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Mar. Drugs 2018, 16(9), 308; https://doi.org/10.3390/md16090308

Petromylidenes A–C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus)

Department of Fisheries and Wildlife, Michigan State University, East Lansing, MI 48824, USA
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Received: 9 August 2018 / Revised: 24 August 2018 / Accepted: 29 August 2018 / Published: 1 September 2018
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Abstract

Three novel bile acid derivatives, petromylidenes A–C (13), featuring uncommon alkylidene adductive scaffolds, were isolated from water conditioned with sexually mature male sea lampreys (Petromyzon marinus). Their structures were elucidated by mass spectrometry and NMR spectroscopy, and by comparison to spectral data of related structures. The identification of compounds 13, further illustrates the structural diversity of the 5α bile salt family. Compounds 13 exhibited notable biological properties as well, including high olfactory potencies in adult sea lampreys and strong behavioral attraction of ovulated female sea lampreys. Electro-olfactogram recordings indicated that the limit of detection for 1 was 10−9 M, 2 was 10−11 M, and 3 was less than 10−13 M. These results suggested 13 were likely male pheromones, which guide reproductive behaviors in the sea lamprey. View Full-Text
Keywords: bile salts; pheromone; electro-olfactogram; behavioral assay; invasive species; cyclostomata bile salts; pheromone; electro-olfactogram; behavioral assay; invasive species; cyclostomata
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Li, K.; Scott, A.M.; Fissette, S.D.; Buchinger, T.J.; Riedy, J.J.; Li, W. Petromylidenes A–C: 2-Alkylidene Bile Salt Derivatives Isolated from Sea Lamprey (Petromyzon marinus). Mar. Drugs 2018, 16, 308.

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