Page last updated: 2024-12-08

1,2,6-tri-o-galloyl-beta-d-glucopyranose

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

Description

## 1,2,6-tri-O-galloyl-beta-D-glucopyranose: A Powerful Antioxidant

**1,2,6-tri-O-galloyl-beta-D-glucopyranose** is a complex polyphenol molecule found naturally in various plants, particularly in the seeds of the **tea plant (Camellia sinensis)**.

**Structure and Composition:**

* **Galloyl groups:** The molecule is composed of a beta-D-glucopyranose core, which is a sugar molecule, and three galloyl groups attached to it at positions 1, 2, and 6. Galloyl groups are esters of gallic acid, a powerful antioxidant.
* **Molecular formula:** C27H22O18

**Importance in Research:**

1,2,6-tri-O-galloyl-beta-D-glucopyranose has attracted significant interest in research due to its potent **antioxidant properties** and potential for various health benefits:

* **Antioxidant Activity:** The galloyl groups are responsible for its strong antioxidant activity. They can effectively scavenge free radicals, protecting cells from oxidative stress and damage. This is crucial for preventing various diseases related to oxidative stress, like cancer, cardiovascular disease, and neurodegenerative disorders.
* **Anti-inflammatory Effects:** Studies suggest that this compound possesses anti-inflammatory properties, which may contribute to its potential therapeutic benefits.
* **Anti-diabetic Effects:** Research indicates that 1,2,6-tri-O-galloyl-beta-D-glucopyranose might help regulate blood sugar levels and potentially improve insulin sensitivity, making it relevant for diabetes research.
* **Anti-microbial Activity:** Some studies suggest that this compound could have anti-microbial effects, potentially combating certain bacterial and fungal infections.

**Research Applications:**

* **Developing novel therapeutic agents:** Scientists are exploring the potential of this compound for developing new drugs or supplements to combat diseases like cancer, diabetes, and inflammatory conditions.
* **Improving food safety:** Research is exploring its use as a natural antioxidant to extend the shelf life of food products and improve their nutritional value.
* **Understanding the role of polyphenols in human health:** Studying this compound helps scientists understand the complex mechanisms of polyphenols and their impact on human health.

**Current Research:**

Ongoing research is focused on:

* **Understanding the specific molecular mechanisms responsible for its diverse biological activities.**
* **Developing efficient and sustainable extraction methods for isolating this compound from natural sources.**
* **Developing safe and effective formulations for its use in various applications.**

**Conclusion:**

1,2,6-tri-O-galloyl-beta-D-glucopyranose holds significant promise for various biomedical and technological applications due to its potent antioxidant properties and potential therapeutic benefits. Ongoing research continues to unravel its potential and explore its applications in improving human health and well-being.

1,2,6-tri-O-galloyl-beta-D-glucopyranose: from Terminalia chebula fruits, effective against multidrug-resistant uropathogens; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,2,6-tris-O-galloyl-beta-D-glucose : A galloyl-beta-D-glucose compound having the galloyl groups in the 1-, 2- 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]

FloraRankFlora DefinitionFamilyFamily Definition
TerminaliagenusA plant genus of the family COMBRETACEAE. Members contain arjunin, an ellagitannin (TANNINS).[MeSH]CombretaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mostly trees and shrubs growing in warm areas.[MeSH]
Terminalia chebulaspecies[no description available]CombretaceaeA plant family of the order Myrtales, subclass Rosidae, class Magnoliopsida. They are mostly trees and shrubs growing in warm areas.[MeSH]

Cross-References

ID SourceID
PubMed CID440308
CHEMBL ID447974
CHEBI ID27395
SCHEMBL ID2370653
MeSH IDM0591768

Synonyms (26)

Synonym
79886-49-0
C04360 ,
1-o,2-o,6-o-trigalloyl-beta-d-glucose
1,2,6-trigalloylglucose
[(2r,3s,4s,5r,6s)-3,4-dihydroxy-5,6-bis[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate
1,2,6-tri-o-gallose-beta-d-glucopyranose
1,2,6-trikis-o-galloyl-beta-d-glucose
bdbm50250504
CHEBI:27395 ,
1,2,6-tris-o-galloyl-beta-d-glucose
1,2,6-tris-o-(3,4,5-trihydroxybenzoyl)-beta-d-glucopyranose
CHEMBL447974 ,
beta-d-glucopyranose, 1,2,6-tris(3,4,5-trihydroxybenzoate)
1,2,6-trigalloyl glucose
SCHEMBL2370653
ncgc00384822-01![(2r,3s,4s,5r,6s)-3,4-dihydroxy-5,6-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Q4545648
DTXSID901000816
1,2,6-tri-o-galloylglucose
PD119278
1,2,6-tri-o-galloyl-beta-d-glucopyranose
1,2,6-tri-galloyl-beta-d-glucose
[4,5-dihydroxy-2-(3,4,5-trihydroxybenzoyl)oxy-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-3-yl] 3,4,5-trihydroxybenzoate
CS-0645777
1,2,6-tri-o-galloyl-|a-d-glucose
HY-N11285
[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)
Genome polyprotein IC50 (µMol)1.89000.70001.95673.8000AID241704
Squalene monooxygenase Rattus norvegicus (Norway rat)IC50 (µMol)0.63000.06102.344610.0000AID357310
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1778694Antibacterial activity against Escherichia coli DSM 1116 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
AID362725Inhibition of Escherichia coli RNase H by FRET assay2008Journal of natural products, Sep, Volume: 71, Issue:9
HIV-1 ribonuclease H inhibitory phenolic glycosides from Eugenia hyemalis.
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.
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
AID241704Inhibitory activity against Hepatitis C virus NS3 protease by ELISA2004Bioorganic & medicinal chemistry letters, Dec-20, Volume: 14, Issue:24
Antiviral compounds from traditional Chinese medicines Galla Chinese as inhibitors of HCV NS3 protease.
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.
AID362726Inhibition of human RNase H by FRET assay2008Journal of natural products, Sep, Volume: 71, Issue:9
HIV-1 ribonuclease H inhibitory phenolic glycosides from Eugenia hyemalis.
AID357310Inhibition of rat squalene epoxidase2001Journal of natural products, Aug, Volume: 64, Issue:8
Ellagitannins and hexahydroxydiphenoyl esters as inhibitors of vertebrate squalene epoxidase.
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.
AID362724Inhibition of HIV2 RNase H by FRET assay2008Journal of natural products, Sep, Volume: 71, Issue:9
HIV-1 ribonuclease H inhibitory phenolic glycosides from Eugenia hyemalis.
AID362723Inhibition of HIV1 RNase H by FRET assay2008Journal of natural products, Sep, Volume: 71, Issue:9
HIV-1 ribonuclease H inhibitory phenolic glycosides from Eugenia hyemalis.
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.
AID399391Inhibition of HIV1 recombinant integrase expressed in Escherichia coli1998Journal of natural products, Jan, Volume: 61, Issue:1
A new flavonol glycoside gallate ester from Acer okamotoanum and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (18.18)18.2507
2000's3 (27.27)29.6817
2010's5 (45.45)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.30

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 Index12.30 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.30)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]