Cyclized 9,11-secosterol enol-ethers from Pseudopterogorgia americana

Chemical investigation of the MeOH extract from the gorgonian Pseudopterogorgia americana afforded two rare sterols, ameristerenol A (1) and B (2), both 9,11-secosterols possesses a seven-membered cyclic enol-ether in ring C, and ameristerol A (3) is the first example of a naturally occurring 9,11-secosterol containing a gorgosterol side chain with a C-24(28) double bond. Ameristerenol A (1) was converted to the sterol derivatives 4–6 to provide additional chemical diversity and comparison for biological screening. The structures of compounds 1–6, along with three related known analogues 7–9, were determined on the basis of extensive spectroscopic analysis and by comparison with literature data. Compound 6 exhibited slight cytotoxicity activity against human breast cancer cell line MDA-MB-231.

DOI: https://doi.org/10.1016/j.steroids.2017.06.008.

Paul D. Scesa

Paul joined the faculty in the Department of Chemistry at the University of South Florida in 2024. Paul is a Florida Native, completing his Associates of Arts at Broward College (formerly Broward Community College), and Bachelors Degree at Florida Atlantic University. He continued at Florida Atlantic University for his PhD, studying the isolation and biomimetic synthesis of coral terpenes with Profs Lyndon West and Stephane Roche. After this, Paul traveled far away to the land of Utah to learn biosynthesis with the Prof Eric Schmidt. This work led to the discovery of terpene biosynthetic gene clusters in soft corals. Paul received an NIH Pathway to Independence Career Award K99/R00 to continue this work. Currently his lab focuses broadly on utilizing biosynthetic knowledge to discover and produce natural products. We are especially interest in terpenes, soft coral and their evolution/ecology and engineering ways to scale natural product production.

Sanjeevan Rajendran

I am a postdoctoral research scholar in the Department of Chemistry at the University of South Florida (USF). My current research focuses on engineering yeast for enhanced production of coral terpenes and transient expression of coral biosynthetic pathways in plant.

I earned my Ph.D. in Natural Products Chemistry from the University of Colombo, Sri Lanka, in 2019. My doctoral research centered on plant- and fungi-derived secondary metabolites, including cyclic peptides, their biological activities, and transcriptomic analyses to elucidate their biosynthetic pathways. During my first postdoctoral appointment at the University of North Texas (UNT), I worked on the production of fungal medicinal compounds in plant and the isolation of metabolites from a bioherbicidal fungus, gaining extensive experience in synthetic biology.