Investigations of Novel Unsaturated Bile Salts of Male Sea Lamprey as Potential Chemical Cues
- 191 Downloads
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.
KeywordsBile salt Agnatha Pheromone
We thank the United States Fish and Wildlife Service, Marquette Biological Station, and the Sea Lamprey Control Centre of Fisheries and Oceans Canada for providing experimental animals. We also thank Dr. A. Dan Jones and Ms. Li Jun Chen for assistance with mass spectrometry analysis. Dr. Ke Li and two anonymous reviewers provided constructive comments which improved the manuscript. This research was funded by Great Lake Fishery Commission. Any use of trade, product, or company names is for descriptive purposes only and does not imply endorsement by the U.S. Government. This article is Contribution 1874 of the U.S. Geological Survey, Great Lakes Science Center.
- Faraway JJ (2005) Linear Models with R. Chapman & Hall, New YorkGoogle Scholar
- Haslewood GAD (1978) The biological importance of bile salts. North Holland Pub Co. P 206Google Scholar
- McMahon TE, Zale AV, Orth DJ (1996) Aquatic habitat measurements. In: Murphy BR, Willis DW (eds) Fisheries techniques, 2nd edn. Maryland, American Fisheries Society, pp 83–120Google Scholar
- Parikh VM (1974) Absorption spectroscopy of organic molecules. Addison Wesley Longman Publishing Co, Reading, MassachusettsGoogle Scholar
- Plesiat P, Grandguillot M, Harayama S, Vragar S, Michel-Briand Y (1991) Cloning, sequencing, and expression of the pseudomonas testosterone gene encoding 3-oxosteroid Δ1 dehydrogenase. J Bacteriol 73:7219–7227Google Scholar
- Tammar AR (1974) Bile salts in fishes. Chem Zool 8:595–612Google Scholar
- Yang Y, Griffiths WJ, Nazer H, Sjovall J (1997) Analysis of bile acids and bile alcohols in urine by capillary column liquid chromatography-mass spectrometry using fast atom bombardment or electrospray ionization and collision-induced dissociation. Biomed Chromatogr 11:240–155PubMedCrossRefGoogle Scholar