Anti-mitotic activity gives moroidin potential as a chemotherapy drug, and this property combined with its unusual chemical structure has made it a target for organic synthesis.
[3] A second approach by Jia and coworkers employed an asymmetric Michael addition and bromination, a stereoselective reaction that gave a compound with the correct configuration and Leu-Trp linkage.
[5] Chen and coworkers demonstrated another stereoselective approach, which coupled iodotryptophan to 8-aminoquinoline by palladium catalysis to give a single diastereomer with the desired Leu-Trp linkage and configuration.
[6] Moroidin is one of several biologically active compounds isolated from the venom of Dendrocnide moroides, a member of the stinging nettle family.
The plant stores its venom in silica hairs that break off when touched, delivering the toxins through the skin and inducing extreme pain.
During mitosis, microtubules form the organizing structure called the mitotic apparatus, which captures, aligns, and separates chromosomes.
[3] The mechanism of tubulin disruption is not known, but the degree of biological activity has been linked to the structure of the right-hand ring containing the Trp-His linkage.
[3] In contrast, stephanotic acid, a cyclic compound analogous only to the left-hand ring and containing the same Leu-His linkage, has no anti-mitotic activity.