1,3,6-tri-o-galloyl-beta-d-glucose
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 Source | ID |
|---|---|
| PubMed CID | 452707 |
| CHEMBL ID | 389895 |
| CHEBI ID | 24182 |
| SCHEMBL ID | 1004538 |
| MeSH ID | M0453766 |
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 |
Protein Targets (2)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus | Potency | 35.4813 | 0.0096 | 10.5250 | 35.4813 | AID1479145 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Other Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Lactoperoxidase | Bos taurus (cattle) | Km | 1.3700 | 0.3000 | 1.5778 | 8.4100 | AID1490876 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (5)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| response to oxidative stress | Lactoperoxidase | Bos taurus (cattle) |
| thiocyanate metabolic process | Lactoperoxidase | Bos taurus (cattle) |
| antibacterial humoral response | Lactoperoxidase | Bos taurus (cattle) |
| hydrogen peroxide catabolic process | Lactoperoxidase | Bos taurus (cattle) |
| cellular oxidant detoxification | Lactoperoxidase | Bos taurus (cattle) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Molecular Functions (5)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| peroxidase activity | Lactoperoxidase | Bos taurus (cattle) |
| calcium ion binding | Lactoperoxidase | Bos taurus (cattle) |
| heme binding | Lactoperoxidase | Bos taurus (cattle) |
| thiocyanate peroxidase activity | Lactoperoxidase | Bos taurus (cattle) |
| lactoperoxidase activity | Lactoperoxidase | Bos taurus (cattle) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Ceullar Components (3)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| virion membrane | Spike glycoprotein | Severe acute respiratory syndrome-related coronavirus |
| extracellular space | Lactoperoxidase | Bos taurus (cattle) |
| cytoplasm | Lactoperoxidase | Bos taurus (cattle) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (19)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1678465 | Anti-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 fluoresce | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678470 | Metal chelating activity assessed as Fe2+-compound complex formation incubated for 5 mins by colorimetry | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678475 | Potency index, ratio of trolox IC50 to test compound IC50 for antioxidant activity assessed as DPPH radical scavenging activity | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678472 | Antioxidant activity in pH 4.5 phosphate buffer assessed as PTIO radical scavenging activity after 1 hr by microplate reader based assay | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678473 | Antioxidant activity assessed as ferric ion reducing activity using FeCl3.H2O and TPTZ incubated for 30 mins by FRAP assay | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678474 | Antioxidant activity assessed as DPPH free radical scavenging activity after 5 mins by microplate reader based assay | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID284211 | Inhibition of HCV NS3 serine protease | 2007 | Bioorganic & 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. |
| AID1678471 | Antioxidant activity in pH 7.4 phosphate buffer assessed as PTIO radical scavenging activity after 1 hr by microplate reader based assay | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678464 | Anti-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 assay | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678468 | Anti-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%) | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678467 | Anti-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%) | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID401340 | Binding affinity to bradykinin | 1996 | Journal of natural products, Feb, Volume: 59, Issue:2 | Natural polyphenols (vegetable tannins) as drugs: possible modes of action. |
| AID1678477 | Metal chelating activity assessed as Fe2+-compound complex formation by measuring red shift by UV-visible spectrophotometry | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678466 | Anti-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%) | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678469 | Anti-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%) | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1678476 | Antioxidant activity assessed as compound-DPPH adduct formation with covalent bridging by UHPLC-ESI-Q-TOF-MS analysis | 2020 | ACS medicinal chemistry letters, Nov-12, Volume: 11, Issue:11 | Covalent Bridging of Corilagin Improves Antiferroptosis Activity: Comparison with 1,3,6-Tri- |
| AID1490878 | Induction 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 plot | 2017 | Journal of natural products, 05-26, Volume: 80, Issue:5 | Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase. |
| AID1490877 | Induction 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 plot | 2017 | Journal of natural products, 05-26, Volume: 80, Issue:5 | Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase. |
| AID1490876 | Induction 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 plot | 2017 | Journal 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)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 1 (16.67) | 18.2507 |
| 2000's | 2 (33.33) | 29.6817 |
| 2010's | 1 (16.67) | 24.3611 |
| 2020's | 2 (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.
| This Compound (12.82) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (16.67%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (83.33%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||