Ilimaquinone

Names

[ Name ]:
Ilimaquinone

[Synonym ]:
2-Hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylenedecahydro-1-naphthalenyl]methyl}-1,4-benzoquinone
Illimaquinone
Ilimaquinone
Imaquinone
2-hydroxy-5-methoxy-3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidenedecahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione
MFCD00274432
2,5-Cyclohexadiene-1,4-dione, 3-[[(1R,2S,4aS,8aS)-decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl]methyl]-2-hydroxy-5-methoxy-

Biological Activity

[Description]:

Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway. Ilimaquinone can induce vesiculation of the Golgi apparatus[1]. Ilimaquinone exerts anti-HIV, anti-microbial, anti-inflammatory, and effects[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Ilimaquinone induces a concentration-dependent anti-proliferative effect in several types of cancer cell lines, including prostate cancer PC-3 and LNCaP, non-small cell lung cancer A549 and hepatocellular carcinoma Hep3B cells. Ilimaquinone (0.3-30 μM; 48 hours) inhibits the proliferation of PC-3 cells, DU145, LNCaP, MG63, A549, Hep3B cells with GI50s of 2.6 μM, 5.8, 4.6, 4.9, 4.1, 12.0μM, respectively[1]. Cell Viability Assay[1] Cell Line: Prostate cancer PC-3 cells Concentration: 0.3, 1, 3, 10, and 30 μM Incubation Time: 48 hours Result: Inhibited the proliferation of PC-3 cells in a concentration-dependent manner.

[In Vivo]

Ilimaquinone exhibits terminal elimination half-lives (T1/2=1.2±0.3 h) due to high plasma clearance (2.95±0.53 L/h/kg) following oral administration (10 mg/kg) in male Sprague-Dawley rats[2].

[References]

[1]. Pin-Hsuan Lu, et al. Ilimaquinone, a Marine Sponge Metabolite, Displays Anticancer Activity via GADD153-mediated Pathway. Eur J Pharmacol. 2007 Feb 5;556(1-3):45-54.

[2]. Heebin Son, et al. Stereo-Selective Pharmacokinetics of Ilimaquinone Epimers Extracted From a Marine Sponge in Rats. Mar Drugs. 2019 Mar 17;17(3):171.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
478.4±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₂H₃₀O₄

[ Molecular Weight ]:
358.471

[ Flash Point ]:
159.9±22.2 °C

[ Exact Mass ]:
358.214417

[ PSA ]:
63.60000

[ LogP ]:
6.38

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.549

MSDS

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Safety Information

[ WGK Germany ]:
3

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds

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