Journal of Undergraduate Chemistry Research
Peer Reviewed Article
Goniothalamin, a natural product extracted from the tree bark of the Goniothalamus genus, has been shown to induce apoptosis in cancer cells. It is hypothesized that goniothalamin's biological activity is due to its ability to react with thiols. Goniothalamin has been shown to decrease levels of glutathione, a natural antioxidant, found in cancer cells. This causes a redox imbalance, which ultimately leads to cell death. Thiol-reactive compounds, like goniothalamin, have also been shown to inhibit nuclear factor-κB (NF-κB). NF-κB is a transcription factor that has been implicated in unregulated cell growth. Through a nine step sequence, a novle analogue of goniothalamin has been prepared that replaces the lactone core of the nature product with a cyclohexenone. The synthetic sequence features a unique enol ether protection of beta-diketone which allows facile preparation of the desired analogue. It is anticipated that the novel goniothalamin derivative will demonstrate increaed cytotoxicity against cancer cells.
Mechelke, Mark F.; Dumke, Addison A.; and Wegwerth, Sarah E., "Design and Synthesis of a Potential Chemotherapeutic Agent Using Goniothalamin as a Natural Product Template" (2013). Chemistry Faculty Publications. 2.