Investigations of novel unsaturated bile salts of male sea lamprey as potential chemical cues

Journal of Chemical Ecology
By: , and 



Sulfated bile salts function as chemical cues that coordinate reproduction in sea lamprey, Petromyzon marinus. 7α, 12α, 24-trihydroxy-5α-cholan-3-one 24-sulfate (3kPZS) is the most abundant known bile salt released by sexually mature male sea lampreys and attracts ovulated females. However, previous studies showed that the male-produced pheromone consists of unidentified components in addition to 3kPZS. Here, analysis of water conditioned with mature male sea lampreys indicated the presence of 4 oxidized, unsaturated compounds with molecular weights of 466 Da, 468 Da, and 2 of 470 Da. These compounds were not detectable in water conditioned with immature male sea lampreys. By using mass spectrometry, 4 A-ring unsaturated sulfated bile salts were tentatively identified from male washings as 2 4-ene, a 1-ene, and a 1,4-diene analogs. These were synthesized to determine if they attracted ovulated female sea lampreys to spawning nests in natural streams. One of the novel synthetic bile salts, 3 keto-1-ene PZS, attracted ovulated females to the point of application at a concentration of 10-12 M. This study reveals the structural diversity of bile salts in sea lamprey, some of which have been demonstrated to be pheromonal cues.

Publication type Article
Publication Subtype Journal Article
Title Investigations of novel unsaturated bile salts of male sea lamprey as potential chemical cues
Series title Journal of Chemical Ecology
DOI 10.1007/s10886-014-0511-4
Volume 40
Issue 10
Year Published 2014
Language English
Publisher Kluwer Academic
Publisher location New York, NY
Contributing office(s) Great Lakes Science Center
Description 10 p.
First page 1152
Last page 1160
Online Only (Y/N) N
Additional Online Files (Y/N) N
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