title: Characterization of a novel bile alcohol sulfate released by sexually mature male sea lamprey (Petromyzon marinus).
abstract: A sulphate-conjugated bile alcohol, 3,12-diketo-4,6-petromyzonene-24-sulfate (DKPES), was identified using bioassay-guided fractionation from water conditioned with sexually mature male sea lamprey (Petromyzon marinus). The structure and relative stereochemistry of DKPES was established using spectroscopic data. The electro-olfactogram (EOG) response threshold of DKPES was 10(-7) Molar (M) and that of 3-keto petromyzonol sulfate (3 KPZS; a known component of the male sea lamprey sex pheromone) was 10(-10) M. Behavioural studies indicated that DKPES can be detected at low concentrations by attracting sexually mature females to nests when combined with 3 KPZS. Nests baited with a mixture of DKPES and 3 KPZS (ratio 1∶29.8) attracted equal numbers of sexually mature females compared to an adjacent nest baited with 3 KPZS alone. When DKPES and 3 KPZS mixtures were applied at ratios of 2∶29.8 and 10∶29.8, the proportion of sexually mature females that entered baited nests increased to 73% and 70%, respectively. None of the sexually mature females released were attracted to nests baited with DKPES alone. These results indicated that DKPES is a component of the sex pheromone released by sexually mature male sea lamprey, and is the second biologically active compound identified from this pheromone. DKPES represents the first example that a minor component of a vertebrate pheromone can be combined with a major component to elicit critical sexual behaviors. DKPES holds considerable promise for increasing the effectiveness of pheromone-baited trapping as a means of sea lamprey control in the Laurentian Great Lakes.
authors.affiliation: Department of Fisheries and Wildlife, Michigan State University, East Lansing, Michigan, United States of America.
authors.forename: Ke
authors.initials: K
authors.lastname: Li
authors.forename: Cory O
authors.initials: CO
authors.lastname: Brant
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Siefkes
authors.forename: Hanna G
authors.initials: HG
authors.lastname: Kruckman
authors.forename: Weiming
authors.initials: W
authors.lastname: Li
mesh_terms: D000818:Animals; D001522:Behavior, Animal; D001646:Bile / Q000737:chemistry / Q000378:metabolism*; D002793:Cholic Acids / Q000096:biosynthesis* / Q000737:chemistry; D005260:Female; D008297:Male; D008824:Michigan; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D048428:Petromyzon / Q000502:physiology*; D012741:Sexual Maturation
chemical_list: D002793:Cholic Acids; C500317:petromyzonol sulfate