title: Isolation and identification of petromyzestrosterol, a polyhydroxysteroid from sexually mature male sea lamprey (Petromyzon marinus L.).
abstract: Petromyzestrosterol (1), a novel polyhydroxylated steroid, was identified from water conditioned with sexually mature male sea lamprey (Petromyzon marinus), a jawless vertebrate animal. Along with this novel steroid, two known steroids, 7α,12α,24-trihydroxy-5α-cholan-3-one-24-sulfate (3k PZS) and 7α,12α,24-trihydroxy-5α-cholan-24-sulfate (PZS), were isolated. Structures of these compounds were unequivocally established by spectroscopic analyses and by comparison with spectra of known compounds. Electro-olfactogram recordings (EOG) showed that 1 at nanomolar concentrations was stimulatory for the olfactory epithelium of adult females. 3k PZS, known to function as a male sex pheromone, was more stimulatory than 1 for the female olfactory epithelia. The concentration-response curve of 3k PZS was exponential in shape with steep slopes between 10(-10) and 10(-6) mol L(-1). The concentration-response curve for 1 was shallower than that for 3k PZS.
authors.affiliation: Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA.
authors.forename: Ke
authors.initials: K
authors.lastname: Li
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Siefkes
authors.forename: Cory O
authors.initials: CO
authors.lastname: Brant
authors.forename: Weiming
authors.initials: W
authors.lastname: Li
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid; D005260:Female; D007798:Lampreys; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D012724:Sex Attractants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012903:Smell / Q000187:drug effects / Q000502:physiology; D013261:Sterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D012724:Sex Attractants; D013261:Sterols