ILIMAQUINONE Chemical Properties

Melting point:

108-110℃ (pentane )

alpha 

D23 -23.2° (c = 1.12 in CHCl3)

Boiling point:

478.4±45.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

DMSO: Soluble; Ethanol: Soluble; Hexane: Soluble; Methanol: Soluble

pka

2.92±0.50(Predicted)

form 

Red solid

color 

Light yellow to brown

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

ILIMAQUINONE Usage And Synthesis

Description

Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. In mammalian cells, 25 μM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC₅₀ = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC₅₀ = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-inducible factor-1.

Uses

Ilimaquinone is an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor.

Uses

Biological probe for intracellular communications and vesicle-mediated transport.

Definition

ChEBI: A natural product found in Dactylospongia elegans.

General Description

A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties. Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. Inhibits cellular methylations through its interaction with S-adenosylhomocysteinase. Blocks the cytotoxicity of ricin and diphtheria toxin. Acts as an inhibitor of the RNase H activity of HIV-1.

Biochem/physiol Actions

Primary TargetInduces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules.

References

[1] H S RADEKE. Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion.[J]. Chemistry & biology, 1999, 6 9: 639-647. DOI: 10.1016/s1074-5521(99)80115-x
[2] P A TAKIZAWA. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone.[J]. Cell, 1993, 73 6: 1079-1090. DOI: 10.1016/0092-8674(93)90638-7
[3] VéRONIQUE CRUCIANI  Svein O M  Edward Leithe. Ilimaquinone inhibits gap-junctional communication prior to Golgi fragmentation and block in protein transport[J]. Experimental cell research, 2003, 287 1: Pages 130-142. DOI: 10.1016/s0014-4827(03)00124-1
[4] BYUNG GYU KIM . A new structural class of S-adenosylhomocysteine hydrolase inhibitors[J]. Bioorganic & Medicinal Chemistry, 2009, 17 18: Pages 6707-6714. DOI: 10.1016/j.bmc.2009.07.061
[5] SHUGENG CAO. Marine Sesquiterpenoids that Inhibit the Lyase Activity of DNA Polymerase β[J]. Journal of Natural Products , 2004, 67 10: 1716-1718. DOI: 10.1021/np049849+
[6] LIN DU  Dale G N  Yu Dong Zhou*. Inducers of Hypoxic Response: Marine Sesquiterpene Quinones Activate HIF-1[J]. Journal of Natural Products , 2013, 76 6: 1175-1181. DOI: 10.1021/np400320r

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