from the formal condensation of the carboxy group of gallic acid (3,4,5-trihydroxybenzoic acid) with an alcoholic or phenolic hydroxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
superpathway of hydrolyzable tannin biosynthesis030
pentagalloylglucose biosynthesis012

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)18.29000.00001.559910.0000AID1872954
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)11.86000.00000.933210.0000AID1872953
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID358166Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358168Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID1872953Inhibition of AChE (unknown origin) by spectrophotometric based Ellman's method2022Bioorganic & medicinal chemistry, 05-01, Volume: 61Advancements in the development of multi-target directed ligands for the treatment of Alzheimer's disease.
AID1778697Antibacterial activity against Mycobacterium smegmatis DSM ATCC 700084 assessed as growth inhibition by serial dilution assay2021Journal of natural products, 05-28, Volume: 84, Issue:5
Cytotoxic Compounds from the Stem Bark of Two subsp. of
AID358167Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358165Cytotoxicity against human PRMI7951 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID1872954Inhibition of BuChE (unknown origin) by spectrophotometric based Ellman's method2022Bioorganic & medicinal chemistry, 05-01, Volume: 61Advancements in the development of multi-target directed ligands for the treatment of Alzheimer's disease.
AID358169Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (25.00)18.7374
1990's3 (37.50)18.2507
2000's0 (0.00)29.6817
2010's1 (12.50)24.3611
2020's2 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.78 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]