Page last updated: 2024-12-11

1,3,6-trihydroxy-2-methyl-9,10-anthraquinone

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-trihydroxy-2-methyl-9,10-anthraquinone is a complex organic molecule with the following chemical properties:

* **Name:** 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone
* **Molecular Formula:** C15H10O5
* **Molecular Weight:** 270.24 g/mol
* **Structure:** It consists of an anthraquinone core (a two-fused benzene ring system with a quinone functional group) with three hydroxyl (-OH) groups at positions 1, 3, and 6, and a methyl group (-CH3) at position 2.

This specific anthraquinone derivative has been the focus of research for its potential applications in various fields, including:

**1. Anti-Cancer Activity:**

* Studies have shown that 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone exhibits significant cytotoxic activity against various cancer cell lines, including leukemia, colon cancer, and breast cancer.
* The mechanism of action is thought to involve the induction of apoptosis (programmed cell death) and inhibition of cancer cell proliferation.

**2. Anti-Inflammatory Activity:**

* This anthraquinone derivative has been found to possess anti-inflammatory properties, potentially acting by inhibiting the production of pro-inflammatory mediators like cytokines.
* This could make it a potential therapeutic agent for treating inflammatory diseases like arthritis and inflammatory bowel disease.

**3. Antioxidant Activity:**

* Anthraquinone derivatives are known for their antioxidant properties, and this specific compound is no exception.
* Its antioxidant activity could be beneficial in protecting cells from damage caused by free radicals, potentially reducing the risk of certain diseases.

**4. Dyeing Applications:**

* Anthraquinones are widely used as dyes in various industries. This specific compound could be investigated for its dyeing properties and potential applications in textiles and other materials.

**5. Pharmaceutical Applications:**

* The diverse biological activities of this anthraquinone derivative make it a promising candidate for further research and development of new pharmaceuticals.

**Research Importance:**

The diverse biological activities of 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone make it a valuable target for research in various fields.

* **Drug discovery:** Investigating its mechanism of action and optimizing its structure could lead to the development of new drugs for cancer treatment, inflammation, and other diseases.
* **Materials science:** Its properties could be utilized in developing novel materials with specific applications, such as dyes, pigments, and antioxidants.
* **Understanding biological processes:** Studying this compound's interactions with biological systems can provide insights into cellular processes and contribute to a better understanding of disease development.

While promising, further research is necessary to fully understand the safety, efficacy, and optimal applications of this anthraquinone derivative.

2-methyl-1,3,6-trihydroxy-9,10-anthraquinone: anthraquinone derivative [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,3,6-trihydroxy-2-methyl-9,10-anthraquinone : A trihydroxyanthraquinone that is 9,10-anthraquinone substituted by hydroxy groups at positions 1, 3 and 6 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis. [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
RubiagenusA plant genus of the family RUBIACEAE. The root is a source of red dyes (madder color and 1,2,4-trihydroxy-9,10-anthracenedione) and ANTHRAQUINONES.[MeSH]RubiaceaeThe Madder plant family of the order Gentianales (formerly Rubiales), subclass Asteridae, class Magnoliopsida includes important medicinal plants that provide QUININE; IPECAC; and COFFEE. They have opposite leaves and interpetiolar stipules.[MeSH]

Cross-References

ID SourceID
PubMed CID5319801
CHEMBL ID251491
CHEBI ID69519
SCHEMBL ID22719980

Synonyms (19)

Synonym
CHEMBL251491
chebi:69519 ,
1,3,6-trihydroxy-2-methylanthracene-9,10-dione
1,3,6-trihydroxy-2-methyl-9,10-anthraquinone
9,10-anthracenedione, 1,3,6-trihydroxy-2-methyl-
6-hydroxyrubiadin
1,3,6-trihydroxy-2-methylanthraquinone
87686-86-0
AKOS028108773
Q27137858
FS-9124
1,3,6-trihydroxy-2-methyl-9,10-anthracenedione; 1,3,6-trihydroxy-2-methylanthraquinone; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone; 2-methyl-1,3,6-trihydroxyanthraquinone
FT-0775879
SCHEMBL22719980
E88682
CS-0023190
DTXSID701257045
2-methyl-1,3,6-trihydroxy-9,10-anthraquinone
HY-N2714
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
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 (1)

ClassDescription
trihydroxyanthraquinoneA member of the class of hydroxyanthraquinones carrying three hydroxy substituents.
[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]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID355821Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 10 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID623563Antibacterial activity against Staphylococcus aureus CGMCC1.2465 after 24 hrs by turbidimetric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis.
AID355820Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 3 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID355819Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 1 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID332370Inhibition of thrombin-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before thrombin challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID355823Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 100 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID312305Chemoprevention index, ratio of IC50 for mouse Hepa lclc7 cells to activity against mouse quinone reductase2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID355825Toxicity in lipopolysaccharide-activated ddY mouse macrophages at 100 uM by MTT method2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
AID312303Induction of mouse quinone reductase in mouse Hepa lclc7 cells assessed as concentration required to double enzyme activity2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID623564Antifungal activity against Candida albicans CGMCC 2.2086 after 24 hrs by turbidimetric method2011Journal of natural products, Oct-28, Volume: 74, Issue:10
Biologically active arborinane-type triterpenoids and anthraquinones from Rubia yunnanensis.
AID332373Inhibition of platelet activating factor-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before platelet activating factor challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID332379Antiplatelet activity against rabbit platelet assessed as inhibition of collagen-induced platelet aggregation treated 3 mins before collagen challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID332371Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before arachidonic acid challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID312304Cytotoxicity against mouse Hepa lclc7 cells2007Journal of natural products, Dec, Volume: 70, Issue:12
Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots.
AID332372Inhibition of collagen-induced platelet aggregation in rabbit platelet assessed as aggregation at 300 uM treated 3 mins before collagen challenge by turbidimetric method1994Journal of natural products, Feb, Volume: 57, Issue:2
Antiplatelet constituents of formosan Rubia akane.
AID355822Inhibition of nitric oxide production in lipopolysaccharide-activated ddY mouse macrophages at 30 uM relative to control2003Journal of natural products, May, Volume: 66, Issue:5
Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis.
[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's1 (20.00)18.2507
2000's2 (40.00)29.6817
2010's2 (40.00)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: 12.87

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 Index12.87 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.87)

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]