Publication Title

Journal of Undergraduate Chemistry Research

Document Type

Peer Reviewed Article

Publication Date

2013

Abstract

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.

Comments

NOTE: This is a PDF of the article as originally published in the Journal of Undergraduate Chemistry Research. It is archived here with the kind permission of the publisher. The original version was published as:

Mechelke, Mark F., Addison A. Dumke, and Sarah E. Wegwerth (2013). "Design and Synthesis of a Potential Chemotherapeutic Agent Using Goniothalamin as a Natural Product Template." Journal of Undergraduate Chemistry Research, Vol. 12, No. 2. Available to subscribers at http://www.vmi.edu/WorkArea/DownloadAsset.aspx?id=10737425866.

NOTE: Addison A. Dumke and Sarah E. Wegwerth were students enrolled in CHEM 489 - Independent Study and conducted the research for this article under the guidance of Dr. Mark Mechelke.

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