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 (IC
50 = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC
50 = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-
inducible factor-
1.
Uses
Biological probe for intracellular communications and vesicle-mediated transport.
Uses
Ilimaquinone is an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor.
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
