Two novel sulfated bile salt-like dienones, featuring either a unique, rearranged side chain or a rare cis-11,12-diol on the steroidal C-ring, herein named petromyzene A (1) and B (2), respectively, were isolated from water conditioned with spawning male sea lamprey (Petromyzon marinus; a jawless vertebrate animal). The structures of these natural products were elucidated by mass spectrometry and NMR spectroscopy. Petromyzenes A and B exhibited high olfactory potency for adult sea lamprey and strong behavioral attraction for spawning females.
Sea lamprey, Petromyzon marinus, rely heavily on chemical cues that mediate their life history events, such as migration and reproduction. Here, we describe petromyzone A-C (1-3), three novel bile alcohols that are highly oxidized and sulfated, isolated from water conditioned with spermiated male sea lamprey. Structures of these compounds were unequivocally established by spectroscopic analyses and by comparison with spectra of known compounds. Electro-olfactogram recordings showed that 1 at 10 M was stimulatory to the adult sea lamprey olfactory epithelium, while 2 and 3 were stimulatory at 10 M. Behavioral assays indicated that 1 is attractive, 2 is not attractive or repulsive, and 3 is repulsive to ovulated female sea lamprey. The results suggest that 1 and 2 may be putative pheromones that mediate chemical communication in sea lamprey. The identification of these three components enhances our understanding of the structures and functions of sex pheromone components in this species and may provide useful behavioral manipulation tools for the integrated management of sea lamprey, a destructive invader in the Laurentian Great Lakes.
Intra-annual reproductive investments may not be predictive of male reproductive success because of the effects of intra- and inter-sexual interactions on sperm depletion. For long-lived iteroparous fish species such as lake sturgeon (Acipenser fulvescens), reproductive effort may affect life-time reproductive success. Radio frequency identification (RFID) antennas were placed at the mouth of the Upper Black River, MI and downstream of spawning locations to quantify male migratory and mating behaviors including upstream migration time (UT), river residence time (RT), number of intra-annual spawning migrations (IM), inter-annual spawning interval (SI), and operational sex ratio during 2017-2018. Computer assisted sperm analysis (CASA) was used to quantify sperm quality. RT had a strong negative influence on sperm concentration and with measures of sperm quality. RT and the number of females encountered were positively associated with male reproductive success (number of offspring sired) across years. RT, IM, and UT were negatively associated with sperm quality, indicating sperm depletion is a reliable measure of sexual activity. Results demonstrate trade-offs between benefits and costs associated with current reproductive effort on future reproduction.
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