Damnacanthal: Difference between revisions

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{{chembox
{{DISPLAYTITLE:Damnacanthal}}
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460112831
| Name = Damnacanthal
| ImageFile = Damnacanthal.svg
| ImageName = Chemical structure of damnacanthal
| ImageAlt = Chemical structure of damnacanthal
| IUPACName = 3-Hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde
| OtherNames = 3-Hydroxy-1-methoxyanthraquinone-2-aldehyde
|Section1={{Chembox Identifiers
| CASNo = 477-84-9
| CASNo_Ref = {{cascite|changed|??}}
| CASNoOther =
| PubChem = 2948
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 212948
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IPDMWUNUULAXLU-UHFFFAOYSA-N
| SMILES = COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2843
| InChI = 1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3
| MeSHName =
}}
|Section2={{Chembox Properties
| C=16 | H=10 | O=5
| Appearance =
| Density = 1.461 g/mL
| MeltingPt =
| BoilingPtC = 532
| Solubility =
}}
|Section3={{Chembox Related
| OtherFunction_label = arylformaldehydes
| OtherFunction = [[Gossypol]]<br />
[[Pyridoxal]]
}}
}}


'''Damnacanthal''' is an [[natural anthraquinone|anthraquinone]] which acts as a p56lck [[tyrosine kinase]] inhibitor.<ref>{{cite journal |vauthors=Faltynek CR, Schroeder J, Mauvais P |title=Damnacanthal is a highly potent, selective inhibitor of p56lck tyrosine kinase activity |journal=Biochemistry |volume=34 |issue=38 |pages=12404–10 |date=September 1995 |pmid=7547985 |doi= 10.1021/bi00038a038|url=|display-authors=etal}}</ref> It can be extracted from ''[[Morinda citrifolia]]''.<ref>{{cite journal |vauthors=Anekpankul T, Goto M, Sasaki M |title=Extraction of anti-cancer damnacanthal from roots of ''Morinda citrifolia'' by subcritical water  |journal=Separation and Purification Technology|volume=55 |issue=3 |pages=343–349 |date=July 2007  |pmid= |doi=10.1016/j.seppur.2007.01.004 |url=|display-authors=etal}}</ref>
== Overview ==
[[File:Damnacanthal.svg|thumb|right|Chemical structure of Damnacanthal]]
'''Damnacanthal''' is a naturally occurring anthraquinone compound found in the roots of the noni plant, ''[[Morinda citrifolia]]''. It is known for its potential biological activities, including anti-inflammatory, anti-cancer, and antimicrobial effects. Damnacanthal has been the subject of various studies due to its ability to interact with cellular pathways and its potential therapeutic applications.


== References ==
== Chemical Properties ==
{{reflist}}
Damnacanthal is classified as an anthraquinone, a type of aromatic organic compound. Its chemical formula is C__H__O_, and it is characterized by a three-ring structure with multiple hydroxyl groups. The presence of these hydroxyl groups contributes to its reactivity and potential biological activity.


{{anthraquinone}}
== Biological Activity ==
Damnacanthal has been studied for its effects on various biological systems. It has shown potential as an inhibitor of certain protein kinases, which are enzymes that play a critical role in cell signaling and regulation. This inhibition can lead to the modulation of cellular processes such as proliferation, apoptosis, and differentiation.


[[Category:Hydroxyanthraquinones]]
=== Anti-Cancer Properties ===
[[Category:Tyrosine kinase inhibitors]]
Research has indicated that damnacanthal may have anti-cancer properties. It has been observed to induce apoptosis, or programmed cell death, in certain cancer cell lines. This effect is thought to be mediated through the inhibition of specific signaling pathways that are often dysregulated in cancer.
[[Category:Aldehydes]]
[[Category:Phenol ethers]]
[[Category:Vinylogous carboxylic acids]]


{{antineoplastic-drug-stub}}
=== Anti-Inflammatory Effects ===
{{aromatic-stub}}
Damnacanthal has also demonstrated anti-inflammatory effects in various studies. It may inhibit the production of pro-inflammatory cytokines and reduce the activation of inflammatory pathways, making it a compound of interest for the treatment of inflammatory diseases.
{{dictionary-stub1}}
 
=== Antimicrobial Activity ===
In addition to its anti-cancer and anti-inflammatory properties, damnacanthal has shown antimicrobial activity against a range of pathogens. This includes bacteria, fungi, and viruses, suggesting its potential use as a natural antimicrobial agent.
 
