Damnacanthal

Damnacanthal is an anthraquinone isolated from the root of Morinda citrifolia, using water[1] or organic solvents.[2]

Damnacanthal
Names
Preferred IUPAC name
3-Hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
Other names
3-Hydroxy-1-methoxyanthraquinone-2-aldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.208.625
PubChem CID
UNII
InChI
  • 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 Y
    Key: IPDMWUNUULAXLU-UHFFFAOYSA-N Y
  • 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
SMILES
  • COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O
Properties
Chemical formula
 C16H10O5
Molar mass 282.251 g·mol−1
Density 1.461 g/mL
Boiling point 532 °C (990 °F; 805 K)
Related compounds
Related arylformaldehydes
 Gossypol

Pyridoxal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Pharmacology

In a 1995 in vitro study, damnacanthal was found to act as a potent and selective inhibitor of p56lck tyrosine kinase.[3]

References
  1. Anekpankul T, Goto M, Sasaki M, et al. (July 2007). "Extraction of anti-cancer damnacanthal from roots of Morinda citrifolia by subcritical water". Separation and Purification Technology. 55 (3): 343–349. doi:10.1016/j.seppur.2007.01.004.
  2. Okusada K, Nakamoto K, Nishida M, Fujita-Hamabe W, Kamiya K, Mizushina Y, Satake T, Tokuyama S (2011). "The antinociceptive and anti-inflammatory action of the CHCl3-soluble phase and its main active component, damnacanthal, isolated from the root of Morinda citrifolia". Biol Pharm Bull. 34 (1): 103–7. doi:10.1248/bpb.34.103. PMID 21212526.
  3. Faltynek CR, Schroeder J, Mauvais P, et al. (September 1995). "Damnacanthal is a highly potent, selective inhibitor of p56lck tyrosine kinase activity". Biochemistry. 34 (38): 12404–10. doi:10.1021/bi00038a038. PMID 7547985.


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