Pop a piece of gum in your mouth—what’s causing that cooling sensation? It’s a compound called cubebol, which is also found in products like aftershave.

The ring structure that forms cubebol is at the center of recent research by Dr. Matthew Siebert and his team.

“We know that there are several compounds containing this ring structure, including cubebol and isovelleral,” said Siebert, assistant professor of chemistry. “Isovelleral, however, has promise as a much more important compound. It has been found to exhibit cytotoxic effects—that may be enhanced by further modification—making this an attractive anti-cancer agent.”

Siebert recently had a paper on the subject of the plurality of pathways in gold published in Organometallics.

“In this work we used quantum chemical calculations to explore the viability of multiple proposed pathways to form naturally occurring ring structures via a gold-catalyzed reaction,” said Siebert. “Before our study, researchers had determined that there are two major events that must take place, but had no justification for which took place first, nor did they understand the details of these events—each event takes multiple chemical steps.”

Ultimately, Siebert’s team found what they believe to be the pathway for developing new compounds. The study provided insight that can be used to duplicate this reaction to form other compounds with this naturally occurring ring structure. This could lead to compounds, such as isovelleral, being used in new anti-cancer medications.

Looking forward

Though the broader purpose of the research is to contribute to the larger chemistry community, Siebert says there is a more specific purpose as well.

“For this particular study, we saw that we could provide answers about which proposed mechanism of action is more likely to take place,” said Siebert. “We were also able to provide directed examples of how one could go about optimizing this reaction in their own work.”

Siebert’s research provides insight into the atomic-level transformations that must take place to synthesize naturally-occurring ring structures in the laboratory.

Siebert hopes that another scientist will take this research and test it in a wet lab, ideally confirming the team’s results.

“We would also like to see our suggestions on optimization put to good use—perhaps by increasing the efficiency with which isovelleral, or other candidate pharmaceuticals, are produced.”