== Sources and Extraction ==
Damnacanthal is primarily extracted from the roots of the noni plant, ''Morinda citrifolia''. The extraction process typically involves the use of organic solvents to isolate the compound from the plant material. The noni plant is native to Southeast Asia and Australasia, and it has been used in traditional medicine for centuries.
 
== Potential Applications ==
Due to its diverse biological activities, damnacanthal is being explored for various therapeutic applications. These include its use as a potential anti-cancer agent, an anti-inflammatory compound, and an antimicrobial treatment. Further research is needed to fully understand its mechanisms of action and to develop effective formulations for clinical use.
 
== Related Pages ==
* [[Anthraquinone]]
* [[Morinda citrifolia]]
* [[Apoptosis]]
* [[Protein kinase]]
 
[[Category:Anthraquinones]]
[[Category:Natural products]]
[[Category:Phytochemicals]]

Latest revision as of 03:36, 13 February 2025


Overview[edit]

Chemical structure of Damnacanthal

Damnacanthal is a naturally occurring anthraquinone compound found in the roots of the noni plant, Morinda citrifolia. It is known for its potential biological activities, including anti-inflammatory, anti-cancer, and antimicrobial effects. Damnacanthal has been the subject of various studies due to its ability to interact with cellular pathways and its potential therapeutic applications.

Chemical Properties[edit]

Damnacanthal is classified as an anthraquinone, a type of aromatic organic compound. Its chemical formula is C__H__O_, and it is characterized by a three-ring structure with multiple hydroxyl groups. The presence of these hydroxyl groups contributes to its reactivity and potential biological activity.

Biological Activity[edit]

Damnacanthal has been studied for its effects on various biological systems. It has shown potential as an inhibitor of certain protein kinases, which are enzymes that play a critical role in cell signaling and regulation. This inhibition can lead to the modulation of cellular processes such as proliferation, apoptosis, and differentiation.

Anti-Cancer Properties[edit]

Research has indicated that damnacanthal may have anti-cancer properties. It has been observed to induce apoptosis, or programmed cell death, in certain cancer cell lines. This effect is thought to be mediated through the inhibition of specific signaling pathways that are often dysregulated in cancer.

Anti-Inflammatory Effects[edit]

Damnacanthal has also demonstrated anti-inflammatory effects in various studies. It may inhibit the production of pro-inflammatory cytokines and reduce the activation of inflammatory pathways, making it a compound of interest for the treatment of inflammatory diseases.

Antimicrobial Activity[edit]

In addition to its anti-cancer and anti-inflammatory properties, damnacanthal has shown antimicrobial activity against a range of pathogens. This includes bacteria, fungi, and viruses, suggesting its potential use as a natural antimicrobial agent.

Sources and Extraction[edit]

Damnacanthal is primarily extracted from the roots of the noni plant, Morinda citrifolia. The extraction process typically involves the use of organic solvents to isolate the compound from the plant material. The noni plant is native to Southeast Asia and Australasia, and it has been used in traditional medicine for centuries.

Potential Applications[edit]

Due to its diverse biological activities, damnacanthal is being explored for various therapeutic applications. These include its use as a potential anti-cancer agent, an anti-inflammatory compound, and an antimicrobial treatment. Further research is needed to fully understand its mechanisms of action and to develop effective formulations for clinical use.

Related Pages[edit]