Page last updated: 2024-12-08

1,3,6-tri-o-galloyl-beta-d-glucose

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

Description

1,3,6-tri-O-galloyl-beta-D-glucose, also known as **1,3,6-trigalloylglucose (1,3,6-TGG)**, is a naturally occurring polyphenol found in plants, particularly in the leaves of oak trees. It's a complex molecule with a glucose core and three galloyl groups attached to it.

Here's why 1,3,6-TGG is important for research:

**1. Biological Activities:**

* **Antioxidant:** 1,3,6-TGG exhibits strong antioxidant properties, which means it can neutralize harmful free radicals in the body. This makes it potentially relevant in fighting oxidative stress and related diseases.
* **Anti-inflammatory:** Studies suggest that 1,3,6-TGG has anti-inflammatory effects, potentially making it beneficial in treating inflammatory conditions.
* **Anti-cancer:** 1,3,6-TGG has shown promising anti-cancer activity in vitro and in some animal studies. It can inhibit tumor growth and induce apoptosis (programmed cell death) in cancer cells.
* **Neuroprotective:** Some research suggests that 1,3,6-TGG may have neuroprotective effects, protecting brain cells from damage and potentially benefiting cognitive function.

**2. Potential Therapeutic Applications:**

* **Dietary Supplement:** The antioxidant and other beneficial properties of 1,3,6-TGG have sparked interest in its potential use as a dietary supplement for promoting overall health.
* **Pharmaceutical Development:** Due to its various biological activities, 1,3,6-TGG is being investigated as a potential drug candidate for treating various conditions, including cancer, inflammatory diseases, and neurodegenerative disorders.

**3. Research Tool:**

* **Understanding Plant Metabolism:** 1,3,6-TGG is a valuable tool for studying plant metabolism and the biosynthesis of polyphenols.
* **Exploring Drug Delivery:** Research is exploring the use of 1,3,6-TGG as a carrier molecule for targeted drug delivery.

**4. Food Chemistry:**

* **Food Preservation:** 1,3,6-TGG's antioxidant properties make it potentially useful as a natural food preservative to extend the shelf life of food products.
* **Sensory Properties:** 1,3,6-TGG contributes to the astringent taste and color of certain foods and beverages.

**It's important to note that while 1,3,6-TGG shows promising potential, more research is needed to understand its full effects and safety in humans before it can be widely used as a therapeutic agent or supplement.**

**Current Research:**

Ongoing research on 1,3,6-TGG focuses on:

* **Mechanism of action:** Understanding how 1,3,6-TGG exerts its biological effects at a molecular level.
* **Optimization and delivery:** Finding efficient ways to extract, synthesize, and deliver 1,3,6-TGG to the body.
* **Clinical trials:** Evaluating the safety and efficacy of 1,3,6-TGG in humans for various conditions.

1,3,6-tri-O-galloyl-beta-D-glucose represents a promising area of research with potential benefits for human health and wellness.

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

Cross-References

ID SourceID
PubMed CID452707
CHEMBL ID389895
CHEBI ID24182
SCHEMBL ID1004538
MeSH IDM0453766

Synonyms (47)

