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

Nicholas S. Johnson; Sang-Seon Yun; Weiming Li

doi:10.1007/s10886-014-0511-4

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

Nicholas S. Johnson·Sang-Seon Yun·Weiming Li

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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.

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Nicholas S. Johnson, Sang-Seon Yun, Weiming Li. 2014-10-30. Investigations of novel unsaturated bile salts of male sea lamprey as potential chemical cues. https://doi.org/10.1007/s10886-014-0511-4

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