O'Brien E T, Asai D J, Groweiss A, Lipshutz B H, Fenical W, Jacobs R S, Wilson L
J Med Chem. 1986 Oct;29(10):1851-5. doi: 10.1021/jm00160a009.
Stypoldione, a marine natural product that possesses an o-quinone functional group, has been shown to inhibit a variety of biological processes including cell division. We found that stypoldione binds covalently to sulfhydryl groups of thiol-containing compounds via addition of sulfur to the C-4' position of the quinone ring. We examined the ability of stypoldione to add to sulfhydryl groups of a number of thiol-containing substances, including glutathione, thiophenol, beta-mercaptoethanol, and the protein tubulin. We suggest that the biological actions of stypoldione may be caused by the addition of this compound to thiol groups of biological molecules.
