Letter abstract
Nature Chemical Biology 1, 324 - 328 (2005)
Published online: 2 October 2005 | doi:10.1038/nchembio739
Mixture of new sulfated steroids functions as a migratory pheromone in the sea lamprey
Peter W Sorensen1, Jared M Fine1, Vadims Dvornikovs2, Christopher S Jeffrey2, Feng Shao2, Jizhou Wang2, Lance A Vrieze1, Kari R Anderson2 & Thomas R Hoye2
The sea lamprey is an ancient, parasitic fish that invaded the Great Lakes a century ago, where it triggered the collapse of many fisheries1. Like many fishes, this species relies on chemical cues to mediate key aspects of its life, including migration and reproduction2, 3. Here we report the discovery of a multicomponent steroidal pheromone that is released by stream-dwelling larval lamprey and guides adults to spawning streams. We isolated three compounds with pheromonal activity (in submilligram quantities from 8,000 l of larval holding water) and deduced their structures. The most important compound contains an unprecedented 1-(3-aminopropyl)pyrrolidin-2-one subunit and is related to squalamine, an antibiotic produced by sharks4. We verified its structure by chemical synthesis; it attracts adult lamprey at very low (subpicomolar) concentrations. The second component is another new sulfated steroid and the third is petromyzonol sulfate, a known lamprey-specific bile acid derivative. This mixture is the first migratory pheromone identified in a vertebrate and is being investigated for use in lamprey control.
- Department of Fisheries, Wildlife and Conservation Biology, University of Minnesota, St. Paul, Minnesota 55108, USA.
- Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Correspondence to: Peter W Sorensen1 e-mail: psorensen@umn.edu
Correspondence to: Thomas R Hoye2 e-mail: hoye@chem.umn.edu