Synonym
AC-20241
NCGC00179867-01
ACON1_002062
MEGXP0_001387
[(2r,3r,4s,5r,6s)-3,5-dihydroxy-4,6-bis[(3,4,5-trihydroxybenzoyl)oxy]tetrahydropyran-2-yl]methyl 3,4,5-trihydroxybenzoate
tannic acid (corilagin)
1,3,6-tri-o-galloyl-b-d-glucopyranose
.beta.-d-glucopyranose, 1,3,6-tris(3,4,5-trihydroxybenzoate)
glucopyranose, 1,3,6-trigallate, .beta.-d-
1,3,6-tri-o-galloyl-b-d-glucose
.beta.-d-glucopyranose 1,3,6-trigallate
18483-17-5
gallotannins
chebi:24182 ,
CHEMBL389895
1,3,6-tri-o-galloyl-beta-d-glucose
C17458
nsc 69861
o8718334xj ,
glucopyranose, 1,3,6-trigallate, beta-d-
beta-d-glucopyranose 1,3,6-trigallate
beta-d-glucopyranose, 1,3,6-tris(3,4,5-trihydroxybenzoate)
unii-o8718334xj
AKOS015965331
SCHEMBL1004538
.tannin
1,3,6-tri-o-galloylglucose
W-201661
1,3,6-tri-o-galloyl glucose
1,3,6-tri-o-galloyl-.beta.-d-glucopyranose
1,3,6-trigalloyl glucose
DTXSID3041667
1,3,6-tri-o-galloyl-beta-d-glucose, analytical standard
J303.464J ,
1,3,6-trigalloylglucose, >=95% (lc/ms-elsd)
1,3,6-tri-o-galloyl-beta-d-glucopyranose
(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(((3,4,5-trihydroxybenzoyl)oxy)methyl)tetrahydro-2h-pyran-2,4-diyl bis(3,4,5-trihydroxybenzoate)
1,3,6-tris(3,4,5-trihydroxybenzoate)beta-d-glucopyranose
Q13423012
CS-0032136
HY-N6006
NCGC00179867-02
MS-30889
1,3,6-tri-o-galloyl--d-glucose
E87143
beta-d-glucopyranose-1,3,6-tris(3,4,5-trihydroxybenzoate
1,3,6-tri-o-galloyl- beta -d-glucose
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency35.48130.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LactoperoxidaseBos taurus (cattle)Km1.37000.30001.57788.4100AID1490876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
response to oxidative stressLactoperoxidaseBos taurus (cattle)
thiocyanate metabolic processLactoperoxidaseBos taurus (cattle)
antibacterial humoral responseLactoperoxidaseBos taurus (cattle)
hydrogen peroxide catabolic processLactoperoxidaseBos taurus (cattle)
cellular oxidant detoxificationLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
peroxidase activityLactoperoxidaseBos taurus (cattle)
calcium ion bindingLactoperoxidaseBos taurus (cattle)
heme bindingLactoperoxidaseBos taurus (cattle)
thiocyanate peroxidase activityLactoperoxidaseBos taurus (cattle)
lactoperoxidase activityLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
extracellular spaceLactoperoxidaseBos taurus (cattle)
cytoplasmLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1678465Anti-ferroptosis activity against erastin-induced ferroptosis in Sprague-Dawley rat bmMSC cells assessed as inhibition of lipid peroxidation at 3 ug/ml preincubated for 12 hrs followed by compound addition and measured after 12 hrs by C11-Bodipy fluoresce2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678470Metal chelating activity assessed as Fe2+-compound complex formation incubated for 5 mins by colorimetry2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678475Potency index, ratio of trolox IC50 to test compound IC50 for antioxidant activity assessed as DPPH radical scavenging activity2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678472Antioxidant activity in pH 4.5 phosphate buffer assessed as PTIO radical scavenging activity after 1 hr by microplate reader based assay2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678473Antioxidant activity assessed as ferric ion reducing activity using FeCl3.H2O and TPTZ incubated for 30 mins by FRAP assay2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678474Antioxidant activity assessed as DPPH free radical scavenging activity after 5 mins by microplate reader based assay2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID284211Inhibition of HCV NS3 serine protease2007Bioorganic & medicinal chemistry, Jan-01, Volume: 15, Issue:1
Prediction of binding for a kind of non-peptic HCV NS3 serine protease inhibitors from plants by molecular docking and MM-PBSA method.
AID1678471Antioxidant activity in pH 7.4 phosphate buffer assessed as PTIO radical scavenging activity after 1 hr by microplate reader based assay2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678464Anti-ferroptosis activity against erastin-induced ferroptosis in Sprague-Dawley rat bmMSC cells assessed as increase in cell viability at 0.47 to 4.7 uM preincubated for 12 hrs followed by compound addition and measured after 12 hrs by CCK8 assay2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678468Anti-ferroptosis activity against erastin-induced ferroptosis in Sprague-Dawley rat bmMSC cells assessed as early cell death at 4.7 uM after 1 hr by AnnexinV-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 10.4%)2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678467Anti-ferroptosis activity against erastin-induced ferroptosis in Sprague-Dawley rat bmMSC cells assessed as late cell death at 4.7 uM after 1 hr by AnnexinV-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 19.9%)2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID401340Binding affinity to bradykinin1996Journal of natural products, Feb, Volume: 59, Issue:2
Natural polyphenols (vegetable tannins) as drugs: possible modes of action.
AID1678477Metal chelating activity assessed as Fe2+-compound complex formation by measuring red shift by UV-visible spectrophotometry2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678466Anti-ferroptosis activity against erastin-induced ferroptosis in Sprague-Dawley rat bmMSC cells assessed as cellular death at 4.7 uM after 1 hr by AnnexinV-FITC/propidium iodide staining-based flow cytometric analysis (Rvb = 3.73%)2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678469Anti-ferroptosis activity against erastin-induced ferroptosis in Spargue-Dawley rat bmMSCs cells assessed as cell viability at 4.7 uM after 1 hr by AnnexinV-FITC/propidium iodide staining based flow cytometry analysis (Rvb = 65.9%)2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1678476Antioxidant activity assessed as compound-DPPH adduct formation with covalent bridging by UHPLC-ESI-Q-TOF-MS analysis2020ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11
Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri-
AID1490878Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring ratio of Kcat to Km for substrate using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1490877Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Kcat using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1490876Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Km using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's1 (16.67)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.82

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 Index12.82 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]