1,2,8-trihydroxy-6-methoxyxanthone
Description
1,2,8-trihydroxy-6-methoxyxanthone, also known as **mangiferin**, is a natural compound found in various plants, particularly in the mango tree (Mangifera indica). It's a polyphenol, meaning it has multiple hydroxyl (OH) groups attached to its structure.
**Here's why it's important for research:**
* **Pharmacological Activities:** Mangiferin has been shown to exhibit a wide range of pharmacological activities, including:
* **Antioxidant:** It protects cells against damage caused by free radicals, which are linked to aging and various diseases.
* **Anti-inflammatory:** It can reduce inflammation by inhibiting certain enzymes and signaling pathways.
* **Anti-cancer:** Studies suggest it may have anti-proliferative effects on various cancer cells, potentially by inducing apoptosis (programmed cell death).
* **Neuroprotective:** It may protect brain cells from damage caused by oxidative stress and neurotoxins.
* **Antidiabetic:** It has shown potential for regulating blood glucose levels and improving insulin sensitivity.
* **Antiviral:** Some research indicates its potential to inhibit the replication of certain viruses.
* **Potential Therapeutic Applications:** Due to its diverse pharmacological activities, mangiferin is being investigated as a potential therapeutic agent for various diseases, including:
* **Cancer:** Research is ongoing to explore its effectiveness against different types of cancer.
* **Neurodegenerative diseases:** Its neuroprotective properties are being explored for Alzheimer's and Parkinson's diseases.
* **Diabetes:** Its potential for blood sugar control is under investigation.
* **Inflammatory diseases:** It's being investigated for its ability to treat conditions like rheumatoid arthritis and inflammatory bowel disease.
* **Natural Source of Bioactive Compounds:** Mangiferin is a natural product that is readily available in mango and other plants. This makes it a promising source for developing new drugs and supplements.
**However, research on mangiferin is still ongoing, and more studies are needed to confirm its efficacy and safety for therapeutic use.** The specific mechanisms of action and optimal dosage for different conditions are still being investigated.
1,2,8-trihydroxy-6-methoxyxanthone: has antidiabetic, antihyperlipidemic, and antioxidant activities; isolated from Swertia corymbosa; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
swertianin : A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 2 and 8 and a methoxy group at position 6. It has been isolated from various species of the genus Swertia and has been found to exhibit antioxidant activities. [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]
Related Flora
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Swertia | genus | A plant genus of the family GENTIANACEAE. It is a source of swertiapuniside and IRIDOID GLYCOSIDES.[MeSH] | Gentianaceae | A plant family of the order Gentianales, subclass Asteridae, class Magnoliopsida.[MeSH] |
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 5281661 |
| CHEMBL ID | 187044 |
| CHEBI ID | 9371 |
| MeSH ID | M000603527 |
Synonyms (32)
| Synonym |
|---|
| nsc289490 |
| swertianine |
| nsc-289490 |
| swertianin |
| 1,2,8-trihydroxy-6-methoxyxanthone |
| 20882-75-1 |
| 6-methoxy-1,2,8-trihydroxyxanthen-9-one |
| 1,2,8-trihydroxy-6-methoxy-9h-xanthen-9-one |
| nsc 289490 |
| gentiakochianin |
| xanthen-9-one, 6-methoxy-1,2,8-trihydroxy- |
| brn 1351024 |
| 9h-xanthen-9-one, 1,2,8-trihydroxy-6-methoxy- |
| bdbm50155435 |
| 1,2,8-trihydroxy-6-methoxy-xanthen-9-one |
| CHEMBL187044 , |
| chebi:9371 , |
| 1,2,8-trihydroxy-6-methoxyxanthen-9-one |
| unii-890wxq4kc0 |
| 890wxq4kc0 , |
| AKOS016010617 |
| xanthen-9-one, 1,2,8-trihydroxy-6-methoxy- |
| gentiakoxianin |
| 1,7,8-trihydroxy-3-methoxyxanthone |
| 1,3,7,8-tetrahydroxyxanthone 3-methyl ether |
| 3-methoxy-1,7,8-trihydroxyxanthone |
| Q-100263 |
| FT-0697995 |
| DTXSID60174998 |
| Q27108364 |
| CS-0018315 |
| HY-N1994 |
Roles (2)
| Role | Description |
|---|---|
| antioxidant | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. |
| plant metabolite | Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. |
| [role 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] | |
Drug Classes (3)
| Class | Description |
|---|---|
| xanthones | Any member of the class of xanthenes based on a xanthone skeleton. |
| polyphenol | Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [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] | |
Protein Targets (1)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Amine oxidase [flavin-containing] A | Homo sapiens (human) | IC50 (µMol) | 8.5000 | 0.0000 | 2.3789 | 9.7700 | AID240726 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (3)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| biogenic amine metabolic process | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| positive regulation of signal transduction | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| dopamine catabolic process | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Molecular Functions (5)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| protein binding | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| primary amine oxidase activity | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| aliphatic amine oxidase activity | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| monoamine oxidase activity | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| flavin adenine dinucleotide binding | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Ceullar Components (3)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| mitochondrion | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| mitochondrial outer membrane | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| cytosol | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| mitochondrion | Amine oxidase [flavin-containing] A | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Bioassays (26)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID384226 | Cell cycle arrest in rat C6 cells assessed as accumulation at G2/M phase at 50 uM after 24 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384229 | Induction necrosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384233 | Induction of reactive oxygen species production in rat C6 cells at 50 uM after 36 hrs by flow cytometry | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384217 | Antiproliferative activity against rat C6 cells assessed as cell number after 24 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384224 | Cell cycle arrest in rat C6 cells assessed as accumulation at G0/G1 phase at 50 uM after 24 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384232 | Induction of mitochondrial membrane potential depolarization in rat C6 cells assessed as increase in green to red fluorescence ratio at 50 uM after 24 hrs by flow cytometry | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID240726 | Concentration required to inhibit monoamine oxidase activity by 50% | 2004 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22 | QSAR modeling of the MAO inhibitory activity of xanthones derivatives. |
| AID384219 | Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384236 | Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as cell number after 48 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384239 | Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as cell number after 48 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384220 | Antiproliferative activity against rat C6 cells assessed as cell number after 72 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384218 | Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384237 | Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as mitochondrial respiration after 48 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384231 | Induction apoptosis in rat C6 cells assessed as caspase activation at 50 uM after 36 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384214 | Antiproliferative activity against human U251 cells assessed as cell number after 24 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384230 | Induction apoptosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384225 | Cell cycle arrest in rat C6 cells assessed as accumulation at S phase at 50 uM after 24 hrs by flow cytometry relative to control | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384222 | Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384216 | Antiproliferative activity against human U251 cells assessed as cell number after 48 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384228 | Induction of apoptosis in rat C6 cells assessed as change in morphology at 50 uM after 48 hrs by bright field microscopy | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384227 | Inhibition of bovine brain tubulin by microtubule depolymerization assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384238 | Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as change in morphology by bright field microscopy | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384215 | Antiproliferative activity against rat C6 cells assessed as cell number after 48 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384240 | Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as mitochondrial respiration after 48 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384223 | Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| AID384221 | Antiproliferative activity against human U251 cells assessed as cell number after 72 hrs by crystal violet assay | 2008 | Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10 | Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (5)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 4 (80.00) | 29.6817 |
| 2010's | 1 (20.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 12.50
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 (12.50) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||