Page last updated: 2024-12-10

1,2,8-trihydroxy-6-methoxyxanthone

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

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]

FloraRankFlora DefinitionFamilyFamily Definition
SwertiagenusA plant genus of the family GENTIANACEAE. It is a source of swertiapuniside and IRIDOID GLYCOSIDES.[MeSH]GentianaceaeA plant family of the order Gentianales, subclass Asteridae, class Magnoliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID5281661
CHEMBL ID187044
CHEBI ID9371
MeSH IDM000603527

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
plant metaboliteAny 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)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
aromatic etherAny 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

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)8.50000.00002.37899.7700AID240726
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID384226Cell cycle arrest in rat C6 cells assessed as accumulation at G2/M phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384229Induction necrosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384233Induction of reactive oxygen species production in rat C6 cells at 50 uM after 36 hrs by flow cytometry2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384217Antiproliferative activity against rat C6 cells assessed as cell number after 24 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384224Cell cycle arrest in rat C6 cells assessed as accumulation at G0/G1 phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384232Induction 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 cytometry2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID240726Concentration required to inhibit monoamine oxidase activity by 50%2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
QSAR modeling of the MAO inhibitory activity of xanthones derivatives.
AID384219Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384236Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384239Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384220Antiproliferative activity against rat C6 cells assessed as cell number after 72 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384218Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 24 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384237Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as mitochondrial respiration after 48 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384231Induction apoptosis in rat C6 cells assessed as caspase activation at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384214Antiproliferative activity against human U251 cells assessed as cell number after 24 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384230Induction apoptosis in rat C6 cells at 50 uM after 36 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384225Cell cycle arrest in rat C6 cells assessed as accumulation at S phase at 50 uM after 24 hrs by flow cytometry relative to control2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384222Antiproliferative activity against rat C6 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384216Antiproliferative activity against human U251 cells assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384228Induction of apoptosis in rat C6 cells assessed as change in morphology at 50 uM after 48 hrs by bright field microscopy2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384227Inhibition of bovine brain tubulin by microtubule depolymerization assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384238Antiproliferative activity against Albino Oxford rat primary astrocytes assessed as change in morphology by bright field microscopy2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384215Antiproliferative activity against rat C6 cells assessed as cell number after 48 hrs by crystal violet assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384240Antiproliferative activity against Albino Oxford rat peritoneal macrophages assessed as mitochondrial respiration after 48 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384223Antiproliferative activity against human U251 cells assessed as mitochondrial dehydrogenase activity after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Antiglioma action of xanthones from Gentiana kochiana: Mechanistic and structure-activity requirements.
AID384221Antiproliferative activity against human U251 cells assessed as cell number after 72 hrs by crystal violet assay2008Bioorganic & 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)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (80.00)29.6817
2010's1 (20.00)24.3611
2020's0 (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.

MetricThis Compound (vs All)
Research Demand Index12.50 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.50)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]