Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

• Published in: Journal of organic chemistry Vol. 72; no. 20; pp. 7544 - 7550
• Main Authors: Hoye, Thomas R, Dvornikovs, Vadims, Fine, Jared M, Anderson, Kari R, Jeffrey, Christopher S, Muddiman, David C, Shao, Feng, Sorensen, Peter W, Wang, Jizhou
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 28-09-2007
• Subjects: Alicyclic compounds, terpenoids, prostaglandins, steroids; Animals; Chemistry; Cholestanes - chemistry; Exact sciences and technology; Molecular Conformation; Nuclear Magnetic Resonance, Biomolecular; Organic chemistry; Petromyzon - metabolism; Pheromones - chemistry; Preparations and properties; Pyrrolidinones - chemistry; Steroids; Steroid; Molecular structure; Pheromone; NMR spectrometry; Cholesterol; Hydrogen 1; Marine environment; Squalamine; Pest; Bile acid; Analog; Model compound; Organic sulfate; Cholestane derivatives; Lamprey; Spectrophotometry; Comparative study
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo070957l

The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of 1H NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.