**ABSTRACT NOT FOR CITATION WITHOUT AUTHOR PERMISSION. The title, authors, and abstract for this completion report are provided below. For a copy of the full completion report, please contact the author via e-mail at liweim@msu.edu. Questions? Contact the GLFC via email at slrp@glfc.org or via telephone at 734-662-3018.**





Technical Assistance to Development of Additional Pheromone-Based Control Agents


Ke Li2, Weiming Li2


2  Department of Fisheries and Wildlife, Room 13 Natural Resources Building,

480 Wilson Road, Michigan State University, East Lansing, MI 48824 U.S.A.


May 2019




We characterized 14 compounds produced by sea lamprey that may play roles in regulation of migration and spawning behaviors.  First, we studied the molecules produced by larvae that act as migratory pheromones. A dihydroxylated tetrahydrofuran fatty acid, (+)-PMA, was isolated from larval sea lamprey washings (LW) with guidance from a bioassay that measured in-stream migratory behaviors. A synthetic copy of (+)-PMA was a potent stimulant of the adult olfactory epithelium, and, at 5 × 10−13 M, replicated the extracts of larval washings in biasing adults into a tributary stream. In addition to PMA, three pairs of related fatty-acid derivatives (PMB, petromyroxols, and iso-petromyroxols) have been characterized from LW. The petromyroxol enantiomers offer a rare example of a non-racemic pheromone mixture, but presented a major challenge in quantifying the compounds in the environmental matrix.  After an extensive study, separation and quantification of the petromyroxol enantiomers was developed and optimized using high-performance liquid chromatography (HPLC) tandem mass spectrometry (MS/MS) on a chiral column. Second, we continued our investigation of the pheromones produced by spermiated males. This effort resulted in the identification of eight bile salt derivatives, categorized into three groups according to their chemical structures. Third, we performed chemistry analyses that played an important role in the discovery that spermine functions as a male sex pheromone in sea lamprey. Furthermore, our technical assistance supported other pheromone-related research activities that produced 16 papers. Lastly, we summarized our experiences in identifying pheromones into a review paper entitle “Discovery and characterization of natural products that act as pheromones in fish” for Natural Product Reports.