Petromyzonol sulfate

FI GURE 4.3 Structures of allocholic acid (petromyzonol sulfate is identical apart from replacement of the carboxyl group with sulfate), taurine-conjugated bile acid, and geosmin. 

Yun, S-S., Scott, A. P., and Li, W. (2003). Pheromones of the male sea lamprey, Petromyzon marinusL. structural studies on a new compound, 3-keto allocholic acid, and 3-keto petromyzonol sulfate. Steroids 68,297-304. 

Petromyzonol sulfate and allocholic acid are commonly produced and released by larval petromyzontid lampreys and likely used as part of a common evolution-arily conserved pheromone. This scenario is reasonable because different lamprey species have similar larval (silt) and spawning (gravel) habitat requirements, and their larvae derive no apparent benefit from producing compounds that serve as an attractant for adults (Fine et al. 2004). However, not all of the activity of the larval pheromone could be explained by these two bile acids released by larvae (Vrieze and Sorensen 2001). A recent study identified two new compounds, petromyzona-mine disulfate and petromyzosterol disulfate, released by larval sea lampreys and hypothesized to function as pheromones (Sorensen et al. 2005). Currently, there is no evidence that crustaceans use long distance pheromones. 

Figure 13 Chromatograms of gall bladder extracts from the pacific lamprey (A), western brook lamprey (B), and sea lamprey (C). Petromyzonol sulfate (PZS) and allocholic acid (ACA) cleanly separate from each other and hyocholic acid (HA) and lithocholic acid (LCA) are the internal standards. (Reprinted with permission from Steroids, 68 (2003) 515-523 Elsevier.)...

Fine, J.M. and Sorensen, P.W (2005) Biologically relevant concentrations of petromyzonol sulfate, a compound of the sea lamprey migratory pheromone, measured in stream water. /. Chem. Ecol, 31, 2205-2210. 

Siefkes, M.J., Winterstein, S.R., and Weiming, L.I. (2005) Evidence that 3-keto petromyzonol sulfate specifically attacks ovulating female sea lampreys, Petromyzon marinus. Anim. Behav., 70, 1037-1049. 

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