Ilimaquinone

Ilimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties.¹ In mammalian cells, 25 µM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway.^2,3 It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC₅₀ = 40 µM).^1,4 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.^5,6

WARNING This product is not for human or veterinary use.

1. Radeke, H.S., Digits, C.A., Casaubon, R.L., et al. Interactions of (−)-ilimaquinone with methylation enzymes: Implications for vesicular-mediated secretion. Chem. Biol. 6(9), 639-647 (1999).

2. Takizawa, P.A., Yucel, J.K., Veit, B., et al. Complete vesiculation of golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone. Cell 73(6), 1079-1090 (1993).

3. Cruciani, V., Leithe, E., and Mikalsen, S.O. Ilimaquinone inhibits gap-junctional communication prior to Golgi fragmentation and block in protein transport. Exp. Cell Res. 287(1), 130-142 (2003).

4. Kim, B.G., Chun, T.G., Lee, H.Y., et al. A new structural class of S-adenosylhomocysteine hydrolase inhibitors. Bioorg. Med. Chem. 17(18), 6707-6714 (2009).

5. Cao, S., Gao, Z., Thomas, S.J., et al. Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase β. J. Nat. Prod. 67(10), 1716-1718 (2004).

6. Du, L., Zhou, Y.D., and Nagle, D.G. Inducers of hypoxic response: Marine sesquiterpene quinones activate HIF-1. J. Nat. Prod. 76(6), 1175-1181 (2013).