title: Investigations of novel unsaturated bile salts of male sea lamprey as potential chemical cues.
abstract: 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.
authors.affiliation: Department of Fisheries and Wildlife, Michigan State University, 13 Natural Resources Building, East Lansing, MI, 48824, USA.
authors.forename: Nicholas S
authors.initials: NS
authors.lastname: Johnson
authors.forename: Sang-Seon
authors.initials: SS
authors.lastname: Yun
authors.forename: Weiming
authors.initials: W
authors.lastname: Li
mesh_terms: D000818:Animals; D001647:Bile Acids and Salts / Q000737:chemistry / Q000378:metabolism*; D005260:Female; D008297:Male; D010060:Ovulation; D048428:Petromyzon / Q000502:physiology*; D012724:Sex Attractants / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001647:Bile Acids and Salts; D012724:Sex Attractants