**ABSTRACT NOT FOR
CITATION WITHOUT AUTHOR PERMISSION.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
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Technical Assistance to Development
of Additional Pheromone-Based Control Agents
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
ABSTRACT:
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.